Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa.
Abstract |
Activity-guided fractionation of a CHCl(3)-soluble extract of the twigs of Aglaia rubiginosa, using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of a new naturally occurring cyclopenta[b]benzofuran, 1-O-acetylrocaglaol (1), along with seven known compounds, methyl rocaglate (2), rocagloic acid (3), 1-O-acetylmethyl rocaglate (4), desyclamide, eryodictiol, 5-hydroxy-3,7,4'-trimethoxyflavone, and naringenin. A CHCl(3) extract of the leaves of A. rubiginosa yielded the new compound (3S,4R,22R)-cholest-7,24-diene-3,4,22-triol (5), as well as 11 known compounds, including 2 and 4 and cabraleone, dammarelonic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid methyl ester, (3beta,4beta,22R)-ergosta-5,24(24')-diene-3,4,22-triol, ocotillone, shoreic acid, beta-sitosterol, and beta-sitosterol glycoside. The structures of 1 and 5 were elucidated by spectral and chemical methods. Isolates were evaluated with a human cancer cell panel, and compounds 1-4 were found to exhibit potent cytotoxic activity.
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Authors | J Fausto Rivero-Cruz, Hee-Byung Chai, Leonardus B S Kardono, Fransisca M Setyowati, Johar J Afriatini, Soedarsano Riswan, Norman R Farnsworth, Geoffrey A Cordell, John M Pezzuto, Steven M Swanson, A Douglas Kinghorn |
Journal | Journal of natural products
(J Nat Prod)
Vol. 67
Issue 3
Pg. 343-7
(Mar 2004)
ISSN: 0163-3864 [Print] United States |
PMID | 15043407
(Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
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Chemical References |
- 1-O-acetylmethyl rocaglate
- Antineoplastic Agents, Phytogenic
- Benzofurans
- Hydroxycholesterols
- cholest-7,24-diene-3,4,22-triol
- cyclopenta(b)benzofuran, 1-O-acetylrocaglaol
- methyl rocaglate
- rocagloic acid
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Topics |
- Aglaia
(chemistry)
- Antineoplastic Agents, Phytogenic
(chemistry, isolation & purification, pharmacology)
- Benzofurans
(chemistry, isolation & purification, pharmacology)
- Drug Screening Assays, Antitumor
- Humans
- Hydroxycholesterols
(chemistry, isolation & purification, pharmacology)
- Indonesia
- KB Cells
- Molecular Structure
- Plant Leaves
(chemistry)
- Plant Stems
(chemistry)
- Plants, Medicinal
(chemistry)
- Stereoisomerism
- Tumor Cells, Cultured
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