Withanolides from Physalis hispida

Abstract

Nine new withanolides (1-9), withahisolides A-I, were isolated along with nine known compounds (10-18) from the aerial parts of Physalis hispida. The structures of 1-9 were elucidated through a variety of spectroscopic techniques, while the structures of 1 and 2 were confirmed by X-ray crystallographic analysis. Compounds 1-3 are the first withanolides with nonaromatic six-membered ring D moieties. In addition, withanolide 8 represents a novel withanolide skeleton due to the absence of a C-13-C-17 bond within the steroidal nucleus.

Withanolides from Leaves of Nicandra physalodes

“…From this species, several withanolides have been reported possessing either the normal or modified skeletons (ring-D aromatic). [6][7][8][9][10][11][12] N. physalodes is considered an ornamental plant possessing insect repellent properties. In fact, its main constituent named as nicandrenone showed antifeedant activity.…”

“…[6][7][8]13 In a continuing effort to isolate active compounds from the Brazilian Solanaceae, the acetone extract from N. physalodes was investigated. As results, five new withanolides (15-oxonicaphysalin B (1), 6β,7α-dihydroxynicandrenone 10 (2), 24α ,25β -dihydroxy-nicandrenone-2 (3 ) and a mixture of the epimers 17-(1α/1β-methylpropanone)-nicandrenone (4a/4b)), in addition to nicandrenone-10 (5), nicandrenone (6), nicandrenone-7 (7), 10 nicandrenone-2 (8), 7 nicaphysalin B (9), 9 and 26R-withahisolide G (10), 12 were isolated. The isolated compounds were evaluated for their antibacterial and antifungal effects.…”

Withanolide Structural Revisions by 13C NMR Spectroscopic Analysis Inclusive of the γ-Gauche Effect

“…63 It was observed that both the OH-17α and OH-17β shield the γpositioned C-12 (∼7−9 ppm decrease), as demonstrated by the 13 C NMR comparison of steroids 65−87: androstanes [65 64 and its 17β-hydroxy derivatives (43 51,64 and 66 64 )], pregnane (67); 65 cholestanes [68, 65 and the related 17β-hydroxy (69) 66 and 17α-hydroxy (70) 67 derivatives]; and withanolides (31,34,37,58, and 71−87) (Figure 3, Tables S1, S3, and S4, Supporting Information). This analysis compared the data of each classic withanolide against their corresponding 17-hydroxy derivatives: (1) withanolide B (37) 46 and the corresponding 17α-hydroxy (31) 16 and 17β-hydroxy (34) 23,24 derivatives; (2) withanolide A (71) 16 and its 17α-hydroxy derivative (72); 16 (3) daturalactone-4 (73) 68 and its 17β-hydroxy derivative (74); 16 (4) withaferin A (58) 59 against its 17α-hydroxy derivative (75); 69 (5) 5β,6β-epoxy-1-oxowitha-3,24-dienolide (76) 59 against jaborosalactone L (77); 70 (6) 16α-acetoxy-5β,6β-epoxy-1-oxowitha-2,24-dienolide (78) 71 and its 17αhydroxy derivative (79); 71 (7) 5,6-deoxywithaferin A (80) 72 against its 17α-hydroxy derivative (81); 73 (8) 27-hydroxy-1oxowitha-2,5,24-trienolide (82) 74 against cilistol A (83); 75 (9) 5α,6β-dihydroxywithaferin A (84) 43,76 against cilistadiol (85); 77 and (10) 6α-chloro-5β-hydroxywithaferin A (86) 10 against 6αchloro-5β,17α-dihydroxywithaferin A (87). 10 In addition, there are insignificant chemical shift differences (<2 ppm) observed on the carbons of the steroid nucleus caused between the αand β-orientation of the 17-hy...…”

“…bipinnatif ida (Dunal) Reiche, 4 Physalis coztomatl Dunal, 5 P. hispida (Waterf.) Cronquist, 6 P. longifolia Nutt., 7,8 Vassobia brevif lora (Sendtn.) Hunz., 9 and Withania somnifera (L.) Dunal.…”

Pharmacological Effects of withanolides

“…In the past decade, with the rapid development and application of various separation techniques and spectral analysis techniques, especially nuclear magnetic resonance spectroscopy, the research speed of the compounds in the solanaceae has been greatly accelerated, and its structural research has made great progress. Up to now, more than 900 kinds of withanolides have been separated from the whole world [5,6].…”