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![Gastroprotective effect of different doses of 5-O-[(β-d-apiopyranosyl-(1 → 6)-(β-d-glucopyranosyl)]-3',4'-dihydroxy-7-methoxy-4-phenylcoumarin (10) (0.1–100 mg/kg p.o.). Bars represent the mean ± SEM (n = 6). *p < 0.05, significantly different from the vehicle; one-way ANOVA followed by the Newman–Keuls multiple comparison test](publication/333956995/figure/fig3/AS:962140626231325@1606403609676/Gastroprotective-effect-of-different-doses-of.png)
Gastroprotective effect of different doses of 5-O-[(β-d-apiopyranosyl-(1 → 6)-(β-d-glucopyranosyl)]-3',4'-dihydroxy-7-methoxy-4-phenylcoumarin (10) (0.1–100 mg/kg p.o.). Bars represent the mean ± SEM (n = 6). *p < 0.05, significantly different from the vehicle; one-way ANOVA followed by the Newman–Keuls multiple comparison test
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The term copalchi has been used in the scientific literature to define a group of plants of the Rubiaceae and Euphorbiaceae families with extremely bitter stem-barks, useful for treating diabetes and malaria. In this review we summarized the most relevant chemical and pharmacological works carried out in the last century with the copalchis of the R...
Citations
... Finally, the copalchi complex is used to control glycemia in diabetes, which includes several species of the Rubiaceae and Euphorbiaceae families, particularly the Hintonia and Exostema genera. These species have been studied chemically and pharmacologically to contribute to quality control procedures and to identify botanical products made with these plants (Mata et al. 1990, Cristians et al. 2014, Rivero-Cruz et al. 2019). ...
Background:
Based on the concept of “plant species complex,”, defined as a group sharing local names and morphological, aromatic, and curative properties, we analyzed the leaves of three species of the genus Oreopanax that are used as wrappers for tamales called “xocos” or “chocos” in Veracruz, Mexico, searching for common traits.
Question:
Do leaves of the genus Oreopanax form an ethnobotanical food complex sharing chemical and anatomical characteristics?
Studied species / data description:
Leaves from three species of the genus Oreopanax: O. capitatus, O. echinops, and O. flaccidus.
Study site and dates:
Leaves of O. capitatus and O. echinops were recollected on January 25 and 26, 2021, in the Clavijero Botanic Garden of the Instituto de Ecología, A. C. in Xalapa, Veracruz; leaves of O. flaccidus were recollected in Atapalchico, Tlacolulan, Veracruz.
Methods:
Chemical analyses consisted of oil extraction of the studied species' leaves, which were then injected into a gas chromatographer coupled to a mass spectrometer (GC-MS). Anatomical analyses included: fixation, paraffin sectioning, and staining of leaf sections of the three species. Observations were performed with a compound microscope using a bright field or UV light.
Results:
For the first time, we are reporting major volatile compounds common in the three analyzed species (several aliphatic and aromatic alcohols, and terpenoids). The three species present resin canals in the mesophyll and the cortex of the midrib of the leaf.
Conclusions:
The studied Oreopanax species form an ethnobotanical food complex since they share similar uses, smells, and tastes.
... Hintonia latiflora: The oldest use of this taxon dates back to the sixteenth century, being used as a febrifuge (Rivero-Cruz et al. 2019). Actually, the bark of Hintonia latiflora has 36 different uses in Mexico, the most popular is as antidiabetic, but decoction of the bark is also used traditionally for the treatment of fevers, blood purifying, internal infections, infected wounds, malaria, purgative, diuretic, anemia, bile, hair loss, nephritis, and kidney diseases (Anaya-Dávila 1991; Aguilar et al. 1994;Argueta et al. 1994). ...
... Hintonia latiflora and H. standleyana conforms a medicinal plant complex together with other Rubiaceae species as Exostema caribaeum and Simira mexicana; altogether are used and commercialized with the same purpose: antidiabetic agents (Cristians et al. 2018;Rivero-Cruz et al. 2019). In some cases, the Hintonia species are mixed with the aforementioned plants, being a matter of attention, since E. caribaeum is a toxic species and can generate health risks if the appropriate quality control is not carried out on the plant material used for therapeutic purposes (Rivero-Cruz et al. 2019). ...
