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Abstract

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.

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... Several species from the Lamiaceae family have been proposed to have an antidiabetic effect, ursolic acid, oleanolic acid and β-sitosterol being the products related with this activity [25,26]. In the case of ursolic acid and oleanolic acid, they have been described as potential α-glucosidase inhibitors using in vitro and in silico experiments [29]. Considering the above and taking into account the constant need for the development of new drugs to treat the hyperglycemia caused by diabetes mellitus, the potential antidiabetic effect of S. polystachya (a species that belongs to the Lamiaceae family) was evaluated, in consideration of a chemotaxonomic criterion. ...
... The administration of the extract from the stems from S. polystachya (EESpS) generated a significative reduction in hyperglycemia in the animals with experimental DM2. These results are similar to those reported in other vegetal species from the Lamiaceae family [25][26][27][28][29][30], where the authors describe the diminution of hyperglycemia after a single administration of ethanolic extracts from the leaves of other Lamiaceae species. Moreover, in some studies, a subchronic administration of extracts results in an adequate control of hyperglycemia accompanied by a reduction in the glycated hemoglobin percentage [20]. ...
... To identify the compounds responsible for the observed effects of the S. polystachya stem extract, a phytochemical screening from EtOAcFr was performed. HPLC-diode array detection (DAD) allowed us to determine the presence of ursolic and oleanolic acid, two terpenoids that have been described as α-glucosidase inhibitors in in vitro and in silico diabetic models [29]. In this sense, 42 terpenoids previously reported in Salvia species were checked in EtOAcFr and SeFr6, including polystachynes A, B, and D, as well as linearolactone, which was previously isolated from S. polystachya [35]; however, only the presence of ursolic acid and oleanolic acid (UA and OA, respectively) was identified. ...
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The antihyperglycemic activity of ethanolic extract from Salvia polystachya (EESpS) and its products was evaluated using in vivo, ex vivo and in silico assays; additionally, an acute toxicity assay was evaluated. EESpS was classified as a nontoxic class 5 drug. EESpS, ethyl acetate fraction (EtOAcFr), secondary-6-fraction (SeFr6), ursolic acid (UA), and oleanolic acid (OA) reduced the hyperglycemia in DM2 mice. α-glucosidase inhibition was evaluated with oral sucrose and starch tolerance tests (OSuTT and OStTT), an intestinal sucrose hydrolysis (ISH) assay and molecular docking studies using acarbose as control. SGLT1 inhibition was evaluated with oral glucose and galactose tolerance tests (OGTT and OGaTT), an intestinal glucose absorption (IGA) assay and molecular docking studies using canagliflozin as the control. During the carbohydrate tolerance tests, all the treatments reduced the postprandial peak, similar to the control drugs. During the ISH, IC50 values of 739.9 and 726.3 µM for UA and OA, respectively, were calculated. During the IGA, IC50 values of 966.6 and 849.3 for UA, OA respectively, were calculated. Finally, during the molecular docking studies, UA and OA showed ∆G values of −6.41 and −5.48 kcal/mol−1, respectively, on α-glucosidase enzymes. During SGLT1, UA and OA showed ∆G values of −10.55 and −9.65, respectively.
... The species is commonly regarded as "insulina" (insulin), referring to its efficacy to improve the diabetic condition [5]. Previous phytochemical studies allowed the isolation of some neo-clerodane diterpenoids, including amarisolide (1) [6], a few seco-clerodane diterpenoids [6][7][8][9][10] and some flavonoids [6,8]. The traditional preparation of the plant collected in Puebla, Mexico, as well as amarisolide (1), and some of the flavonoids showed inhibitory activity against mammal α-glucosidases in vitro and in vivo. ...
... The species is commonly regarded as "insulina" (insulin), referring to its efficacy to improve the diabetic condition [5]. Previous phytochemical studies allowed the isolation of some neo-clerodane diterpenoids, including amarisolide (1) [6], a few seco-clerodane diterpenoids [6][7][8][9][10] and some flavonoids [6,8]. The traditional preparation of the plant collected in Puebla, Mexico, as well as amarisolide (1), and some of the flavonoids showed inhibitory activity against mammal α-glucosidases in vitro and in vivo. ...
