10048. Withaferin A

Nomenclature

CAS number: 5119-48-2
(4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid δ-lactone; 4β,27-dihydroxy-1-oxo-5β,6β-epoxywitha-2,24-dienolide.
C28H38O6; mol wt 470.60.
C 71.46%, H 8.14%, O 20.40%.

Description and references

Isolated from the leaves of Withania somnifera Dun., Solanaceae: Lavie, Yarden, J. Chem. Soc. 1962, 2925; Kirson et al., Tetrahedron 26, 2209 (1970); Subramanian, Sethi, Indian J. Pharm. 32, 16 (1970); from roots of Withania coagulans: eidem, Curr. Sci. 38, 267 (1969); from Acnistus arborescens (L.): Kupchan et al., J. Org. Chem. 34, 3858 (1969). Structure: Lavie et al., J. Chem. Soc. 1965, 7517; Kupchan, loc. cit. Crystal structure: McPhail, Sim, J. Chem. Soc. C 1968, 962. Antitumor activity studies: B. Shohat et al., Cancer Chemother. Rep. 51, 271 (1967); B. Shohat, H. Joshua, Int. J. Cancer 8, 487 (1971). Synthetic studies: M. Hirayama et al., J. Chem. Soc. Perkin Trans. 1 1981, 88. Stereoselective synthesis: eidem, Tetrahedron Lett. 23, 4725 (1982).

Chemical structure

Properties

White prisms from acetone-petroleum ether, mp 252-253° (Kupchan). Also reported as mp 243-245° (ethyl acetate). [α]D28 +125° (c = 1.30 in CHCl3). uv max (ethanol): 214, 335 nm (ε 17300, 165).