... Hintonia latiflora and H. standleyana conforms a medicinal plant complex together with other Rubiaceae species as Exostema caribaeum and Simira mexicana; altogether are used and commercialized with the same purpose: antidiabetic agents (Cristians et al. 2018;Rivero-Cruz et al. 2019). In some cases, the Hintonia species are mixed with the aforementioned plants, being a matter of attention, since E. caribaeum is a toxic species and can generate health risks if the appropriate quality control is not carried out on the plant material used for therapeutic purposes (Rivero-Cruz et al. 2019). ...
... In particular, 4-arylcoumarin (C) was isolated from Exostema species (of the family Rubiaceae) and displayed cytotoxic activity against various cancer cell lines [26]. These neoflavones are abundant components that widely exist naturally in plants and have anticancer properties [27,28]. Studies reported that microtubule inhibition by 4-arylcoumarin derivatives was similar to that of combretastatin A-4, both of which bind to the colchicine-binding site [29,30]. ...
... Almost all compounds of the class, 5,6,7-methoxy-substituted 4-phenylquinolin-2(1H)one (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32), had IC 50 anticancer activities of more than 50 µM. However, these 4-PQ derivatives showed potential anti-proliferation against the COLO205 and H460 cell lines with IC 50 values ranging 0.32-47.1 µM. ...
... In particular, 6-methoxy-4-(3 -methoxy phenyl)quinolin-2(1H)-one (22) showed excellent anticancer activity, which was highly active against the COLO205 (IC 50 = 0.32 µM) and H460 cell lines (IC 50 = 0.89 µM). In addition, 4-(2 ,4dimethoxyphenyl)-5,7-dimethoxy quinolin-2(1H)-one (27) showed moderate anticancer activity against the COLO205 cell line (IC 50 = 7.85 µM). Interestingly, a previous study indicated that the 3,4,5-trimethoxyphenyl moiety is commonly employed in antimitotic agents [34]; however, our results showed that a tri-methoxy substitution on 4-PQs (29)(30)(31)(32) seemed to have no anticancer effects (IC 50 > 50 µM). ...
Our previous study found that 2-phenyl-4-quinolone (2-PQ) derivatives are antimitotic agents, and we adopted the drug design concept of scaffold hopping to replace the 2-aromatic ring of 2-PQs with a 4-aromatic ring, representing 4-phenyl-2-quinolones (4-PQs). The 4-PQ compounds, whose structural backbones also mimic analogs of podophyllotoxin (PPT), maybe a new class of anticancer drugs with simplified PPT structures. In addition, 4-PQs are a new generation of anticancer lead compounds as apoptosis stimulators. On the other hand, previous studies showed that 4-arylcoumarin derivatives with 5-, 6-, and 7-methoxy substitutions displayed remarkable anticancer activities. Therefore, we further synthesized a series of 5-, 6-, and 7-methoxy-substituted 4-PQ derivatives (19–32) by Knorr quinoline cyclization, and examined their anticancer effectiveness. Among these 4-PQs, compound 22 demonstrated excellent antiproliferative activities against the COLO205 cell line (50% inhibitory concentration (IC50) = 0.32 μM) and H460 cell line (IC50 = 0.89 μM). Furthermore, we utilized molecular docking studies to explain the possible anticancer mechanisms of these 4-PQs by the docking mode in the colchicine-binding pocket of the tubulin receptor. Consequently, we selected the candidate compounds 19, 20, 21, 22, 25, 27, and 28 to predict their absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles. Pharmacokinetics (PKs) indicated that these 4-PQs displayed good drug-likeness and bioavailability, and had no cardiotoxic side effects or carcinogenicity, but we detected risks of drug–drug interactions and AMES toxicity (mutagenic). However, structural modifications of these 4-PQs could improve their PK properties and reduce their side effects, and their promising anticancer activities attracted our attention for further studies.
... Note the inner bark of yellow color once the cork is detached by harvest flowers hexameric, axillary, solitary, and hermaphroditic ( Fig. 3), fragrant, 5-7 cm in length; pedicel with a pair of bracteoles not connected by stipules; lobes of calyx greenish-yellowish, linear, closely triangular or rarely leafy, expanded or involuntary; corolla tube creamy white in anthesis, infundibuliform; anthers latrorse dehiscence, with parallel arrangement of teak, glabrous or pubescent; ovary inferior, with the entire stigma or slightly bilobed; ovule anthropic; capsule septicidal, bilocular, sub-cylindrical to subspherical, slightly compressed, 1.5-3.5 cm long, 1.2-1.8 cm wide, with six or no ribs, with or without lenticels (Fig. 2); seed laterally compressed and embedded in the ovary, with rough surface, raphe, and small thread (Ochoterena-Booth 2000;Borhidi 2012;Beltrán-Rodríguez et al. 2015;Rivero-Cruz et al. 2019;Fig. 1). ...
