5,20α(R)-dihydroxy-6α,7α-epoxy-1-oxo-(5α) witha-2,24-dienolide, a new steroidal lactone from withania coagulans

Subramanian, S.Sankara; Sethi, P. D.; Glotter, E.; Kirson, I.; Lavie, David

doi:10.1016/s0031-9422(00)94725-3

Cited by 47 publications

(33 citation statements)

References 8 publications

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“…The chemical shift of the hydrogens of this methylene and that of a methine at 02.89 (dd, J = 13.4 Hz) suggested the corresponding carbons were attached to a sulphur atom, a suggestion which was supported by a carbon resonance at 031.2 (t) and 47.9 (d). Based on these findings, withaperuvin H was formulated as (166) which was found to be in agreement with the 13C-NMR data. It has been conjectured that cysteine-derived cx-mercaptoacetaldehyde provides the extra two carbon atoms and the sulphur atom present in the molecule.…”

Section: Withanolide Ysupporting

confidence: 72%

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

Ray¹,

Gupta²

1994

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Section: Withanolide Ysupporting

confidence: 72%

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

Ray¹,

Gupta²

1994

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Molecular evidences of its ability to induce nerve development and improve nervous system function have been reported. 7,11) However, its usual very low levels in the natural plant 8,21,22) along with restriction of its occurrence mainly in the roots in W. somnifera require attempts to explore its production in in vitro cultures. Because of the rootspecific production of withanolide A, root cultures, particu-larly hairy roots, that can grow rapidly in simple media and can be easily upscaled in a bioreactor form the first choice for production in vitro.…”

Section: Resultsmentioning

confidence: 99%

Withanolide A Biogeneration in in Vitro Shoot Cultures of Ashwagandha (Withania somnifera DUNAL), a Main Medicinal Plant in Ayurveda

et al. 2007

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Multiple shoot cultures of two experimental lines of Withania somnifera plants (RS-Selection-1 and RS-Selection-2) were established using nodal segments as explants. The hormonal combinations of benzyl adenine and kinetin not only influenced their morphogenetic response but also differentially modulated the level of biogeneration of withanolide A in the in vitro shoots of the two lines. Interestingly, withanolide-A, that was hardly detectable in the aerial parts of field-grown Withania somnifera (explant source), accumulated considerably in the in vitro shoot cultures of the plant. The productivity of withanolide A in the cultures varied considerably (ca. 10-fold, 0.014 to 0.14 mg per gram fresh weight) with the change in the hormone composition of the culture media as well as genotype used as source of the explant. The shoot culture of RS-Selection-1 raised at 1.00 ppm of BAP and 0.50 ppm of kinetin displayed the highest concentration of withanolide A in the green shoots of 0.238 g per 100 g dry weight tissue. This was a more analytical concentration keeping in view the isolation yields so far reported from the dried roots of the field-grown plant (ca. 0.015 g per 100 g dry weight), even if isolation losses are considered during purification. The enhanced de novo biogenesis of withanolide A in shoot cultures was corroborated with radiolabel incorporation studies using [2-(14)C] acetate as a precursor. Production of withaferin A was also found in the in vitro shoot cultures. As this compound is a predominant withanolide of native shoots as well and has been already reported to be accumulated in in vitro shoot cultures, its biogeneration observed in these shoot cultures is not discussed in detail.

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“…By comparison with the reported data, fourteen known compounds were identified as withanolide A (2), 4) (20S,22R)-5a,27-dihydroxy-6a,7a-epoxy-1-oxowitha-2,24-dienolide (3), 5) lycium substance B (4), 6) withacoagin (5), 7) (20S,22R)-4b,5b,6a,27-tetrahydroxy-1-oxowitha-2,24-dienolide (6), 8) withanolide D (7), 9) and withaferin A (8), 10) withanosides V (13), 8,11) IV (14), 11) VI (15), 11) III (18), 11) and II (19), 11) coagulin Q (16), 12) and physagulin D (17). 13) Compound 1 was obtained as a white powder.…”

Section: )mentioning

confidence: 99%