The roots of <i>Salvia rhytidea:</i> a rich source of biologically active diterpenoids

Jassbi, Amir Reza; Eghtesadi, Farrokh; Hazeri, Nourallah; Ma’sumi, Hashem; Valizadeh, Jafar; Chandran, Jima N.; Schneider, Bernd; Baldwin, Ian Thomas

doi:10.1080/14786419.2016.1188096

Cited by 19 publications

(6 citation statements)

References 21 publications

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“…Further purification by a combination of silica gel CC, and preparative and semipreparative RP-HPLC afforded 17 abietane, icetexane, and isopimarane diterpenoids. Fourteen of them were identified as known compounds, including 12-hydroxy-20-norabieta-8,11,13-triene (1) [21], carnosol (3) [22], 7α-ethoxyrosmanol (4) [23], miltirone (5) [24], Δ 9 -dehydro-ferruginol (7) [25], ferruginol (8) [26], miltiodiol (10) [22], and galdosol (17) [23] (▶ Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Antiprotozoal Diterpenes from Perovskia abrotanoides

et al. 2018

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As part of a screening for new antiparasitic natural products from Iranian plants, -hexane and ethyl acetate extracts from the aerial parts of were found to exhibit strong inhibitory activity against and. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1: -17: ), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5,10)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2: ), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6: ), and 12-methoxybarbatusol (9: ) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against , and. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7-ethoxyrosmanol (4: ) with an IC of 0.8 µM against (SI 14.9) and an IC of 1.8 µM (SI 6.9) against , ferruginol (8: ) with an IC of 2.9 µM (SI 19.2) against , and miltiodiol (10: ) with an IC of 0.5 µM (SI 10.5) against . None of the compounds exhibited selective toxicity against (SI ≤ 1.6).

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Section: Resultsmentioning

confidence: 99%

Antiprotozoal Diterpenes from Perovskia abrotanoides

et al. 2018

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“…Some of the species possess antimicrobial, antimalarial, anti-oxidant and antiproliferative activities (Loizzo et al 2014; Russo et al 2015; Jassbi et al 2016; Moridi Farimani & Abbas-Mohammadi 2016). Salvia apiana , commonly known as white sage, can be found scattered throughout southwestern North America, with the highest concentration in Southern California (Borek et al 2006).…”

Section: Introductionmentioning

confidence: 99%

Phytochemical and biological evaluation of Salvia apiana

Radhakrishnan

Hayes

Ross

2016

Natural Product Research

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Salvia apiana (white sage, Lamiaceae family) plant is native to southern California and parts of Mexico. Some Native American tribes local to this region consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections and poison oak rashes. The aqueous ethanolic extract of S. apiana showed moderate CB1 activity (58.3% displacement). Chromatographic purification of the ethanolic extract on silica gel column led to isolation of nine compounds: rosmadial (I), carnosol (II), 16-hydroxycarnosol (III), sageone (IV), cirsimaritin (V), salvigenin (VI), oleanolic acid (VII), 3β,28-dihydroxy-urs-12-ene (VIII), and ursolic acid (IX). The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding.

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“…[34], S. rhytidea Benth. [35] and S. reuterana Boiss [36] which grow in Europe or the Middle East. This is the first time that labdane type diterpenoids have been isolated from a sage of the subgenus Calospahce.…”

Section: Resultsmentioning

confidence: 99%

Structural Elucidation of Malonylcommunol and 6β-Hydroxy-trans-communic Acid, Two Undescribed Diterpenes from Salvia cinnabarina. First Examples of Labdane Diterpenoids from a Mexican Salvia Species

et al. 2020

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The aerial parts of Salvia cinnabarina afforded two undescribed labdane diterpenoids 1 and 2 (malonylcommunol and 6β-hydroxy-trans-communic acid) along with two known labdane diterpenoids, trans-communic acid (3) and trans-communol (4). Additionally, seven known metabolites were also isolated; two isopimarane diterpenoids 5 and 6, two sesquiterpenoids identified as β-eudesmol (7) and cryptomeridiol (8), and three aromatic compounds identified as phthalic acid (9), a mixture of tyrosol fatty acid esters (10) and the flavone salvigenine (11). While compounds compounds 1-3 showed significant inhibition of yeast α-glucosidase, compounds 2, 3 and 7 had no anti-inflammatory activity in the edema model induced by TPA. This paper is not only the first report on a wild population of Salvia cinnabarina, but also of the presence of labdane-type diterpenoids in a Mexican Salvia sp.Molecules 2020, 25, 1808 2 of 17 spectroscopic and X-ray diffraction analysis [7,8]. Compound 12 has been tested in several in vitro and in vivo models and exhibits a wide array of biological activities, such as antispasmodic in the isolated guinea-pig ileum model, inhibition of urinary bladder contractility in rats [9] and intestinal motility in mice [10]. Hypotensive activity in a rat model [11], along with anxiolytic and anti-depressive effects in the elevated plus-maze and the forced swimming tests in mice have also been described [12]. Compound 12 showed antimutagenic activity in the Ames test on Salmonella typhimurium and Escherichia coli [13] and also had an anticlastogenic effect in human lymphocytes of its sodium salt [14]. It should be noted that, up to now, all the studies on S. cinnabarina, have been carried out solely on cultivated material from different Botanical Gardens.Continuing with our systematic study of the genus Salvia in Mexico, and ongoing investigation for biological activity diterpenes of chemosystematic importance [15], we report herein the first study on a wild population of S. cinnabarina collected in the State of Puebla (Mexico). Several diterpenoids of the labdane (1-4) and isopimarane (5-6) skeletons were isolated, as well as two eudesmane-type sesquiterpenoids (7-8), phtalic acid (9), tyrosol derivatives (10) and the flavone salvigenin (11). Compounds 1-2 proved to be undescribed labdane-type diterpenoids related to trans-communic acid (3) and trans-communol (4), also isolated from this plant, and their structures were established as malonylcommunol (1) and 6β-hydroxy-trans-communic acid (2). While compounds 1-3 showed significant inhibition of yeast α-glucosidase, compounds 2,3 and 7 showed no anti-inflammatory activity in the edema model induced by TPA. Results and DiscussionThe aerial parts of Salvia cinnabarina afforded 11 compounds (Figure 1) after extensive chromatographic separation and purification.Molecules 2020, 25, x FOR PEER REVIEW 2 of 17

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The roots of Salvia rhytidea: a rich source of biologically active diterpenoids

Cited by 19 publications

References 21 publications

Antiprotozoal Diterpenes from Perovskia abrotanoides

Antiprotozoal Diterpenes from Perovskia abrotanoides

Phytochemical and biological evaluation of Salvia apiana

Structural Elucidation of Malonylcommunol and 6β-Hydroxy-trans-communic Acid, Two Undescribed Diterpenes from Salvia cinnabarina. First Examples of Labdane Diterpenoids from a Mexican Salvia Species

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