... Hintonia latiflora: The oldest use of this taxon dates back to the sixteenth century, being used as a febrifuge (Rivero-Cruz et al. 2019). Actually, the bark of Hintonia latiflora has 36 different uses in Mexico, the most popular is as antidiabetic, but decoction of the bark is also used traditionally for the treatment of fevers, blood purifying, internal infections, infected wounds, malaria, purgative, diuretic, anemia, bile, hair loss, nephritis, and kidney diseases (Anaya-Dávila 1991; Aguilar et al. 1994;Argueta et al. 1994). ...
... Hintonia standleyana: The stem-bark infusion is originally used for treating malaria fevers, also is popularly used as antiparasitic and for treating gastrointestinal ailments such as gastritis and gastric ulcers, nowadays their main use is antidiabetic (Díaz 1976;González-Chevez et al. 2000;Monroy and Castillo-España 2007;Rivero-Cruz et al. 2019). ...
... In the Danish Pharmacopoeia from 1805 are listed four different cinchona barks: Cortex Carabaeus harvested from Cinchona caribaea, which is a synonym of Exostema caribaeum (Jacq) Schult (Rubiaceae). The bark is known to be extremely bitter because of the presence of 4-phenylcoumarins, but cinchona alkaloids have not been found [44]. Cortex Peruvianus, harvested from Cinchonae officinalis L., Cortex Peruvianus Flavus (yellow or royal bark) and Cortex Peruvianus Ruber (red bark). ...
... The product showed exc no toxic effects on mice. The active principles turned out 15,[42][43][44][45][46][47][48][49]. The most active compounds appeared to be containing a 5-hydroxyl group [90]. ...
Until the end of the 19th century all drugs were natural products or minerals. During the 19th century chemists succeeded in isolating pure natural products such as quinine, morphine, codeine and other compounds with beneficial effects. Pure compounds enabled accurate dosing to achieve serum levels within the pharmacological window and reproducible clinical effects. During the 20th and the 21st century synthetic compounds became the major source of drugs. In spite of the impressive results achieved within the art of synthetic chemistry, natural products or modified natural products still constitute almost half of drugs used for treatment of cancer and diseases like malaria, onchocerciasis and lymphatic filariasis caused by parasites. A turning point in the fight against the devastating burden of malaria was obtained in the 17th century by the discovery that bark from trees belonging to the genus Cinchona could be used for treatment with varying success. However isolation and use of the active principle, quinine, in 1820, afforded a breakthrough in the treatment. In the 20th century the synthetic drug chloroquine severely reduced the burden of malaria. However, resistance made this drug obsolete. Subsequently artemisinin isolated from traditional Chinese medicine turned out to be an efficient antimalarial drug overcoming the problem of chloroquine resistance for a while. The use of synthetic analogues such as chloroquine or semisynthetic drugs such as artemether or artesunate further improved the possibilities for healing malaria. Onchocerciasis (river blindness) made life in large parts of Africa and South America miserable. The discovery of the healing effects of the macrocyclic lactone ivermectin enabled control and partly elimination of the disease by annual mass distribution of the drug. Also in the case of ivermectin improved semisynthetic derivatives have found their way into the clinic. Ivermectin also is an efficient drug for treatment of lymphatic filariasis. The serendipitous discovery of the ability of the spindle toxins to control the growth of fast proliferating cancer cells armed physicians with a new efficient tool for treatment of some cancer diseases. These possibilities have been elaborated through preparation of semisynthetic analogues. Today vincristine and vinblastine and semisynthetic analogues are powerful weapons against cancer diseases.
... Compounds 109 and 116 stimulated AMPK phosphorylation in vitro in C2C12 myoblast cells. Thus, these compounds activate the AMPK pathway, which, in turn, could stimulate insulin secretion [127]. Based on these structures, Wang and collaborators in 2017 [128] synthesized a few substituted 4-phenylcoumarins derivatives analogs of compound 109; their pharmacological investigation showed that those 4-phenylcoumarins possessing adjacent 7,8-dihydroxy groups were equipotent to the standard drug glibenclamide as hypoglycemic agents in vivo. ...
