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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...
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... C-4 location of the hydroxy group was indicated by the HMBC correlations of HO-4 with C-3, C-4, C- 5, and C-18. In addition, the relative configuration of 10 was established by the analysis of the NOESY spectrum (Figure 4), taking into account the same criteria as for 1 and 2. The NOE correlations of the HO-4 with H-6β suggested a β-disposition of the hydroxy group, and this correlation together with those of H-19β with H 3 -20 indicated the presence of a cis-fused γ- lactone moiety. The cross-peak of H 3 -20 with H-8 established the presence of a cis-fused δ-lactone, and the cross-peaks of H- 14 and H-15 with H-11α suggested an α-oriented furan ring. ...
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Abstract: Background: Plants belonging to the genus Kaempferia (family: Zingiberaceae) are
distributed in Asia, especially in the southeast region, and Thailand. They have been widely used
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Citations
... br s, H-15). The duplicity of the signals in this second functional group confirmed the epimeric relation in compounds 1/2 as occurs with other diterpenoids derived from Salvia species, and suggested that both compounds differed with 3 by the oxidation degree in the C-13 to C-16 lateral chain of the neo-clerodane framework (Bautista et al. 2017). The signal in the 1 H NMR spectrum at δ H 4.45 (d, J = 8.0 Hz, H-1′) was assigned to the anomeric proton of the d-glucose residue, which correlated in the HSQC spectrum with a signal at δ C 103.37/103.31 ...
... (Toscano et al. 2020), and S. polystachia Cav. (Bautista et al. 2017). The diterpenoids with this structural feature can occur as a single enantiomer (methyl ethers), and as diastereomeric or epimeric mixtures due to the opening in solution of the 5-hydroxy-furan-2(5H)-one moiety, followed by the subsequent epimerization at C-15 or C-16 of the neoclerodane framework, and by the eventual epimerization at C-4 or C-8 when their biosynthesis occurs. ...
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.
... Some of the Mexican species are well known due to their documented nutritional properties (i.e., S. hispanica L.; Cahill, 2003;Mohd Ali et al., 2012;Ullah et al., 2016) or for their psychoactive properties that are of pharmacological interest due to their antinociceptive effects (i.e., Salvia divinorum Epling and Jativa; Jenks et al., 2011;Tlacomulco-Flores et al., 2020). The most commonly reported bioactive constituents within the subgenus have been characterized as diterpenoids-abietanes and clerodanes- (Bautista et al., 2016;Jiang et al., 2016;Bautista et al., 2017;Esquivel et al., 2017;Campos-Xolalpa et al., 2021). ...
... Clerodanes. A number of clerodanes have been characterised in the following species of subgenus Calosphace: Salvia amarissima, S. divinorum, S. dugesii Fernald, S. hispanica, S. leucantha, and S. polystachia (Shirota et al., 2006;Gang et al., 2011;Jiang et al., 2016;Bautista et al., 2017;Fan et al., 2020). ...
Salvia is the most diverse genus within the mint family (Lamiaceae), many of its species are well-known due to their medicinal and culinary uses. Most of the ethnopharmacological and phytochemical studies on Salvia are centred on species from the European and Asian clades. However, studies about the most diverse clade, the Neotropical sages (Salvia subgenus Calosphace; 587 spp.), are relatively scarce. This review aims to compile the information on the traditional medicinal uses, pharmacological and phytochemistry properties of the Neotropical sages. To do so, we carried out a comprehensive review of the articles available in different online databases published from the past to 2022 (i.e., PubMed, Scopus, and Web of Science, among others) and summarized the information in tables. To uncover phylogenetic patterns in the distribution of four different groups of metabolites (mono-, sesqui-, di-, and triterpenes), we generated presence-absence matrices and plotted the tip states over a dated phylogeny of Salvia. We found several studies involving Mexican species of Salvia, but only a few about taxa from other diversity centres. The main traditional uses of the Mexican species of Calosphace are medicinal and ceremonial. In traditional medicine 56 species are used to treat diseases from 17 categories according to the WHO, plus cultural-bound syndromes. Pharmacological studies reveal a wide range of biological properties (e.g., antinociceptive, anti-inflammatory, anxiolytic, cytotoxic, and antidiabetic, etc.) found in extracts and isolated compounds of 38 Neotropical sages. From extracts of these species, at least 109 compounds have been isolated, identified and evaluated pharmacologically; 73 of these compounds are clerodanes, 21 abietanes, six flavonoids, five sesquiterpenoids, and four triterpenoids. The most characteristic metabolites found in the Neotropical sages are the diterpenes, particularly clerodanes (e.g., Amarisolide A, Tilifodiolide), that are found almost exclusively in this group. The Neotropical sages are a promising resource in the production of herbal medication, but studies that corroborate the properties that have been attributed to them in traditional medicine are scarce. Research of these metabolites guided by the phylogenies is recommended, since closely related species tend to share the presence of similar compounds and thus similar medicinal properties.
