Journal
TETRAHEDRON
Volume 56, Issue 35, Pages 6401-6405Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00584-6
Keywords
Exostema acuminatum; Rubiaceae; norditerpenoids; 4-phenylcoumarins; X-ray crystallography; cytotoxic activity; in vivo evaluation
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Bioassay-guided phytochemical investigation of the roots of Exostema acuminatum (Rubiaceae) using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of two norditerpenoids, namely, (16R)-ent-16,17-dihydroxy-19-nor-kaur-4-en-3-one (1) and (16S)-ent-16,17-dihydroxy-19-nor-kaur-4-en-3-one (2), and six previously known 4-phenylcoumarins (3-8). The structure and relative stereochemistry of the novel compound 1 were determined by X-ray crystallography. All isolates were tested against a panel of human tumor cell lines, and the 4-phenylcoumarins showed significant cytotoxicity, with 3'-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin (5) and 8-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin (6) exhibiting the most potent activity. Two of the 4-phenylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (3) and 6, were evaluated in an in vivo P388 murine leukemia model. (C) 2000 Elsevier Science Ltd. All rights reserved.
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