... The species is commonly regarded as "insulina" (insulin), referring to its efficacy to improve the diabetic condition [5]. Previous phytochemical studies allowed the isolation of some neo-clerodane diterpenoids, including amarisolide (1) [6], a few seco-clerodane diterpenoids [6][7][8][9][10] and some flavonoids [6,8]. The traditional preparation of the plant collected in Puebla, Mexico, as well as amarisolide (1), and some of the flavonoids showed inhibitory activity against mammal α-glucosidases in vitro and in vivo. ...
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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.
... Phytochemical studies of S. circinata have reported the presence of diterpenoids such as amarissinins A-E (Bautista et al. 2016, Fragoso-Serrano et al. 2019) and teotihuacanin (Bautista et al. 2015, Fragoso-Serrano et al. 2019, and glucoside diterpenoids as amarisolides A-F (Maldonado et al. 1996, Flores-Bocanegra et al. 2017, Fragoso-Serrano et al. 2019. Flavonoids like pedalitin (Maldonado et al. 1996), apigenin-7-O-β-D-glucoside, the flavone 2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-one, and new biflavone (Flores-Bocanegra et al. 2017). ...
... Phytochemical studies of S. circinata have reported the presence of diterpenoids such as amarissinins A-E (Bautista et al. 2016, Fragoso-Serrano et al. 2019) and teotihuacanin (Bautista et al. 2015, Fragoso-Serrano et al. 2019, and glucoside diterpenoids as amarisolides A-F (Maldonado et al. 1996, Flores-Bocanegra et al. 2017, Fragoso-Serrano et al. 2019. Flavonoids like pedalitin (Maldonado et al. 1996), apigenin-7-O-β-D-glucoside, the flavone 2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-one, and new biflavone (Flores-Bocanegra et al. 2017). ...
... Allowed purifying by crystallization a pure compound (m.p. 206 ºC, Fisher Johns equipment) that was analyzed by ESIMS in positive mode with a Cap LC coupled MicromassVR Q-ToF Ultima ESI system (Waters Corp., Milford, MA), as well as 1 H NMR and 13 C NMR analysis (Bruker, Avance DPX400). The NMR signals matched with that previous reported for this compound preliminary isolated from S. amarissima (Maldonado et al. 1996, Flores-Bocanegra et al. 2017. ...
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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
... The phytochemical profiles of three populations of this plant species have been determined; from the first two populations, distributed in the states of Puebla and Oaxaca, the glucoside diterpenoids amarisolides A−E (11−15) were isolated. 5,8 From a third population, distributed in the valley of Teotihuacan, state of Mexico, the diterpenoids amarissinins A−C (3−5) and teotihuacanin (6) were isolated. 7,9 Furthermore, as a continuation of the studies of the phytochemistry of the Salvia genus and search for new bioactive natural products, scale-up of the isolation of teotihuacanin (6) to obtain semisynthetic derivatives as potential MDR modulators was performed. ...
... Note trans-diaxial dispositions of all the involved protons in the spin system, as is common for a β-glucopyranoside. 8 In addition, the NMR data of the sugar moiety and furan ring of 1 were similar to those of O-acetylglucoside diterpenoids from Salvia chamaedryoides. 10 The C-6 location of the acetoxy group in the sugar moiety was established by the HMBC correlations between H 2 -6′ (δ H 4.30, d, J = 3.9 Hz) and C-1″ (δ C 170.8). ...
... Crystallization from acetone/hexanes gave crystalline 7, which was used to perform a single-crystal X-ray diffraction study. The Flack parameter of 0.03 (8) 14 permitted definition of the configuration as (4R,5S,8S,9R,10S) ( Figure 2). Spectroscopic and spectrometric data of the remaining epimeric mixture of compounds 7/8 were acquired. ...
