Constituents of the Bark and Twigs of Artocarpus dadah with Cyclooxygenase Inhibitory Activity

Abstract

Fractionation of an ethyl acetate-soluble extract of the bark of Artocarpus dadah has led to the isolation of three new prenylated stilbenoid derivatives, 3-(gamma,gamma-dimethylallyl)resveratrol (1), 5-(gamma,gamma-dimethylallyl)oxyresveratrol (2), 3-(2,3-dihydroxy-3-methylbutyl)resveratrol (3), and a new benzofuran derivative, 3-(gamma,gamma-dimethylpropenyl)moracin M (4), along with six known compounds, oxyresveratrol, (+)-catechin, afzelechin-3-O-alpha-L-rhamnopyranoside, (-)-epiafzelechin, dihydromorin, and epiafzelechin-(4beta-->8)-epicatechin. From an ethyl acetate-soluble extract of the twigs of the same plant were isolated compound 4 and two new neolignan derivatives, dadahols A (5) and B (6), as well as 10 known compounds, oxyresveratrol, (+)-catechin, afzelechin-3-O-alpha-L-rhamnopyranoside, resveratrol, steppogenin, moracin M, isogemichalcone B, gemichalcone B, norartocarpetin, and engeletin. The structures of compounds 1-6 were determined using spectroscopic and chemical methods. Isolates were evaluated for their inhibitory effects against both cyclooxygenase-1 (COX-1) and -2 (COX-2) and in a mouse mammary organ culture assay.

Secondary metabolites of Bagassa guianensis Aubl. wood: A study of the chemotaxonomy of the Moraceae family

“…The stilbenoids trans-resveratrol (7) (Lee et al, 2001;Su et al, 2002), trans-oxyresveratrol (8) (Likhitwitayawuid and Sritularak, 2001;Lee et al, 2001;Su et al, 2002;Li et al, 2007), arachidin 2 (9) (Orsini et al, 2004) and artogomezianol (13) (Likhitwitayawuid and Sritularak, 2001) were identified by comparison of the spectral and chemical data with the literature (Fig. 1).…”

Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agent

“…Structures for 14 known compounds were identified by comparison with the literature data as dihydromorin [18], steppogenin [19], norartocarpetin [8], artocarpanone [9], artocarpesin [20], artocarpin [21], cycloartocarpin [22], cycloartocarpesin [23], artocarpetin [9], brosimone I [24], cudraflavone B [25], carpachromene [26], isoartocarpesin [27], and cyanomaclurin [9]. Their structures are shown in Fig.…”

Prenylated Stilbenes and Their Novel Biogenetic Derivatives from Artocarpus chama

“…The IR spectrum showed absorptions for hydroxy groups (ν = 3375 cm -1 ) and benzene rings (ν = 1592, 1514, and 1442 cm -1 3 , and four methyl carbon signals. These NMR spectroscopic data suggest that 1 is a diprenylated and tetrahydroxylated (E)-stilbene.…”