Nic-1-lactone, a minor steroidal constituent of Nicandra physaloides (Solanaceae)

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

“…8a,17a (80,84,88,91) Nicandrenolactone ( = Nic-l lactone) (190) 8a (92) Salpichrolide A (191) 10a (159) F. Jaborols (Ring A Aromatic Withanolides and Precursor) laborol (192) 6d (72,75) laborosalactone Q (193) 6c…”

“…Sominolide (92) 13e (176) Vamonolide (S7) ge (116) Viseosalaetone A (Sl) 91 (155) Viseosalaetone B (S2) 91 (155) Withacnistin (113) la, Sa (19) Withaeoagin (127) 13b (/68) 20-Deoxy-I7cx-hydroxywithaeoagin (US) 13e (184) Withafastuosin A (40) 2a (31) Withafastuousin B (41) 2a (31) Withaferin A (64) la, Ie, Sa, 91, 13a, 13b, 13e, 13e (2,18,19,190) …”

Withanolides and related ergostane-type steroids

“…When such an opening takes place in a 4-unsubstituted withanolide, e.g. withanolide E, the diol is diaxial (108), but the chlorohydrin is diequatorial, e.g. 4-deoxyphysalolactoneg3 (1 lo), a SP-hydroxy-6a-chloro-2en-1-one isolated from the leaves of P. peruviana and of W. somnifera chemotype III.69 When the opening occurs in 4Phydroxywithanolide E (1 13), the chlorohydrins, as well as the diols, are diequatorial, (5P-OH, 6a-OH and 5P-OH, 6a-Cl).…”

Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review

“…According toand 13C nmr data, this ring exists in a twistchair conformation.2 B.-Epoxylactones. The first epoxylactone isolated in this series was Nic-1lactone, a minor component of Nicandra physaloides (37). It is one of the few natural ring D aromatic steroids.…”

“…Several new compounds related to withanolide E and 4/3-hydroxywithanolide E were isolated from a variety of Phy salts peruviana that grotvs near Varanasi (India). Extraction of the roots afforded withaperuvin (37) (29), the product of diequatorial hydrolytic opening of (36), whereas the leaves afforded inter alia psysalolactone (38) (30) and 4-desoxyphysalolactone (39) (29), the chlorohydrins derived from 4/3-hydroxywithanolide E (36) and withanolide E (7), respectively.1 The diequatorial opening of the epoxide ring in (36) to give the glycol (37) and the chlorohydrin (38) could have been anticipated from previous knowledge on the behavior of 4/3-hydroxy-5/3,6/3-epoxy-steroids (31) under acidic conditions. However, the formation in nature of the diequatorial chlorohydrin 39 from withanolide E contradicts the known behavior of this compound.…”