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Phylogenetic and Chemical Analyses of the Medicinal Plant Salvia circinnata: an Approach to Understand Metabolomics Differences
Abstract
Salvia circinnata Cav. (Syn. S. amarissima Ortega), Lamiaceae, is a Mexican medicinal plant used in traditional medicine for the treatment of gastrointestinal illness, cancer, and diabetes. Samples of ten natural populations were analyzed by application of a systematic approach which involved the combination of DNA barcoding, GC–MS, HPLC–DAD, and HPLC-FLD for differentiation of their chemical profiles. Taxonomic and phylogenetic analyses indicated that all of them belong to the same analyzed plant species. The GC–MS analysis showed the presence of alkanes, amides, anthraquinones, and sesquiterpenoids in the volatile fraction of the extracts. HPLC–PDA and HPLC-FLD analyses indicated that at least four chemotypes exist for the analyzed species, diverging in the production of clerodane diterpenes: (i) an amarissinin A–rich population; (ii) another single population producer of amarisolide A; (iii) producing populations of teotihuacanin and amarissinin A, (iv) while another population only produced alkanes and sesquiterpenes as distinctive constituents not previously reported for this plant. The multivariate statistical analysis suggests that this chemical diversity depends on environmental factors.Graphical abstract
... The different territorial, geographic, and climatic conditions provoke changes in the metabolites, and it may affect all the Salvia species that have a wide distribution in the country, even in the same species with different geographical distribution. These changes are a significant area of study to determine the impact of the different conditions in synthesizing metabolites of pharm acological interest [28,30]. ...
... Considering the similarity observed in the distinct Salvia species, it is essential and necessary to take special care in the taxonomic identification to avoid correlation errors and extrapolation [26], which could put in risk the reproducibility and continuation of pharmacological and chemical studies with these species [2,30]. The chemical composition varies between species, seasons, and habitats, as well as the stage of development or the plant organ (ontogeny of leaves, flowers, and fruits), factors that lead to significant qualitative differentiations where the composition can undergo significant changes. ...
... This, in turn, could generate a different activity that can be observed in biological assays [28]. Besides, some of the same compounds in different species could not be at the same concentration [30,69] and might affect the expected effect. ...
The Salvia genus is one of the most extensive in the Lamiaceae family. The Salvia genus comprises approximately 900 species worldwide, 33 of which exist in the Valle de México, the most populated region of Mexico. The taxonomic identification of these species often represents a problem because they present a great variety of synonyms or variations in their nomenclature, like S. polystachya with 12 synonymies. The traditional medicinal uses of Salvia species in Mexico are varied and include treatment for around 97 diseases. At least 20 species of the Salvia genus have well-documented medicinal ethnobotanical information with various uses, including gastrointestinal disorders, gynecological problems, promoting childbirth, antipyretic, disinfecting wounds, diabetes, and respiratory issues. The phytochemistry of the Salvia species from the Valle of Mexico is also vast and diverse; at least 315 chemical compounds have been identified, mainly terpenoids, that have received significant attention due to their multifaceted biological activities. Among the activities mentioned are anticancer, anti-hyperglycemic, anti-fungal, anti-inflammatory, or anti-microbial. Some of the compounds present more than one biological activity. Given their extensive structural diversity, terpenoids represent a great source of compounds for developing new therapeutic agents. However, additional clinical and experimental studies are still needed to elucidate the mechanisms of action, optimal doses, and potential toxicity of the isolated compounds. Resumen. El género Salvia es uno de los más extensos en la familia Lamiaceae. El género Salvia comprende aproximadamente 900 especies alrededor del mundo, de las cuales 33 se encuentran en el Valle de México, la región más poblada de México. La identificación taxonómica de estas especies representa frecuentemente un problema al presentar una gran cantidad de sinonimias o variaciones en su nomenclatura, como S. polystachya que tiene 12 sinonimias. Los usos en medicina tradicional de Salvias en México son variados, incluyendo tratamiento para alrededor de 97 enfermedades. Por lo menos 20 especies del género Salvia tienen información bien documentada de sus usos médicos y etnobotánicos, con una amplia variedad de usos que incluye desórdenes gastrointestinales, problemas ginecológicos, promotores de parto, antipirético, para desinfectar heridas, diabetes o problemas respiratorios. La fitoquímica de las especies de Salvia del Valle de México es también amplia y diversa. Por lo menos 315 compuestos químicos han sido identificados y aislados, principalmente terpenoides, que han recibido gran atención debido a sus actividades biológicas multifacéticas, como anticancerígenas, antihiperglucémicas, antifúngica, antiinflamatorias o antimicrobianas. Algunos de los compuestos presentan más de una actividad biológica. Dada su extensa diversidad estructural, los terpenoides representan una amplia fuente de compuestos para el desarrollo de nuevos agentes terapéuticos. Sin embargo, estudios clínicos y experimentales adicionales son necesarios para elucidar el mecanismo de acción, dosis óptimas y toxicidad potencial de los compuestos aislados.
... The final temperature was maintained for 9 min. Each analysis was repeated in triplicate, and the volatile compounds were identified by deconvolution, using the W10N11 database (Wiley10Nist11) and the % area normalized (Sepúlveda-Cuellar et al. 2021). ...
... The PDA detector acquires the chromatograms at 240 and 330 nm, and the FL detector operates with an excitation longwave of 250 nm, and an emission longwave of 410 nm. All experiments were repeated in triplicate according to Sepúlveda-Cuellar et al. (2021). ...
Background:
Salvia urica Epling is taxonomically and phylogenetically related to Salvia amarissima Ortega. The last species has pharmacological relevance by its contents of bioactive metabolites. Nowadays, Salvia urica has no reports about its chemical constituents and pharmacological activities.
Hypothesis:
Does the close relationship between S. amarissima and S. urica led both species produce similar specialized metabolites? Does Salvia urica display similar pharmacological effects as S. amarissima?
Studied species:
Salvia urica Epling (Lamiaceae).
Study site and dates:
The plant material was collected in Teopisca, Chiapas, Mexico, in December 2021.
Methods:
Metabolites of the acetone extract from Salvia urica were identified by GC-MS and HPLC-PDA profiling. In parallel, a phytochemical study was conducted, and the individual constituents purified, previously characterized by 1D NMR, were assayed on antihyperglycemic effect in diabetic mice and a charcoal-gum arabic-induced hyperperistalsis model in rats.
Results:
The volatile compounds identified by GC-MS were alkanes, aromatics and triterpenes. The principal constituents of the acetone extract of Salvia urica were amarissinin A and 5,6-dihydroxy-7,3',4'-trimethoxyflavone, which were also quantified by HPLC-PDA. The extract and both metabolites isolated showed an antihyperglycemic effect on streptozotocin-induced diabetic mice, suggesting a possible synergic effect. In addition, the compound 5,6-dihydroxy-7,3',4'-trimethoxyflavone (IC50 = 0.79 mg/kg) showed a better antipropulsive effect than loperamide (IC50 = 16.6 mg/kg).
Conclusions:
The phytochemical composition of an acetone extract of Salvia urica was determined by first time. The metabolites isolated from this plant support the phylogenetic relationship of S. urica with Salvia amarissima, and they showed antipropulsive and antihyperglycemic effects.
The HPLC–PDA profiling of an acetone-soluble extract of the leaves of Salvia circinnata Cav. (Syn. Salvia amarissima Ortega), Lamiaceae, collected at Patzcuaro, Michoacan, Mexico, indicated this population corresponds to the chemotype “amarisolide A.” The phytochemical study of the extract led to the isolation of two new diterpenoid glucosides, amarisolide H and 15-epi-amarisolide H, which were obtained as an epimeric mixture, together with the known compounds amarisolides A, D, G, 16-epi-amarisolide G, and 5,6-dihydroxy-7,3′,4′-trimethoxyflavone. The structures of compounds amarisolide H and 15-epi-amarisolide H were determined by the analyses of their NMR and HRMS data. The cytotoxicity and anti-multidrug resistance (MDR) effects of compounds amarisolide H, 15-epi-amarisolide H, amarisolide A, amarisolide G, and 16-epi-amarisolide G in MCF-7 cancer cells sensible and resistant to vinblastine were essayed.
