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The Jalap Roots: A Herbal Legacy from the Neotropics to the World

January 2025
Journal of Ethnopharmacology 341(1):119316

DOI:10.1016/j.jep.2024.119316

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CC BY 4.0

Authors:

Adriana Hernández

National Autonomous University of Mexico

Mabel Fragoso

National Autonomous University of Mexico

Rogelio Pereda

National Autonomous University of Mexico

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The jalap roots: A herbal legacy from the neotropics to the world

Adriana C. Hern´

andez-Rojas , Mabel Fragoso-Serrano , Rogelio Pereda-Miranda

Departamento de Farmacia, Facultad de Química, Universidad Nacional Aut´

onoma de M´

exico, Ciudad Universitaria, 04510, Mexico City, Mexico

ARTICLE INFO

Handling Editor: D M Leonti

Keywords:

Anthelmintic

Convolvulaceae

Cytotoxicity

Ipomoea

Laxative

Operculina

Purgative

Resin glycosides

ABSTRACT

Etnopharmacological relevance: The Convolvulaceae or morning glory family, with about 2000 species in the

world’s Tropics and subtropics, stands out among the plants used in traditional medicine. Medicinal plant

complexes with important purgative properties have been developed in Mexico and Brazil from members of the

genera Ipomoea and Operculina with storage roots. Popularly known as the jalap roots, their resin glycosides

cause purgative and laxative activities that facilitate bowel movements.

Aim of the study: This article reviews the importance of the Convolvulaceae family in herbal medicine with a

holistic approach that includes a historical perspective, as well as descriptions of crude drugs, phytopharma-

ceuticals, and chemical constituents. It further considers the family’s distribution and biological properties, such

as documented purging and cytotoxic activities of the Mexican and Brazilian jalap roots. The main aim of this

review is to afford insights into the use and management of medicinal jalap roots for their potential development

as herbal medicines.

Materials and methods: A search for available information on the genera and species that constitute the jalap roots

was conducted using scientic databases, including PubMed, Google Scholar, ScienceDirect, and the Interna-

tional Plant Names Index. Also, numerous historical European herbals, botanical books, and pharmacopeias were

reviewed using the Biodiversity Heritage Library and Internet Archive.

Results: The review establishes that from the initial introduction of the medicinal jalap roots to Europe in the 16th

century, various types of Neotropical purging roots were confused. The misunderstanding resulted from similar

traditional uses of several species with common morphological features, organoleptic characteristics, and

vernacular names. Subordinate species were also frequently used as substitutes for the signature or ofcinal

crude drug. A compendium of contemporary uses of Mexican and Brazilian jalaps in herbal medicine is also

presented.

Conclusions: Mexican and Brazilian jalap roots, still in use in traditional medicine, offer great potential as sources

of biologically active principles. Research should prioritize the investigation on their chemical markers, toxicity,

mechanisms of action, ecological requirements, and ecological networks. An integrated ethnopharmacological

approach, which has not been adequately explored, would promote their proper management as novel

phytopharmaceuticals.

1. Introduction

Mexico and Brazil are biologically diverse countries (Mittermeier

and Goettsch-Mittermeier, 1997) that also display a multiplicity of

native indigenous languages and traditions, including medical treat-

ments and natural resource management. This overlap between global

biological richness and areas of multiculturalism makes them pivotal

geographic regions in plant-human interaction and of exceptional in-

terest from ethnobotanical and ethnopharmacological perspectives

(Toledo, 2013). As such, Mexican and Brazilian ethnoora used in

traditional medicine has not been adequately explored as a source of

biodynamic principles.

Within the vast world of plants used ancestrally in the tropical

Americas, the Convolvulaceae Juss. or morning glory family stands out,

with about 2000 species and 60 genera in the world’s tropical and

subtropical regions (Sim˜

oes et al., 2022). Brazil and Mexico contain the

highest number of these species, also of the genus Ipomoea L., with a

total of about 640–800 species (B´

anki et al., 2024;Wood et al., 2020).

In both countries, various species in the morning glory family had

been used for generations as remedies, food, and entheogens by their

* Corresponding author.

E-mail address: pereda@unam.mx (R. Pereda-Miranda).

Contents lists available at ScienceDirect

Journal of Ethnopharmacology

journal homepage: www.elsevier.com/locate/jethpharm

https://doi.org/10.1016/j.jep.2024.119316

Received 22 July 2024; Received in revised form 30 December 2024; Accepted 31 December 2024

Journal of Ethnopharmacology 341 (2025) 119316

Available online 2 January 2025

indigenous peoples, colonizers, and later settlers. Cross-cultural inter-

action has persistently yielded recognition to the importance of

exchanging knowledge about the therapeutic healing properties of

plants and valued Materia Medica (Leonti et al., 2020). The legacy of the

jalap roots with important purgative properties in the traditional med-

icine of the Neotropics comes from this practice.

The jalaps constitute a taxonomically and ecologically heteroge-

neous group of bindweeds within the Convolvulaceae, mainly in the

genera Ipomoea and Operculina Silva Manso. A conspicuous morpho-

logical feature of this family is the occurrence of secretory structures of

resins in dermal tissues of stems, leaves, owers, seeds, and, especially,

in the periderm of roots with strong laxative effects for humans

(Pereda-Miranda et al., 2010). These medicinal species have been

recognized in two independent medicinal plant complexes in the tradi-

tional medicine systems as the Mexican and Brazilian jalap roots. They

include various species with tuber-shape storage roots of convolvula-

ceous bindweeds. Though taxonomically distinct, their crude drugs

share morphological features, certain organoleptic characteristics, and

vernacular names (Pereda-Miranda et al., 2006). A medicinal plant

complex usually includes a signature, dominant species or “label”

(ofcinal) species, which possess the most effective properties, and

several subordinate species of lesser quality. These secondary species are

used when the signature species is not accessible, but they are not

adulterants (Linares and Bye, 1987).

One of the oldest concepts of traditional medicine worldwide has

been the need to purge the body from toxic products (Lewis and

Elvin-Lewis, 2003). In pre-Hispanic Mexican medicine, purgative and

laxative herbals were commonly used to achieve the “purication of the

body”. The idea was that a balance must be maintained between

opposite forces articulated in a fundamental cosmological duality, the

hot and cold dichotomy. This systems classied not only bodily condi-

tions and medicines but also other spheres of life, such as states of the

natural and ritual environments, human life stages, emotions, and world

views (Colson and de Armellada, 1983;García-Hern´

andez et al., 2023;

L´

opez Austin, 1988;Messer, 1981).

Purgatives, laxatives, diaphoretics, diuretics, emetics, and digestives

were basic to pre-Hispanic herbal remedies because the Aztecs perceived

illnesses as caused by accumulated phlegms and infected uids pene-

trating the nerves, head, chest, and all parts of the body. Those needed to

be expelled to improve health and cure diseases (L´

opez Austin, 1974;

Ortiz de Montellano, 1990). Francisco Hern´

andez de Toledo, during the

rst scientic expedition to the Americas (1570–1577), described the

cacam´

otic tlanoquiloni or purging potatoes. Hern´

andez, a physician of the

court of Spain’s King Philip II, was the rst European naturalist to

compile ethnobotanical evidence from indigenous medical practitioners

in central Mexico (Hern´

andez, 2000). He described the properties of this

medicinal complex of purgative bindweed roots as “benign remedies and

hot medicines”to purge the stomach and expel offending humors “with

wonderful gentleness and safety and remove bilious and other humors

from the veins”(Hern´

andez, 1959). Hern´

andez stated that Aztecs

believed that heat illnesses must be cured by the ingestion of contrary

cold remedies to achieve a healthy equilibrium. His perceptions of folk

medicine in ancient Mexico were shaped to t the Hippocratic-Galenic

humoral doctrine of the double opposites hot/cold and wet/dry, prev-

alent in the Mediterranean countries at the time of the conquest

(L´

opez-Austin, 1995;Ortiz de Montellano, 1975). Today, the Aztec

hot-cold theory is widely applied by contemporary traditional healers or

curanderos in Mexico and the United States (Cruz et al., 2022;L´

opez,

2005). Nevertheless, anthropologists have considered the Aztec hot and

cold dualism as a syncretism between 16th century European concepts

and the native Mesoamerican cosmology (García-Hern´

andez et al.,

2023).

Laxatives and purgatives were aimed at alleviating constipation,

contemplated as a hot illness, through bowel movements for the elimi-

nation of internal heat (Foster, 1994). These medicinal herbs have been

known and marketed as jalap root (raíz de jalapa in Spanish) since the

beginning of the Spanish colony (New Spain, present-day Mexico). The

colonists used xalapa or jalapa as the vernacular name for the signature

species (ofcinal jalap or Rhizoma Jalapa). Xallapan is a Nahuatl word,

the language of the Aztecs, that means spring in the sand (xalli: sand and

apan: sufx for place names where there is a spring or river). In this

region, jalaps were abundant in the surrounding highlands of Xalapa in

Veracruz. Ipomoea purga (Wender) Hayne is the authentic root of jalap or

signature species (Fig. 1). Ipomoea orizabensis (Pelletan) Lebed. ex Steud.

(Mexican scammony or false jalap), Ipomoea stans Cav. (tumbavaqueros),

and Ipomoea simulans D.Hanb (Tampico jalap) were recognized as sub-

ordinate or succedaneum species.

In Brazil, several ethnobotanical and phytopharmaceutical publica-

tions cite the uses of the roots of jalapa-de-purga or batata-de-purga

(Brazilian jalap) as laxatives, anthelmintics, blood puriers, agents

against stupor (loss of consciousness), or as a treatment for uterine

infection. Dried sliced roots, pulverized crude drugs, tinctures, herbal

syrups, ours (tapioca and jalap˜

ao or batat˜

ao powders), and tablets are

sold at low cost as purgatives in municipal markets, street markets, local

pharmacies, and health food stores. This large selection of Brazilian

jalap therapeutic commercial products is manufactured from a bind-

weed with yellow owers and large storage roots, identied as Oper-

culina hamiltonii (G.Don) D.F. Austin &Staples. The species is

extensively disseminated in the north and northeast of Brazil. Another

Brazilian jalap with white owers, Operculina macrocarpa Urb., was

formerly considered the ofcinal species but has been discontinued

(Montiel-Ayala et al., 2021).

This article outlines the important and diverse value the Con-

volvulaceae family has had in herbal medicine as a purgative drug

throughout human history. We relate how after the European Conquest,

Mexican and Brazilian jalaps and their roots, already in use among

indigenous peoples, gained acceptance and trade with Europe. We

illustrate various contemporary uses of these roots in herbal medicine

and offer a relatively brief compendium of known species of Mexican

and Brazilian jalaps. The text concludes with a review of past and

ongoing pharmacognostic research associated with these plants,

including some insights into possible applications, such as in carcer

treatment.

2. Reviewing methodology

The species used as part of the Mexican and Brazilian jalap root

medicinal complexes were researched from December 2023 to

September 2024. The valid scientic names and synonyms obtained

from the International Plant Names Index (IPNI), facilitated on the

Internet (http://www.ipni.org) by The Royal Botanic Gardens, Kew,

Harvard University Herbaria &Libraries, and Australian National Her-

barium, were used for the literature search. Additionally, bindweed,

Convolvulaceae, Ipomoea,Operculina,Distimake, and purgative were

used to do the search in PubMed, Google Scholar, and ScienceDirect, as

well as the following keywords: history, biogeography, ecology, taxon-

omy, phylogeny, chemistry, and chemical constituents. The search also

included the name for the crude drugs: jalap, jalapa, jalap root, Mexican

scammony radix, Orizabae Tuber,Jalapae Tuber, Orizaba jalap, Brazilian

jalap, Veracruz jalap, Tampico jalap, ruibarbo blanco, mechoacan, rui-

barbo negro,jalapa macho, and Jalappenwurzel. Medical botany books

and historic publications were revised using the Biodiversity Heritage

Library (BHL) and Internet Archive. The search was not limited by

language and spanned relevant literature in order to cover archaeolog-

ical, historical, and present-day information on purging bindweeds. Data

on species distribution were downloaded from the Botanical Information

Network and Ecology Network (BIEN) and further checked with avail-

able literature.

3. Purgative morning glories: a historical survey

Knowledge of the purgative uses of the Convolvulaceae family is

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

probably older than the information accessible from the limited

archaeological, ethnohistorical, and ethnobotanical sources available

from the earliest civilizations. In ancient Egypt, a species of bindweed

associated with papyrus stems had religious symbolism and was often

found in oral ornaments in tombs; it has been identied as Convolvulus

arvensis L. This plant is native from Eurasia (Austin, 2000) into Medi-

terranean Africa, and is now distributed worldwide as a signicant

introduced weedy pest (Al-Sna, 2016;Sosnoskie et al., 2020). The

exact botanical identication of the depicted plant has been under

debate, but palaeobotanists have recognized a convolvulaceous bind-

weed as the archetype for these ancient Egyptians representations

(Fig. S1). Aufr`

ere and Lopez-Moncet (2001) concluded that depiction of

the leaves as triangular or in the shape of an arrowhead was essentially

for its symbolic character as an expression of vigor. Further, its

distinctive enormous multi-branched storage root of several meters −

and thus with a strong vegetative reproductive potential −may argue

for evidence of its representation in funeral imagery as a symbol of

rebirth. As early as the 16th century CE, the medicinal uses of C. arvensis

were described in European herbals and natural history or medical

botany books (Fig. S2), with its aerial parts and roots indicated for

stimulating bowel movements (Fuchs, 2001). Holm et al. (1977) and

Barker (2001) provided recent descriptions for the traditional uses of

this bindweed as a purgative agent.

Dioscorides Pedanius, whose De Materia Medica (Classical Gr. Π

ερ

ὕλ

ης

ἰ

ατρι

κή

) of around 65 CE, is the Greek precursor of modern

pharmacopeias, described about 600 medicinal plants, 90 minerals, and

30 substances of animal origin. The oldest surviving illustrated manu-

script of this medical treatise dates from the early 6th century CE, the

Vienna Dioscorides, now in the National Library of Austria. It includes a

bindweed with irregularly arrow-shaped leaves and a thick storage root

as well as a description of how to prepare its resin for consumption as a

powerful purgative (Fig. S3). The image is labeled with its vernacular

name in Greek

αμων

−scammony −at the folio upper center and

copied in brown-ink script calligraphy to the right as

αμων

. Greek

and Roman philosophers and physicians including Hippocrates (ca. 460

BCE), Theophrastus (ca. 300 BCE), Pliny (23–79 CE), Celsus (ca. 25

BCE–50 CE), and Rufus of Ephesus (70–110 CE) were acquainted with a

resin known as scammonium (Flückiger and Hanbury, 1874;Kotenberg,

1920) obtained by incising and cutting the fresh root of scammony

(Gunther, 1968;Pereira, 1840).

