Steroids and Flavonoids from Physalis alkekengi var. franchetii and Their Inhibitory Effects on Nitric Oxide Production

Abstract

Four new steroidal compounds possessing a rare 13,14-seco-16,24-cycloergostane skeleton, physalin Y ( 1), physalin Z ( 2), physalin I ( 6), and physalin II ( 7), were isolated from the 80% EtOH extract of calyces from Physalis alkekengi var. franchetii together with 11 known steroids ( 3- 5 and 8- 15) and eight flavonoids ( 16- 23). The structures of the new compounds were elucidated primarily on the basis of 1D and 2D NMR and mass spectroscopic studies. The relative configuration of the 3-OH group of 3, 4, and 5 was also established or re-established. The inhibitory effects of compounds 1- 23 on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.

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

“…The presence of this compound in the aerial part of P. alkekengi is being reported here for the first time, whereas physalin D has been previously isolated from the aerial parts of P. minima, P. angulata, and P. lancifolia (Row et al, Kawai et al, 1987Kawai et al, , 2001Makino et al, 1995a). The isolation of physalin D from the calyces of the plant is consistent with the results reported by Qiu et al (2008). According to our results, the methanol extract of P. alkekengi has strong antibacterial activity against Gram-positive bacteria.…”

“…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). In the present study, physalin D was isolated from the extracts of P. alkekengi.…”

Three new physalins from Physalis alkekengi var. franchetii

“…The molecular formula of 2 was determined to be C 28 H 32 O 12 on the basis of HREIMS (m/z 560.1854, [M] + ; calcd 560.1894) and NMR data ( Table 1). The NMR data of 2 were similar to those of physalin Z 22 , and the differences between them were two of the double-bond carbon signals in physalin Z were replaced by two oxygenated methine signals in 2 located at C-6 and C-7, which were deduced by (Figure 2) of H-6/H-7 and H-7/H-8β revealed that OH-C(6) and OH-C(7) were α-oriented. So the structure of compound 2 was deduced and named as physalin IV (2).…”

“…Hence, the structure of compound 3 was identified to be 3-O-methylphysalin X (3). The structures of five known steroidal compounds, physalin Z (4) 22 , physalin C (5) 24 , physalin I (6) 25 , physalin P (7) 26 , 25,27-dihydro-4,7-dedehydro-7-deoxyneophysalin A (8) 27 , were elucidated in comparison to their spectroscopic data with those reported in the literature.…”

Withanolides and Related Steroids

“…franchetii. Physalins W (306) and X (307) were initially isolated by Chen et al (147) and their structures revised by Qiu and coworkers (139). The latter authors also reported the isolation of the 3-methoxy analogues physalin I (308) and physalin II (309).…”