Article
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.
... 14 This species is used in folk medicine for treating ulcers, helminthiases, and diabetes. 15 Previous phytochemical studies led to the isolation of some clerodane diterpenoids such as amarisolide (6), 16,17 several seco-clerodane diterpenoids, 10 and the flavone pedalitin (7). 16 Some of the compounds obtained were cytotoxic against human cancer cell lines and had modulatory activity in a breast cancer cell line resistant to vinblastine. ...
... 15 Previous phytochemical studies led to the isolation of some clerodane diterpenoids such as amarisolide (6), 16,17 several seco-clerodane diterpenoids, 10 and the flavone pedalitin (7). 16 Some of the compounds obtained were cytotoxic against human cancer cell lines and had modulatory activity in a breast cancer cell line resistant to vinblastine. 17,18 ■ RESULTS AND DISCUSSION Acute toxicity analysis in animals is the first step during the assessment of the efficacy of phytopreparations. ...
... 22 In order to isolate the active principles, a nonpolar extract from the aerial parts of S. circinata was prepared. Extensive chromatography of this extract yielded new compounds 1−5, along with the known substances 6, 16 7, 16 8, 23 and 9, 24 which were identified by comparison with physical and spectroscopic data previously reported. ...
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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 HRESIMS spectrum displayed a cationized molecule at m/z 547.21273 [M + Na] + , suggesting a molecular formula C 26 H 36 O 11 Na (calcd 547.21498) and indicating 9 indices of hydrogen deficiency. Comparison of their 1 H and 13 C NMR data (Table 1) with those described previously for amarisolide A (3) indicated that compounds 1/2 are structurally related with 3 (Maldonado et al. 1996). The 1D NMR spectra displayed the presence of a 18,19-γ-lactone (δ C 171.48,72.54,δ ...
... The structures of amarisolides A (3), D (4), and G (6) together with their corresponding C-16 epimers 5 and 7 were deduced by comparison with their 1 H and 13 C NMR data described in the literature (Maldonado et al. 1996;Flores-Bocanegra et al. 2017;Salinas-Arellano et al. 2020). The structure of flavone 8 was established as 5,6-dihydroxy-7,3′,4′-trimethoxyflavone using the same procedure applied to identify the know glucoside diterpenoids (Chemesova and Boiko 1990;Nagao et al. 2002). ...
Article
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.
... The target compounds of the analyses for this study were amarisolide A (1), amarissinin A (7), and teotihuacanin (11). Amarisolide A (1) was kindly provided by Prof. Dr. Alfredo Ortega (Maldonado et al. 1996). Amarissinin A (7) and teotihuacanin (11) were isolated according to previously described methodologies (Bautista et al. , 2016. ...
... It is used in traditional medicine for treating cancer, diabetes, diarrhea, helminthiases, rheumatism, and stomach ulcers (Fragoso-Serrano et al. 2019;Moreno-Pérez et al. 2019;Solares-Pascasio et al. 2021). The first chemical study of S. circinnata was conducted more than two decades ago (Maldonado et al. 1996). However, recent investigation of the pharmacological potential of several secondary metabolites of S. circinnata has been conducted according to their traditional uses. ...
Article
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
... In this context, the same behavior was observed in S. amarissima, an endemic herb in Mexico. A previous phytochemical study of the non-polar extract obtained from its leaves, collected in Oaxaca valley, leads to the isolation of amarisolide, a glycosylated clerodane diterpene [15]. Recently, further investigation of the acetone extract of the leaves and flowers from S. amarissima, collected in the mountains surrounding the Teotihuacan Valley, State of Mexico, leads to the identification of teotihuacanin (4), a rearranged clerodane diterpene with potent modulatory activity of MDR in the MCF-7 cancer cell line resistant to vinblastine. ...
... The constituents from fraction C were separated by successive silica gel CC (2.5 × 22.0 cm, 40 mL) eluted with mixtures n-hexane-EtOAc 1:1 (frs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] and nhexane-EtOAc 3:7 (frs. [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. ...
