Steroidal constituents of Physalis minima(Solanaceae)

Antiproliferative and Anti-inflammatory Withanolides from Physalis angulata

“…The molecular formula of physangulatin I (9) was assigned as C 31 ; δ C 73.9 (C-3)] in 9 and the absence of an olefinic unit [δ H 6.70 (1H, ddd, J = 10.0, 6.0, 2.0 Hz, H-3) and 6.14 (1H, dd, J = 10.2, 2.0 Hz, H-2); δ C 145.9 (C-3) and 128.5 (C-2)] in 24, suggesting the methoxylation of the Δ 2,3 double bond at C-3. This finding was confirmed through an HMBC experiment showing a correlation from OMe-3 to C-3 ( Figure 2).…”

Antileishmanial Physalins fromPhysalis minima

“…Comparison of the spectroscopic data of compounds 4 ± 6 with those reported led to their identification as physalin H [28], isophysalin B [17], and 5b,6b-epoxyphysalin B, respectively [3] [29]. These compounds had first been reported from P. angulata, P. alkekengi, and P. minima, respectively.…”

“…The signal at d(H) 3.22 (J(6a,7b) 2.2) was assigned to HÀC(6), geminal to an oxirane ring. The low J value and comparison of the chemical shift with a known physalin (5b,6b-epoxyphysalin B) suggested a-orientation of HÀC(6) [3]. A downfield three-proton singlet at d(H) 3.26 was assigned to the 3-MeO group.…”

“…1 H-and 13 C-NMR spectra: Bruker Avance-400 and -500 spectrometers at 400/100 and 500/125 MHz, resp., in CDCl 3 Leishmanicidal in vitro Activity. L. major (DESTO) promastigotes were grown at 22 ± 258 in RPMI-1640 (Sigma) medium containing 10% of heat-inactivated (56 o for 30 min) fetal bovine serum.…”

“…Normal withanolides like withaferin A are C 28 steroidal compounds possessing a relatively highly oxidized ergostane-type skeleton characterized by a six-membered lactone ring in the side chain [2] [3]. The physalins are biogenetically related to the withanolides from which they are formally derived by a) oxidative bond cleavage between C(13) and C (14) to yield a nine-membered ring, b) formation of a new six-membered carbocycle between C(16) and C (24), and c) oxidation of the Me group at C(13) to a COOH group, which results in 18,20-lactonization [3]. Physalins are commonly named as 16,24-cyclo-13,14-secosteroids [1].…”