This pre-Christian medicinal herb’s designation is now identied as

Convolvulus scammonia L., native to and widely distributed in the eastern

Fig. 1. The jalap (Rhizoma Jalapae,Ofcinal Jalapae), the root of Ipomoea purga (Wender) Hayne. A) Vines, stems herbaceous, perennial, glabrous to 7 m and leaves

petiolate, 4-12 ×3–8 cm. B) Stems green or purple, corolla hypocrateriform, 4–6 cm long, red purple to magenta, stamens and style exserted up to a 1 cm

(photograph courtesy of Sarahí Díaz-Mota). C) Fresh roots (photograph Rogelio Pereda-Miranda). D) Dried, smoked storage roots (photograph courtesy of Alberto

Linajes). (For interpretation of the references to color in this gure legend, the reader is referred to the Web version of this article.)

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

part of the Mediterranean basin into Asia Minor, and in Southern Russia

(Flückiger and Hanbury, 1874). Smyrna and Aleppo provided it during

the 18th and 19th centuries (Bouillon-Lagrange and Vogel, 1811). Thus,

it was also known as Syrian or purging bindweed in European herbals

(Fig. S4). The variable quality of the dried milky juice, known as virgin

scammony, led to the use of Resina Scammoniae, as specied in the

United States and British pharmacopeias at the beginning of the 20th

century (Wood et al., 1918). This was obtained from the dried root by

macerating it with alcohol and further precipitating the resin with water

(Power and Rogerson, 1912). The drug was employed as an anthelmintic

and a cholagogue agent. The juice, applied in wool to the womb, was an

abortifacient (Osbaldeston and Wood, 2000). It is no longer used in the

Western Hemisphere, but until the early 20th century, it was widely

dispensed as an effective treatment for severe constipation, especially in

purgation of children, and for the catharsis of adults (purication by

purgation) (Lewis and Elvin-Lewis, 2003). The resin is an important

drug used in Unani medicine, a Perso-Arabic system of traditional

medicine, practiced in the Muslim culture in South Asia and Central

Asia, where physicians prescribe saqmunia as treatment for skin diseases,

chronic headache, bilious fever, conjunctivitis, and jaundice, among

others (Ansari et al., 2022). The drug is also part of many other Unani

herbal formulations, and widely commercialized in India, including

through the Internet (Fig. S5).

Several other members of the morning glory family have been

traditionally used as laxatives in treating acute constipation, which is

one of the most common gastrointestinal conditions in the world (Akram

et al., 2022). Thus, they are indicated as purgative, anti-spasmodic, and

antiparasitic medications (Al-Sna, 2016). An example is Cuscuta epi-

linum Weihe or ax dodder, which is generally associated with culti-

vated ax throughout Europe and elsewhere (Costea and Tardif, 2006).

The seeds of Ipomoea nil L. (Roth) and I. purpurea L. (Roth), native to the

tropical Americas (Austin et al., 2001), are now popular in traditional

Chinese and Unani medicines to purge the bowels, relieve constipation,

and kill intestinal parasites (Gao et al., 2023). Among indigenous peo-

ples of North America, some Ipomoea species were also used as purga-

tives and for stomach ailments, e.g., Ipomoea pandurata G.Mey., an

endemic species from the Eastern United States (Austin, 2011;Barton,

1818;Moerman, 2009). Similarly, the prairie’sIpomoea leptophylla

Torr., yielded a gum containing anti-tuberculosis resin glycosides

(Barnes et al., 2003). These medicinal bindweeds have massive storage

roots, sometimes reaching the size of a human body but with a mild

action as a hydragogue that made them inferior commercial competitors

of the jalap root (Stanford and Ewing, 1919).

The limited ethnobotanical sources on uses of Mesoamerican morn-

ing glories species before the arrival of the Europeans describe essen-

tially two usages other than the edible sweet potato, I. batatas (L.) Lam

(Austin, 1978, 1988). The rst is the use of the seeds of several species

with hallucinogenic properties in divination and religious rituals

(Alrashedy and Molina, 2016). The subject seeds contain small quanti-

ties of ergot alkaloids (similar to the LSD drug), produced by the fungal

symbiont Periglandula species (Clavicipitaceous) associated to Ipomoea

and Turbina Raf. (Beaulieu et al., 2015;Cook et al., 2019;Steiner and

Leistner, 2018). The second known pre-European property pertains to

the storage roots of several species used as purgative crude drugs

(Bernatzik, 1865;Coxe, 1830;Desfontaines, 1809;Farwell, 1920;

Flückiger, 1890;Pereda-Miranda et al., 2006).

The Libellus of Medicinalibus Indorum Herbis (Codex Cruz-Badianus),

written during 1552 and 1553 CE, is the oldest source in the New

World in which botanists can nd illustrations of native medicinal

Mexican plants. It is a treatise on herbal, animal, and mineral-based

remedies of the Aztecs and the rst text of Materia Medica that informs

about the uses of the pre-Hispanic Mexican ora. The author, Aztec

healer Martín de la Cruz, dictated his account of remedies against dis-

eases in Nahuatl. It was translated into Latin by the indigenous

nobleman Juan Badiano, a student associated with the College of Santa

Cruz de Tlatelolco, the rst institution of higher education in the New

World created for the Aztec nobility (Emmart, 1940). De la Cruz-Ba-

diano’s work was completed in July 1553 and sent to Spain as a gift to

Holy Roman Emperor Charles V (King Charles I of Spain) and deposited

in the royal library where it remained unknown until it became the

property of the apothecary Diego de Cortavila y Sanabria in 1623. Later,

Cardinal Francesco Barberini, ambassador of the Vatican in Spain

(1624–1626), became the owner and brought it to Rome. In 1902, the

manuscript, sometimes referred to as the Codex Barberini, became part of

the Vatican Library. In 1929, the Libellus was found by Charles Upson

Clark, a history professor at Columbia University. Pope John Paul II

returned the Libellus to Mexico in 1990, where it is in the library of the

National Institute of Anthropology and History in Mexico City

(Reyes-Chilpa et al., 2021;Tucker and Janick, 2020); digital and print

facsimiles are now available (Emmart, 1940;Bye and Linares, 2013;

Miranda and Vald´

es, 1964).

The Codex Cruz-Badianus gives the Nahuatl names of medicinal

plants in a phonetic transcription in Latin, an illustration of the labeled

species, and their uses in indigenous recipes and formulations for

treating various illnesses (Emmart, 1940;Tucker and Janick, 2020).

Folio 32 recto illustrates

elicpahtli (Nahuatl language, uelic: savory and

pahtli: medicine), a morning-glory with red-owers and large storage

Fig. 2. Illustration (Folio 32 recto) from the Badiano Manuscript depicts the

vine “

elicpahtli”(Nahuatl, uelic =tasty, pahtli =medicine). This morning

glory has been identied as the jalap root, the purgative crude drug of pre-

Hispanic medicine. The description for purging the stomach in Latin (Purgatio

ventris), in addition to the anatomical characteristics of the vine with storage

roots and red campanulate owers, facilitated its taxonomic identication as

Ipomoea purga. Reproduced with permission by the National Institute of An-

thropology and History, Mexico from Libellus de Medicinalibus Indorum Herbis,

Manuscrito Azteca de 1552; Instituto Mexicano del Seguro Social, Mexico City,

1964. (For interpretation of the references to color in this gure legend, the

reader is referred to the Web version of this article.)

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

roots (Fig. 2). Its legend reads Purgatio ventris (purge for the abdomen)

and the recipe in Latin states, “when the abdomen is purulent, the pa-

tient must drink to drive out the pus a portion of the ground root of the

herb

elicpahtli in hot water before mid-day meal”(Emmart, 1940;

Tucker and Janick, 2020). This therapeutical description is comparable

to the one outlined by Dr. Francisco Hern´

andez for the purging potatoes

(cacam´

otic tlanoquiloni) (Hern´

andez, 2000).

Modern interpretations of this Aztec remedy have identied this

purgative species as I. purga (Emmart, 1940;Bye and Linares, 2013;

Miranda and Vald´

es, 1964). The Latin adjective purga means purgative

and was used as the specic epithet for the scientic name of this widely

used medicinal herb, which is the ofcinal jalap root. The species has

been referred to with different botanical synonyms: Exogonium purga

(Wender) Benth. (Fig. S6), Batatas purga (Wender) Peterm, Convolvulus

ofcinalis Pelletan, Convolvulus jalapa Scheide, Convolvulus purga

Wender, Ipomoea schiedeana Zucc., and Ipomoea jalapa Nutt. &Cox.

(Wood et al., 2020). The valid taxonomical description for the signature

species was done by Friedrich Gottlob Hayne (1763–1832), as illustrated

in Fig. 3 (Hayne, 1830), and is based on the lectotype for Convolvulus

purga (Fig. S7; NY Botanical Garden barcode: 00318916). The descrip-

tion for Ipomoea purga (Wender.) Hayne is as follows: perennial vines,

with storage roots, and stems herbaceous, glabrous to 7 m, green or

purple; leaves petiolate, 4-12 ×3–8 cm; owers usually 1 or 2 per

inorescence with corolla hypocrateriform, 4–6 cm long, red-purple to

magenta waxy transparent color; stamens and style somewhat exserted

(Fig. 1) (Wood et al., 2020).

Another remarkable colonial 16th century manuscript, an encyclo-

pedic work about the people and culture of central Mexico in which

morning glory species were illustrated, is The General History of the

Things of New Spain compiled and written during 1576–1577 by the

Franciscan Friar Bernardino de Sahagún and indigenous collaborators

from the same College of Santa Cruz de Tlatelolco (Sahagún, 2023). It

consists of 12 vol or books with 2000 illustrations. Book XI is dedicated

to natural history and comprises the preparation of remedies from

plants, including their native names, as well as minerals and animals

used in several medicinal formulations. The manuscript was sent to

Europe where it entered the Medici family’s library in Florence and thus

is commonly referred to as the Florentine Codex, now in the Laurentian

Library of Florence, Italy. Sahagún wrote about the ololiuhqui or xix-

icamatic application: “… The grated root is useful for those that have

swollen bellies and whose intestines rumble; when drunk while fasting,

it purges, and lowers fever …The root is somewhat sweet, and one

makes enough to drink three times (an infusion) …[sic]”(Dibble and

Anderson, 1963;Sahagún, 2023). It is important to note here that the

name ololiuhqui was generalized to many species of Convolvulaceae and

not only for Ipomoea corymbosa (L.) Roth (Rivea corymbosa Osmond), as

mentioned in the Florentine Codex in the description of the xixicamatic

and identied as Ipomoea tuberosa L. by Daniel F. Austin (1998), now

Distimake tuberosus (L.) A.R.Sim˜

oes &Staples (Fig. S8), and the

elicpahtli (uei patli as mentioned by Sahagún) (Fig. 2), the authentic

jalap root (I. purga).

4. The confusion among Mexican jalap roots

The rst treatise on medicinal plants of the Americas written in

Europe, widely known in the Old World during the early 17th century,

was La Historia medicinal de las cosas que se traen de nuestras Indias

Occidentales (1565–1574), by Nicol´

as Monardes (1512–1588). It was

translated into English by John Frampton with the title Joyfull Newes out

of the Newfound World (1596). In it, the Sevillian physician and botanist

proposed to study and experiment with American plant remedies in

order to explore their therapeutic properties, taking advantage of Sev-

ille’s role as the port of entry for the Old World goods brought from the

West Indies out of the port of Villa Rica de la Vera Cruz (The Rich Village

of the True Cross). The city of Veracruz on the coast of the Gulf of Mexico

was founded in 1519, which made it the rst municipal prefecture in

Fig. 3. Illustrations of the protologue of the Mexican Jalap root, Ipomoea purga (Wender) Hayne. Friedrich G. Hayne described this species in "Getreue Darstellung und

Beschreibung der in der Arzneykunde Gebr¨

auchlichen Gew¨

achse" (1805–1837), Volume XII (1830) with two hand-colored engraved plates by Friedrich Guimpel. Left

plate: aerial parts; Right plate: roots and reproductive organs. Reproduced from Hayne (1830) https://doi.org/10.5962/bhl.title.114846.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

Mexico and the Americas.

So, Monardes cultivated American plants in his garden and described

many species for the rst time, such as the jalap root, maize, sweet

potatoes, and tobacco, among others. His contribution helped to intro-

duce the purgative Mexican jalaps in the practices of Hippocratic hu-

moral medicine (Von Staden, 2007) and Galenic pharmacy in the

colonial empires of Spain and Portugal, in which the theory of four

humors was accepted until the early 18th century (Hajar, 2021). Thus,

these New Word remedies became valuable substitutes for scammony in

the composition of purgative drugs (Chipman, 2012). This transfer of

therapeutical knowledge from the Americas happened without any

conceptual reserve or restriction (Risse, 1984). The practice of purgation

was still commonplace until a few years ago.

A striking example of the spread of these Mexican species beyond the

Iberian Peninsula is the treatise by the English naturalist John Gerard,

Great Herball or Generall Historie of Plantes (1597), the most inuential

book of medical botany in English until the beginning of the 20th cen-

tury, with an illustration of the Indian rhubarb, the root of Mechoacan

(Fig. S10A) from another Nahuatl word, Michihuac´

an, meaning place of

shermen. Because of its mild purgative effects, this subordinate species

became popular in European medicine as a New World succedaneum for

scammony.

