Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa.
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.
Rivero-Cruz
J Fausto
JF
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.
Chai
Hee-Byung
HB
Kardono
Leonardus B S
LB
Setyowati
Fransisca M
FM
Afriatini
Johar J
JJ
Riswan
Soedarsano
S
Farnsworth
Norman R
NR
Cordell
Geoffrey A
GA
Pezzuto
John M
JM
Swanson
Steven M
SM
Kinghorn
A Douglas
AD
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
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