Withaphysalins

Most of the known withanolides belong to group A, which may be further divided into 11 subgroups withanolides with an unmodified skeleton, withaphysalins, physalins, acnistins, withajardins, withametelins, sativolides, subtriflora-5-lactones, ring-D aromatic withanolides, ring-A aromatic withanolides and norbomane-type withanolides, Fig. (2). 

Compounds 13-22 are structurally related to the withaphysalins, isolated from Physalis minima, which have been regarded as intermediates in the formation of the physalins. Recently Tomassini et al. published a review on withanolides isolated from the Physalis genera [21]. 

Physalis species. They were appropriately named as withaphysalins... 

Hypothetic biogenetic scheme to withaphysalin C (114) to physalin C (191) by E. Glotter is shown in Chart VI. 

Carbon No. Daturilin (138) Witha- minimln (164) 23-hydrcxy physalo- lactcne (180) Physalc— lactone (175)1 Witha- peruvin (181)1 Wltha-peruvin D Withaphysalin E (144) (+) Jabarcl (187) ° ... 

A series of ten withanolides, isolated from Physalis minima, were evaluated for their cytotoxic properties against HCT-116 and NCI-H460 cell lines. It was found that withaphysalin C (31) was active against both the cell lines [72]. The stmcture-activity relationship (SAR) studies of the C3dotoxic withanolides from Physalis minima and Physalis angulata indicate that the a,)S-unsaturated ketone moiety in ring A and 5jS-6/i oxirane moiety in ring B are important contributors in the cytotoxicity of withanolides. The absence of these two structural features may result in a loss or reduction of the cytotoxicity of withanohde [4]. 

Veras ML, Bezerra MZB, Braz-Filho R, Pessoa OD, Monteaiegro RC, De- Moraes MO, Costa-Lutufo LV (2004) Cytotoxic epimtaic withaphysalins from leaves of Acnistus arborescens. Planta Med 70 551-555... 

Sinha SC, Ray AB, Oshima Y, Bagchi A, Hikino H (1987) Withaphysalin E, a withanolide of Physalis minima var. indica. Phytochemistry 26 2115-2117... 

Withaphysacarpin, 3484 Withaphysalins, 3468 Withaphysalins A, 3468 Withaphysalins E, 3468 Withaphysalins M, 3478 Withaphysalins O, 3478 Without fertility disruption, 2421 Wittig reaction, 3079 WNT5a, 2404 Wnt signaling, 2194 Women s Health Initiative (WHI), 2407 World Anti-Doping Agency (WADA), 290... 

Secowithanolides. Withaphysalin C, a derivative of withaphysalin A, as well as the physalins, e.g., physalins C and H (Fig. 7.29) belong to the most studied withanolides 13,14-Seco congeners isolated from various Physalis spp. Due to an initial oxidative cleavage of the withanolide skeleton between C-13 and C-14 the main difference of withaphysalin C to its congener A is represented by a... 

Veleiro AS, Oberti JC, Burton G (2005) Chemistry and bioactivity of withanolides from South American Solanaceae. In Atta-ur-Rahmtm (ed) Studies in natural products chemistry, vol 32 (part L). Elsevier, Amsterdam, NL, pp 1019-1052 Veras ML, Bezerra MZB, Lemos TLG, Uchoa DEA, Braz-Frlho R, Chai HB, Cordell GA, Pessoa ODL, (2004a) Cytotoxic withaphysalins from the leaves of Acnistus arborescens. J Nat Prod 67 710-713... 

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