As a result, since the late 16th century, substantial misunderstanding

has persisted between the various types and varieties of the Meso-

american jalap roots. This misunderstanding was due in part to the

traditional uses of several morning glory species, the frequent adulter-

ation of the drugs at their geographical and habitat sources (Linajes

et al., 1994), the addition of subordinate species (Alsberg et al., 1919),

as well as lack of knowledge on the origin of the signature plant. Sig-

nicant confusion, for both common names and scientic nomenclature,

has resulted from taxonomists’attempts to classify the variety of Mes-

oamerican jalaps. In addition, other plants were used as jalaps or adul-

terants, including Phytolacca octandra L., P. decandra L., Phytolaccaceae,

and Mirabilis jalapa L., Nyctaginaceae. Like John Gerard, some German

authors even supposed that jalap was rhubarb (Scheuber, 1894), a

species unrelated taxonomically to Ipomoea (Bernatzik, 1865;De Gas-

sicourt, 1817;Youngken, 1940).

Edible roots eaten by native North Americans were considered po-

tatoes (Solanum tuberosum L.) by the colonizers, including diverse un-

related species (Austin, 2011). One of these roots was I. pandurata,

confused with both potatoes and Mechoacan root for more than 200

years. This endemic plant was also mistaken for other Convolvulaceae,

such as Ipomoea macrorhiza Michx., an endemic coastal night-owering

species with white owers and often three-lobed leaves with no me-

dicinal properties as yet recognized, and even with other families of

plants such as Apios americana Medik., Fabaceae (Austin, 2011;Wood

et al., 2020).

Monardes was the rst to describe the laxative and purgative prop-

erties of the jalap root and, at the same time, brought attention to the

difference between this purgative plant and the other known Meso-

american laxative crude drug, the Mechoacan or Rayz de Michoacan

(Bernatzik, 1865). Many attempts, mainly by non-native expeditionary

botanists, to make the inventories of the natural resources of the New

World resulted in signicant misunderstandings of the diversity of the

Mexican jalaps. The confusion between jalaps is illustrated by the lith-

ographs of Jean-Th´

eodore Descourtilz (1796–1855) published in the

Flore pittoresque et m´

edicale des Antilles, ou Trait´

e des plantes usuelles des

colonies françaises, anglaises, espagnoles et portugaises (Descourtilz, 1833)

by Michel Etienne Descourtilz (1775–1835). In it, Mirabilis jalapa

(Figs. S11A and S11B) was described with the following vernacular

names: white rhubarb, American scammony, root of Mechocan, jalap,

nyctage or nyctage dychotome, and nyctage faux jalap (Nictago jalapae DC.)

(Fig. S11C), and identied as Jalapa ofcinarum (Descourtilz, 1833).

Mirabilis dichotoma L. is now a synonym of M. jalapa. Another drastic

purgative root of a plant with yellow owers was illustrated with the

synonyms designated as Convolvulus jalapa L. and I. macrorhiza

(Fig. S11D) and the common names of liseron jalap (French), xalapa

(Mexican Spanish), jalapa (Portuguese and European Spanish), and jalap

(English). Based on the simplied illustration for the oral elements by

Descourtilz, plus the description of the therapeutical use of this purga-

tive root, it can be suggested that this vine is one of the members of

Operculina, with a distribution that includes South America and the

Caribbean islands, and that was identied putatively in Brazil as the

yellow-owered O. hamiltonii, not the Mexican jalap root (I. purga).

The confusion with Mirabilis resulted from a false assignment by the

German medical practitioner Gregorious Horstius in his De natura motus

(1617), among other causes. Horstius’mistake inuenced Charles

Plumier (1646–1704) and consequently Joseph Pitton de Tournefort

(1656–1708). Wenzel Bernatzik (1821–1902) considered that the erro-

neous identication was perhaps inuenced by the similar mode of ac-

tion of both herbs (Bernatzik, 1865). In fact, M. jalapa is a bushy

perennial herb that typically reaches heights of 1 m with a moderately

thickened storage root (Fig. S11B) (Liya et al., 2021), not an herbaceous

vine with a very thick and bulbous root with an oval or pear-like form as

does the authentic Mexican jalap (Fig. 1) (McDonald, 1989). In tradi-

tional medicine, the root of M. jalapa is used as a purgative and diuretic

drug, as well as in treating gastrointestinal ailments and abdominal

colics (Liya et al., 2021). Mirabilis roots contain 3% of a polysaccharide

resin that on hydrolysis yields galactose and arabinose (Liya et al.,

2021). The total resin glycosides for the Mexican jalap root corresponds

to 9–12% and on hydrolysis afforded hydroxylated fatty acids, in addi-

tion to glucose, quinovose, fucose, and rhamnose (Pereda-Miranda et al.,

2006).

Other reasons for this misperception could be the inuence of

important botanical authorities who incorrectly identied jalaps, the

easy availability of Mirabilis in the Mexican landscape, and the more

accurate knowledge of Mirabilis than of the Ipomoea members of the

jalap root complex. Taxonomy, as a science of classication as it is

currently known, was in its infancy with the rst signicant botanical

works of Caspar Bauhin (Prinax Theatri Botanici, 1623), Leonard Plu-

kenet (Phytographia, 1691–1696), and Linnaeus (Systema Naturae,

1735), among others. At that point, various classication were mistakes.

For example, Bauhin (1560–1624) mentioned the Radix Mechoacan

(root of Mechoacan) with the polynomial name Bryonia Mechoacana

alba, the jalap root as B. Mechiocana nigricans, and another B. Mechiocana

sylvestris with a milder purgative effect,although the genus Bryonia L.

now is known to belong to the Cucurbitaceae. Misled by Plumier,

Tournefort attributed the jalap to a species of Mirabilis, an error adopted

by Nicolas L´

emery (1645–1715) in his work published in 1714, Trait´

universel des drogues simples or Universal Treaty on Simple Drugs

(Grifth, 1835).

Most of the jalap records in botanical and pharmacognostic works

during the rst half of the 18th century placed the Mexican jalaps in the

Nyctaginaceae as Mirabilis jalapa. Even Linnaeus in the rst edition of his

Materia medica (1749) described Mirabilis longiora L., as the signature

plant for the jalap root complex, but later in the second edition (1767),

he recognized this species as a member of Convolvulus (Scheuber, 1894),

thanks to the botanist Dr. William Houstoun (1695–1733). In his travels

to America (1728–1732), Houstoun, employed as a ship’s surgeon for

the British South Sea Company, collected plants in Mexico, Jamaica,

Cuba, and Venezuela. He transported the true jalap from Veracruz to

Jamaica, as part of a plan to cultivate the plant and try to break the

Spanish monopoly on this purgative drug (Dorner, 2019). At the same

time, he was employed by the physician and naturalist Hans Sloane

(1660–1753) to collect samples from the Neotropical ora. In March

1731, he informed his successful acquisition of the jalap root through

the help of indigenous people. After the Spanish authorities denied him

the opportunity to explore the province of Xalapa, he was shipwrecked

in the port of Veracruz, and his collections of dried specimens were lost

(Johnston, 1941;Rose, 2023). The jalap was later identied by

Antoine-Laurent de Jussieu (1748–1836) as a member of Convolvulus

(Bernatzik, 1865). Thus, many botanists subsequently accepted the jalap

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

root as a member of this genus, e.g., Philip Miller (1691–1771), Leonard

Plukenet (1641–1706), and John Ray (1627–1705) mentioned it as

Convolvulus americanus jalapium dictus or C. americanus volubilis.

The modern legitimate description of the signature species is based

on its rediscovery by the German botanists Christian Julius Wilhem

Schiede (1798–1836) and Ferdinand Deppe (1795–1861) during an

expedition to the foggy mountains of Cofre de Perote, Veracruz. They

were successful in nding the true mother plant of the jalap drug, which

was known as purga de jalapa (Fig. 1), in the Chiconquiaco Sierra

(Schiede, 1830). The German botanist Georg Wihelm Franz Wenderoth

(1774–1861) published the communication between Diederich Franz

Leonhard von Schlechtendal (1794–1866) and Schiede in 1830,

providing a description of the species under the name C. purga (Fig. S7),

in which he distinguished the authentic jalap drug from I. macrorhiza,

the name given by Thierry de Menonville (1739–1780), Ren´

e Louiche

Desfontaines (1750–1833), and Andr´

e Michaux (1746–1802), because

of its growth habits “in the cold region of the Mexican Andes in the

forests near Chiconquiaco [sic]”, the Sierra Madre Oriental (Wenderoth,

1830). This species was formally published by Hayne (1830) as I. purga.

Prior to the ndings of Schiede and Deppe, John Redman Coxe

(1773–1864) managed to cultivate the plant that produced the ofcinal

jalap and described it as I. jalapa var. macrorhiza from a culture of

samples transported from Veracruz, Mexico, and maintained it during

three successive years in his garden in Pennsylvania (Coxe, 1830). This

description, supported by Thomas Nuttall (1786–1859), included two

plates (Fig. S12) that distinctly showed the same anatomical features

that were identied at almost the same time by Hayne (1830). However,

his morphological analysis and interpretations were ignored by the

scientic community because it was thought to be another bindweed

unrelated to the signature species.

The rst purging root ofcially described was I. tuberosa (Fig. S8) by

Linnaeus (1753), as only distributed in Jamaica (Linnaeus, 1753).

Recently, Austin (1998) reported its use as one member of the Mexican

jalap root complex, notwithstanding the pre-Columbian knowledge of its

purgative properties. Ipomoea jalapa (L.) Pursh described by Linnaeus, in

Mantissa plantarum (1767) as C. americanus jalapium or Jalapa ofcina-

rum Martyn (Fig. S13), is another of the species included in the confu-

sion. McDonald (1989) worked on the neotypication of this species. In

the words of Robert Eglesfeld Grifth (1798–1850), the name C. jalapa

leads to much confusion and uncertainty from is having been applied to

many totally distinct plants (Grifth, 1835). The root of Mechoacan, as

mentioned and illustrated in European herbals (Fig. S10A), was identi-

ed as Ipomoea jalapa by Friedrich Traugott Pursch (1774–1820). The

differences with I. macrorhiza and a detailed characterization and

illustration were provided in Pursch’sFlora Americae Septentrionalis

(Pursch, 1813). Nevertheless, this medicinal jalap root was also

continually confused with I. purga. Another jalap, used in the traditional

medicine to treat epileptic seizures and nervous disorders, was described

in 1794 by Antonio J. Cavanilles (1745–1804) as Ipomoea stans Cav

(Herrera-Ruiz et al., 2007), with no mention of its purgative properties

in this description (Fig. S13A).

Great demand for the signature jalap root, and uctuating supply, led

to commerce with Europe and the United States with other wild roots

similar in effect (Alsberg et al., 1919), including subordinate con-

volvulaceous species with wider distribution such as I. orizabensis (Pel-

letan) Lebed. ex Steud. This subordinate species for jalap root was

described in 1834 by Gabriel Pelletan. It is known as the Mexican

scammony, false jalap or light jalap because of the mild purgative effects

of its resins with a higher yield than the true scammony’s resin (Alsberg

et al., 1919). Another species, known as the Tampico jalap, which is less

rich in resin and less purgative than true jalap, quickly entered in trade

internationally because of its lower price (Hanbury, 1869). Daniel

Hanbury (1825–1875) described it in 1869 as I. simulans D.Hanb. and

mentioned that its root was collected in the Guanajuato State in central

Mexico along the Sierra Gorda near San Luis Potosí. There and in nearby

villages, it was purchased from indigenous peoples and carried by

muleteers to Tampico, a port in the southeastern Tamaulipas state on the

Gulf of Mexico and north to the state of Veracruz. It was also known as

purga de Sierra Gorda (Sierra Gorda’s purge).

5. Commercial exchange between Mexico and Europe

Linajes et al. (1994) described a detailed traditional production

system of I. purga in the localities of Coxmatla and Tlacuilolan (Xico,

Veracruz) (Fig. 4A), by observing the advanced knowledge of the ecol-

ogy of the species among farmers of indigenous ancestry. Their knowl-

edge of the phenology and germination of seeds was remarkable. They

could anticipate the dehiscence of the capsular fruit and scaried the

seeds efciently with a small incision on the testa opposite to the

micropyl that yielded a 90–95 % germination rate. The post-harvest

process to prepare the drug included smoke-drying the roots with

wood, the same method observed by Schiede (1830) in Chiconquiaco,

where locals grew up the purging bindweed in their gardens. This

traditional production system was passed on orally through generations

of farmers (Linajes et al., 1994).

Jalap root production was highly important in the Xico region of

Veracruz during the colonial period from the 16th through 18th century,

and New Spain (now Mexico) provided the raw material for maintaining

the Spanish Crown’s monopoly on this important substitute for Europe’s

supply of Syrian or purging bindweed (C. scammonia). The economic

importance of the purging roots for the Spanish Empire was reected in

the 1791 royal decree by Charles IV of Spain that granted Xalapa the title

Villa and a coat of arms. That heraldic shield in part depicts six purging

roots with leaves from a bindweed (seis rayces ´

o frutos con sus [h]ojas ´

guías, [sic]) illustrated as four long, tuberous, moderately thickened

roots at the right and left and two thick, bulbous roots at the center

above and below (Fig. S14).

In 1828, the production of I. purga root was around 140 614 tons per

year (Lerdo de Tejada, 1853), while Linajes et al. (1994) using the same

source cited more than 1.67 million tons exported to Europe between

1761 and 1851. About 40 tons of dried jalap roots were still exported

yearly to the United States from Veracruz’s Xico region from the 1940’s

until the 1990’s, when the production fell to almost nothing (Linajes

et al., 1994).

The global demand for jalap root has waned due to increased use of

other laxatives derived from the mucilage of other plant species (Plan-

tago L., Senna Mill., and Cassia L.) for short-term treatment of con-

stipation and irritable bowel syndrome. Also, the world market has come

to be dominated by Italian and German exports of plant drugs based on

dried roots and resins from Brazil (O. hamiltonii) and India. Turpeth or

the Indian jalap (Akbar, 2020), celebrated by the ayurvedic physicians

(Ahmad et al., 2017;Austin, 1982;Staples et al., 2020), is now identied

as Operculina turpethum (L.) Silva Manso (Fig. S9). Nonetheless, sliced

dried roots of jalaps are still sold in health-food stores and markets for

medicinal plants in Mexico (Fig. 4D). The current suggested pre-

scriptions for the jalap root per liter of water are 1–3 g of powder,

0.2–0.4 g of dried hydroalcoholic extract, 0.1–0.6 g of resin extracted

with alcohol and precipitated with water. A teaspoon of the root, cut

small or granulated, is taken per cup of boiling water, or 10 to 20 drops

every 4 h in tincture. If given in sugar or jelly, this preparation is an

innocuous purge for children (Pereda-Miranda et al., 2006).

