Chemistry and genetics of withanolides in Withania somnifera hybrids

Nittala, S. Sarma; Lavie, David

doi:10.1016/0031-9422(81)85278-8

Cited by 50 publications

(44 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…22 C-NMR data with those reported in the literature. 24) Comparison of the spectral data of compounds 3-6 with the reported values led to their identification as known withanolides, withaferin-A (3), 22,23) 2,3-dihydrowithaferin-A (4), 23) 6a,7a-epoxy-5a,20-dihydroxy-1-oxowitha-2,24-dienolide (5), 19) and 5b,6b-epoxy-4b-hydroxy-1-oxowitha-2,14,24-trienolide (6). 22) Compounds 1-6 were screened for their anti-cholinesterase activity in a mechanism-based assay (Table 2).…”

Section: Resultsmentioning

confidence: 99%

Cholinesterase Inhibiting Withanolides from Withania somnifera

et al. 2004

View full text Add to dashboard Cite

A total of two new (1, 2) and four known (3-6) withanolides were isolated from the whole plant of Withania somnifera. Their structures were elucidated on the basis of spectroscopic techniques and were characterized as 6a a,7a a-epoxy-3b b,5a a,20b b-trihydroxy-1-oxowitha-24-enolide (1), 5b b,6b b-epoxy-4b b,17a a,27-trihydroxy-1-oxowitha-2, 24-dienolide (2), withaferin-A (3), 2,3-dihydrowithaferin-A (4), 6a a,7a a-epoxy-5a a,20b b-dihydroxy-1-oxowitha-2,24-dienolide (5), and 5b b,6b b-epoxy-4b b-hydroxy-1-oxowitha-2,14,24-trienolide (6), respectively. Compounds 2, 3, 5, and 6 displayed inhibitory potential against butyrylcholinesterase, but only compounds 3, 4, and 6 were found to be active against acetylcholinesterase.

show abstract

Section: Resultsmentioning

confidence: 99%

Cholinesterase Inhibiting Withanolides from Withania somnifera

et al. 2004

View full text Add to dashboard Cite

show abstract

“…The fragmentation mode of ixocarpalactone B (202) is slightly different due to its spiroketal structure. Cleavage of the 20,22-bond initiates the fragmentation and leads to a peak at mjz 142 and a peak at [M-142-OH] +.…”

Section: :~Andohmentioning

confidence: 98%

“…Acnistins Acnistin A (195) Id (30) Acnistin E (1%) Id (30) Tubocaposide A (197) 12a (161,162) Tubocaposide B (198) 12a (161,162) Withajardin A (199) 3b (54) Withajardin B (200) 3a (53) H. Ixocarpalactones Ixocapalactone A (201) 9d, ge, 9j, 91 (119) Ixocarpalactone B (202) 9d, ge, 9j, 91 (119) laborochlorodiol (203) 6d (73) laborochlorotriol (204) 6d (73) laborolone (205) 6d (73) laborosalactone P (212) 6e (76) laborotetrol (206) 6d (73) Taccalonolide A (209) 15a (204) Taccalonolide B (210) 15a (204) Taccalonolide D (211) 15a (205) Trechonolide A ( = laborosalactone M-magellanica) (207) 6d,lla (73,74,160) Trechonolide B (208) lla (160) I. Perulactones Perulactone A (213) 9i (136) Perulactone B (214) 9i (145) their isolation from marine organisms (soft coral) and from members of Taccaceae and Leguminosae suggest that they are much more widely distributed. The various sources so far known to yield withasteroids are listed in Table 1.…”

Section: Namementioning

confidence: 99%

“…2,3-Dihydrowithaferin A (75) Ie, 13a, 13e, 13e (2) 2,3-Dihydro-5,6-deoxywithaferin A (115) Ie (27a) 2,3-Dihydro-27-deoxywithaferin A (76) Ie (27a) 24,25-Dihydro-27 -deoxywithaferin A (116) Ie,13e (183) 14cx-Hydroxy-27-deoxywithaferin A (66) 13e (181) 17cx-Hydroxy-27-deoxywithaferin A (67) 13e (184) (96) l3e (196,202) (186,187) Withanolide Y (129) 13e (177) Withanone (12) 13e (184) 141X-Hydroxywithanone (13) 13e (197) 14~-H ydroxywithanone (14) 13e (197) Withastramonolide (15) 2f,2h (51) 12-Deoxywithastramonolide ( = 27-Hydroxywithanolide B) (16) 2c, 13e (39,184) 41X-27-Dihydroxy-5~,6~-epoxy-…”

Section: Namementioning

confidence: 99%

“…71X,171X-Dihydroxy-5~,6~-epoxyl-oxowitha-2,24-dienolide (84) l3e (11) 51X,141X,17ct-Trihydroxy-6~-7~ epoxy-l-oxowitha-2,24-dienolide (130) l3e (197) 4~, 7~,20-Trihydroxy-l-oxo-…”

Section: Namementioning

confidence: 99%

See 2 more Smart Citations

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

View full text Add to dashboard Cite

New Withanolides and Other Constituents from the Fruit of Withania somnifera

Abou-Douh

2002

Arch. Pharm. Pharm. Med. Chem.

View full text Add to dashboard Cite

Two new steroidal lactones of the withanolide‐type, 5β, 6α, 14α, 17β, 20β‐pentahydroxy‐1‐oxo‐20 S, 22R‐witha‐2, 24‐dienolide (1)and 6α, 7α‐epoxy‐5α, 14α, 17α, 23β‐tetrahydroxy‐1‐oxo‐22R‐witha‐2, 24‐dienolide (2), were isolated from the fruit of Withania somnifera (L.) Dunal (Solanaceae) growing in Southern Egypt, together with two known coumarins, scopoletin (3)and aesculetin (4), a known triterpene, viz. β‐amyrin (5), and two known phytosterols, viz. stigmasterol (6) and sitosterol (7). The structures of the isolated compounds have been elucidated by spectroscopic methods including UV, IR, 1H‐, 13C‐NMR, DEPT experiments, HRFAB‐, FAB‐, and EI‐mass spectrometry. The in vitro antimicrobial activity of the new withanolide (1) and the alcoholic fruit extract are discussed.

show abstract

Chemistry and genetics of withanolides in Withania somnifera hybrids

Cited by 50 publications

References 12 publications

Cholinesterase Inhibiting Withanolides from Withania somnifera

Cholinesterase Inhibiting Withanolides from Withania somnifera

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

New Withanolides and Other Constituents from the Fruit of Withania somnifera

Contact Info

Product

Resources

About