... Three of these were preliminarily identified as terpene compounds, which could be inferred by their positive reaction to ceric sulphate, in which the color observed changed from purple to red. Plants of this family (Lamiaceae) contain a high quantity of terpenoids (monoterpenes, diterpenes, and triterpenes) [37][38][39][40], as in the case of S. amarissima, having been identified as neo-clerodane diterpenes, such as amarisolides, amarissinins, and teotihuacanine [24][25][26]38,41]. ...
Article
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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.
... A partir de los aceites esenciales de S. amarissima la especie más estudiada de las salvias, se aisló el amarisólido, un neoclerodano glicósido diterpenico con actividad antiinflamatoria (Maldonado, 1996). Este compuesto se aisló también en S. rubescens (Muñoz, et al., 2009). ...
Article
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Salvia amarissima es una planta mexicana a la que se le atribuyen actividades hipoglicemiantes, anti ulcerosas y anti helmínticas. En el presente trabajo se evaluó por primera vez la actividad antimicrobiana de los extractos hexánico, metanólico y acuoso obtenidos de la planta, los cuales se probaron en 8 cepas de microorganismos de referencia por las técnicas de Kirby- Bauer y la de dilución del antimicrobiano en agar. No se detectó actividad antimicrobiana de los extractos con las técnicas ensayadas. Por último, se llevó a cabo un análisis preliminar espectroscópico de los compuestos presentes en cada extracto.
Article
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.
Article
Ethnopharmacological relevance Mexico is considered an ancestral center of diversity of Salvia species, however many of them lack scientific information. Salvia circinnata Cav. (syn. Salvia amarissima Ortega) is an endemic species used in traditional medicine to treat disorders attributed to a cold state like anxiety in the central nervous system, as well as gastrointestinal ailments and pain relief. Aim of the study To give preclinical evidence about the pharmacological properties of this species by investigating its antinociceptive and anti-inflammatory effects, the chemical nature of at least one metabolite, and a possible mechanism of action and adverse effects, using different experimental models of pain. Material and methods Different crude extracts of Salvia circinnata Cav. aerial parts were prepared using increasing polarity and evaluated in the formalin test in mice. This screening allowed to select and evaluate an ethyl acetate extract (EtOAc), as the most bioactive extract, and a metabolite. Antinociceptive and anti-inflammatory activities were confirmed using the plantar test and carrageenan-induced edema. The antinociceptive effects of the extracts were compared to that observed with morphine (1 mg/kg), tramadol (20 mg/kg) or indomethacin (20 mg/kg) as reference drugs. Participation of opioids and TRPV1 receptors was investigated, as well as acute toxicity and adverse effects of sedation and gastric damage. Results EtOAc (0.1–10 mg/kg) of S. circinnata Cav. showed a dose-dependent and significant antinociceptive activity, associated in part with the presence of a neo-clerodane glycoside amarisolide A (0.01–1 mg/kg), in the neurogenic and inflammatory phases of the formalin test. Central action of both treatments was corroborated in the plantar test, whereas anti-inflammatory effects were confirmed with the extract (1 and 10 mg/kg) and amarisolide A (1 mg/kg) in the carrageenan-induced edema test. An opioid mechanism in both treatments, and the TRPV1 receptor modulation in the extract were involved. No acute toxicity and adverse effects were noticed with the extract and pure compound in comparison to the reference drugs. Conclusion These results provide preclinical evidence of the ethnopharmacological antinociceptive S. circinnata Cav. properties, in which the neo-clerodane diterpene glycoside amarisolide A was partially responsible involving the participation of the opioid receptors, while TRPV1 receptor modulation was implicated in the anti-inflammatory activity may be because of the presence of other constituents. This information supports the use of this species in folk medicine for pain therapy.
Article
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.
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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.