The root of the tumbavaqueros (I. stans) is also distributed in several

phytopharmaceuticals sold as over-the-counter medicines as sliced

roots, alcoholic infusion, pills, and herbal mixtures for treating anxiety

and insomnia, as well as to promote relaxation (Fig. S15).

6. Jalap herbal medicines in Brazil

The history of the path that the word jalapa (jalap) of Mexican origin

followed to Brazil and conformed to the designation jalapa-do-Brasil

(Brazilian jalap) is related to that of the Mexican jalap. Purging plants

for the Convolvulaceae family were documented from the beginning of

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

the colonies in Latin America by conquistadors, friars, physicians, and

travelers who were naturalists. Thus, the vernacular name of jalap was

brought to Brazil through the medicinal plant manuscripts of the 16th

and 17th centuries.

In the practice of European Hippocratic-Galenic medicine, which

gave great therapeutic importance to purgative remedies, the laxative

and purifying properties of these perennial vines with storage roots and

acrid taste were recognized. These indigenous purgative convolvula-

ceous roots, widely distributed in Brazil’s Tropics, gained quick accep-

tance because they were remedies with a mild effect, similar to some of

the Mexican jalaps. Seen then as a panacea, they continue to be widely

used in north and northeastern Brazil. Coelho Elder (2013) reported that

the root of Mechoacam (Michoac´

an) was mentioned as early as the 17th

century in Pierre Pomet’s reference Histoire G´

en´

erale des Drogues

(Fig. S10B). In Jo˜

ao da Silva Feij´

o’sDescriptive Collection of Plants of the

Captaincy of Cear´

a(1799), the use of jalap root is indicated by the

vernacular Mexican name of Mechoacam. This reference is one of the

oldest on the traditional use of the jalapa-do-Brasil in the Brazilian

Northeast.

The Brazilian jalap root’s scientic name is Operculina macrocarpa, a

bindweed with white owers. In recognition of its important therapeutic

benets, the colonizers of South America called this laxative root with

the common name of batata-de-purga (purging potato). Its distribution is

limited to the thickets of the Atlantic Forest of Brazil’s northeast and

southeast (Fig. S16A). In the rst edition of the Pharmacopoeia of the

United States of Brazil (1929), it is mentioned as jalapa-do-Brasil and

that should contain at least 15% resin (Brand˜

ao et al., 2009).

Today, the common names of batata-de-purga,jalap˜

ao (big jalap) or

batat˜

ao (big potato) correspond to O. hamiltonii (Fig. 5), a different

species with yellow owers, distributed in the north and northeast of

Brazil. Sliced roots are easily found in many herbal and open-air mar-

kets, and it is widely sold in isolated communities in the Amazon River

Basin. Its distribution is wider than that of the species O. macrocarpa

(Fig. S16B),facilitating access to the various communities of the region,

in the states of Amazonas, Par´

a, Maranh˜

ao, Piauí, and Cear´

a, among

others. Its grated root is used in purgatives for amoebic dysentery and

other intestinal diseases (Staples et al., 2020). This climbing purging

jalap with yellow owers gave its name to the Jalap˜

ao State Park in

Tocantins state and can be found in all the Cerrado or savanna vegetation

of this extensive northern region. This Brazilian jalap (O. hamiltonii) is

not mentioned in the 1929 edition of the Brazilian Pharmacopoeia,

indicating that its use is recent, subsequent to the expansion of popu-

lation into the northern regions (Montiel-Ayala et al., 2021).

Another species of the jalap complex is also widely distributed in the

Brazilian savannas and into Bolivia and Paraguay. It is an erect under-

shrub with somewhat thickened storage roots and funnel-shaped pink

owers with a pubescent corolla (Fig. S17), known as jalap and identi-

ed as I. aprica House (syn I. angustifolia Choisy) (Wood et al., 2015).

Fig. 4. Authentic jalap root, Ipomoea purga. A) Jalap root plantation in Xico, Veracruz (Photograph courtesy of Alberto Linajes). B) Resin extraction in methanol from

a dried root. C) Sliced dried jalap roots found in Mexico City medicinal plant markets. Photographs: Rogelio Pereda-Miranda.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

Brazilian jalapa-de-purga is used as an anthelmintic, in blood-

purifying remedies, against stupor, and as a treatment for uterine

infection. In municipal markets, street markets, local pharmacies and

naturist shops, dried sliced roots, pulverized crude drugs, tinctures,

herbal syrups and liquors, ours, and tablets are sold as inexpensive

purgatives (Fig. 6). The roots are cut into slices averaging 5–7 cm in

diameter, and about 0.5 cm thick, rough and dark at the edges and of a

pale brown to dark grayish color on the surfaces of cut sections that

reveal several concentric rings (Fig. 6B). They bear considerable

resemblance to the ofcinal Mexican jalap. Recommended use a cup of

cold decoction drunk before bedtime. One teaspoon of the root, cut small

or pulverized, per cup of boiling water is a safe purgative for children.

Powders (jalapa or batat˜

ao p´

o,Fig. 6C) and ours (tapioca) and are also

sold with a recommended dosage of 1–3 g in a liter of water.

Jalap tincture is used to treat constipation and is widely marketed in

various presentations of registered herbal medicines, as Tintura de jalapa

Sobral and Tintura de jalapa D1 Lapon. These tinctures, formulated as

hydroalcoholic extracts of O. hamiltonii roots with a concentration of the

active resins of 15–19 mg/ml, are sold in pharmacies throughout Brazil

(Fig. 6D). As a powerful purge, the recommended dosage for its action is

30–45 ml (2–3 tablespoons) of the tincture in a bottle of sugar water,

once a day for seven days; as a milder laxative to ease constipation, 15

ml (one tablespoon) of the tincture in sugary water is indicated.

Various herbal syrups containing jalapa-de-purga are known as

aguardente alem˜

a(German brandy) and sold as Hyp´

olito liquor remedy

(Fig. 6D), Tiro Seguro (Safe Shot), Santa Fe German brandy, indicated for

treating stomach indigestion, circulatory problems, stroke, liver and

spleen disorders, facial paralysis, as well as for trembling hands, legs,

and arms, plus as a blood cleanser. The dosage for these syrups is usually

one tablespoon once a day. Tiro Seguro syrup contains jalap root powder,

mastruz juice (Dysphania ambrosioides (L.) Mosyakin &Clemans), Indian

mastruz juice (Lepidium virginicum L.), star anise (Illicium verum Hook.f.),

S˜

ao Caetano melon (Momordica charantia L.), small mint (Mentha spicata

L.), propolis, honey, and a water-alcohol solution. Artisanal spirits made

with fermented jalap roots are also sold.

Anti-stupor pills are also sold without labels, in small plastic and/or

cardboard packages of 20 tablets that appear to be hand-molded

(Fig. 6D). Some packages bear only the name of the product, the

manufacturer, or use instructions, others show the ingredients. These

anti-stupor pills contain jalap, extract of Luffa operculata (L.) Cogn.

(buchina or purga-de-bocho), and dry extracts of Aloe vera (L.) Burm.f.

(aloe vera).

Fig. 5. The species Operculina hamiltonii D.F. Austin &Staples is an annual climbing plant with yellow owers, distributed mainly in the shrublands of the tropical

regions of the north and northeast of Brazil, where it is known as batata-de-purga (purging potato). A) Root, stem with leaves and ellipsoid immature fruits with

capsules surrounded by enlarged sepals. B) Flower. C) Mature operculated fruit. Photographs: Rogelio Pereda-Miranda. (For interpretation of the references to color

in this gure legend, the reader is referred to the Web version of this article.)

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

7. Taxonomic notes and phylogenetic connections

Convolvulaceae is sister to Solanaceae. A structural change in the

chloroplast genome of this family strongly supports its monophyly with

the absence of the rpl2 intron as a molecular synapomorphy. The con-

volvulaceous plants are the only asterid family with this deletion

(Stefanovi´

c et al., 2002), and their seeds are physically dormant (Baskin

et al., 2000). The generic delimitation for the morning glories has been

historically problematic by grouping supercially similar species into

genera, leading to non-monophyletic groups and highly polymorphic

genus concepts (Staples et al., 2020). The biggest species group in

Convolvulaceae is Ipomoea, which was described by Linnaeus in his

Species Plantarum (1753) but never monographed until the work by

Wood et al. (2020), who considered the group as an expanded mono-

phyletic genus recognized by its spiny pollen. However, the genus was

not clearly dened, and Linnaeus and his successors placed species in

both Convolvulus and Ipomoea without clear separation criteria. Jacques

Denys Choisy, in his work Convolvulaceae orientales (1834), separated

the two genera permanently based on ovary and fruit characters (Wood

et al., 2020). During the 20th century the boundaries between the

genera that include the jalap roots remained unclear over the years; the

same species had repeatedly been classied in different genera

(Convolvulus, Batatas, Exogonium, Ipomoea, Merremia, and Operculina).

Two species, now considered to belong to Operculina, were rst named

by Linnaeus (1753) as Convolvulus turpethum L. and C. macrocarpus. In

1836, Silva Manso proposed the generic name Operculina for these

species on the basis of their different fruit type with a dehiscent cap,

called “operculum”(Silva Manso, 1836), which he considered “a transi-

tion from capsule to drupe”and a synapomorphy for the genus (Fig. S9).

Pressed herbarium specimens had ruined the three-dimensional

arrangement of the fruit, making it impossible to interpret this struc-

ture correctly. Operculina is monophyletic as the genus is currently cir-

cumscribed. Other characteristics useful for recognizing the genus are its

large, pear-shaped sepals, accrescent and persistent calyx, broad at the

base with upward tapers, anthers that coil spirally strongly after

dehiscence, and stems, petioles, peduncles, and pedicels frequently

winged (Staples et al., 2020).

Austin (1982) was the rst to formally recognize Merremieae, a

grouping in which he included Merremia and Operculina, among other

genera. Early molecular phylogenetic studies suggested that the tribe

Merremieae and the genus Merremia were polyphyletic (Stefanovi´

et al., 2002). Sim˜

oes et al. (2022) further demonstrated that Merremia is

not monophyletic by using a comprehensive species-level sampling from

all genera in Merremieae. Later, these genera were re-assigned in several

monophyletic groups with new generic entities, such as Camonea Raf.,

Daustinia Buril &A. R. Sim˜

oes, Decalobanthus Ooststr., Distimake,Mer-

remia, and Operculina,inter alia (Sim˜

oes et al., 2022). Recently, Distimake

was fully recognized as the largest genus segregated from Merremia sensu

lato and the sister clade that contains both Decalobanthus and the tribe

Ipomoeeae (Sim˜

oes et al., 2022). So, Ipomoea tuberosa, later considered

as Merremia tuberosa, now belongs to the genus Distimake.

At the species level, jalaps are distantly related phylogenetically,

belonging to different well supported monophyletic groups. The storage

root they share is a characteristic that evolved independently in the

family multiple times (Eserman et al., 2014;Mu˜

noz-Rodríguez et al.,

2019) and thus does not imply a phylogenetic link. Wood’s taxonomic

monograph included 425 Ipomoea species in different clades (Wood

et al., 2020). Ipomoea jalapa belongs to the clade A1 (Arborescens), a

group of species with a pubescent corolla that spread through South

America. Ipomoea orizabensis and I. simulans belongs to the clade B1

Fig. 6. The root of the Brazilian jalap, jalapa-do-brasil. (A) Roots. B) Dried roots cut into slices. C) Batat˜

ao powder (our or tapioca) and pulverized jalapa for sale in a

public market. D) German brandy or syrup (Hip´

olito), jalap root tincture (Indústria Farmacˆ

eutica Sobral) and pills. All products were purchased at Mercado

Municipal 2000, Santar´

em, Par´

a, Brazil in September 2015. Photographs: Rogelio Pereda-Miranda.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

(Pharbitis), while I. purga and I. stans are in the clade B2 (Quamoclit). In

both groups no obvious morphological feature characterizes the clades

(Wood et al., 2020). Molecular studies suggest that I. orizabensis consists

of more than one taxon (Mu˜

noz-Rodríguez et al., 2019). McDonald

(2001) and Wood et al. (2020) included four varieties for this species.

8. Biogeography

Although the morning glory family is distributed throughout the

world, the distribution of many of its members is quite restricted. Nar-

row endemism occurs at the generic and species levels in almost every

continent (Stefanovi´

c et al., 2002). Given that their seeds are not ef-

cient at long distance dispersal, the widespread distribution at the family

level suggests a very old origin of the group. It is possible that the family

was at one time cosmopolitan but lost its presence in the northern

hemisphere when it became drier and cooler during the Eocene Epoch

(McDonald, 1991). Though a proper analysis does not exist, there is

much evidence for the probability that the morning glory family has

endemics of evolutionary old lineages and endemics of more recent

origin (paleo and neoendemics).

McDonald (1991) recognized four major centers of diversity for the

family: Mexico, South America, tropical Africa, and Southeast Asia. As

the most abundant member of the family, the genus Ipomoea has an

amphitropical distribution, with its species diversity rising away from

the Equator with the greatest diversity of species between the latitudes

of 15–30◦, notably in Mexico and Brazil (Austin et al., 2015;Wood et al.,

2020). Both countries have 60 endemics, including the jalap species.

Brazil is the richest country in Ipomoea, but it remains the least explored

and it is the only country in the Americas from where signicant

numbers of new species are expected (Wood et al., 2020). In Mexico,

Ipomoea stands out uniquely for tropical endemics occurring along a

humid coastal plain, in eastern Mexico, with more than twice the

number of Mexico’s arid-zone endemics, with the arid central Mexican

plateau as a secondary source of endemism in the genus (McDonald,

1991).

In general, the biogeographic distribution of the family, including

the jalaps, has been altered by anthropogenic dispersal, which compli-

cates any assessment of biogeographic patterns (Eserman et al., 2014).

The jalaps of the genus Ipomoea are ancestrally Neotropical but have

likely been dispersed by humans to the paleotropics (Austin et al., 2015).

The species of Operculina and Distimake now have pantropical distribu-

tions but are thought to be of paleotropical origins (Austin et al., 2015).

Many species of these genera were distributed by humans for use as

medicine or ornamentals (Austin, 2000;Austin et al., 2013;2015).

The species belonging to the Mexican and Brazilian jalap roots are

divided in two groups of pantropical distribution and endemic elements.

