1371. Constituents of Withania somnifera Dun. Part IV. The structure of withaferin A

Lavie, David; Glotter, E.; Shvo, Youval

doi:10.1039/jr9650007517

Cited by 124 publications

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“…The Cotton effects of 2 (Deϩ6.03 at 248 nm and DeϪ0.87 at 352 nm) were similar to those of withaperuvin E, 22) bearing the same structure of rings A, B, and the a,bunsaturated d-lactone moiety, indicating a 22R configuration and cis-fusion of rings A and B. Based on the above evidence, compound 2 was assumed to be 4-oxowithangulatin A, which was confirmed by manganese dioxide oxidation 21) of 1 to 2. Therefore the structure of withangulatin I (2) was considered to be (20S,22R)-15a-acetoxy-5b,6b-epoxy-14a-hydroxy-1,4-dioxo-witha-2,16,24-trienolide.…”

Section: Resultsmentioning

confidence: 65%

Withangulatin I, a New Cytotoxic Withanolide from Physalis angulata

et al. 2008

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Physalis angulata L. is an annual herb belonging to the family Solanaceae and is widely distributed in tropical and temperate regions. It is a common herbal plant, known in Chinese as kuzhi, which has been used as a folk medicine with antiinflammatory, antitussive, antipyretic, diuretic, antidotal, and antitumor effects in Taiwan. 1) The extracts and components of this plant were found to have antitumor, 2,3) cytotoxic, [4][5][6][7][8] inhibition of the ubiquitin-proteasome pathway, 9) immunomodulatory, 10) antimycobacterial, 11) antinociceptive, antiinflammatory, and antiallergic activities. 12)Physalis angulata is known to contain a wide variety of pharmacologically important steroidal compounds, such as withasteroids.4) To date, phytochemical studies of this plant have described the isolation of numerous phytochemicals, including withasteroids, [4][5][6]8,[13][14][15][16][17] flavonoid glycoside, 18) and alkaloids. 19) In a previous study, we isolated a withanolide, withangulatin A (1), 15) with significant biological activities 20) from this plant as a part of our search for bioactive constituents from natural sources. Here, we report the isolation and structural elucidation of a minor withanolide, withangulatin I (2), from this plant. Its structure was established as (20S,22R)-15a-acetoxy-5b,6b-epoxy-14a-hydroxy-1,4-dioxo-witha-2,16,24-trienolide on the basis of extensive spectroscopic data interpretation, chemical transformation, and circular dichroism (CD) experiments. The cytotoxic activities of compounds 1 and 2 against human colorectal carcinoma COLO 205 and human gastric carcinoma AGS cell lines were also evaluated in vitro. Results and DiscussionAs in the previously reported procedure, 15) the fractions containing withanolides were combined. The combined fractions were further purified by repeated column chromatography and preparative TLC to afford a minor withanolide, withangulatin I (2). The structure of 2 was established based on detailed spectral analyses, chemical transformation, and comparison with the spectral data reported in the literature.Compound 2 was isolated as a pale yellow, amorphous powder. The IR spectrum of 2 displayed absorption bands of hydroxyl (3450 cm 22) The EI-MS spectrum showed a base peak at m/z 125 which confirmed the presence of the a,b-unsaturated d-lactone moiety.23) These data revealed that compound 2 is a typical withanolide bearing an acetoxyl group and a D 2 -1,4-dione moiety. The deshielding proton A new withanolide, withangulatin I (2), was isolated from the whole plant of Physalis angulata. Its structure was established as (20S,22R)-15a a-acetoxy-5b b,6b b-epoxy-14a a-hydroxy-1,4-

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Section: Resultsmentioning

confidence: 65%

Withangulatin I, a New Cytotoxic Withanolide from Physalis angulata

et al. 2008

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“…Much of pharmacological activity in this plant has been attributed to two main withanolides i.e. withaferin A and withanolide D. 7 Hence the present study was designed to investigate the nephroprotective as well as nephrocurative activity of W. somnifera because this herb is easily available throughout the country and being very common in nature hence not costly.…”

