Halogenated monoterpenes having a cyclohexadienone from the red alga Poilieria homemanni

被引：5

作者：

Kuniyoshi, M ^{[1
]}

Oshiro, N ^{[1
]}

Miono, T ^{[1
]}

Higa, T ^{[1
]}

机构：

[1] Univ Ryukyus, Dept Chem Biol & Marine Sci, Nishihara, Okinawa 9030213, Japan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2003年 / 50卷 / 01期

关键词：

red alga; Portieria hornemanni; monoterpene; cyclohexadienone; cytotoxin; aromatization mechanism;

D O I：

10.1002/jccs.200300023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Five new ochtodane class monoterpenes have been isolated from two collections of the red alga Portieria hornemanni and their structures elucidated by spectroscopic analysis. These compounds contained 4,4-dimethylcyclohexa-2,5-dienone in common and differed in the C-2 side chain structure. Some of them showed mild cytotoxicity. Also discussed is the mechanism of the transformation of 2-chloro-1-hydroxyochtoda-3(8),5-dien-4-one, a related labile compound reported previously, into 4,5-dimethylbenzo[b]furan.

引用

页码：167 / 170

页数：4

共 10 条

[1]

BURRESON BJ, 1975, TETRAHEDRON LETT, P2155

[2]

COLL JC, 1987, AUST J CHEM, P1893

[3] BIO-ACTIVE MONOTERPENES FROM RED SEAWEEDS [J].

CREWS, P ;

MYERS, BL ;

NAYLOR, S ;

CLASON, EL ;

JACOBS, RS ;

STAAL, GB .

PHYTOCHEMISTRY, 1984, 23 (07) :1449-1451

[4] A PENTAHALOGENATED MONOTERPENE FROM THE RED ALGA PORTIERIA-HORNEMANNII PRODUCES A NOVEL CYTOTOXICITY PROFILE AGAINST A DIVERSE PANEL OF HUMAN TUMOR-CELL LINES [J].

FULLER, RW ;

CARDELLINA, JH ;

KATO, Y ;

BRINEN, LS ;

CLARDY, J ;

SNADER, KM ;

BOYD, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (16) :3007-3011

[5] 2-(1-CHLORO-2-HYDROXYETHYL)-4,4-DIMETHYLCYCLOHEXA-2,5-DIENONE - A PRECURSOR OF 4,5-DIMETHYLBENZO[B]FURAN FROM THE RED ALGA DESMIA-HORNEMANNI [J].

HIGA, T .

TETRAHEDRON LETTERS, 1985, 26 (19) :2335-2336

[6]

Higa T., 1989, Studies in Natural Products Chemistry, V5, P341

[7]

HIGA T, 1987, Patent No. 4708962

[8] NEW HALOGENATED MONOTERPENES FROM DESMIA-(CHONDROCOCCUS)-HORNEMANNI [J].

ICHIKAWA, N ;

NAYA, Y ;

ENOMOTO, S .

CHEMISTRY LETTERS, 1974, (11) :1333-1336

[9]

WARING AJ, 1966, ADV ALICYCL CHEM, V1, P207

[10]

WOOLARD FX, 1978, TETRAHEDRON LETT, P2367

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