For Ipomoea and Distimake, a natural delimitation of the territories is

followed, rather than the simple political division, using the biogeo-

graphic province of Mega-Mexico proposed by Rzedowski (1993). In

addition to Mexico’s current delimitation, it includes the areas of the

Sonoran Desert, the Chihuahuan Desert, and the Tamaulipan scrub that

lie in the United States, as well as some portions of Central America as

far south as northern Nicaragua. Fig. S18 illustrates the distribution of

the medicinal complex of purgative jalap roots in Mexico.

8.1. Distribution of the Mexican jalaps

8.1.1. Ipomoea purga (Wender.) Hayne

This medicinal root is a Mexican endemic species with a distribution

centered on Hidalgo (Huasteca High Sierra), Puebla (Sierra Norte), and

Veracruz (Fig. 4) (Hayne, 1830). It grows in pine and oak forests at al-

titudes of around 1900–2400 above sea level. It occurs on the mountains

of Acajete, Chiconquiaco, Huayacocotla, Ixhuac´

an de los Reyes,

Tonay´

an, Las Vigas, and Xico among other places in Veracruz

(McDonald, 1994). This signature jalap’s distribution probably includes

the tropical moist broadleaf forest ecoregion on the northern and

northeastern slopes of the Chiapas highlands in southern Mexico with

cold climate mountainous areas (Corrales et al., 2015). Villase˜

nor

(2016) in his compendium for the Mexican ora does not mention

I. purga as endemic, probably because of its presence in Jamaica and

other countries of central and south America, where it was introduced

(Flückiger, 1890). It is not a coastal plant as was thought for centuries

(Williams, 1970).

Dried specimens, herbarium sheets, and records in databases of

I. purga at altitudes below 1300 m typically belong to I. dumosa (Benth.)

L.O.Williams, a species that is widely distributed from Panama to central

Mexico in tropical climates (Wood et al., 2020). This bindweed does not

have the globose storage root as I. purga, its sepals are uneven, acute, and

it has leaves that wrap around the base of the corolla tube in the terminal

fertile branches (McDonald, 1994). In Xalapa, Xico, and Coatepec,

Veracruz, this edible morning glory is known as xonequi and its leaves

are used for the preparation of a bean broth with maize masa dumplings.

8.1.2. Ipomoea jalapa (L.) Pursh

Historically, this species was known in European herbals and

botanical books as the root of Mechoacan or raíz de michoac´

(Fig. S10A). It grows at altitudes of up to 1700 m, but more often close to

the coast. The distribution is similar to that of Ipomoea trida but Wood

et al. (2020) mentioned that I. jalapa is very common yet unrecorded in

several countries, where it might be expected to occur; examples are the

Caribbean islands including the Dominican Republic, as well as Central

America. It has, essentially, a Mesoamerican distribution, probably

extended by humans for the medicinal properties of the species.

8.1.3. Ipomoea orizabensis (Pelletan) Ledeb. ex Steud

In the Mexican traditional medicine, this morning glory has been

known as male or Orizaba jalap, (Farwell, 1920;Shellard, 1951). Very

variable in indumenta, sepals, and leaf division, it may be a complex of

several species. McDonald (2001) divided it into four varieties and

Wood et al. (2020) maintained this division: Ipomoea orizabensis subsp.

orizabensis,Ipomoea orizabensis subsp. collina (House) J.R.I.Wood &

Scotland, Ipomoea orizabensis subsp. austromexicana (J.A.McDonald) J.R.

I.Wood &Scotland, and Ipomoea orizabensis subsp. novogaliciana (J.A.

McDonald) J.R.I.Wood &Scotland. The species is often found in stony

areas and is distributed from the north of Mexico to Guatemala, at 1500

to 2500 m and is endemic to Megamexico.

8.1.4. Ipomoea simulans D. Hanb

This species is the source of the Tampico jalap (Wood et al., 2020).

The specic epithet was chosen in allusion to the resemblance that the

plant bears in foliage, storage roots, and habit to the true jalap (I. purga).

The funnel-shaped corolla and pendent ower-buds of the Tampico jalap

distinguish the species from I. purga and allow the morphological

discrimination between the two species (Hanbury, 1869). It is endemic

to the central states of Mexico, mainly Guanajuato, Quer´

etaro, Hidalgo,

and Morelos, and along the Mexican Pacic Coast in the states of

Michoac´

an, Guerrero, and Oaxaca at altitudes of 1500–2500 m. This

species thrives in high oak and pine forests. Its tuber was rst exported

from Tampico in Tamaulipas and therefore called Tampico jalap

(Hanbury, 1869), as mentioned above.

8.1.5. Ipomoea stans Cav

Tumbavaqueros is an herbaceous perennial and erect plant common

in open pine forest (Fig. S15A), grasslands, xerophilous scrublands, and

secondary vegetation, at 1300–2700 m. It is endemic to central Mexico

and distributed in the Bajío region of the western and central states,

occurring in around 20 states overall, but mainly in Coahuila, Mexico

City, Durango, Guanajuato, Hidalgo, M´

exico State, Jalisco, Michoac´

an,

Morelos, Oaxaca, Puebla, San Luís Potosí, Quer´

etaro, Tlaxcala, and

Veracruz (Rzedowski and Carranza-Gonz´

alez, 2023).

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

8.1.6. Distimake tuberosus (L.) A.R.Sim˜

oes &Staples

Distimake is a sister clade of Operculina and a genus of approximately

48 species with a pantropical distribution, segregated from Merremia.

Mexico has 12 species (Rzedowski and Carranza-Gonz´

alez, 2023). This

species is endemic to southern Mexico and nearby Central America, was

introduced to the Old World, and is often cultivated as an ornamental

plant (Austin, 1998). A rare species, it is found in disturbed sites at sea

level to 1200 m from Florida in the United States through Mexico and

Central America into South America, as well as in the West Indies.

8.2. Distribution of the Brazilian jalaps

Operculina Silva Manso is a genus with 13 species distributed in the

tropics of the Americas and Asia, Madagascar, Australia, and the South

Pacic Islands. For this genus, no evidence exists for its presence in

Africa before human migrations. Oceanic dispersal has also played a role

in its distribution (Staples et al., 2020). Fig. S16 illustrates the distri-

bution of the Brazilian jalap root medicinal plant complex.

8.3. Operculina macrocarpa (L.) Urb

This species is present in the Atlantic Forest in northeastern and

southeastern Brazil, and the West Indies (Guadeloupe and Martinique).

It was possibly introduced long ago in tropical West Africa (Ivory Coast,

Ghana, and Togo) and is now naturalized. This amphi-Atlantic distri-

bution implies that O. macrocarpa could have been dispersed by the

natural ocean currents (McDonald, 1991), or more likely carried across

the Atlantic from Brazil, possibly by Portuguese slave traders or mis-

sionaries. Heine (1960) proposed that Roman Catholic missionaries

leaving Brazil intentionally introduced O. macrocarpa seeds to Africa to

make rosary beads. Two additional causes for the anthropogenic

dispersal were its transport in ship ballasts and as contaminants of crop

seeds (Eserman et al., 2014).

8.3.1. Operculina hamiltonii (G. Don) D.F. Austin &Staples

Operculina hamiltonii var. hamiltonii, occurs in Central America (from

Costa Rica to Panama), the West Indies (Cuba, Dominican Republic,

Haiti, and the Lesser Antilles), and South America (Bolivia, Brazil,

Colombia, Ecuador, French Guiana, Guyana, Paraguay, Peru, and Suri-

name) at elevational ranges from 100 to 200 m. This Brazilian jalap with

yellow owers thrives on human-disturbed openings and margins of

primary dry tropical forest, along roadsides, and near to streams.

Currently, all phytopharmaceuticals commercialized in various pre-

mises in northern Brazil are only manufactured with this jalap root

(Montiel-Ayala et al., 2021).

Staples et al. (2020) strongly suspect that this species does not occur

in Mexico. Its only recorded collection in Mexico was of a poorly

localized specimen in the city of Campeche by William Houstoun in

1730 during an expedition across the Mexican Yucatan peninsula and

into parts of Spanish America. In Cuba, the expedition collected samples

of the species Ipomoea ampliata Choisy (syn. Operculina hamiltonii var.

hamiltonii) with yellow owers, so there might have been an unfortunate

confusion with that collection site. O. hamiltonii has never again been

reported as collected in Mexico. Operculina hamiltonii var. mucronata D.

F. Austin &Staples is only known from the holotype collected in Serra

das Araras, in the Brazilian state of Mato Grosso by Carl Axel Magnus

Lindman in 1894 and deposited in the Department of Botany at the

Swedish Museum of Natural History (accession number: S07-4342).

9. Resin glycosides

Resin glycosides belong to a large family of specialized plant me-

tabolites identied as acyl sugars (Kruse et al., 2022). These glycolipids

are characterized by a profuse variety of oligomers of hydroxylated fatty

acids assembled on individual saccharide cores (Pereda-Miranda et al.,

2010). These distinctive secondary metabolites of the Convolvulaceae

family act as a chemical defense in the species’s natural resistance to

bacterial and fungal pests, against herbivores (Leckie et al., 2016), and

in plant-plant interactions (Lotina-Hennsen et al., 2013).

These acyl sugars are amphiphilic agents because of the occurrence

of lengthy aliphatic chains (aglycones) joined to a polar oligosaccharide

(glycone). They are always present as complex mixtures of homologues,

having the same glycosidic acid core and differing in the chain length of

their esterifying alkyl substituents (Pereda-Miranda et al., 2010). Thus,

their isolation and purication are difcult to achieve by conventional

chromatography (Pereda-Miranda et al., 2024). Resin glycosides were

classied into two groups according to their solubility in ether: jalapin

or soluble portion and convolvulin or insoluble part (Power and Rog-

erson, 1912).

9.1. Chemical diversity

More than 400 structures have been entirely puried from several

species of the morning glory family (Fan et al., 2022;Pereda-Miranda

et al., 2010). Most of these share three signicant structural features: (i)

a polysaccharide core of up to seven sugar residues, including aldo-

hexoses, mainly D-glucose or D-galactose, and epimers of pentoses such

as D-fucose, L-rhamnose, D-quinovose, and D-xylose in their pyranose

forms, which are constituted with no more than four individual mono-

saccharides; (ii) monohydroxy and dihydroxy fatty acids at the C-11 or

C-12 positions with chains lengths of C

-C

that may generate an

intramolecular macrolactone; and (iii) sugar cores acylated by aromatic

or aliphatic fatty acids that can be of C

–C

carbons long (Fan et al.,

2022;Pereda-Miranda et al., 2010). Some oligomers undergo intermo-

lecular condensations when they form larger, complex ester-type di-

mers, like those described from the Mexican morning glory, Ipomoea

tricolor Cav., (Bah and Pereda-Miranda, 1997), the Mexican jalap root,

I. purga (Casta˜

neda-G´

omez and Pereda-Miranda, 2011;Casta-

neda-G´

omez et al., 2013), the arborescent morning glory I. wolcottiana

Rose (Corona-Casta˜

neda et al., 2016), and the sweet potato, I. batatas

(Escalante-S´

anchez and Pereda-Miranda, 2007;Rosas-Ramírez and

Pereda-Miranda, 2013).

To explore the chemical diversity of the convolvulaceous herbal

drugs, the HPLC techniques of column overloading, heart-cutting, and

peak shaving have been applied. These procedures, individually or

combined, are performed in semi- or preparative reversed-phase col-

umns, mainly C-18 or NH

(amino for carbohydrate analysis). The

chromatography system has been frequently operated in the recycle

mode with mixtures of CH

CN-MeOH-H

O to allow the purication of

individual resin glycoside samples with a purity 99%, as demonstrated

by NMR and MS methods (Pereda-Miranda et al., 2024).

9.1.1. The Mexican jalap roots

Resin glycosides have been examined chemically since the 19th

century (Bernatzik, 1865;De Gassicourt, 1817;Scheuber, 1894). During

the early 1960s, the products of saponication, the volatile acids

(esterifying groups), and the glycosidic acids (oligosaccharide cores)

were prepared for their systematic analysis. These glycosidic cores are

sufcient to distinguish the producing crude drugs and normally named

after the generic or species name of the plant (Shellard, 1961a,1961b,

1961c). Acid hydrolysis of the saponied resin liberates the hydroxyl-

ated fatty acids (aglycones) and the individual sugars (Shellard, 1961a,

1961b,1961c). Gas chromatography coupled to mass spectrometry by

electron impact (GC-EIMS) has been widely used for structural charac-

terization of the aglycones, while the identication of sugars and their

sequence of glycosylation are determined by permethylation, acetolysis,

and partial acid hydrolysis (Wagner, 1974). Based on their behavior

towards acids and alkalis, Mannich and Schumann (1938) proposed a

polymeric structure of high molecular weight for the resin glycoside

from Exogonium purga (Fig. S19). However, these authors analyzed

commercially available resins obtained from the Brazilian jalap

(O. macrocarpa) rather than the genuine crude drug (Eich, 2008). Errors

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

in the authentication of Mexican and Brazilian jalap resins, as detailed in

the results also obtained by Votocek and Prelog (1929) and Auterhoff

and Demleitner (1955), were explained by Shellard (1961a,b) based on

the aglycones released from each individual authentic crude drug

through acid hydrolysis.

A modern chemical analysis of some commercial samples of the

Mexican jalap roots was performed by generating HPLC and

C NMR

spectroscopic proles of the glycosidic acids obtained through alkaline

hydrolysis of the resin-glycoside-rich MeOH extracts (Pereda-Miranda

et al., 2006). These proles were able to differentiate the three jalap

crude drugs still in frequent use in Mexico and could be practical

analytical tools for the quality control of these herbal purgatives (Fig. 7).