... Mexico harbors a third of the Salvia species identified to date (306 taxa) from which 75% are endemic ). These species have been used as sources of food and medicines since pre-Columbian times (Cahill 2003) and they are still used for treating dermatological, gastrointestinal, gynecological, and neurological disorders (Bautista et al. 2014(Bautista et al. , 2017Calzada et al. 2015). Among these species, S. circinnata Cav. ...
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 structures of the isolated compounds were established by the analyses of their NMR spectroscopic and MS spectrometric data and were compared with those described in the literature (Nagao et al. 2002;Gecibesler et al. 2019). Curiously, during the isolation procedure, sesquiterpenoids and diterpenoids were not isolated as is common in Salvia species (Bautista et al. 2017;Fragoso-Serrano et al. 2019). The subsequent evaluation of the antiprotozoal properties of isolates 1-3 showed that compounds 1 and 2 had moderate antiprotozoal activity against both protozoa, with IC 50 values of 40.4 (40.9-39.8) ...
Salvia connivens Epling, Lamiaceae, is an annual herbaceous plant used as a traditional medicine in Mexico for the treatment of diarrhea, which out can be caused by bacterial, viral, and protozoal infections, as well as toxins mainly. Mexican medicinal plants with anti-diarrheic activity represent a source of potential antiprotozoal agents. The phytochemical isolation of the constituents of an acetone-soluble extract led to the isolation of the known flavonoids: eupatorin, cirsiliol, and nuchensin. The structures of these compounds were elucidated by the analysis of their NMR and MS data. Nuchensin displayed potent antiprotozoal activity against Entamoeba histolytica (IC50 0.072 ± 0.006 μM) and Giardia lamblia (IC50 0.118 ± 0.006 μM), which was comparable to metronidazole.Graphical abstract
... We postulated that compounds present on Sp extract, besides lowering the stress oxidative-induced damage, might allow adaptations on gene regulation. For example, aerial parts of Sp contain eleven neo-cleorodane difepenoids; some of these compounds augmented the expression of extracellular matrix components (e.g., genes codifying type I, II, and V collagens and elastin) [57], which are critical for vascular basement membrane function and play a central role in cerebrovascular diseases [58]. Compounds in S. mitiorrhiza can also inhibit the expression of adhesion molecules in vascular endothelium and in leukocytes that help to prevent the development of vascular damage induced by ischemia and reperfusion [59]. ...