Essential oils extracted from aromatic and medicinal plants have been known since antiquity for their biological, antibacterial, antifungal, and cosmetic properties. Most essential oils consist in their majority of a complex mixture of monoterpenes, sesquiterpenes, alcohols, esters, aldehydes, oxides, etc… Essential oils generally manifest pharmaceutical properties: they are antiseptic, digestive stimulator, antispasmodic, or neuro-sedative. In this work, we found that essential oils of Lavandula officinalis L. and Rosmanirus Officinalis L. are widely used in the cosmetics and perfumery industry and also aromatherapy, in particular by therapeutic techniques such as massage, inhalation, or bath. The principal chemotypes of Rosmarinus officinalis are as follow: α-pinene, Camphene, 1,8-cineole, Camphor, Borneol, α-terpineol, and β-caryophyllene. About the chemotypes of Lavandula officinalis we had Linalool, 1,8-cineole, Camphor, Linalyl acetate, Borneol, α-Terpineol. They are also used as ingredients in the pharmaceutical industry to flavor oral forms, to perfume dermo-pharmaceutical preparations, and to ensure the preservation of pharmaceutical forms.
The essential oil obtained by hydrodistillation from the aerial parts of Salvia aegyptiaca L. (Lamiaceae) growing wild in pre-Saharan region of Algeria, was analysed by GC-MS. Forty-one compounds were detected, representing 87.9% of the whole oil. The essential oil of S. aegyptiaca is characterized by the predominance of monoterpene derivatives (70.6%). The major constituents were tricyclene (22.9%), followed by limonene (17.5%), β-pinene (7.4%), caryophyllene oxide (3.2%) and β-caryophyllene (3.1%). Tricyclene, the main component in our analysis is generally absent in the volatile oils from other Salvia species, therefore, the Algerian accession of S. aegyptiaca may be categorized as a new chemo-type.
Salvia amarissima Ortega was evaluated to determinate its antihyperglycemic and lipid profile properties. Petroleum ether extract of fresh aerial parts of S. amarissima (PEfAPSa) and a secondary fraction (F6Sa) were evaluated to determine their antihyperglycemic activity in streptozo-cin-induced diabetic (STID) mice, in oral tolerance tests of sucrose, starch, and glucose (OSTT, OStTT, and OGTT, respectively), in terms of glycated hemoglobin (HbA1c), triglycerides (TG), and high-density lipoprotein (HDL). In acute assays at doses of 50 mg/kg body weight (b.w.), PEfAPSa and F6Sa showed a reduction in hyperglycemia in STID mice, at the first and fifth hour after of treatment, respectively, and were comparable with acarbose. In the sub-chronic test, PEfAPSa and F6Sa showed a reduction of glycemia since the first week, and the effect was greater than that of the acarbose control group. In relation to HbA1c, the treatments prevented the increase in HbA1c. In the case of TG and HDL, PEfAPSa and F6Sa showed a reduction in TG and an HDL increase from the second week. OSTT and OStTT showed that PEfAPSa and F6Sa significantly lowered the postprandial peak at 1 h after loading but only in sucrose or starch such as acarbose. The results suggest that S. amarissima activity may be mediated by the inhibition of disaccharide hydrolysis, which may be associated with an α-glucosidase inhibitory effect.
An infusion prepared from the aerial parts of Salvia amarissima Ortega inhibited the enzyme protein tyrosine phosphatase 1B (PTP-1B) (IC50~88 and 33 μg/mL, respectively). Phytochemical analysis of the infusion yielded amarisolide (1), 5,6,4′-trihydroxy-7,3′-dimethoxyflavone (2), 6-hydroxyluteolin (3), rutin (4), rosmarinic acid (5), isoquercitrin (6), pedalitin (7) and a new neo-clerodane type diterpenoid glucoside, named amarisolide G (8a,b). Compound 8a,b is a new natural product, and 2–6 are reported for the first time for the species. All compounds were tested for their inhibitory activity against PTP-1B; their IC50 values ranged from 62.0 to 514.2 μM. The activity was compared to that of ursolic acid (IC50 = 29.14 μM). The most active compound was pedalitin (7). Docking analysis predicted that compound 7 has higher affinity for the allosteric site of the enzyme. Gas chromatography coupled to mass spectrometry analyses of the essential oils prepared from dried and fresh materials revealed that germacrene D (15) and β-selinene (16), followed by β-caryophyllene (13) and spathulenol (17) were their major components. An ultra-high performance liquid chromatography coupled to mass spectrometry method was developed and validated to quantify amarisolide (1) in the ethyl acetate soluble fraction of the infusion of S. amarissima.
Clary sage (Salvia sclarea L.), known for its aromatic and medicinal properties, belongs to the Lamiaceae family. Although the species grows wild throughout Sicily, knowledge of its production and qualitative properties is limited. The aim of this study was to evaluate the agronomic behavior of the species over two years of testing and to characterize the chemical properties of its wild counterparts in order to identify the most promising accessions for cropping or for use in breeding programs. Tests were carried out during 2008, 2009, and 2010. During the first year, the plot was established. Subsequently, the main parameters for bio-agronomic evaluation were taken in 2009 and 2010. Regarding qualitative characterization, essential oils (EO) were extracted from flowering samples of clary sage. The accessions in the study showed satisfactory adaptation capacity to cropping. The accessions examined belong to the “linalyl acetate” (range 36–43%) chemotype. Test results show good potential for Mediterranean cropping systems, helping to increase the range of medicinal and aromatic species in cultivation.
Common thyme (Thymus vulgaris L.) is a Mediterranean evergreen shrub of the Lamiaceae that shows chemical polymorphism in its natural populations. In Mediterranean habitats six basic chemotypes have been described according to the main component in its essential oil: thymol, carvacrol, linalool, geraniol, α-terpineol, thuyanol-4, of which the thymol chemotype is widely used in cultivation and as a spice. In this study ten selected clones were analysed in terms of chemical composition of the volatile oil and genetic fingerprint. The study question was whether individual chemotypes can be distinguished by molecular markers. Chemical composition was analysed by GC-MS, and for assessing the genetic polymorphism ISSR marker system was chosen as it is reliable and easy to use even in case of less studied species. The studied T. vulgaris clones represented five different chemotypes and could be distinguished using 12 ISSR primers. Clones belonging to the thymol chemotype showed the most distinct separation. The study shows the potential of using molecular markers in breeding and selection of T. vulgaris, being able to differentiate different chemotypes.
We present the latest version of the Molecular Evolutionary Genetics Analysis (MEGA) software, which contains many sophisticated
methods and tools for phylogenomics and phylomedicine. In this major upgrade, MEGA has been optimized for use on 64-bit computing
systems for analyzing bigger datasets. Researchers can now explore and analyze tens of thousands of sequences in MEGA. The
new version also provides an advanced wizard for building timetrees and includes a new functionality to automatically predict
gene duplication events in gene family trees. The 64-bit MEGA is made available in two interfaces: graphical and command line.
The graphical user interface (GUI) is a native Microsoft Windows application that can also be used on Mac OSX. The command
line MEGA is available as native applications for Windows, Linux, and Mac OSX. They are intended for use in high-throughput
and scripted analysis. Both versions are available from www.megasoftware.net free of charge.