Ipomoea purga yielded two hexasaccharides of 11S-hydroxyte-

tradecanoic (convolvulinolic) and 11S-hydroxyhexadecanoic (jalapi-

nolic) acids, purgic acids A and B, respectively (Fig. 7). The chemical

structure for purgic acid A was elucidated as tetradecanoic acid,

(11S)-[(O-6-deox-

y--

β-D-glucopyranosyl-(12)-O-β-D-glucopyranosyl-(13)-O-[6-deox-

y--

β-D-galactopyranosyl-(14)]-O-6-deox-

y--

-L-mannopyranosyl-(12)-O-β-D-glucopyranosyl-(12)-6-deox-

y-β-D-glucopyranosyl)oxy], while purgic acid B has

(11S)-hydroxyhexadecanoic acid as its aglycon but having the same

glycosidation sequence in the oligosaccharide core (Pereda-Miranda

et al., 2006). Ipomoea orizabensis afforded scammonic acid A, a tetra-

saccharide of jalapinolic acid (Fig. 7), as the only glycosidic acid, which

was originally identied as the major glycosidic core from the resin

glycosides of the scammony (Noda et al., 1990;Kogetsu et al., 1991).

The structure of scammonic acid A was found to be hexadecanoic acid,

(11S)-[(O-6-deox-

y--

β-D-glucopyranosyl-(14)-O-6-deox-

y--

-L-mannopyranosyl-(12)-O-β-D-glucopyranosyl-(12)-6-deox-

y-β-D-glucopyranosyl)oxy] (Noda et al., 1990). Finally, Ipomoea stans

afforded operculinic acid B, initially identied in Ipomoea operculata,

syn. Operculina macrocarpa (Ono et al., 1989b), and characterized as

operculinic acid B (hexadecanoic acid, (11S)-[(O-6-deox-

y--

-L-mannopyranosyl-(14)-O-[β-D-glucopyranosyl-(13)]-Ο-6-deox-

y--

-L-mannopyranosyl-(14)-O-6-deox-

-L-mannopyranosyl-(12)-β-D-glucopyranosyl)oxy]).

Early investigation of the authentic Mexican jalap root by the con-

ventional degrative processes afforded the following results. The volatile

residues corresponded to tiglic, acetic, propionic, iso-butyric, methy-

butyric, iso-pentanoic, and n-pentanoic acids, which were obtained after

alkaline hydrolysis of both the ether insoluble portion (convolvulin) and

Fig. 7. Chemical structures for the glycosidic acids obtained from the MeOH extracts of the Mexican jalaps. Expansion at 90–110 ppm of

C NMR ngerprint after

saponication of the MeOH extracts: 1)Ipomoea purga (Rhizoma Jalapae); 2)Ipomoea orizabensis (Mexican scammony); 3)Ipomoea stans (tumbavaqueros root,

a substitute).

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

the soluble portion (jalapin) of the resin prepared by the usual method.

The oligosaccharidic acids consisted of two parts: the insoluble fraction

in ether (convolvulinic acid) which on acid hydrolysis yielded ipurolic,

(3S,11S)-dihydroxytetradecanoic, and convolvulinolic acids. The solu-

ble part in ether (purginic acid) on acid hydrolysis gave ipurolic acid.

Both fractions afforded the saccharides glucose, fucose, and rhamnose

(Shellard, 1961a). These initial explorations were carried out with

simple analytical techniques available at the time such as GC-EIMS, but

the limitation of this conventional analysis by the fact that intact resin

constituents are nonvolatile hampered their complete examination.

Even so, these degrative methods provided the basic structural infor-

mation to achieve the correct assembly of the intact structures of these

acyl sugars by the application of high resolution non-degrative proced-

ures as NMR and MS in recent years (Pereda-Miranda et al., 2010).

From the chloroform-soluble extract prepared with the aerial parts of

I. purga, through recycling HPLC (Casta˜

neda-G´

omez and

Pereda-Miranda, 2011;Casta˜

neda-G´

omez et al., 2013), oligosaccharides

derivatives of jalapinolic acid named purginosides I-IV, macrocyclic

pentasaccharides (Fig. 8), and the purgins I-III, ester-type dimers, were

isolated (Fig. 9). High-eld nuclear magnetic resonance spectroscopy

(NMR) and mass spectrometry (FAB, ESI) were used to characterize all

isolated compounds. Saponication of the crude resin glycoside mixture

yielded operculinic acid A, hexadecanoic acid, (11S)-[(O-6-deox-

-L-mannopyranosyl-(14)]-O-[β-D-glucopyranosyl-(13)]-O-6-deoxy-

-L-manno-pyranosyl-(14)-O-6-deoxy-

-L-mannopyranosyl-(12)-6-

deoxy-β-D-galacto-pyranosyl)oxy] as the major glycosidic acid compo-

nent, whereas the fatty acids 2-methylbutyric, n-hexanoic, n-decanoic,

n-dodecanoic, and trans-cinnamic were identied as the esterifying

residues on the oligosaccharide cores (Casta˜

neda-G´

omez and

Pereda-Miranda, 2011). Purginosides I-IV are pentasaccharide lactones

of operculinic acid A and their differences are due to the acylating res-

idues in the positions C

or C

and C

of the last rhamnose unit, which

were esteried by cinnamic, methylbutyric, and hexanoic acids.

The structural characterization of the purgins I-III indicated that

these molecules have dimeric structures consisting of two units of the

operculinic acid A in the case of purgin I (Casta˜

neda-G´

omez and

Pereda-Miranda, 2011), and two units of the operculinic acid B, hex-

adecanoic acid, (11S)-[(O-β-D-glucopyranosyl-(14)-O-6-deoxy-

-L-ma

nnopyranosyl-(12)-Ο-β-D-glucopyranosyl-(12)-6-deoxy-β-D-glucopyra

nosyl)oxy]), for purgins II and III (Casta˜

neda-G´

omez et al., 2013).

The main difference between purgin II and III is due to the acylating

residue on C

of the terminal rhamnose unit of both monomeric units

with methylburic acid for purgin II and hexanoic acid for purgin III

(Fig. 9). The isolation of purgins I-III demonstrated the complexity of the

chemical diversity of resin glycosides contents in I. purga and conrmed

the previous hypothesis of Mannich and Schumann about the

complexity of the resin glycosides as high-molecular weight oligosac-

charides glycosidically linked to a hydroxylated fatty acid.

From the MeOH-soluble extracts, two partially acylated macrocyclic

bisdesmoside resin glycosides were isolated, named as jalapinosides I

and II. They have the same glycosidation sequence in the oligosaccha-

ride core as purgic acids A and B, although differing from each other in

their aglycone: ipurolic acid, (3S,11S)-dihydroxytetradecanoic acid in

jalapinoside I (Bautista et al., 2015), and ipolearic acid, (3S,11S)-dihy-

droxyhexadecanoic acid in jalapinoside II (Bautista et al., 2016). In

addition, the second sugar linkage of an additional quinovose moiety

was established at C-3 of the aglycone. Jalapinoside I possess

(+)-methylbutiric acid as the acylating residue at C-3 of the terminal

quinovose unit in contrast to jalapinoside II with a residue of (−)-nylic

acid. Both compounds shared the same acylation pattern of the

Fig. 8. Chemical structures for purginosides I-IV isolated from the CHCl

-ex-

tracts of the authentic Mexican jalap aerial parts, Ipomoea purga.

Fig. 9. Chemical structures for purgins I-III, ester-type dimers, isolated from

the CHCl

-extracts of the authentic Mexican jalap aerial parts, Ipomoea purga.

For abbreviations of the esterifying residues, see Fig. 8.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

oligosacharide core, with an acetyl group at C-6 of the rst internal

glucose and a (+)-methylbutyrate at C-2 of the rhamnose unit (Fig. 10).

For the Mexican scammony or false jalap (I. orizabensis), Shellard

(1961c) described the application of the alkaline hydrolysis to the ether

soluble portion (orizabin), which afforded the volatile acids tiglic, ace-

tic, propionic, isobutyric, isovaleric, methylbutyric, and n-valeric. The

liberated oligosaccharidic acid, on acid hydrolysis, afforded jalapinolic

acid, glucose, fucose, and rhamnose. HPLC separation was used to

separate and purify the remarkably complex diastereoisomeric mixtures

of resin glycosides from the CHCl

-soluble extracts of the false jalap,

denominated as the orizabin series (Hern´

andez-Carlos et al., 1999;

Pereda-Miranda and Hern´

andez-Carlos, 2002).

All isolated tetrasacchrides from the orizabin series were esteried

by isobutiric (iba), tiglic (tga), and (+/−)-3-hydroxy-2-methylbutanoic

acids (nilic acid, nla) with a macrocyclic structure similar to those of the

scammonic acid A-based resin glycosides from C. scammonia (Noda

et al., 1990). Saponication of 12 diasteroisiomeric glycolipids, oriza-

bins X-XXI, proved that each diastereomeric pair resulted from esteri-

cation by both threo (+/−)-nilic acid enantiomers (Pereda-Miranda

and Hern´

andez-Carlos, 2002). The application of Mosher’s method

(Pereda-Miranda et al., 2023) determined the absolute conguration of

each liberated nilic acid residue.

For example, the nal resolution into pure orizabins X-XIII was

accomplished by peak shaving and recycling HPLC through an amino

column. Orizabins X and XI yielded after alkaline hydrolysis, the levo-

rotatory (2R,3R) and dextrorotatory (2S,3S) niloyl (nla) residues (3-

hydroxy-2-methylbutanoic acid), respectively. Individual saponication

of orizabins XII and XIII delivered the same enantiomers, i.e, threo (−)-

and (+)-nilic acid. This isomerism resulted from the interchange of the

chiral residues esterifying positions C-2 of rhamnose and C-6 of glucose

(Pereda-Miranda and Hern´

andez-Carlos, 2002). Consequently, orizabins

X and XI represented a positional isomeric pair in relation to orizabins

XII and XIII by exchanging the ( ±)-nilic and isobutyric residues

(Fig. 11).

9.1.2. The Brazilian jalap roots

The resin of Brazilian jalap was originally obtained from the dried,

sliced roots of the morning glory species with white owers,

O. macrocarpa. This purgative drug resembled the resin from the

Mexican jalap root, for which it was frequently substituted in the global

herbal market. However, its marginal solubility in ether was recognized

by Shellard (1951) and diverged from the other convolvulaceous resins,

such as those from the Mexican jalaps and from the second Brazilian

jalap of yellow owering O. hamiltonii, by its abnormal prominent water

solubility (Shellard, 1961b). This early observation was recently

conrmed by the preparation of the jalapin (CH

-soluble fraction)

and convolvulin (MeOH-soluble fraction) from O. macrocarpa dried

roots (50 g) to afford 0.65 g of the lipophilic total resins and 6.75 g of the

ether-insoluble polar fraction (Fig. S20).

Saponication of the convolvulin fraction afforded exogonic acid,

which represented 7% of the resin, and its structure was elucidated by

Fig. 10. Chemical structures for jalapinosides I and II, bisdesmoside resin glycosides, isolated from the MeOH-extracts of the authentic Mexican jalap aerial parts,

Ipomoea purga.

Fig. 11. Chemical structures for orizabins X-XIII isolated from the CHCl

-ex-

tracts of the Mexican false jalap roots, Ipomoea orizabensis.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

Graf and Dahlke (1964) as an epimeric mixture of 2-(carbox-

ymethyl)-7-methyl-1,6-dioxaspiro[4.4]nonan (Fig. 12), present in the

two major congurations, E,E3S,6S,9Rand Z,Z3S,6R,9R, but also with

minor amounts of the E,Zand Z,Ediastereoisomers were also present

(Lawson et al., 1992), in addition to the volatile residues tiglic and

isovaleric acids. A branched-chain hexasaccharide of 3,12-dihydroxy

hexadecanoic (operculinolic) acid was rst isolated by Wagner and

Kazmaier (1977), designated as operculinic acid (rhamnocolvolvulinolic

acid), and composed by glucose and rhamnose (2:1), which was char-

acterized as 3,12-dihydroxyhexadecanoic acid 12-O-

-D-gluco

pyranosyl-(1 →4)-[O-

-L-rhamnopyranosyl-(1 →6)]-O-

-D-glucop

yranosyl-(1 →3)-O-

-L-rhamnopyranosyl-(1 →2)-[O-β-D-glucopy

ranosyl-(1 →3)]-O-β-D-glucopyranoside. From these initial chemical

investigations, both operculinic and exogonic acids were dened as the

chemical marker for the resin of O. macrocarpa (Mannich and Schu-

mann, 1965).

A re-examination of the operculinic acid structure was done by Ono

et al. (2009), mainly by degradative and spectroscopic evidence (high

resolution NMR and MS). Thus, this glycosidic acid was recognized to be

3S,12S-dihydroxyhexadecanoic acid 12-O-β-D-glucopyranosyl-(1 →

3)-O-

-L-rhamnopyranosyl-(1 →2)-[O-β-D-glucopyranosyl-(1 →

3)]-O-β-D-glucopyranosyl-(1 →2)-[O-

-L-rhamnopyranosyl-(1 →

6)]-O-β-D-glucopyranoside, and renamed as operculinic acid H.

A chemical analysis of the MeOH-soluble resin glycosides from the

roots of O. macrocarpa was assessed by generating NMR proles of its

glycosidic acids obtained through saponication, acetylation, and

recycling HPLC purication. Three intact resin glycosides related to

operculinic acid H, macrocarposidic acids A-C with isovaleroyl, tigloyl,

and exogonoyl groups as esterifying residues were puried (Fig. 13).

Saponication and peracetylation of the crude drug afforded operculinic

acid H as the major glycosidic acid in this fraction (Lira-Ric´

ardez et al.,

2019). These results provided support for the atypical, elevated solubi-

lity in water of O. macrocarpa resin glycosides due to their hex-

asaccharide sugar cores as well as the non-macrocyclic nature of their

aglycone as free acids.

Procedures were recently described for the isolation, purication by

recycling HPLC, and structure elucidation of six undescribed resin gly-

cosides from Operculina hamiltonii. Two acyclic pentasaccharides of

(11S)-hydroxyhexadecanoic acid, named hamiltoniosides I and II, were

isolated (Moreno-Velasco et al., 2022) with a previously known and

commonly found glycosidic acid in the morning glory family, oper-

culinic acid A (Fig. 14). The pentasaccharide core in these compounds

was esteried by one unit of n-decanoic or n-dodecanoic acid. Four

structural related tetrasaccharide macrolactones were also isolated

(Moreno-Velasco et al., 2024). Hamiltonin I represented a macrocyclic

structure of a tetrasaccharide of (11S)-hydroxyhexadecanoic acid, pre-

viously identied and named as operculinic acid C. This glycosidic core

was diacylated by n-decanoic acid and the unusual n-hexadecanoic acid

moiety (Fig. 15). The hamiltonins II-IV demonstrated a structural

isomeric relation as one residue of n-dodecanoic acid esteries the tet-

rasaccharide core on a different position in each compound. Hamiltonin

V was characterized as an ester-type homodimer of hamiltonins II and III (Fig. 16).

