Chemistry of carpesterol, a novel sterol from Solanum xanthocarpum

Abstract

The structure of carpesterol (1) has recently been shown to be (22ñ)-22-hydroxy-6-oxo-4a-methyl-5a:-stigmast-7-en-3/3-yl benzoate. The present work describes some chemical transformations of the sterol as well as its degradation to 4a-methyl-5a-stigmast-8( 14)-en-3/?-ol (10) from which the 24R configuration of the stigmasterol ethyl group was confirmed. The possible implications of 1 to the biogenesis of steroidal alkaloids and sapogenins are presented. The ORD spectra of 1 and some of its derivatives are contrasted with the spectra of the ecdysterols.

Lipase Inhibitor from Fruits of <i>Solanum stramonifolium</i> Jacq.

“…Only fraction 4 showed anti-pancreatic lipase activity and then was further purified by preparative TLC on silica gel plates using n-hexane/ethyl acetate (8:2 v/v) as developing solvent to give compound 1. The 1 H, 13 C NMR and MS analyses of compound 1 indicated it was (22R)-3β-benzoyloxy-22-hydroxy-4α-methyl-5α-stigmast-7-en-6-one or carpesterol (Figure 1) [15][16][17][18]. Compound 1 showed lipase inhibition activity of 62.3% ± 6.2% at concentration of 0.125 mg/mL.…”

“…xanthocarpum [25]. Carpesterol was also found in S. sisymbrifolium [18], S. xanthocarpum [17,26] and S. indicum [16]. It showed anti-inflammatory activity and hypoglycaemic activity in rats and mice [14].…”

Cytotoxic Principles and Their Derivatives of Formosan Solanum Plants

“…int. )[M + H]+ 578(53), 560(4), 444(2), 416(4), 398 (10), 138(40), 125(67), 115(100);irvmax(KBr)3400(OH)cm-1;'Hnmrseetext; 13Cnmr(CD3OD) see Table 1. Compound 1 was hydrolyzed to yield capsimine whose identity was confirmed by direct comparison of mp, ir, nmr, and ms spectra with those of an authentic sample.…”

Correlative study of heavy metal content with biological importance of Solanum virginianum leaf extract

“…The plant has long been used to treat coughs, asthma, toothache, hair loss, skin diseases, and respiratory diseases [20][21][22]. Secondary metabolites like diosgenin and β-sistosterol were isolated in 1968 [23], Carpesterol in 1971 [24], and 11 more in 1973 [25]. Further, Β2-Solamargine, Solamargine, Solasonine, solasodine, Caffeic acid, oleanolic acid are also reported [26][27][28].…”