Sage phylogenies have not resolved many shallow level clades within problematic Salvia subgenus Calosphace, hindered by the difficulty in finding sufficiently variable loci. We assembled fifteen chloroplast genomes and nuclear ribosomal cistrons from non-target reads of a nuclear hybrid enrichment project to assess the phylogenetic utility for a closely related group of mainly Mexican sections. Chloroplast synteny is confirmed with 10 Lamiales chloroplasts, supporting a map to reference assembly. Salvia miltiorrhiza Bunge chloroplast was used as a reference for assemblies, averaging 25,970 reads with mean depth of 20.71 reads; genomes ranged from 141,451 to 150,339 bp. The S. carduacea Benth. nuclear ribosomal cistron (18S, ITS1, 5.8S, ITS2 and 26S) was used as a reference for assembly, averaging 66,387 reads and mean depth of 1508 reads. We evaluated several partitioning schemes for plastid, plastid and nrDNA and reduced sampling, to assess whether these would render the same phylogenetic inferences. Maximum likelihood inferences resulted with high bootstrap support and two main clades with interspersed species from Salvia sect. Scorodoniae: clade A with species from S. sects. Atratae and Mitratae and clade B from S. sects. Sigmoideae and Uricae. Only S. sect. Uricae is monophyletic in every analysis supporting its identity, not merged into S. sect. Scorodoniae; S. sect. Sigmoideae is inferred monophyletic only if the ribosomal DNA sequences are included. Greater resolution and higher branch support are obtained with the entire plastome and nrDNA, rather than subsampling highly variable regions; thus we recommend this approach with expanded taxon sampling, coupled with a morphological review to better solve sectional circumscription in closely related S. subgenus Calosphace species.
p align="left"> Background : Salvia circinata is an endemic species of Mexico used in the folk medicine of Santiago Huauclilla, Oaxaca, mainly as remedy for gastrointestinal diseases.
Hypothesis : If the extracts of Salvia circinata have secondary metabolites with antinociceptive activity, then the behavior of nociception in the model of “whriting” in mice will decrease.
Specie studied : Salvia circinata Cav. (Lamiaceae).
Study site and years of study : Salvia circinata was collected in Santiago Huauclilla, Oaxaca, in July 2014.
Methods : Firstly, the acute toxicity of S. circinata extracts was evaluated to calculate the LD50 with OECD method. Then, dose-response curves of the antinociceptive effect of S. circinata organic and aqueous extracts (1, 10, 30, 100, and 300 mg/kg) were obtained in the writhing test in mice. Furthermore, chromatographic techniques were applied to isolate the compounds and were identified by comparison of the values of 1H NMR, 13C NMR and ESIMS reported in the literature.
Results : Our data showed significant antinociceptive activity in all the tested extracts. Amarisolide A and pedalitin were isolated in the ethyl acetate and methanol extracts, respectively and assayed at doses of 1, 5 and 10 mg/kg, i.p. All the compounds decreased nociception in mice in at least 50 % from a minimal dosage of 1 mg/kg, i.p. and in a similar manner than the reference drug ketorolac (1 mg/kg, i.p.).
Conclusions : Our findings give evidence that Salvia circinata possesses antinociceptive activity depending on the presence of several known bioactive constituents, reinforcing its use in the Mexican traditional medicine to alleviate abdominal pain.</p
Galphimia glauca is a plant that is endemic to Mexico and has been commonly used since pre-Hispanic times to treat various illnesses, including central nervous system disorders and inflammation. The first studies investigating a natural population of G. glauca in Mexico showed that the plant has anxiolytic and sedative activities in mice and humans. The plant’s bioactive compounds were isolated and identified, and they belong to a family of nor-secofriedelanes called galphimines. The integration of DNA barcoding and thin-layer chromatography analysis was performed to clarify whether the botanical classification of the populations in the study, which were collected in different regions of Mexico, as G. glauca was correct or if the populations consist of more than one species of the genus Galphimia. We employed six DNA barcodes (matK, rbcL, rpoC1, psbA-trnH, ITS1 and ITS2) that were analyzed individually and in combination and then compared each other, to indicate differences among the studied populations. In the phylogenetic analysis, ITS1 and ITS2 markers as well as the combination of all DNA regions were the most efficient for discriminating the population studied. The thin-layer chromatography analysis exhibited four principal chemical profiles, one of which corresponded to the populations that produced galphimines. DNA barcoding was consistent and enabled us to differentiate the populations that produce galphimines from those that do not. The results of this investigation suggest that the studied populations belong to at least four different species of the genus Galphimia. The phylogenetic analysis and the thin-layer chromatography chemical profiles were convenient tools for establishing a strong relationship between the genotype and phenotype of the studied populations and could be used for quality control purposes to prepare herbal medicines from plants of the genus Galphimia.
Plant secondary metabolites (SMs) are not only a useful array of natural products but also an important part of plant defense system against pathogenic attacks and environmental stresses. With remarkable biological activities, plant SMs are increasingly used as medicine ingredients and food additives for therapeutic, aromatic and culinary purposes. Various genetic, ontogenic, morphogenetic and environmental factors can influence the biosynthesis and accumulation of SMs. According to the literature reports, for example, SMs accumulation is strongly dependent on a variety of environmental factors such as light, temperature, soil water, soil fertility and salinity, and for most plants, a change in an individual factor may alter the content of SMs even if other factors remain constant. Here, we review with emphasis how each of single factors to affect the accumulation of plant secondary metabolites, and conduct a comparative analysis of relevant natural products in the stressed and unstressed plants. Expectantly, this documentary review will outline a general picture of environmental factors responsible for fluctuation in plant SMs, provide a practical way to obtain consistent quality and high quantity of bioactive compounds in vegetation, and present some suggestions for future research and development.
Antecedentes:
Lamiaceae es una de las familias con mayor riqueza de especies en México. Sin embargo, aún se carece de un estudio detallado sobre su diversidad en el país y de una revisión taxonómica global y actualizada. Como resultado, el aprovechamiento y conservación de los integrantes de esta familia es limitado.
Preguntas:
¿Qué avances se han logrado en el estudio y entendimiento de la riqueza, endemismo y distribución de las Lamiaceae mexicanas? ¿Qué estrategias deben ejecutarse para consolidar el conocimiento de la familia en el país?
Taxon:
Lamiaceae
Sitio de estudio:
México
Métodos:
Se hizo una revisión exhaustiva de las Lamiaceae mexicanas en la literatura, bases de datos y herbarios. Se sintetizó el estado de su conocimiento. Se aplicaron análisis cuantitativos para evaluar su riqueza, endemismo y distribución geográfica.
Resultados:
México cuenta con 33 géneros y 598 especies, de las cuales el 66.2 % son endémicas. El género más diverso es Salvia, con 306 especies. El estado más diverso es Oaxaca, mientras que Jalisco alberga el mayor número de especies endémicas.
Conclusiones:
En México, Lamiaceae es la octava familia más diversa y el número de sus especies representa el 5.5 % de la familia a nivel mundial, por lo que el país puede considerarse uno de los centros de diversificación más importante. Debido a lo anterior, y al endemismo elevado que presenta, México es crucial para la conservación in situ de la familia. Si bien se ha logrado un avance considerable de su conocimiento y en la actualidad hay un repunte en su estudio, es necesario diversificar los campos de investigación.
Eleven neo-clerodane diterpenoids (1–11) including the new analogues 1, 2, and 10, and 3′,5,6,7-tetrahydroxy-4′-methoxyflavone (12) were isolated from the aerial parts of Salvia polystachya. Polystachyne G (1) and 15-epi-polystachyne G (2) were isolated as an epimeric mixture, containing a 5-hydroxyfuran-2(5H)-one unit in the side chain at C-12 of the neo-clerodane framework. Polystachyne H (10) contains a 1(10),2-diene moiety and a tertiary C-4 hydroxy group. The structures of these compounds were established by analysis of their NMR spectroscopic and MS spectrometric data. The absolute configurations of compounds 3, 4, and 10 were determined through single-crystal X-ray diffraction analysis. The antibacterial, antifungal, and phytotoxic activities of the diterpenoids were determined. In addition, the stimulatory effect of the expression of extracellular matrix components of nine of the isolates (1–8 and 11) was assayed. Compounds 1–4, 8, and 11 increased the expression of the genes codifying for type I, type III, and type V collagens and for elastin.