This study aimed to compare the antioxidant activities of extracts obtained from three plant families and evaluate their therapeutic effect on strokes. Ethanol extracts were obtained from either the leaf or the aerial parts of plants of the families Annonaceae (Annona cherimola, A. diversifolia, A. muricata, A. purpurea, and A. reticulata), Lamiaceae (Salvia amaríssima and S. polystachya), and Geraniaceae (Geranium niveum and G. mexicanum). Extracts were analyzed in terms of hydroxyl radical (OH•), peroxyl radical (ROO•), and superoxide anion (O2•⁻). The efficiency of the extracts to prevent neuronal death induced by excitotoxicity was tested with the tetrazolium assay, the O2•⁻ scavenging capacity was evaluated with the dihydroethidium dye, and the protective effect of the extracts with the highest antioxidant activity was tested on a stroke experimental model. The extracts’ IC50 values (μg/mL) of scavenging varied from 98.9 to 155.04, 4.5 to 102.4, and 20.2 to 118.97 for OH•, ROO•, and O2•⁻, respectively. In the excitotoxicity model, Annonaceae extracts were highly cytotoxic while Lamiaceae and Geraniaceae reduced intracellular O2•⁻ production and protect neurons against oxidative stress. Salvia polystachya reduced cerebral damage, as well as improved survival and behavior after ischemia. Our results encouraged the use of plant extracts as natural antioxidants to minimize neuronal injury following stroke.
... In the HMBC spectrum ( Fig. 2a) there were observed correlations of H-7 with C-6, C-8, C-9 (δ C 40.5), and a signal at δ C 119.2 (C). The chemical shift and multiplicity of the later signal was characteristic of acetalic or cetalic moieties (Bautista et al., 2017;Maldonado et al., 2016), suggesting the presence of three oxygen bridges in 1, and was therefore assigned to C-1' (Bautista et al., 2012;Liao et al., 2009;Zhao et al., 2018). This was supported by the HMBC correlation of a sixth methyl group at δ H 1.59 (s) with C-1′ and by the low shifted signals of C-6 and C-7 in comparison with the data of galphimine E (6) (Cardoso-Taketa et al., 2004). ...
Both DNA barcoding and phylogenetic data of the studied botanical material suggested the existence a new population of Galphimia glauca. Their leaves afforded three new nor-3,4-seco-friedelanes named galphimines M-O, together with known galphimines D, E, G, and I. Galphimines M and N possess bicyclic orthoacetates which are the first examples of orthoesters found in the Malpighiaceae family, while galphimine O has a 27,20-δ-lactone moiety. The structures elucidation followed from spectroscopic means and the absolute configuration followed from single crystal X-ray diffraction analyses. Tests for antibacterial and antifungal activities of galphimines N and M showed no promising effects.
... Polystachyne G (125), 15-epi-polystachyne G (126), and salvifilines A -D (127 -130) ( Figure 2) were isolated from Salvia polystachya. [31] Lycopersicum esculentum, Capsicum annuum, and L. sativa seeds were used to evaluate the phytotoxic activity of compounds 125 -130 using a seed germination inhibition bioassay. However, none of them showed detectable activity at all the assayed concentrations of 100, 10, and 1 μM. ...
Phytotoxic natural products with either unique or various structures are one of the most abundant sources for the discovery of potential allelochemicals, natural herbicides, and plant growth regulators. Phytotoxic diterpenoids, a relatively large class of natural products, play an important role in the plant‐plant or plant‐microorganism interactions. This article argues that the phytotoxic diterpenoids isolated from the plants and microorganisms can either inhibit the seed germination and the growth of plant seedlings or lead to some disease symptoms on the tested plant tissues and plant seedlings.
Salvia L. (Sage) is a therapeutically important plant genus with over 1000 species worldwide. They are a rich source of novel diterpenes. In this present study, we tried to review the chemistry and pharmacology of the Salvia diterpenes between 2016 and 2024. Therefore, we collected information from various scientific databases, including Scopus and PubMed, using key words “Salvia” AND “Diterpene” OR “Diterpenoid”. This updated review article discussed the phytochemistry and pharmacology of 258 undescribed diterpenes isolated from the Salvia genus between 2016 and October 2024. Studies showed that these diterpenes could be structurally divided into subclasses such as abietanes, clerodanes, icetexanes, labdanes, and fusicoccanes. The reported diterpenes have exhibited various pharmacological effects such as anticancer, antibacterial, antiviral, antiparasitic, anti-inflammatory, analgesic, anti-oxidant, antidiabetic, and neurotrophic activities. According to the results, these diterpenes of Salvia can be the lead compounds for drug discovery, especially for cancer and microbial diseases.
Graphical abstract
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.