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The antinociceptive effect of extracts, fractions and compounds of Critoniella acuminata, Physalis peruviana and Salvia rubescens were evaluated by the follow methods: Hot Plate test, acetic acid induced abdominal writhing and Formalin test. The fraction of Critoniella acuminata at doses of 100mg/kg p.o. exhibited antinociceptive effect in the hot plate test; while Physalis peruviana fraction at doses of 100 mg/kg p.o., showed an antinociceptive effect against the pain chemically induced. This fraction produced 40% inhibition of the acetic acid induced writhing (acute visceral nociception) and the licks during phase II (acute inflammatory nociception) of the formalin test. The findings of this experimental study suggest that fractions of Critoniella acuminata and Physalis peruviana possess antinociceptive activity with opioid and nsaid-like mechanisms respectively.
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The leaves of Zuelania guidonia yielded eight new clerodane diterpenes, namely, zuelaguidins A-H (1-8), and the known clerodane diterpene esculentin A (9). Some of these structures contained a 3,6-dihydro-1,2-dioxin moiety. The new compounds were isolated and identified using 1D- and 2D-NMR experiments. All compounds were evaluated for cytotoxicity against the CCRF-CEM (human acute lymphocytic leukemia), CEM-ADR5000 (human acute lymphocytic leukemia resistant to doxorubicin), and MIA-PaCa-2 (human pancreatic carcinoma) cell lines as well as for their selectivity against peripheral blood mononuclear cells from healthy human subjects. Zuelaguidins B, C, and E were the most potent compounds against the CCRF-CEM cell line, with IC50 values ranging from 1.6 to 2.5 μM.
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The investigation of Salvia thymoides afforded, in addition to known triterpenes and flavones, four neo-clerodane diterpenoids, 7α-hydroxy-neo-cleroda-3,13-dien-18,19: 15,16-diolide, 7-oxo-neo-cleroda-3,13-dien-18,19: 15,16-diolide, 6α,18,19-trihydroxy-neo-cleroda-3,13-dien-15,16-olide (thymonin) and 6α,7β,18,19-tetrahydroxy-neo-cleroda-3,13,-dien-15,16-olide (7β-hydroxythymonin). The last two compounds have not been previously described. The structures of these compounds were established by chemical and spectroscopic methods. The absolute stereochemistry of thymonin was determined by X-ray analysis of a bromo derivative.
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In addition to several known compounds, the new languidulane diterpene, tonalenin (8β-hydroxy-7-epi-8,17-dihydrolanguiduline), was isolated from the aerial parts of Salvia tonalensis. The structures were elucidated by spectroscopic means. © 1997 Elsevier Science Ltd. All rights reserved
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The investigation of Salvia thymoides afforded, in addition to known triterpenes and flavones, four neo-clerodane diterpenoids, 7α-hydroxy-neo-cleroda-3,13-dien-18,19: 15,16-diolide, 7-oxo-neo-cleroda-3,13-dien-18,19: 15,16-diolide, 6α,18,19-trihydroxy-neo-cleroda-3,13-dien-15,6-olide (thymonin) and 6α,7β,18,19-tetrahydroxy-neo-cleroda-3,13,-dien-15,16-olide (7β-hydroxythymonin). The last two compounds have nor been previously described. The structures of these compounds were established by chemical and spectroscopic methods. The absolute stereochemistry of thymonin was determined by X-ray analysis of a bromo derivative.
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The absolute configuration of the neoclerodane glycoside amarisolide, presented here as the monohydrate, C26H36O9·H2O, has been determined by association with the known configuration of the glucose moiety. Its structure was established as 2β-(O-β-d-gluco­pyran­osyl)­neocleroda-3,13(16),14-trien-15,16-epoxy-18,19-olide. Extensive hydrogen bonding among the hydroxyl groups of the sugar moiety forms layers which are interconnected by water mol­ecules.