Salvia subg. Calosphace (Lamiaceae, Lamiales) is a highly diverse clade endemic to the New World. The phylogenetic relationships of Calosphace have been previously investigated using DNA sequences of nuclear ITS region and plastid psbA–trnH intergenic spacer, but the resulting trees lack resolution and support for many clades. The present paper reassesses the phylogenetic relationships of subgenus Calosphace, including a broader taxon sampling, with a special focus on representing previously unsampled sections, and using an additional plastid marker (trnL–trnF region). Our results show increased resolution and overall patterns of support, recovering ten main clades. Within core Calosphace, the most inclusive of these main clades, 17 new subclades were identified. Of the 42 sections for which more than one species was analysed, only 12 are monophyletic. Our biogeographical analysis identified at least twelve migrations to South America from Mexican and Central American lineages, in agreement with previous suggestions of multiple origins of South American Calosphace diversity. This analysis also confirmed a colonization of the Antilles by Andean lineages. The reconstruction of ancestral states of pollination syndromes showed multiple shifts to ornithophily from melittophily and one reversal to the latter.
Common sage (Salvia officinalis) is a popular culinary and medicinal herb.
A literature survey has revealed that sage oils can vary widely in their chemical compositions.
The purpose of this study was to examine sage essential oil from different sources/origins and to
define the possible chemotypes of sage oil. Methods: Three different samples of sage leaf essential
oil have been obtained and analyzed by GC-MS and GC-FID. A hierarchical cluster analysis was
carried out on 185 sage oil compositions reported in the literature as well as the three samples in this
study. Results: The major components of the three sage oils were the oxygenated monoterpenoids
α-thujone (17.2–27.4%), 1,8-cineole (11.9–26.9%), and camphor (12.8–21.4%). The cluster analysis
revealed five major chemotypes of sage oil, with the most common being a α-thujone > camphor >
1,8-cineole chemotype, of which the three samples in this study belong. The other chemotypes are a
α-humulene-rich chemotype, a β-thujone-rich chemotype, a 1,8-cineole/camphor chemotype, and a
sclareol/α-thujone chemotype. Conclusions: Most sage oils belonged to the “typical”, α-thujone >
camphor > 1,8-cineole, chemotype, but the essential oil compositions do vary widely and may have a
profound effect on flavor and fragrance profiles as well as biological activities. There are currently no
studies correlating sage oil composition with fragrance descriptions or with biological activities.
A dried infusion prepared from the aerial parts of Salvia circinata did not provoke acute toxicity in mice (LD50 > 5 g/kg). This infusion showed poor hypoglycemic and antihyperglycemic effects (100–570 mg/kg) when tested in normal and hyperglycemic mice using acute and oral glucose tolerance tests, respectively. However, this infusion possessed antihyperglycemic action in vivo during an oral sucrose tolerance test (31.6–316 mg/kg), suggesting the presence of α-glucosidase inhibitors in S. circinata. Fractionation of a nonpolar extract of the aerial parts of the plant yielded a new biflavone (1) and four new neoclerodane diterpenoid glucosides (2–5) along with the known compounds amarisolide (6), pedalitin (7), apigenin-7-O-β-d-glucoside (8), and the flavone 2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-one (9). Compounds 1 and 6–9 were active against mammalian α-glucosidases; 6 and 7 were also active against a recombinant α-glucosidase from Ruminococcus obeum and reduced significantly the postprandial peak during an oral sucrose tolerance test in healthy mice, consistent with their α-glucosidase inhibitory activity. Molecular docking and dynamic studies revealed that compounds 6 and 7 might bind to α-glucosidases at the catalytic center of the enzyme.
The genetic characterization of Native American groups provides insights into their history and demographic events. We sequenced the mitochondrial D-loop region (control region) of 520 samples from eight Mexican indigenous groups. In addition to an analysis of the genetic diversity, structure and genetic relationship between 28 Native American populations, we applied Bayesian skyline methodology for a deeper insight into the history of Mesoamerica. AMOVA tests applying cultural, linguistic and geographic criteria were performed. MDS plots showed a central cluster of Oaxaca and Maya populations, whereas those from the North and West were located on the periphery. Demographic reconstruction indicates higher values of the effective number of breeding females (Nef) in Central Mesoamerica during the Preclassic period, whereas this pattern moves toward the Classic period for groups in the North and West. Conversely, Nef minimum values are distributed either in the Lithic period (i.e. founder effects) or in recent periods (i.e. population declines). The Mesomerican regions showed differences in population fluctuation as indicated by the maximum Inter-Generational Rate (IGRmax): i) Center-South from the lithic period until the Preclassic; ii) West from the beginning of the Preclassic period until early Classic; iii) North characterized by a wide range of temporal variation from the Lithic to the Preclassic. Our findings are consistent with the genetic variations observed between central, South and Southeast Mesoamerica and the North-West region that are related to differences in genetic drift, structure, and temporal survival strategies (agriculture versus hunter-gathering, respectively). Interestingly, although the European contact had a major negative demographic impact, we detect a previous decline in Mesoamerica that had begun a few hundred years before.
Terpenoids from Salvia species have been identified to possess biological properties as antiprotozoal agents. Here, we evaluated the antiamoebic and antigiardial activities of 14 known clerodane and modified clerodane-type diterpenes isolated from five Mexican Salvia species against Entamoeba histolytica and Giardia lamblia, and analyzed the effects of the functionalities in decalin ring or in the whole clerodane framework to visualize the structural requirements necessary to produce an antiprotozoal activity. Among these, linearolactone was the most active clerodane diterpene against both protozoa with IC50 values of 22.9 μM for E. histolytica and of 28.2 μM in the case of G. lamblia. In this context it may be a lead compound for the development of novel therapeutic agent for the treatment of diarrhea and dysentery. The remaining diterpenes assayed showed moderate to weak activity against both protozoa. These findings give support to the use of Salvia species in the traditional medicine from México for the treatment of diarrhea. Copyright © 2015 John Wiley & Sons, Ltd.
Copyright © 2015 John Wiley & Sons, Ltd.
Teotihuacanin (1), an unusual rearranged clerodane diterpene with a new carbon skeleton containing a spiro-10/6 bicyclic system, was isolated from the leaves and flowers of Salvia amarissima. Its structure was determined through spectroscopic analyses. Its absolute configuration was established by single-crystal X-ray diffraction. Compound 1 showed potent modulatory activity of multidrug resistance in vinblastine-resistant MCF-7 cancer cell line (reversal fold, RFMCF-7/Vin+ > 10703) at 25 μg/mL.
Two new 5,10-seco-neo-clerodanes, salvimicrophyllins A and B (1 and 2), and two new neo-clerodanes, salvimicrophyllins C and D (3 and 4), were isolated from the leaves and flowers of Salvia microphylla. The structures of these compounds were elucidated mainly by analysis of their NMR spectroscopic and mass spectrometric data. The relative configurations of the salvimicrophyllins were determined by analysis of NOESY spectra and ECD curves, and the relative configuration of compound 2 was confirmed by single-crystal X-ray diffraction crystallography.
