title: 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.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
authors.forename: J Fausto
authors.initials: JF
authors.lastname: Rivero-Cruz
authors.forename: Hee-Byung
authors.initials: HB
authors.lastname: Chai
authors.forename: Leonardus B S
authors.initials: LB
authors.lastname: Kardono
authors.forename: Fransisca M
authors.initials: FM
authors.lastname: Setyowati
authors.forename: Johar J
authors.initials: JJ
authors.lastname: Afriatini
authors.forename: Soedarsano
authors.initials: S
authors.lastname: Riswan
authors.forename: Norman R
authors.initials: NR
authors.lastname: Farnsworth
authors.forename: Geoffrey A
authors.initials: GA
authors.lastname: Cordell
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D031602:Aglaia / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006888:Hydroxycholesterols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007214:Indonesia; D007624:KB Cells; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
chemical_list: C483990:1-O-acetylmethyl rocaglate; D000972:Antineoplastic Agents, Phytogenic; D001572:Benzofurans; D006888:Hydroxycholesterols; C483987:cholest-7,24-diene-3,4,22-triol; C483988:cyclopenta(b)benzofuran, 1-O-acetylrocaglaol; C483989:methyl rocaglate; C428175:rocagloic acid