Cytotoxic Withaphysalins from Physalis minima

Abstract

A novel withanolide, withaphysalin P (1) with a nine‐membered ring, and six other new withaphysalins, 2–7, together with the three known withaphysalins 8–10 were isolated from Physalis minima L. The structures were deduced by means of spectroscopic analyses, and that of withaphysalin P (1) was confirmed by a single‐crystal X‐ray diffraction analysis. Plausible biosynthetic pathways were postulated (Scheme 1). All compounds were tested for their antiproliferative activities toward the human colorectal‐carcinoma HCT‐116 cells and human nonsmall‐cell lung‐cancer NCI‐H460 cells (Table 4). Compounds 1–3, 7–10, 7a, and 7b displayed moderate cytotoxic activity against the two human cancer cell lines.

Anti-cancer potential of South Asian plants

“…The chloroform extract of P. minima also exhibited remarkable cytotoxic activities in NCI-H23 human lung adenocarcinoma cell line via apoptotic cell death 99 . Moreover, Ma et al 100 isolated a panel of withanolides from this plant, which have moderate cytotoxic activity against human colorectal-carcinoma HCT-116 and human non small-cell lung-cancer NCI-H460 cell lines. 106,107 .…”

Antiproliferative and Anti-inflammatory Withanolides from Physalis angulata

“…The ECD spectrum showed a positive Cotton effect at 252 nm, indicating a (22R)-configuration 27. Thus, the structure of physangulatin L (12) w a s d e fi n e d a s ( 5 R , 6 R , 8 R , 9 S , 1 0 R , 1 3 S , 1 4 S , 1 5 S , -16S,17R,20R,22R)-16,17-epoxy-5,6,14,15-tetrahydroxy-1-oxowitha-2,24-dienolide.Physangulatin M (13) was shown to have the molecular formula C30 H 42 O 7 by HRESIMS (m/z 537.2830 [M + Na] + , calcd for C 30 H 42 O 7 Na, 537.2828) and 13 C NMR data. The IR spectrum showed the presence of hydroxy (3398 cm −1 ), carbonyl (1681 cm −1 ), and olefinic (1647 cm −1 ) functionalities.The 1 H and 13 C NMR for rings A−C and E of 13 closely resembled those of 12.…”

“…The ECD spectrum suggested a (22R)-configuration and an α-orientation of OH-5 due to the positive and negative Cotton effects at 252 and 330 nm, respectively. 27 The NOESY spectrum of 2 was also recorded in DMSO-d 6 30 H 40 O 7 Na, 535.2672) and 13 C NMR data. The IR spectrum of 3 showed absorption bands of hydroxy (3395 cm −1 ) and olefinic (1646 cm −1 ) functionalities.…”

“…Its molecular formula was established as C 30 13 C NMR data. The NMR data for rings A−E of 4 were similar to those of physagulin Q isolated from P. angulata L. var.…”

Leishmanicidal Active Withanolides from a Pakistani Medicinal Plant, <i>Withania coagulans</i>

“…plants belonging to Solanaceae. [11][12][13] Withanolides are C28 steroids based on an ergostane skeleton having characteristic functional groups, 14) and have also been isolated from several Solanaceae plants, such as Physalis, 15,16) 25,26) Withanolides were reported to have various interesting biological activities, such as antitumore activity, 16,27,28) cell differentiative activity, 29) neurite outgrowth activity, 30) trypanocidal activity, 31) apoptosis activity and inhibition of invasion, 32) and anti-feedant activity. 33) We tried to isolate leishmanicidal compounds from the aerial parts of W. coagulans collected in Pakistan.…”