Crops and other plants in natural conditions are routinely affected by several stresses acting simultaneously or in sequence. In areas affected by drought, plants may also be exposed to enhanced UV-B radiation (280-315nm). Each of these stress factors differently affects cellular metabolism. A common consequence of plant exposure to the separate action of water deficit and UV-B radiation is the enhanced generation of reactive oxygen species (ROS) causing damage to proteins, lipids, carbohydrates and DNA. Despite this destructive activity, ROS also act as signalling molecules in cellular processes responsible for defence responses. Plants have evolved many physiological and biochemical mechanisms that avoid or tolerate the effects of stress factors. Water deficit avoidance leads to stomatal closure, stimulation of root growth, and accumulation of free proline and other osmolytes. Secondary metabolites (flavonols, flavones and anthocyanins) that accumulate in epidermal cells effectively screen UV-B irradiation and reduce its penetration to mesophyll tissue. The coordinated increased activity of the enzymatic antioxidant defence system such as up-regulation of superoxide dismutase, catalase, guaiacol peroxidase, ascorbate peroxidase and glutathione reductase is an important mechanism of tolerance to water deficit and UV-B radiation. The accumulation of low molecular antioxidants (proline, glycine betaine, ascorbate and glutathione) can also contribute to tolerance to water deficit. Polyamines, tocopherol, carotenoids, alkaloids, flavonoids and other secondary metabolites participate in the removal of ROS under conditions of increased UV-B radiation. The combination of water deficit and UV-B radiation induces responses that can be antagonistic, additive or synergistic in comparison with the action of single stresses. UV-B radiation may enhance resistance to water deficit and vice versa. Hydrogen peroxide, nitric oxide (NO), abscisic acid (ABA), jasmonic acid, ethylene, and salicylic acid participate in the activation of defence mechanisms. The involvement of these molecules in cross-resistance may rely on activation of enzymatic and non-enzymatic antioxidant systems, enzymes of flavonoid biosynthesis and the accumulation of low-molecular-weight osmolytes as well as regulation of stomatal closure. However, under the conditions of prolonged action of stressors or in the case where one of them is severe, the capacity of the defence system becomes exhausted, leading to damage and even death.
Ethnopharmacological relevance:
The species of Salvia subgenus Calosphace are used medicinally and ritually in numerous traditions of folk healing among indigenous cultures of North and South America with more than 500 species. These species contain numerous bioactive terpenes and terpenoids, some active at human opioid and GABA receptors, which may contribute to their effectiveness as folk medicines. Medicinal plant complexes contain species which share common names, morphological and/or aromatic properties, and medicinal uses; these complexes are found in traditional systems of medicine. Our research looks for complexes within Calosphace and the secondary metabolites they contain.
Materials and methods:
Several studies have combined molecular phylogenetics and ethnopharmacology to successfully target active medicinal species. In this paper, we have selected a monophyletic clade, Salvia subgenus Calosphace, and performed a literature search to identify medicinal plant complexes within it. We created a database from over 200 references, found using keywords, and herbarium sheets. To identify medicinal plant complexes within the database, all species with shared vernacular names were first grouped. If the species sharing common names had similar medicinal uses and morphological similarity, they were concluded to be a complex. In order to determine the accuracy and validity of this approach, the chia complex was used as control, and we more species than reported by all of the published references combined. After identifying complexes and species within each, we searched the phytochemical literature to identify all reported secondary metabolites for each.
Results:
We identify four previously unidentified complexes. Mirto (5 species) is used extensively in the treatment of the folk illness susto and other illnesses in Mexico, and is characterized by red flowers. Ñucchu (7 species) used as a symbolic element in religious processions and in the treatment of respiratory ailments in Peru and characterized by red flowers. Cantueso (2 species), with blue flowers, is used for respiratory ailments in Mexico, and Manga-paqui (3 species) is used for kidney and liver diseases in Ecuador. For the species of each complex we report all traditional preparations, other vernacular names, and known secondary metabolites. Among these complexes, Mirto and Ñucchu appear to have exceptional levels of cultural significance.
Conclusions:
Our results support our hypothesis that species within Salvia subgenus Calosphace will assort into complexes of medicinal plants that share common names, appearances, and medicinal uses. We have identified four new complexes within this monophyletic lineage, mirto, ñucchu, cantueso, and manga-paqui.
Selaginella lepidophylla is one of only a few species of spike mosses (Selaginellaceae) that have evolved desiccation tolerance (DT) or the ability to 'resurrect' from an air-dried state. In order to understand the metabolic basis of DT, S. lepidophylla was subjected to a five-stage, rehydration/dehydration cycle, then analyzed using non-biased, global metabolomics profiling technology based on GC/MS and UHLC/MS/MS2 platforms. A total of 251 metabolites including 167 named (66.5%) and 84 (33.4%) unnamed compounds were characterized. Only 42 (16.7%) and 74 (29.5%) of compounds showed significantly increased or decreased abundance, respectively, indicating that most compounds were produced constitutively including highly abundant trehalose, sucrose, and glucose. Several glycolysis/ gluconeogenesis and tricarboxylic acid (TCA) cycle intermediates showed increased abundance at 100% relative water content (RWC) and 50% RWC. Vanillate, a potent antioxidant was also more abundant in the hydrated state. Many different sugar alcohols and sugar acids were more abundant in the hydrated state. These polyols likely decelerate the rate of water loss during the drying process as well as slow water absorption during rehydration, stabilize proteins, and scavenge reactive oxygen species (ROS). In contrast, nitrogen-rich and γ-glutamyl amino acids, citrulline and nucleotide catabolism products (e.g., allantoin) were more abundant in the dry states, suggesting that these compounds might play important roles in nitrogen remobilization during rehydration or in ROS scavenging. UV-protective compounds such as 3-(3-hydroxyphenyl)propionate, apigenin and naringenin, were more abundant in the dry states. Most lipids were produced constitutively with the exception of choline phosphate, which likely plays a role in membrane hydration and stabilization. In contrast, several polyunsaturated fatty acids were more abundant in the hydrated states, suggesting that these compounds likely help maintain membrane fluidity during dehydration. Lastly, S. lepidophylla contained 7 unnamed compounds that displayed 2-fold or greater abundance in dry or rehydrating states, suggesting that these compounds might play adaptive roles in DT.
Ethnopharmacology relevance:
Galphimia glauca (Malpighiaceae) is a Mexican plant popularly used as a tranquilizer in the treatment of nervous system disorders, although it is also used to treat other common illnesses.
Aim of the study:
The aim of this investigation is to find out if populations of Galphimia glauca collected in different regions and ecosystems in Mexico actually belong to the same species by using the contemporary technique of DNA barcodes. Our previous metabolic profiling study demonstrates that different collections of this plant obtained from various geographical areas exhibited diverse chemical profiles in terms of the active compounds named Galphimines. We expected the DNA barcodes apart from indicating the different species of Galphimia would indicate the active populations.
Materials and methods:
We employed matK, rpoC1 and rbcL DNA barcodes to indicate the different species. Furthermore to investigate the possible impact of the several different ecosystems where the seven populations were collected, thin layer chromatography was employed to create a partial chemical profile, which was then compared with the metabolic profiles obtained by (1)H-NMR and multivariate data analysis.
Results and conclusions:
This study showed that the seven populations here analyzed contain at least three different species of the genus Galphimia, although each individual population is homogeneous. Interestingly our TLC analysis clearly showed that the active populations displayed a distinctively unique chemical profile. This work also showed that the use of DNA barcodes combined with chemical profile analysis is an excellent approach to solve the problems of quality control in the development of Galphimia-based medicines as well as for any breeding programs for this species.