Section: Introductionmentioning

confidence: 99%

Biochemical assessment of nephroprotective and nephrocurative activity of Withania somnifera on gentamicin induced nephrotoxicity in experimental rats

et al. 2016

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Background: Renal diseases are among the commonest cause of hospitalization in most of the countries. Acute renal failure (ARF) is a common and serious renal problem having high morbidity and mortality rate. So, prevention of occurrence and progression of acute renal failure (ARF) has become a very important issue. However modern system of medicine lacks reliable nephroprotective drugs. Ashwagandha (Withania somnifera), a traditional Indian plant having antioxidant property may be used for nephroprotection. Methods: The study was carried out in two phases. In phase 1, evaluation of nephroprotection was done. 54 rats were randomised in 3 groups named G10, G20 and G30 according to 10, 20 and 30 days of treatment. In each of the main groups, rats were randomly assigned to any of the three subgroups i.e. control C group (received normal saline (2ml/100gm/day) orally once a day consecutively for test duration), gentamicin treated GT (received normal saline (2ml/100gm/day) orally once a day consecutively for test duration, Injection gentamicin (40mg/kg) was given intraperitonealy once daily for last five days) and W. Somnifera treated WST group (received W. somnifera orally (500mg/kg/day) as a single dose in morning for the test duration and injection gentamicin (40mg/kg) was given intraperitonealy once daily for last five days). Rats were sacrificed 24 hours after the last dose of gentamicin injection (on 11 th , 21 st and 31 st day). In Phase-2 nephrocurative activity of W. somnifera was compared with the spontaneous reversal of gentamicin induced nephrotoxicity. 72 rats were randomized into two groups. In Group-1: 36 rats received intra-peritoneal gentamicin for five days in a dose of 40 mg/kg. In Group-2: 36 rats received intra-peritoneal gentamicin for five days in a dose of 40 mg/kg. From the 5 th day onward these rats received W. Somnifera orally in a dose of 500mg/kg/day till the rats are sacrificed. Six rats from each group were sacrificed on 3 rd , 5 th , 7

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“…1. ) (3). This compound represented the first member of a new class of phytosteroids, the withanolides.…”

Section: Introductionmentioning

confidence: 99%

A biologically active constituent of withania somnifera (ashwagandha) with antistress activity

Kaur

Mathur

Sharma

et al. 2001

Indian J Clin Biochem

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In Ayurvedic medicine, Withania somnifera (Ashwagandha) is wall known for its anti-stress activity. A passive rat experimental model, where the animals are subjected to multiple stress of cold, hypoxia, restraint (C-H-R) has been developed to evaluate adaptogenic properlJes of vadous fracUons of W. somnifera root extracts. We have carded out extraction of roots of W. somnifera with water and further Isolated one of the active constituents called compound X and also tested its anti-stress activity in C-H-R model. The effect of administration of W. somnifera water suspension (350 mglKg bw) and compound X (20mglKg bw) on the fall and recovery of colonic temperature was noted. There was an increase of -38% and -64% in the time taken to attain T,= 23~ by rats given a single dose of fresh aqueous suspension and biologically active constituent (Compound X) respectively, where as decrease in the recovery time to attain T,r 37~ is -13% and -33% respectively, as compared to control group. It is clear that rats treated with the fresh aqueous suspension and compound X of Virdhania somnifera, could withstand the multiple stress of C-H-R better than control group.

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1371. Constituents of Withania somnifera Dun. Part IV. The structure of withaferin A

Cited by 124 publications

References 0 publications

Withangulatin I, a New Cytotoxic Withanolide from Physalis angulata

Withangulatin I, a New Cytotoxic Withanolide from Physalis angulata

Biochemical assessment of nephroprotective and nephrocurative activity of Withania somnifera on gentamicin induced nephrotoxicity in experimental rats

A biologically active constituent of withania somnifera (ashwagandha) with antistress activity

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