3β-Hydroxy-28-P-Coumaroyloxy-lup-20(29)-en-27-oic Acid From Caraipa Densifolia

Abstract

Caraipa densifolia Mart. (Clusiaceae) has afforded the new lupene derivative 3 beta-hydroxy-28-p-coumarolyoxy-lup-20(29)-en-27-oic acid (8), whose structure was deduced by chemical correlation with betulin (6). Simiarenol (1), taraxerone (2), friedelin (3), lupeol (4), betulinic acid (5), betulin (6), and beta-sitosterol-beta-D-glucoside (7) were also isolated in this study.

Antibacterial and cytotoxic activity of Brazilian plant extracts - Clusiaceae

“…(Lokvam et al 2000, Porto et al 2000, anthraquinones with antiprotozoal activity were found in V. orientalis (Mbwambo et al 2004), and cytotoxic compounds were isolated from three species of Vismia (Hussein et al 2003). A lupane derivative was isolated from C. densifolia (Gunasekera et al 1983). Xanthones (Mahabusakaram et al 2005) and benzophenones (Baggett et al 2005) were isolated from Garcinia species, and some of them showed antibacterial activity (Rukachaisirikul et al 2003).…”

“…Drugs derived from unmodified natural products or drugs semi-synthetically obtained from natural sources corresponded to 78% of the new drugs approved by the FDA between 1983 and 1994(Cragg et al 1997). This evidence contributes to support and quantify the importance of screening natural products.…”

Chemistry and Pharmacognosy of the Genus Durio

“…Since these compounds are all closely related, compound 7 might have the same configuration as the literature [11][12][13]. Further, 3-O-trans-caffeoyl-2hydroxyurs-12-en-28-oic acid (8) [15]. Biogenetically, the ursane skeleton of compound 8 and related triterpenes is likely derived from the same oleane precursor, hence this suggests that 8 may have the same absolute configuration as jacoumaric acid.…”

“…The attachment of p-coumaroyl, feruloyl, caffeoyl, or benzoyl moieties at C-3 or at C-27 of lupeol derivatives may influence the sign of their specific rotation. For example, 3-O-trans-pcoumaroyl betulinic acid, 3-O-cis-p-coumaroyl betulinic acid, 3-O-trans-feruloyl betulinic acid, and 3-O-cis-feruloyl betulinic acid have [] D values of +32.4 (c 0.28, EtOH), +18.0 (c 0.65, EtOH), +27 (c 0.33, EtOH), and +16.1 (c 0.37, EtOH), respectively [7], while the value measured for 3-O-trans-caffeoyl betulinaldehyde was +48 (c 1.0, MeOH) [8]. In contrast, 27-O-transcaffeoylcylicodiscic acid, 3-hydroxy-27-benzoyloxylup-20(29)-en-28-oic acid, and 3-hydroxy-27-benzoyloxylup-20(29)-en-28-oic acid methyl ester have [] D values of -33.8 (c 1.28, MeOH), -2.2 (c 0.31, CHCl 3 ), and -5.8 (c 0.38, CHCl 3 ), respectively [9][10].…”

“…Biogenetically, the ursane skeleton of compound 8 and related triterpenes is likely derived from the same oleane precursor, hence this suggests that 8 may have the same absolute configuration as jacoumaric acid. By comparison of their NMR spectroscopic and optical rotation data, compounds 3, 5-6, and 7-8 were suggested to have the same stereochemistry as known triterpenes [4][5][6][7][8][9][10][11][12][13][14][15].…”