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More than 550 diterpenoids have been isolated from Salvia species widely distributed in Mexico, Turkey, Spain and China. 23 species grow in Algeria, five of them are endemic. We've recently isolated five abietane diterpenoids from each of the endemic species S. jaminiana and S. verbenaca subsp. clandestina and seven diterpenoids, from which three are new, from the endemic species S. barrelieri. We've recently reported the antibacterial activity of the roots of S. jaminiana while the antioxidant activity have been established for the seven diterpenoids isolated from S. barrelieri. Salvia diterpenoids could be divided into 2 categories. The first category includes one monocyclic and bicyclic diterpenoids containing labdanes, clerodanes, neo-clerodanes, seco-clerodanes and other rearranged clerodanes. The second category concerns tricyclic and tetracyclic diterpenes represented by pimaranes and abietanes including quinone abietanes, nor-abietanes, rearranged nor-abietanes, dinor-abietanes, seco-abietanes, tanshinones and other particular rearranged abietanes. A great number of the described Salvia diterpenoids exhibited interesting biological activities e.g anti-tuberculous, antitumour, antimicrobial, antibacterial, antileishmanial and antispasmolytic.
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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.
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Three diterpenoid derivatives were isolated from the acetone extract of Baccharis flabellata. Their structures were elucidated as 2,19;15,16-diepoxy-neo-clerodan-3,13(16),14-trien-18-oic acid, 15,16-epoxy-5,10-seco-clerodan-1(10),2,4,13(16),14-pentaen-18,19-olide and 15,16-epoxy-neo-clerodan-1,3,13(16),14-tetraen-18,19-olide through spectroscopic analyses.
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The structure of four diterpenoid glucosides, designated as salvigresides A-D (1-4), isolated from the aerial parts of Salvia greggii, have been confirmed by spectroscopic and chemical investigation.
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A flavonoid, isolated from the leaves of sesame (Sesamum indicum L. ), was determined as 5, 3', 4'-trihydroxy-6-methoxyflavone 7-glucoside.
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The known ursolic and oleanolic acids, the abietane quinone diterpenes, sessein, and deacetylsessein, together with the also known clerodane diterpenes hardwickiic and clerodermic acids were isolated from the aerial parts of Salvia regla. The structure of a novel compound, reglin, present in this species was established by spectral means as deacetyloxysessein-7α-(3β-hydroxy-olean-12-en-28-oate).
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The structure and configuration of salvianduline C, a novel 5,6-secoclerodane diterpenoid isolated fromSalvia lavanduloides, have been established by high resolution NMR spectroscopy and X-ray crystallographic analysis.
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High-field 2D NMR studies were performed on nine neo-clerodane diterpenoids. Unambiguous assignments of the 13C signals and proton chemical shifts were achieved which led to the revision of some previous assignments.
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A novel non-cyanogenic cyanoglucoside, 1-cyano-3-β-d-glucopyranosyloxy-(Z)-1-methyl-1-propene, was isolated from the latex of Jatropha multifida. The compound was named multifidin.
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From the aerial parts of Baccharis macraei two new clerodane diterpenes, bacchasmacranone and 2β-hydroxybacchasmacranone, were isolated besides the known hardwickiic and hautriwaic acids. The structures of the new compounds were elucidated by spectroscopic methods.
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From a cytotoxic extract of Eupatorium semiserratum DC., five flavones were isolated. Three of the compounds were characterized as the previously-known pectolinarigenin, and two new flavones, eupatorm and eupatilin. Structural studies are described which have led to assignment of the 5,3′-dihydroxy-6,7,4′-trimethoxyflavone structure (1) for eupatorin, and the 5,7-dihydroxy-6,3′,4′-trimethoxyflavone structure (11) for eupatilin. From a cytotoxic extract of Eupatorium cuneifolium (TOURN.) L., two flavones were isolated. The compounds were characterized as the previously-known hispidulin and a new flavone, eupafolin. Structural studies are described which have led to assignment of the 5,7,3′,4′-tetrahydroxy-6-methoxyflavone structure (18) for eupafolin. The earlier assignment of structure 18 for pedalitin is shown to be incorrect, and the alternative 5,6,3′,4′-tetrahydroxy-7-methoxyflavone structure (24) is proposed for pedalitin.
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