The South African Salvia species, Salvia africana-lutea, S. lanceolata and S. chamelaeagnea, are widely used to treat fever and inflammation associated with skin and lung infections. The aim of this study was to explore the non-volatile secondary metabolites and the phytochemical variation within these lesser known species, to support product development and commercialisation. Chemical profiles of the methanol extracts of 81 wild-harvested samples were obtained using ultra performance-quadrupole-Time-of-Flight-mass spectrometry (UPLC-qToF-MS). Forty-one compounds, including caffeic acid, rosmarinic acid, carnosol, carnosic acid and ursolic acid, were detected and confirmed across the three species. Nineteen compounds were tentatively identified of which 14 have not been reported in these species. Principal component analysis revealed distinct clusters corresponding to the three species, confirming chemical differences. Marker compounds for each species were revealed using orthogonal projection to latent structures-discriminant analysis. Further chemometric analysis reflected a degree of intraspecies variation, although the chemistry within populations was mostly conserved. Potential chemotypes for each species were identified through unique compounds associated with each group. The concentrations of medicinally important metabolites, namely, rosmarinic acid, carnosol, carnosic acid and ursolic acid, were determined, using validated UPLC-PDA methods. Ursolic acid was present at levels up to 38.2 mg/g, confirming that these species are a rich source of this compound. No similar studies combining liquid chromatography with chemometric analysis, and utilising a large sample size from various habitats, have been reported for these three Salvia species. The results will guide selection of cultivars with the best attributes for the intended therapeutic application, thereby protecting wild populations from over-exploitation.
The phytochemical study on ten populations of Salvia multicaulis Vahl. revealed that their essential oil qualitative profiles contained a significant amount of monoterpene hydrocarbons, which were the most abundant compounds. Besides, α-Pinene was the major constituent in all studied populations' essential oils. Significant correlations were observed between edaphic parameters and some major essential oil compounds. According to clustering analyses of the chemical data, the S. multicaulis populations were divided into three chemotypes: β-caryophyllene, camphene and camphor, and limonene. The population genetics study showed significant molecular differences among the populations. The Mantel test indicated a significant positive correlation between the geographical distances and genetic diversity, exhibiting a low amount of gene flow and a considerable genetic differentiation value. We also detected four genotypes based on the Nei's genetic distance and structure analysis. The identified chemical and genetic similarities/differences among these populations were correlated with edaphic parameters and geographic distances, suggesting that environmental factors are the primary drivers of the chemical polymorphism of essential oils in S. multicaulis populations.
Medicinal plants have been used for thousands of years and nowadays are extensively employed to treat diverse illnesses. The increasing consumption of medicinal plants and its derivative products has led to an increase of adulterant material during the manufacturing process. The quality of the medicinal active products could be affected by reducing the concentration of bioactive metabolites, and by the presence of toxic compounds. DNA barcoding has become a robust methodology to identify and authenticate medicinal plants. In the present paper, we reviewed 366 manuscripts of medicinal plants published in the last 10 years, and the results of applying DNA barcoding were analyzed. We are also providing taxonomical information, medicinal properties, distribution of investigated material by country, and some representative active compounds. Overall, it was possible to identify 17 different barcode regions that were used to study medicinal plant material. Particularly, the use of ITS2 has increased due to its high discrimination rates at low taxonomic level; however, a multilocus DNA barcode approach could be a better tool to properly identify medicinal plants. Some emerging technologies that allow facing the limitations of DNA barcoding as DNA mini-barcoding, metabarcoding and bar-HRM technology, were reviewed. Future challenges will be the global application of the improved DNA barcoding technologies to properly authenticate and identify medicinal plants. DNA barcoding must be used in countries with a high consumption of herbal remedies in order to provide safe and effective medicinal products.
Salvinorin A is the main bioactive compound in Salvia divinorum, an endemic plant with ancestral use by the inhabitants of the Mazateca mountain range (Sierra Mazateca) in Oaxaca, México. The main use of la pastora, as locally known, is in spiritual rites due to its extraordinary hallucinogenic effects. Being the first known nonalkaloidal opioid-mediated psychotropic molecule, salvinorin A set new research areas in neuroscience. The absence of a protonated amine group, common to all previously known opioids, results in a fast metabolism with the concomitant fast elimination and swift loss of activity. The worldwide spread and psychotropic effects of salvinorin A account for its misuse and classification as a drug of abuse. Consequently, salvinorin A and Salvia divinorum are now banned in many countries. Several synthetic efforts have been focused on the improvement of physicochemical and biological properties of salvinorin A: from total synthesis to hundreds of analogues. In this Review, we discuss the impact of salvinorin A in chemistry and neuroscience covering the historical relevance, isolation from natural sources, synthetic efforts, and pharmacological and safety profiles. Altogether, the chemistry behind and the taboo that encloses salvinorin A makes it one of the most exquisite naturally occurring drugs.
Linearolactone (1) and kaempferol (2) have amebicidal activity in in vitro studies. The type of cell death induced by 1 and 2 and their effects on the virulence of E. histolytica were analyzed by transmission and confocal electron microscopy, reactive oxygen species (ROS) production, and apoptosis, detected by flow cytometry with dichlorofluorescein 2',7'-diacetate and annexin-V binding, respectively, and confirmed by TUNEL. The interaction of 1 and 2 with actin was analyzed by docking, and the in vivo amoebicidal activity was established with the Mesocricetus auratus model; amebic liver abscess (ALA) development was evaluated by magnetic resonance (MR) and validated post mortem. In vitro, compounds 1 and 2 caused chromatin condensation, intracellular ROS, and loss of actin structures. Coupling analysis showed that they bind to the allosteric and catalytic sites of actin with binding energies of -11.30 and -8.45 kcal/mol, respectively. Treatments with 1 and 2 induced a decrease in ALA formation without toxic effects on the liver and kidney. Thus, compound 1, but not 2, was able to induce apoptosis-like effects in E. histolytica trophozoites by intracellular production of ROS that affected the actin cytoskeleton structuration. In vivo, compound 1 was more active than compound 2 to reduce the development of ALA.
Salvia limbata C.A. Meyer (Lamiaceae) is an aromatic medicinal herb growing wild in various parts of Iran. In the current study, variations in the trichomes morphology and density, and composition of the hydro-distilled obtained essential oils of eight wild S. limbata populations were assessed. Essential oil yield showed a high degree of variability among the populations. The major constituents of essential oil were similar in all of the examined populations, except for Damavand population. In this population, two oil components were detected to be higher than 78% of total oil constituents. According to the principal components and cluster analysis, four groups identified with regard to the essential oil compositions: populations containing isospathulenol and aromadendrene (group I), populations with the presence of linalool, spathulenol and δ-elemene (group II), populations containing the high percentage of 1, 8-cineol (group III) and populations were characterized by the high percentage of α-pinene (group IV). The leaves of plants from all populations were covered by villous indumentum, except for Damavand population, which showed tomentose indumentum. Two types of trichomes such as glandular (peltate, capitate and digitate) and non-glandular (unbranched oneto nine-celled) were registered. The analysis of variance revealed significant variations for some of them. Totally, group I had the unique indumentum and essential oil composition, therefore, has been defined as a new chemotype for this species. Such indumentum and chemical differences clearly revealed the environmental impact on the micromorphological and essential oil compositions among the populations. The presence of high isospathulenol content in plants of Damavand population suggests their potential as strong antibiotics. However, the findings also indicate that a proper exploitation of the medicinal properties in this plant highly related to the location of sampling site, which positively contributes to its medicinal value.
The hydrodistilled essential oils from eighteen samples of Salvia rosmarinus Spenn. collected in six localities of Elba Island (Tuscany, Italy) during three different seasonal periods were analyzed by GC-MS for the first time. Fifty-five components were identified, representing 96.8-99.6% of the total chemical composition. All the tested essential oils were characterized by a high content of monoterpenes (oxygenated 49.2-80.3%; hydrocarbons 18.7-48.3%). Among them, 1,8-cineole (26.4-49.1%), α-pinene (4.5-34.8%), camphor (1.1-18.8%) and borneol (1.7-16.2%) were the main constituents. The high amount of 1,8-cineole/α-pinene/camphor/borneol may suggest the presence of an intermediate rosemary chemotype. Statistical analysis was also performed on the essential oil (EO) composition evidenced an expected difference depending on the collection seasons, to the geographical areas and soil composition. A comparison with the essential oil composition from S. rosmarinus collected in all the other islands of Tuscan Archipelago (Italy) was also reported, together with a Multivariate Statistical Analysis.