The CH

and MeOH-soluble extracts from this plant material did

not provide any of the chemical markers previously recognized for the

resins from the Brazilian jalap root (Wagner and Kazmaier, 1977), which

now is identied as O. macrocarpa (Staples et al., 2020). The saponi-

cation of the resins from O. hamiltonii afforded only operculinic acids

A-C (Moreno-Velasco et al., 2024), which were rst isolated from a

commercial sample of O. macrocarpa (Ono et al., 1989a,1989b). These

results thus indicated that the commercial sample previously studied by

Ono represented a mixture of both members of the Brazilian jalap root

complex, the one with white owers (O. macrocarpa), and the other of

yellow owers (O. hamiltonii). In order to provide an experimental

validation for this assumption, HPLC-ESIMS conditions were optimized

for the qualitative detection of the selected marker (Montiel-Ayala et al.,

Fig. 12. Exogonic acid diastereoisomers were recognized as the chemical

markers for the resin of Operculina. macrocarpa.

Fig. 13. Chemical structures for the macrocarposidic acids A-C isolated from

the MeOH-soluble extracts of the Brazilian jalap with white owers, Oper-

culina macrocarpa.

Fig. 14. Chemical structures for the hamiltoniosides I and II isolated from the

-soluble extracts of the Brazilian jalap with yellow owers, Oper-

culina hamiltonii.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

2021), operculinic acid A (Fig. 17), in the crude drugs as well as in some

phytopharmaceutical products acquired in different commercial pre-

mises in northern Brazil (Fig. 6).

In this context, the analytical effectiveness was veried for the

sequence of reactions that included a saponication followed by

Fig. 15. Chemical structures for the hamiltonins I-IV isolated from the CH

-soluble extracts of the Brazilian jalap with yellow owers, Operculina hamiltonii.

Fig. 16. Chemical structure for the hamiltonin V isolated from the CH

soluble extracts of the roots of the Brazilian jalap with yellow owers, Oper-

culina hamiltonii.

Fig. 17. Chemical structure for operculinic acid A isolated from the CH

soluble extracts of the roots of the Brazilian jalap with yellow owers, Oper-

culina hamiltonii.

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

peracetylation of total extracts for the qualitative identication of the

chemical marker. HPLC-ESIMS proles from 15 commercial samples

were generated through retention times and mass values. The HPLC

analysis included: 1) whole crude drugs collected at sites located along

the Amazon River for the Brazilian jalap with yellow owers

(Fig. S21A); 2) whole or sliced crude drugs purchased in popular mar-

kets in Northern Brazil; 3) commercial powdered crude drugs

(Fig. S21B); 4) commercial herbal products, such as tinctures

(Fig. S21C); and 5) an authentic sample of O. macrocarpa (Fig. S21D) on

deposit at the Pharmacognosy Drug Collection, Faculdade de Farmacia,

Universidade Federal do Rio de Janeiro (Lira-Ric´

ardez et al., 2019). This

allowed the generation of representative chromatographic proles for

each sample (Montiel-Ayala et al., 2021).

Signicant differences were identied between the analyzed com-

mercial products and crude drugs in terms of their glycosidic acid con-

stituents. However, all commercial samples contained operculinic acid

A, as the major glycosidic acid. Therefore, these results recognized that

O. hamiltonii was the raw material in the preparation of all the Brazilian

phytopharmaceuticals (Fig. 6). The crude drug samples contained not

only operculinic acid A, but also a greater complexity in their chro-

matographic elution (15–20 min) reecting a structural hyperdiversity

in terms of the oligosaccharide cores of the species studied (Fig. S21B).

The authentic sample of O. macrocarpa presented a chromatographic

prole dissimilar (14–16 min) to that obtained for the analyzed crude

drugs prepared with O. hamiltonii. This sample contained only a major

peak (Fig. S21D), which was not observed in any of the other extracts. As

expected, the two Brazilian jalap root species differed. In the subject

analysis, operculinic acid H was identied as the major chemical marker

in the bindweed with white owers (Lira-Ric´

ardez et al., 2019). This

analysis conrmed that the commercial crude drug analyzed by Ono

et al. (1989a,b) essentially was a mixture of both members of the Bra-

zilian jalap root complex with an almost identical root morphology,

which made their microscopical identication in a dried, pulverized

form impossible. The limited distribution of O. macrocarpa, caused by

deforestation of the Atlantic Forest in northeastern and southeastern

Brazil due to urban expansion, has made this raw material inaccessible

for the production and marketing of phytopharmaceuticals. This situa-

tion explains why the traditional use of this jalap was discontinued

across Brazil during the second half of the 20th century, as demonstrated

by the analytical proling detailed by Montiel-Ayala et al. (2021).

After hydrolysis and peracetylation of the EtOH-soluble extract

prepared from a commercial sample of pulverized roots, the known

operculinic acids A and B and turpethic acid C, in addition to three

undescribed glycosidic acids, operculinic acids L-N, tetrasaccharide or

pentasaccharide cores with unusual 12-hydroxy fatty acid aglycones of

and C

chain lengths were puried (Montiel-Ayala et al., 2021).

Turphetic acid C was the oligosaccharide core previously reported for

turpethosides A and B, major resin glycosides from the Indian Jalap,

O. turpethum (Wagner et al., 1978), with the oligosaccharide core

established to be (S)-12-hydroxyheptadecanoic acid

12-O--

β-D-glucopyranosyl-(13)-[

-L-rhamnopyr-

anosyl-(14)]-O-

-L-rhamnopyranosyl-(14)-O-

-L-rhamnopyr-

anosyl-O-(12)-β-D-glcucopyranosyl (Ding et al., 2012). Therefore,

12-hydroxylated C

fatty acids seems to be restricted to Operculina and

could be used as chemical markers.

9.2. Purging activity

Resin glycosides from the morning glory family have been shown to

increase membrane permeability. They modify the transport of ions,

causing an imbalance in cellular homeostasis by forming pores (Fan

et al., 2014;Zhu et al., 2019b). This could be the mechanism of action

for the cathartic activity, acting as osmotic drastic laxatives or purga-

tives that could also cause an increase in water elimination and intes-

tinal peristalsis (Fig. S22), that facilitates the evacuation and the

elimination of gastrointestinal worms. The Mexican and Brazilian jalap

roots essentially act as hydragogues, cathartic agents that causes copious

watery discharges from the bowels along practically the entire intestinal

canal. The jalap tincture Sobral, formulated with the roots of

O. hamiltonii registered by the Brazilian Health Regulatory Agency as a

traditional phytotherapeutic product, is used to treat constipation

(Fig. S23A). Studies have established its laxative and purgative actions

in mice (Michelin and Salgado, 2004;Gonçalves et al., 2007) and lack of

toxicity in humans (Cunha et al., 2011;Santos et al., 2012).

Recently, it has been shown that the treatment with crude resins

from the seeds of Ipomoea nil, or Pharbitidis Semen in the traditional

Chinese medicine (Gao et al., 2023), increased the fecal excretion and

fecal water content in a dose-dependent manner in rats by increasing the

small intestine peristaltic rate, in a way similar to the effects of Mexican

and Brazilian jalaps (Zhou et al., 2022). The treatment boosts the in-

testinal ora and enhances the expression of relevant neurotransmitters

in the colon (Chen et al., 2022). Treatment with resin glycosides

inhibited the expression of the enzyme aquaporin-3 (AQP3), both in the

colon of rats and in HT-29 cells. It also activated production of

COX-2-mediated prostaglandin 2 (PGE2), which inhibits the expression

of AQP3 and thus decreases the absorption of water from the intestine

into the blood vessels, with a laxative effect (Zhu et al., 2019a).

The purgative and laxative mechanisms of resin glycosides have not

been entirely understood. But a resin-glycoside-based drug traditionally

used in South Korea for gastrointestinal disorders won regulatory

approval there in May 2011 (Kwon and Son, 2013). DA-9701 (Motili-

tone tablets; Dong-A ST Co. Ltd., Seoul, South Korea), a botanical drug

formulated as a 50% ethanol extract from Pharbitidis Semen and Coryd-

alis Tuber, the root of Corydalis yanhusuo (Y.H.Chou &Chun C.Hsu) W.T.

Wang ex Z.Y.Su &C.Y.Wu (Papaveraceae) for treatment of functional

dyspepsia (Fig. S23B). The pharmacological effects of this novel proki-

netic agent include stimulating the stomach’s emptying and modulating

visceral hypersensitivity through the antagonistic action at 5-hydroxy-

tryptamine (HT)

or dopamine (D)

receptors, or agonistic action at

the 5-HT

receptor in both animal and human studies (Choi et al., 2015;

Jin and Son, 2018;Lee et al., 2022).

9.3. Cytotoxic activity

The cytotoxicity of tricolorin A (P-388: IC

2.2

g/ml), a tetra-

saccharide of 11S-hydroxyhexadecanoic acid from I. tricolor, the

Mexican morning glory (Pereda-Miranda et al., 1993), prompted the

search for constrained macrocyclic oligosaccharides in an effort to

discover potent chemotherapeutics (Cao et al., 2005,2007).

An important observation for the cytotoxicity in resin glycosides is

their lipophilicity/hydrophilicity balance, as demonstrated by the IC

values against many cancer cell lines for ipomoeassins and their semi-

synthetic derivatives with nanomolar growth-inhibitory activity (IC

4.2–36 nM) (Fig. S24). Ipomoeassin F was isolated from the leaves of

I. squamosa in the Suriname rainforest (Cao et al., 2005). It binds to the

central Sec61

subunit of the Sec61 complex and induces cytotoxicity by

disrupting multiple aspects of Sec61-mediated protein biogenesis at the

endoplasmic reticulum, mainly protein translocation (Roboti et al.,

2021;Zong et al., 2019).

This universally conserved heterotrimeric Sec61 complex (SecY in

prokaryotes) plays essential roles in biosynthesis of more than one-third

of proteins in all living species and mediates membrane integration of

many proteins, including most cell surface receptors and cell adhesion

molecules (Itskanov et al., 2023). In eukaryotes, secretory proteins are

rst translocated into the endoplasmic reticulum by the Sec61 complex

then reach the cell surface by vesicular trafcking. This prevents the cell

from replenishing its endoplasmic reticulum lumenal stress-inducible

cytosolic chaperones, Hsp70 and Hsp90; an unfolded protein response

precludes the restoration of the endoplasmic reticulum homeostasis.

Ipomoeassin F demonstrated to be a selective inhibitor of the

triple-negative breast cancer cells, one of the most aggressive types of

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

cancer and for which no successful therapy has been established (Tao

et al., 2023). Ring-size-expansion analogues of ipomoeassin F have been

synthesized and evaluated, which improved cytotoxicity (IC

: from 36

to 1.8 nM) and in vitro protein translocation inhibition (IC

: 35 nM), as

well as in vivo with a maximum-tolerance dose of 3 mg/kg in C57BL76

female mice (Zong et al., 2020).

Most of the amphiphilic acyl sugars are noncytotoxic. They have

been described as inhibitory agents of efux pumps, which perform a

signicant function in the extrusion of xenobiotics outside the cells. This

mode of action delivers a protective mean expressed as the multidrug

resistance phenotype in gram-positive (Pereda-Miranda et al., 2006) and

gram-negative bacteria (Corona-Casta˜

neda and Pereda-Miranda, 2012),

as well as in mammalian cancer cells (Casta˜

neda-G´

omez et al., 2013;

Figueroa-Gonz´

alez et al., 2012).

Consequently, resin glycosides could have signicant therapeutically

advantages for the introduction of new options in treating refractory

diseases (Lira-Ric´

ardez and Pereda-Miranda, 2020). For example, purgin

II (Fig. 9) exerted a pronounced potentiation effect by 2140 reversal fold

(RF) for a vinblastine-resistant human breast carcinoma cells

(MCF-7/Vin) at 25 mg/mL. This was greater than the effect of reserpine

(RF 4.4), an indole alkaloid isolated from the dried root of Rauvola

serpentina (L.) Benth. ex Kurz, Apocynaceae (Indian snakeroot) that is

used as an efux pump inhibitor (Casta˜

neda-G´

omez et al., 2013). Jala-

pinosides I and II (Fig. 10) were also exceptionally potent (RF

MCF-7/Vin

>1906) (Bautista et al., 2015,2016), as purgin II, a proven substrate by

ow cytometry and intracellular efux of rhodamine 123 for glyco-

protein P (Casta˜

neda-G´

omez et al., 2013), the chief plasma

membrane-associated translocase responsible for the MDR phenotype

(Lira-Ric´

ardez and Pereda-Miranda, 2020).

Finally, a combination of the individual resin glycosides from

O. hamiltonii (1–50

M) with a sublethal concentration of the clinically

used antineoplastic drugs vinblastine and podophyllotoxin (0.003

in multidrug-resistant breast carcinoma epithelial cells (Fig. S25)

demonstrated an improvement of the entire cytotoxicity from both

independently tested samples, i.e., the acyl sugars and the antineoplastic

drugs (Moreno-Velasco et al., 2022,2024). For instance, while

vinblastine and podophyllotoxin at 0.003

M (a sublethal concentra-

tion) induced no cell death, the supplementation of 10

M of hamiltonin

IV, an ester-type dimer (Fig. 16), increased the cytotoxicity of the former

drug to 55% (IC

10.6

M) and of the latter to 15% (IC

14.3

M),

respectively, Therefore, this potentiation by non-cytotoxic acyl sugar

appeared to modulate drug internalization (Hu et al., 2016) by

increasing intracellular concentration of the these two tested drugs.

Thus, the inhibition of drug efux by resin glycosides and the subse-

quent accumulation of the cytotoxic agents in the cytoplasm of the target

cells would help to maximize the effectiveness of the associate cytotoxic

drugs (Duarte and Vale, 2020;Duarte et al., 2021). The macrocyclic

glycolipid cores seem to be an important requirement for the inhibition

of drug efux, they favor the accumulation of cytotoxic agents in order

to destabilize microtubules by binding tubulin and thus preventing cell

division (Moreno-Velasco et al., 2022,2024).

