Cabraleahydroxylactone

A new sesquiterpene and other terpenoid constituents of Chisocheton penduliflorus.[Pubmed:18277603]

Arch Pharm Res. 2008 Jan;31(1):21-7.

A new aromadendrane sesquiterpene, allo-aromadendrane-10alpha, 14-diol (3), was isolated from Chisocheton penduliflorus (Meliaceae), along with two known sesquiterpenes: allo-aromadendrane-10beta, 14-diol (2) and allo-aromadendrane-10beta, 13, 14-triol (7). Six dammarane triterpenoids, including cabraleadiol (1), eichlerialactone (4), Cabraleahydroxylactone (5), cabralealactone (6), hollongdione (8) and dammaradienone (9), the coumarins scoparone and scopoletin, and vanillic acid were also isolated from the wood and leaves of this plant. Compounds 1-7 displayed antimycobacterial activity against Mycobacterium tuberculosis. Compounds 1, 4, 5 and 6 were weakly cytotoxic to a breast cancer (BC) cell line; whereas, compound 6 was moderately active against a small-cell lung cancer (NCI-H187) cell line.

Activity-guided isolation of cytotoxic constituents from the bark of Aglaia crassinervia collected in Indonesia.[Pubmed:16216518]

Bioorg Med Chem. 2006 Feb 15;14(4):960-72.

Activity-guided fractionation of a CHCl(3)-soluble partition of the MeOH extract of the bark of Aglaia crassinervia collected in Indonesia led to the isolation of three new glabretal-type triterpenoids, aglaiaglabretols A-C (1-3), as well as nine known compounds, 3-epi-Cabraleahydroxylactone (4), Cabraleahydroxylactone (5), rocaglaol (6), 2beta,3beta-dihydroxy-5alpha-pregn-17(20)-(E)-16-one, scopoletin, and mixtures of cabraleadiol and epicotillol and of beta-sitosterol and stigmasterol. The structures of compounds 1-3 were determined on the basis of spectroscopic and chemical methods. The structure of aglaiaglabretol A (1) was confirmed by single-crystal X-ray analysis, and the absolute stereochemistry of this isolate was established by the Mosher ester method. The cytotoxic activity of all isolates and several chemical transformation products obtained in the present study was evaluated. The known cyclopenta[b]benzofuran, rocaglaol (6), was found to be significantly active and comparable in potency to the positive controls, paclitaxel and camptothecin. Aglaiaglabretol B (2) was further tested in an in vivo hollow fiber model.

Biologically active constituents of Aglaia erythrosperma.[Pubmed:22011221]

Nat Prod Res. 2011 Oct;25(17):1621-8.

From the fruits and leaves of Aglaia erythrosperma (Meliaceae), 10 chemical constituents were isolated and identified, i.e. the dammarane triterpenoids cabraleadiol (1), Cabraleahydroxylactone (2), ethyl eichlerianoate (3), eichlerialactone (4), aglinin A (5), cabralealactone (6), the aglaialactone 5,6-desmethylenedioxy-5-methoxy-aglalactone (7), the flavagline 4'-demethoxy-3',4'-methylenedioxy-methyl rocaglate (8) and two coumarins: scoparone and scopoletin. Flavagline 8 exhibited antimalarial activity with an IC(50) value of 7.30 microg mL(-1) and was strongly cytotoxic against small cell lung cancer (NCI-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines, with IC(50) values of 2.17, 2.10 and 0.11 microg mL(-1), respectively. Aglinin A (5) displayed moderate cytotoxicity against all the three cancer cell lines, whereas ethyl eichlerianoate (3), cabralealactone (6) and the aglaialactone 7 were exclusively cytotoxic to NCI-H187 cell line. Cabraleahydroxylactone (2) showed antiviral activity against herpes simplex virus type-1 with an IC(50) value of 3.20 microg mL(-1), in comparison with the standard acyclovir (IC(50) = 1.90 microg mL(-1)). When tested for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra, compounds 1-4 and 6-8 displayed minimum inhibitory concentration in the range of 25-50 microg mL(-1).