Salvia circinata Cav., Lamiaceae, is commonly used in Mexican traditional medicine to treat gastrointestinal ailments, including diarrhea. An acetone-soluble extract from the aerial parts of S. circinata was suspended in a 9:1 methanol–water mixture and fractionated by partition with hexane and EtOAc. The hexane, EtOAc, and aqueous fractions were evaluated for their antiprotozoal activities, where the EtOAc-soluble fraction displayed the best antiprotozoal activity. Resolution of this fraction by chromatographic methods afforded the known diterpenoids amarissinins A–C (1–3), teotihuacanin (4), and amarisolide F (5), along with two flavones, apigenin (6) and 5,6-dihydroxy-7,3′,4′-trimethoxy flavone (7). Compound 7 was the most active one, with IC50 values of 0.05 μM and 0.13 μM against Entamoeba histolytica and Giardia lamblia, respectively. Interestingly, it was even more active than metronidazole and emetine, used as positive controls. Compounds 1–6 showed moderate antiprotozoal activity with IC50 values ranging from 23.9 to 67.8 μM against Entamoeba histolytica, and 39.4 to 127 μM against Giardia lamblia. These results provide evidence-based support for the traditional use of S. circinata, and suggest that the 5,6-dihydroxy-7,3′,4′-trimethoxy flavone (7) may have an important role in the antidiarrheal activity of the plant.
Graphical abstract
Galphimia glauca Cav., Malpighiaceae, is used as a tranquilizer in Mexico. Its active compounds are nor-secofriedelane triterpenes known as galphimines. Using metabolic profiling, we previously demonstrated that individuals obtained in two localities out of the seven analyzed, exhibited accumulation of galphimines. In the present work, we tested the hypothesis that this accumulation responds to genetic control. Galphimia sp. individuals were collected from six previously studied populations, located in five Mexican states (Doctor Mora in Guanajuato, Jalpan in Querétaro, Cuernavaca and Tepoztlán in Morelos, Guadalajara in Jalisco, and Tuxtla Gutiérrez in Chiapas), and transplanted to grow under uniform greenhouse conditions, for a period of 11 months. A phytochemical analysis using chromatographic procedures was performed for all individuals upon arrival and after 11 months of controlled growth. Results indicated that only two populations (Doctor Mora, Guanajuato, and Jalpan, Querétaro), out of the six that were collected, produced galphimines before and after controlled growth, exhibiting the same chemotype pattern in the greenhouse, as in the wild. However, evident changes in foliar morphology, probably due to phenotypic plasticity, were observed in all the acclimatized plants.
Graphical abstract
Nine terpenoids were isolated from the leaves and flowers of Salvia amarissima, including a new acylated diterpenoid glucoside, amarisolide F (1), a new neo-clerodane diterpenoid, amarissinin D (2), which was isolated as an acetyl derivative (2a), and four known diterpenoids. The structure of amarisolide F (1) was elucidated by NMR and MS data analyses, as well as its methanolysis products 7 and 8, which also constituted new diterpenoids, named amarissinin E and 8-epi-amarissinin E, respectively. The absolute configuration of compound 7 was established by single-crystal X-ray diffraction. The cytotoxicity and anti-MDR effect of 1 in three phenotypes of the MCF-7 cell lines were assayed. Compound 1 was 2-3.6-fold more active than amarissinins A (3) and B (4), but several orders of magnitude less active than teotihuacanin (6) and reserpine. © 2018 American Chemical Society and American Society of Pharmacognosy.
Plants have developed a plethora of signals to interact with other organisms, finally building up a sophisticate language for communication. In this context, we investigated Salvia verticillata L. (Lamiaceae), with the primary goal to link secondary metabolites and actual biotic relationships. We specifically analysed the volatile organic compounds (VOC) spontaneously emitted by leaves and flowers and determined the composition of the essential oils obtained from the aerial parts across 2015 and 2016. We merged information of chemical analyses to a micromorphological investigation on the glandular indumentum and to focal observations on the pollinator assemblage.
The VOC profiles were highly variable, with the floral bouquet being the most complex. Flowers and leaves showed 37 and 20 exclusive compounds, dominated by 1,8-cineole (10.4%) and germacrene D (38.4%), respectively. Sesquiterpene hydrocarbons prevailed (83.3% leaves; 73.7% flowers) and 19 common compounds were detected.
The oil profiles proved to be consistent across the two years: sesquiterpene hydrocarbons invariably dominated, with germacrene D, bicyclogermacrene and β-caryophyllene as main compounds.
The whole plant epidermis is thickly covered by two types of glandular hairs: peltates and small capitates, both responsible for the synthesis of terpenes, finally resulting in the VOC emission and in the essential oil production.
S. verticillata attracted mainly bees belonging to two functional groups: medium-sized and large bees, notwithstanding the small size of its flowers. At the site, Apis mellifera and different Bombus species were recorded, mainly interested in feeding on nectar. The literature survey on the isolated volatile compounds confirmed the hypotheses on the seduction strategies towards Apoidea.
We conducted a pilot study using Anchored Hybrid Enrichment to resolve relationships among a mostly Neotropical sage lineage that may have undergone a recent evolutionary radiation. Conventional markers (ITS, trnL-trnF and trnH-psbA) have not been able to resolve the relationships among species nor within portions of the backbone of the lineage. We sampled 12 representative species of subgenus Calosphace and included one species of Salvia's s.l. closest relative, Lepechinia, as outgroup. Hybrid enrichment and sequencing were successful, yielding 448 alignments of individual loci with an average length of 704 bp. The performance of the phylogenomic data in phylogenetic reconstruction was superior to that of conventional markers, increasing both support and resolution. Because the captured loci vary in the amount of net phylogenetic informativeness at different phylogenetic depths, these data are promising in phylogenetic reconstruction of this group and likely other lineages within Lamiales. However, special attention should be placed on the amount of phylogenetic noise that the data could potentially contain. A prior exploration step using phylogenetic informativeness profiles to detect loci with sites with disproportionate high substitution rates (showing "phantom" spikes) and, if required, the ensuing filtering of the problematic data is recommended. In our dataset, filtering resulted in increased support and resolution for the shallow nodes in maximum likelihood phylogenetic trees resulting from concatenated analyses of all the loci. Additionally, it is expected that an increase in sampling (loci and taxa) will aid in resolving weakly supported, short deep internal branches.
Covering: 1990 to 2015The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.
To elucidate relationships at deep levels within Saxifragaceae we analyzed phylogenetically a data set of sequences for six DNA regions, four representing the chloroplast genome (rbcL, matK, trnL-trnF, psbA-trnH) and two from the nuclear genome (ITS and expansion segments of the 26S rDNA). A total of 6676 bp was aligned per taxon, 4559 bp and 1878 bp from the chloroplast and nuclear genomes, respectively. Chloroplast and nuclear trees agreed closely, prompting analysis of a combined, six-gene data set. Application of both parsimony and maximum likelihood methods yielded similar topologies. The use of different ITS alignments and the exclusion of hard-to-align ITS regions had little impact on either the final nuclear-based topology, or the shortest trees from the analysis of six genes. The affinities of two monotypic genera (Saxifragella and Saxifragodes) endemic to Tierra del Fuego were elucidated. Saxifragella is an early branching member of the North Temperate genus Saxifranga s. str.; Saxifragodes is sister to Cascadia, a genus endemic to Oregon and Washington. Long-distance dispersal from east Asia or western North America to South America may have played an important role in forming these and ether similar disjunctions in the family. A number of well-supported clades are present, including Saxifroga s. str., Micranthes, Saxifragopsis/Astilbe, Chrysosplenium/ Peltoboykinia, and the Boykinia and Heuchera groups. The use of additional characters has provided greatly increased resolution and internal support at deep levels. Saxifragaceae comprise two major lineages: Saxifroga s. str. (including Saxifragella) and all other genera of the family (the heucheroids). This major split is accompanied by general biogeographical and morphological differences. Whereas Saxifraga s. str. is largely arctic to alpine in occurrence, the heucheroid clade is largely temperate in distribution. Saxifraga s. str. has a relatively uniform floral morphology (generally actinomorphic; 5 sepals, 5 petals, 10 stamens, 2 carpels), whereas the heucheroid clade encompasses actinomorphic and zygomorphic forms, as well as variation in the number of sepals, petals, stamens, and carpels. Deep-level relationships within both Saxifraga s. str. and the heucheroid clade are well resolved and supported. A phylogenetic classification of the family is provided.