10. Conclusions and perspectives

As outlined in the present review, the family Convolvulaceae has had

important and diverse value and use in herbal medicine throughout

human history. However, this ethnobotanical knowledge has not been

properly studied scientically. In fact, it is difcult to provide a

comprehensive account of the basic ecological requirements of Mexican

and Brazilian jalaps and their often-potent purgative roots. There is not

even accurate knowledge for the phenology, rootstock, and seeds of

some species as Operculina hamiltonii var. mucronata. Collecting her-

barium specimens with ethnobotanical and ecological information

should be a priority for the Neotropical morning glories. For the

moment, the Convolvulaceae remains an enigmatic taxon that is urged

to seek out and document.

Although, the DNA barcode sequences of all members of the Brazil-

ian and Mexican jalaps are in the GenBank data base, that information

has not been correlated to other relevant ecological or chemical aspects.

Thus, further investigations are necessary to identify the chemical

markers, toxicity, and mechanisms of action of these drugs. Molecular

studies are required to detangle the species complex under the name

Ipomoea orizabensis, consisting of more than one taxon, now reported as

four varieties. Additional chemical, ecological, and biogeographical

data can be used to achieve this objective. Biogeographical data are far

too incomplete, and many records should be rened to represent the true

range of the species. A detailed study on the distributional data of the

family is suggested. The association of the jalaps with heritable fungal

endosymbionts has not been sufciently explored, which has toxico-

logical implications for humans and foraging mammals.

The lack of detailed modern ecological and other relevant studies of

the Mexican and Brazilian jalaps is but a small sample of the vast world

of under-explored plant resources with potential in treatment one of the

major social, public-health, and economic problem in the 21st century,

multidrug resistant diseases like cancer. Already, the potential of the

oligosaccharides as inhibitors of efux pumps (such as glycoprotein G, a

membrane translocase responsible for the resistant phenotype) has

encouraged the search for constrained macrocyclic acyl sugars as che-

motherapeutics. These plant metabolites might be coadjutants in com-

bination therapy to evade drug resistance and reinstate the utility of

clinical drugs in treating refractive infections and cancer.

Therefore, further chemical analysis is encouraged of inadequately

studied jalap species, including Ipomoea jalapa,Ipomoea simulans,Ipo-

moea stans, and Distimake tuberosus, as well of other members of the

morning glory family with medicinal properties, especially species in

regions with high diversity in the Convolvulaceae that have ethno-

pharmacological history, as suitably exemplied in the present review

by the jalap roots in Mexico and Brazil.

Finally, an interdisciplinary holistic approach with archaeological,

ethnopharmacological, and sociocultural contextualization is desirable

to achieve proper integration and consolidation of knowledge of me-

dicinal oras from the corpus that resides in the memory of indigenous

peoples.

CRediT authorship contribution statement

Adriana C. Hern´

andez-Rojas: Writing –original draft, Investiga-

tion, Formal analysis, Conceptualization. Mabel Fragoso-Serrano:

Writing –review &editing, Writing –original draft. Rogelio Pereda-

Miranda: Writing –review &editing, Writing –original draft, Meth-

odology, Conceptualization.

Funding

Financial support was provided by Direcci´

on General de Asuntos del

Personal Acad´

emico, UNAM, M´

exico (DGAPA: IN202123).

Declaration of competing interest

The authors declare that they have no known competing nancial

interests or personal relationships that could have appeared to inuence

the work reported in this paper.

Acknowledgments

Adriana C. Hern´

andez-Rojas acknowledges Direcci´

on General de

Asuntos del Personal Acad´

emico, UNAM, for a postdoctoral scholarship

(February 2024–January 2025) in the Programa de Becas Posdoctorales

(POSDOC). Authors are grateful to Drs. Jhon F. Casta˜

neda-G´

omez,

Beatriz Hern´

andez-Carlos, and Elihú Bautista for their contributions to

the chemistry of the Mexican jalap roots. Drs. Jesús Lira-Ric´

ardez, María

Emma Montiel-Ayala, Armando Moreno-Velasco, and Pedro Flores-

A.C. Hern´

andez-Rojas et al. Journal of Ethnopharmacology 341 (2025) 119316

Tafoya provided substantial contributions to the chemistry of the Bra-

zilian jalap roots. Prof. John Wood, Royal Botanic Gardens, Kew,

Richmond, London, UK, conrmed the taxonomical identication of

Ipomoea aprica. Additional information on the taxonomy of this jalap

was provided by Dr. Maria Teresa Buril, Department of Biology, Uni-

versidade Federal Rural de Pernambuco, Brazil.Dr. Suzana Leit˜

ao,

Facultade de Farm´

acia, Universidade Federal do Rio de Janeiro, Brazil,

was an indispensable collaborator during an expedition to collect

authentic samples of the Brazilian jalap with yellow owers along the

Tapaj´

os and Trombetas tributaries of the Amazon River in the Santar´

and Oriximin´

a regions of Brazil’s Par´

a state. Authors gratefully

acknowledge Dr. Casta˜

neda-G´

omez, Universidad Surcolombina, for

drawing the chemical structures and to Mr. Morris Thompson for his

help in copy editing.

Appendix A. Supplementary data

Supplementary data to this article can be found online at https://doi.

org/10.1016/j.jep.2024.119316.

Data availability

No data was used for the research described in the article.

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Full-text available

Nov 2023

Background The hot–cold classification system for things and concepts is widely used by many human groups in Mexico. We conducted a comprehensive review to understand the history, themes, and distribution of this system. Methods We analyzed publications based on field work in Mexico, considering publication date, research approach, study depth, and conceptual domains. We identified the ethnic groups that use the system and the places where they live. A map illustrates the geographic and cultural distribution of the system. Results The hot–cold system has been documented in 101 academic publications spanning almost a century, particularly for traditional medicine and food. Initially dominated by anthropological studies, ethnobotanists have increasingly contributed to the research. The hot–cold system is utilized by at least 56 indigenous ethnic groups (81% of the total) and mestizos (whose primary or sole language is Spanish) across most of Mexico. Discussion Anthropologists laid the foundation for understanding the hot–cold system, on which current ethnobotany builds. However, there are still knowledge gaps, for example on some domains (human beings, landscape) and on patterns by regions or linguistic families. The geographic and cultural distribution presented here is approximate, as group ethnicity is imprecise. Conclusions The hot–cold system is widely applied in Mexico, although some variations exist. Further exploration of understudied domains, and variations between ethnic groups and regions, would contribute to a comprehensive explanation of this interconnected worldview.

ER translocon inhibitor ipomoeassin F inhibits triple-negative breast cancer growth via blocking ER molecular chaperones

Article

Full-text available

Jul 2023
INT J BIOL SCI

Triple-negative breast cancer (TNBC) is an aggressive type of breast cancer where no effective therapy has been developed. Here, we report that the natural product ER translocon inhibitor ipomoeassin F is a selective inhibitor of TNBC cell growth. A proteomic analysis of TNBC cells revealed that ipomoeassin F significantly reduced the levels of ER molecular chaperones, including PDIA6 and PDIA4, and induced ER stress, unfolded protein response (UPR) and autophagy in TNBC cells. Mechanistically, ipomoeassin F, as an inhibitor of Sec61α-containing ER translocon, blocks ER translocation of PDIA6, inducing its proteasomal degradation. Silencing of PDIA6 or PDIA4 by RNA interferences or treatment with a small molecule inhibitor of the protein disulfide isomerases in TNBC cells successfully recapitulated the ipomoeassin F phenotypes, including the induction of ER stress, UPR and autophagy, suggesting that the reduction of PDIAs is the key mediator of the pharmacological effects of ipomoeassin F. Moreover, ipomoeassin F significantly suppressed TNBC growth in a mouse tumor xenograft model, with a marked reduction in PDIA6 and PDIA4 levels in the tumor samples. Our study demonstrates that Sec61α-containing ER translocon and PDIAs are potential drug targets for TNBC and suggests that ipomoeassin F could serve as a lead for developing ER translocon-targeted therapy for TNBC.

Empire and the Theology of Nature in the Cambridge Botanic Garden, 1760–1825

Article

Full-text available

May 2023

Edwin Rose

Founded in 1760, the Cambridge Botanic Garden was designed to serve the theological interests of the university by developing a collection of living plants from across the globe. Exploring the construction and layout of the garden, its global network, methods of managing information, and the accessibility of the collection during the professorship of Thomas Martyn between 1762 and 1825, this article casts new light on the motivations for founding and managing a botanic garden in Cambridge. It shows how communication structures adapted as the British Empire contracted in the Americas and expanded into Asia and the Pacific, classifying species in the physical garden later inventoried in a series of published catalogues. It suggests that growing interests in natural theology intertwined the university with the expanding British Empire, developing a collection designed to educate students in the influence of divine providence on the vegetable kingdom.

A common mechanism of Sec61 translocon inhibition by small molecules

Article

Full-text available

May 2023
NAT CHEM BIOL

The Sec61 complex forms a protein-conducting channel in the endoplasmic reticulum membrane that is required for secretion of soluble proteins and production of many membrane proteins. Several natural and synthetic small molecules specifically inhibit Sec61, generating cellular effects that are useful for therapeutic purposes, but their inhibitory mechanisms remain unclear. Here we present near-atomic-resolution structures of human Sec61 inhibited by a comprehensive panel of structurally distinct small molecules—cotransin, decatransin, apratoxin, ipomoeassin, mycolactone, cyclotriazadisulfonamide and eeyarestatin. All inhibitors bind to a common lipid-exposed pocket formed by the partially open lateral gate and plug domain of Sec61. Mutations conferring resistance to the inhibitors are clustered at this binding pocket. The structures indicate that Sec61 inhibitors stabilize the plug domain in a closed state, thereby preventing the protein-translocation pore from opening. Our study provides the atomic details of Sec61–inhibitor interactions and the structural framework for further pharmacological studies and drug design.

Inhibition of multidrug-resistant MCF-7 breast cancer cells with combinations of clinical drugs and resin glycosides from Operculina hamiltonii

Article

Nov 2023
PHYTOCHEMISTRY

Indigenous Peoples and Biodiversity

Chapter

Jan 2013

Víctor M. Toledo

Synopsis of the family Convolvulaceae in Mexico

Article

Jul 2023

The Convolvulaceae is a diverse family and it is particularly well represented in Mexico. The current inventory confirms the presence of 313 species within Mexico, and this quantity represents nearly 20% of the family’s global diversity. Convolvulaceae species are found in all states of our country but are most frequent at elevations below 1500 m. The preferred habitat is tropical deciduous forest and secondary communities derived from it. Whereas most species are herbaceous to woody climbers, it is noteworthy that some species are arborescent, and the distribution of this growth form is essentially Mexican, with a few species in the Andes.

Pharbitidis Semen: A review of botany, traditional uses, phytochemistry, pharmacology, and toxicology

Article

May 2023
J ETHNOPHARMACOL

Ethnopharmacological relevance: Pharbitidis Semen (the seeds of Ipomoea nil (L.) Roth or Ipomoea purpurea (L.) Roth), a popular traditional Chinese medicine, is also known as "Heichou" or "Baichou" (Chinese: , ). It can purge the bowels, promote diuresis, remove stagnated accumulation, and kill worms. It can be used for treating anasarca with constipation and oliguria; dyspnea and cough caused by retained fluid; abdominal pain because of intestinal parasitosis; ascariasis; and taeniasis. Aims: This review discusses the botany, ethnopharmacology, phytochemistry, pharmacological activities, toxicology, and quality control of Pharbitidis Semen, to obtain a complete understanding of its effects and provide a basis for further research and the development of new drugs. Materials and methods: The literature on Pharbitidis Semen is mainly obtained from pharmacopoeias of different countries, masterpieces of traditional Chinese medicine, Master's and Ph.D. theses, and published articles obtained from literature retrieval websites, such as CNKI, PubMed, SciFinder, WanFang data, Web of Science, Springer, ScienceDirect, Wiley, ACS Publications, Taylor & Francis, J-STAGE, and Google Scholar. Its botany, ethnopharmacology, phytochemistry, pharmacological activities, toxicology, and quality control are discussed to understand its effects and provide a basis for further research. Results: Pharbitidis semen has been used ethnomedically in many tropical and subtropical countries as deobstruents, diuretics, and anthelmintics. About 170 chemical compounds, including terpenoids, phenylpropanoids, resin glycosides, fatty acids and other compounds, have been isolated. It has been reported to have different effects, including laxative, renal-protective, neuroprotective, insecticidal, antitumor, anti-inflammatory, and antioxidant. Moreover, a brief introduction to processing, toxicity, and quality control is provided. Conclusions: The traditional efficacy of Pharbitidis Semen in diarrhea has been confirmed, but its bioactive and toxic ingredients are not entirely clear. It is necessary to strengthen the research and identification of effective parts or natural active components of Pharbitidis Semen, clarify the molecular mechanism of its toxicity and change rule of endogenous substances to make Pharbitidis Semen better used in clinical practice. Additionally, the imperfect quality standard is also a challenge that must be solved urgently. The study of modern pharmacology has broadened the application of Pharbitidis Semen and provided ideas for better utilization of this resource.

From Relative to Absolute Stereochemistry of Secondary Metabolites: Applications in Plant Chemistry

Article

Dec 2022

Structural elucidation of specialized metabolites or natural plant products, especially the stereochemical features of chiral bioactive metabolites, is the most important stage for all investigations in pharmacognosy and phytochemistry. Numerous methods have been established to solve the absolute configuration of natural products, including direct methods such as X-ray diffraction, chiroptical spectroscopy, stereo-controlled partial or total organic synthesis, and chemical correlation by simple organic reactions for derivatization, as well as indirect methods using a standard chiral compound or a derivatizing agent with known absolute configuration, for example, nuclear magnetic resonance by utilization of anisotropic effects of chiral agents. Once the relative configuration of a natural product is resolved, the absolute stereochemistry can be determined with the assistance of chiroptical spectroscopies supported by quantum mechanical-NMR prediction of chemical shifts, scalar coupling constants and simulation of optical rotatory dispersion, in addition to electronic and vibrational circular dichroism spectra. This review summarizes the most practical methods employed in the assignment of absolute stereochemistry of natural plant products with selected examples focused on multichiral center bioactive small molecules from the mega-diverse Brazilian and Mexican flora.Graphical Abstract

The Jalap Roots: A Herbal Legacy from the Neotropics to the World

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