Like in many developing countries, in Mexico, the use of medicinal plants is a common practice. Based on our own field experience, there are at least 800 plants used for treating diabetes nowadays. Thus, their investigation is essential. In this context, this work aims to provide a comprehensive and critical review of the molecules isolated from Mexican hypoglycemic plants, including their source and target tested. In the last few years, some researchers have focused on the study of Mexican hypoglycemic plants. Most works describe the hypoglycemic effect or the mechanism of action of the whole extract, as well as the phytochemical profile of the tested extract. Herein, we analyzed 85 studies encompassing 40 hypoglycemic plants and 86 active compounds belonging to different classes of natural products: 28 flavonoids, 25 aromatic compounds, other than flavonoids, four steroids, 23 terpenoids, 4 oligosaccharides, and 1 polyalcohol. These compounds have shown to inhibit α-glucosidases, increase insulin secretion levels, increase insulin sensitivity, and block hepatic glucose output. Almost half of these molecules are not common metabolites, with a narrow taxonomic distribution, which makes them more interesting as lead molecules. Altogether, this analysis provides a necessary inventory useful for future testing of these active molecules against different hypoglycemic targets, to get a better insight into the already described mechanisms, and overall, to contribute to the knowledge of Mexican medicinal plants.
... 4 From 1890 to 1913, the stem bark of H. latiflora was subjected to pharmacological investigations at the IMN. [44][45][46][47][48] These studies included the isolation of a glycoside (called "coutareoside") that was later rediscovered by German and French researchers. The compound was devoid of toxic effects and provoked diuresis and an increase in the body weight of the patients. ...
... 59 A study by Korec et al. (2000) 60 confirmed the antidiabetic effect of the neoflavonoid coutareagenin from H. latiflora bark in streptozotocininduced diabetes in rats. A vasodilative effect of Sucontral, which supports its antidiabetic effect, was described by Vierling (2005) 33 48 summarized findings that support copalchi bark's antinociceptive and antimicrobial effects in addition to its antidiabetic, vasodilative, and gastroprotective effects. Unpublished studies by Slijepčević and Kraus (1986) 63 and Westendorf and Kraus (1987) 64 investigated acute, chronic, and genotoxicity of copalchi bark. ...
... 38 68 reported a battery of toxic effects of a methanolic extract of H. latiflora stem bark in mice in a dose-dependent manner. 48 According to the Diabetes Canada Clinical Practice Guidelines Expert Committee, dry extract of H. latiflora bark, an NHP for treatment of co-morbidities and complications of diabetes, has been shown to be able to lower glycated hemoglobin (A1C) by at least 0.5% in adults with type 2 diabetes. 69 The expert committee cited a clinical study that concluded that there was a positive effect of a dry extract of H. latiflora bark (extraction solvent ethanol 32%; DER 2.4:1) on blood glucose levels, suggesting a potential benefit in the management of type 2 diabetes. ...
Chikungunya and Mayaro fevers are viral infectious diseases characterized by fever and arthralgia, for which there are currently no effective vaccines or treatments. The urgent need for novel antiviral agents against Chikungunya virus (CHIKV) and Mayaro virus (MAYV) has led to interest in plant-based compounds that can disrupt the viral replication cycle. Chiococca alba (L.) Hitchc., a Neotropical plant traditionally used by Yucatec Maya healers as an antipyretic and antirheumatic, may hold potential as a source of antiviral agents. This study aimed to evaluate the antiviral potential of C. alba methanolic extracts (CAH21 and CAH24) against CHIKV and MAYV through preliminary in vitro and in silico analyses. The cytotoxicity of two methanolic extracts from C. alba roots was assessed in Vero cells using the neutral red assay, and their viral activity was determined via plaque assay post-treatment. Given the observed antiviral effects, we used computational predictions to explore interactions between the multifunctional nsP2 proteases and secondary metabolites identified in C. alba extracts. The metabolites were identified using high-performance liquid chromatography (HPLC) and gas chromatography–mass spectrometry (GC-MS). Phytochemical analysis revealed the presence of flavonoids, coumarins, and phenolic acids in the C. alba extracts. In vitro assays demonstrated that both extracts inhibited over 70% of activity against CHIKV and MAYV at a concentration of 60 µg/mL. In silico predictions suggested that the flavonoids naringin and vitexin had the highest affinity for the nsP2 proteases of CHIKV and MAYV, indicating their potential as viral inhibitors. Our findings revealed that C. alba extract represents a promising source of novel antiviral compounds.