DNA barcodes are becoming an integral tool for the identification of species and the understanding of the evolution and ecology of biodiversity.•Although the specification of a single short DNA region as a universal identifier for all of biodiversity has not materialized, a few genetic markers have now been identified to assist in the DNA barcode endeavor.•DNA barcodes are providing resolved local phylogenies of plant taxa to aid understanding of the principles of how species are assembled into communities and the evolution of functional traits in these assemblages.•Previous attempts to resolve multispecies interactions have been enhanced through use of DNA barcodes in investigations of trophic interactions and ecological forensics.
Leaves of Plantago major L. (common plantain) have been used for centuries almost all over the world as a wound healing remedy, and for other medicinal purposes. Polyphenols have been proposed to be responsible for many of the medicinal properties attributed to P. major. In this study, plants from 19 subpopulations (offspring families), derived from a total of five populations of P. major collected from different parts of Sweden, were screened for genetic variation with molecular markers, and for contents of major polyphenolic compounds. In addition to plantamajoside, four novel poplyphenolic compounds were identified and quantified. RAPD analysis demonstrated considerable between-population variation and very sparse within-population and within-subpopulation variation, just as expected for inbreeding species. Differentiation among populations was associated with the geographical distances between the sampled populations. Differences between populations and subpopulations in polyphenol contents did not reflect the DNA-marker based pattern, suggesting that the expression of the studied polyphenols was affected by, e.g., epigenetic inheritance or a very early environmental influence on the newly germinated seedlings, before potting and randomization.
Sage plants (Salvia offcinalis) were self-pollinated for three consecutive generations. The essential oil composition of 70 plants of the third generation, originating from four different mother plants, was analyzed. The content of α-pinene showed higher variation than all other compounds. The plants segregated into three distinct groups regarding the content of α-pinene: a low-level group around 2% α-pinene, a mid-level group around 9% and a high level group around 15%. This clear segregation into three groups proves the polymorphism (chemotype formation) of α-pinene in sage.Furthermore, the enantiomeric composition of α-pinene shifted from 35:65 [(−)-α-pinene:(+)- α-pinene] in the low level to 15:85 in the mid- and high level.
A new neo-clerodane glycoside, amarisolide, has been isolated from the aerial parts of Salvia amarissima. Its structure was established as 2β-O-β-D-glucopyranosyl neo-cleroda-3,13(16),14-trien-15,16-epoxy-18,19-olide by chemical and spectroscopic means.
Phytochemical and genetic variability of Casearia sylvestris Sw. from São Paulo State Atlantic Forest and Cerrado populations. Two botanical varieties have been considered in Casearia sylvestris species: C. sylvestris var. lingua, with a shrubby characteristic, occurring in bushy Cerrado (savannah) and C. sylvestris var. sylvestris, with an arboreous type in forest or shrubby vegetation. The limits of these varieties based on morphological parameters are very tenuous, though suggesting the reliability of applying molecular and phytochemical to characterize such differences. This work aimed to identify genetic and chemical differences between C. sylvestris varieties in six natural populations of from Cerrado and São Paulo State Atlantic Forest, using RAPD (Random Amplification of Polymorphic DNA) and chemical markers. Georeferenced samples have been collected in order to characterize geographic location data (altitude, latitude and longitude). Nine primers were selected for the RAPD reactions. The dendrogram was obtained from the matrix of pairwise distances through the Jaccard's similarity index using the UPGMA (Unweighted Pair Group Method with Arithmetic Mean) grouping method. A Mantel test was used to analyze correlations between genetic and geographical distances, while the molecular variance analysis and the Shannon index were used to determine the intra- and interpopulation divergences. For the phytochemical study, leaves of both species were submitted to rutin extraction in methanol and quantification was carried out using a high-performance liquid chromatographer. Most soil indicator values showed diversity among populations of savannah and Atlantic Forest. There is a high variability in the rutin content among accessions within and among the study populations. The proposed comparisons among populations and the two study biomes in relation to the rutin content showed that the savannah populations have presented significant higher values. A positive correlation between altitude and rutin content has been clearly shown, i.e., higher altitudes are associated with higher rutin content and Cerrado biome. Partitioning of the diversity indicated that 84% of the variation occurred within populations and only 15% between populations. In order to establish a germplasm bank of the species, it is necessary to collect a higher number of individuals within each population so that the existing variability in the species could be represented.
The Lamiaceae, a widespread family, comprises 220 genera and 4000 species distributed throughout most of the world as annuals and perennial plants. The increasing number of commonly known crops in this family reflects the intensification of taxonomical and ethnobotanical research in this field. The genus Salvia is widely distributed in various regions of the world including the temperate and warmer zones of the world such as the Mediterranean, Central Asia, the Pacific Islands, tropical Africa, and America. It has also been indicated for hemorrhage, dysmenorrhea, miscarriage, swelling, and insomnia, as well as inflammatory diseases such as edema, arthritis, and endangitiis. Chronic hepatitis and liver fibrosis have also been treated with Tanshen for centuries. The alcohol extract of Danshen is particularly rich in abietanoids and diterpene quinone pigments.
Salvia hispanica L., was an important staple Mesoamerican food and medicinal plant in pre-Columbian times. Unlike other Mesoamerican pseudocereal crops such as Amaranthus and Chenopodium, it has received comparatively little research attention. An ethnobotanical review of this Mesoamerican crop plant Salvia hispanica has been undertaken to examine changes in use accompanying Spanish colonization. A comparative analysis of accounts of use from the 16th century codices of Mexico and subsequent publications has revealed subtle changes in medicinal, culinary, artistic, and religious uses. Several hypotheses surrounding changes in use through time and the original use(s) that led to domestication are developed and tested through collection of ethnobotanical data in the highlands of western Mexico and Guatemala. A general decline in ethnobotanical knowledge associated with wild populations coupled with a loss of habitat in some locations has degraded important germplasm and knowledge resources for a species with great economic potential.
Plant secondary metabolites are unique sources for pharmaceuticals, food additives, flavors, and industrially important biochemicals. Accumulation of such metabolites often occurs in plants subjected to stresses including various elicitors or signal molecules. Secondary metabolites play a major role in the adaptation of plants to the environment and in overcoming stress conditions. Environmental factors viz. temperature, humidity, light intensity, the supply of water, minerals, and CO2 influence the growth of a plant and secondary metabolite production. Drought, high salinity, and freezing temperatures are environmental conditions that cause adverse effects on the growth of plants and the productivity of crops. Plant cell culture technologies have been effective tools for both studying and producing plant secondary metabolites under in vitro conditions and for plant improvement. This brief review summarizes the influence of different abiotic factors include salt, drought, light, heavy metals, frost etc. on secondary metabolites in plants. The focus of the present review is the influence of abiotic factors on secondary metabolite production and some of important plant pharmaceuticals. Also, we describe the results of in vitro cultures and production of some important secondary metabolites obtained in our laboratory.