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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.
AuthorsJ 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
JournalJournal of natural products (J Nat Prod) Vol. 67 Issue 3 Pg. 343-7 (Mar 2004) ISSN: 0163-3864 [Print] United States
PMID15043407 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
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
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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