Antileishmanial Physalins fromPhysalis minima

Abstract

Three new physalins (1-3) and a new withanolide 7 have been isolated from the whole plant of Physalis minima, along with three known physalins: physalin H (4), isophysalin B (5), and 5beta,6beta-epoxyphysalin B (6). Their structures were deduced on the basis of in-depth spectroscopic analyses. Compounds 1-6 showed significant in vitro leishmanicidal activities (0.92-19.4 microg/ml) against promastigotes of Leishmania major.

Antimicrobial activity of the extracts and physalin D fromPhysalis alkekengiand evaluation of antioxidant potential of physalin D

“…12.2 ± 1.5 14.0 ± 0.7 32.4 ± 1.2 -E. faecalis 9.0 ± 1.9 9.8 ± 1.9 21.6 ± 1.1 -B. subtilis 11.2 ± 1.9 13.8 ± 1.3 30.4 ± 1.1 -B. cereus 14.4 ± 0.5 14.8 ± 1.5 27.2 ± 2.4 -Gram(-) bacteria E. coli 6.0 ± 2.4 8.2 ± 1.8 28.4 ± 1.1 -P. aeruginosa 7.6 ± 1.1 10.2 ± 2.6 25.0 ± 1.9 -E. cloacae 9.8 ± 2.7 10.6 ± 0.5 22.8 ± 3.7 -K. pneumoniae 7.8 ± 2.0 7.8 ± 0.4 25.0 ± 2.5 -P. vulgaris 6.0 ± 1.0 7.8 ± 1.3 22.0 ± 1.6 -Fungi C. albicans -6.2 ± 0.8 -23.8 ± 0.8 C. krusei -3.8 ± 0.4 -26.6 ± 1.5 C. glabrata -6.2 ± 0.4 -29.2 ± 1.9 C. tropicalis ---21.2 ± 1.9 C. paraphilosis ---22.6 ± 2.5 a In the literature, there is no report about the antioxidant activity of physalins or the extracts of Physalis species. Our report is the first for physalin D. Previous phytochemical studies on the aerial parts of Physalis plants have led to the identification of physalins, which are believed to be the bioactive compounds of the genus Physalis (Januário et al, 2002;Dos Santos et al, 2003;Wu et al, 2004;Choudhary et al, 2005;Lee & Houghton, 2005;Magalhaes et al, 2006;Damu et al, 2007;Castro et al, 2008). However, there is relatively little information in the literature regarding the steroid content of the calyces of Physalis species (Dinan et al, 1997;Qiu et al, 2008).…”

“…Previous studies have focused on the isolation and characterization of secondary metabolites, whereas it has been demonstrated that some of the extracts or active principles obtained from Physalis species have a broad spectrum of biological activities, including antileukemic, antitumor, immunomodulator, cytotoxic, antimycobacterial, antimicrobial, molluscicidal, antihepatoma, and antinociceptive activities in recent studies (Chiang et al, 1992a(Chiang et al, , 1992bJanuário et al, 2002;Shim et al, 2002;Su et al, 2002;Dos Santos et al, 2003;Soares et al, 2003;Wu et al, 2004;Choudhary et al, 2005;Lee & Houghton, 2005;Silva et al, 2005;Bastos et al, 2006;Magalhaes et al, 2006;Damu et al, 2007;Castro et al, 2008). It has been previously reported that the crude extract (i.e.…”

Withanolides and Related Steroids

“…D 16 -Withanolides with oxygen substituents at C-14 and C-15 have the appropriate functionalities for cleavage of the 13,14-bond, and the occurrence of such withanolides in physalin-rich plants strongly suggests that they are either precursors or shunt products in the biosynthesis of physalins (59). A D 14 -withanolide, 107, was also reported from P. minima collected in Pakistan (60). (115), and a 14a,20-epoxywithanolide (116) (65).…”

“…while physalins 298, 300, 301, physalin H (312), isophysalin B (474), and 5b,6b-epoxyphysalin B (502) also had significant activity. The 3-methoxy derivative physalin U (304) and withanolide 107 with an unmodified skeleton were only marginally active (60,145). Removal of the C-6 hydroxy group of physalin H (312) to give either the dehydration product 473 or the deoxygenated physalin 475 (see Sect.…”

Effects of seco-steroids purified from Physalis angulata L., Solanaceae, on the viability of Leishmania sp

“…Previous studies have shown that physalin H, isophysalin B, 5 beta, 6 beta-epoxyphysalin B and others isolated of Physalis minima have in vitro antileishmanial activitiy against promastigotes of L. major (Choudhary et al, 2005;Choudhary et al, 2007). In the present study we demonstrated the antileishmanial activity of physalins B, F, and G isolated from Physalis angulata in vitro in axenic cultures of different Leishmania species, including L. amazonensis, L. braziliensis, L. chagasi (New World), and L. major (Old World).…”