Amarisolide F, an Acylated Diterpenoid Glucoside and Related Terpenoids from Salvia amarissima

Fragoso‐Serrano, Mabel; Ortíz-Pastrana, Naytzé; Luna-Cruz, Norma; Toscano, Rubén A.; Alpuche-Solís, Ángel G.; Ortega, Alfredo; Bautista, Elihú

doi:10.1021/acs.jnatprod.8b00565

Cited by 18 publications

(8 citation statements)

References 13 publications

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“…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].…”

Section: Discussionmentioning

confidence: 99%

Antihyperglycemic and Lipid Profile Effects of Salvia amarissima Ortega on Streptozocin-Induced Type 2 Diabetic Mice

et al. 2021

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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.

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Section: Discussionmentioning

confidence: 99%

Antihyperglycemic and Lipid Profile Effects of Salvia amarissima Ortega on Streptozocin-Induced Type 2 Diabetic Mice

et al. 2021

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“…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) and 42.7 (43.1-41.8) μM against E. histolytica; and 61.6 (66.1-60.4) and 60.3 (62.1-59.4) μM against G. lamblia, respectively.…”

Section: Resultsmentioning

confidence: 99%

Salvia connivens, a Source of Bioactive Flavones with Amoebicidal and Giardicidal Activity

Bautista

Calzada

Yépez‐Mulia

et al. 2020

Rev. Bras. Farmacogn.

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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 (IC 50 0.072 ± 0.006 μM) and Giardia lamblia (IC 50 0.118 ± 0.006 μM), which was comparable to metronidazole.

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“…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).…”

Section: High Performance Liquid Chromatography (Hplc-dad)mentioning

confidence: 99%

Amarisolide A and pedalitin as bioactive compounds in the antinociceptive effects of Salvia circinata

et al. 2019

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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.

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Amarisolide F, an Acylated Diterpenoid Glucoside and Related Terpenoids from Salvia amarissima

Cited by 18 publications

References 13 publications

Antihyperglycemic and Lipid Profile Effects of Salvia amarissima Ortega on Streptozocin-Induced Type 2 Diabetic Mice

Antihyperglycemic and Lipid Profile Effects of Salvia amarissima Ortega on Streptozocin-Induced Type 2 Diabetic Mice

Salvia connivens, a Source of Bioactive Flavones with Amoebicidal and Giardicidal Activity

Amarisolide A and pedalitin as bioactive compounds in the antinociceptive effects of Salvia circinata

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