Pestalotiopsins A and B: New caryophyllenes from an endophytic fungus of Taxus brevifolia

被引：95

作者：

Pulici, M

Sugawara, F

Koshino, H

Uzawa, J

Yoshida, S

Lobkovsky, E

Clardy, J

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

[2] CORNELL UNIV,BAKER LAB,DEPT CHEM,ITHACA,NY 14853

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 06期

关键词：

D O I：

10.1021/jo951736v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new caryophyllene sesquiterpenes have been isolated from Pestalotiopsis sp., an endophytic fungus associated with the bark and leaves of Taxus brevifolia. Pestalotiopsin A (1) has a novel oxatricyclic ring system while pestalotiopsin B (3) exists as two slowly equilibrating atropisomers (6:5 ratio of beta beta:beta alpha) in chloroform solution at room temperature. Structures of 1 and 3 were determined by spectroscopic analyses and single-crystal X-ray diffraction.

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页码：2122 / 2124

页数：3

相关论文

共 11 条

[1] METABOLITES OF THE HIGHER FUNGI .23. THE PUNCTAPORONINS - NOVEL BI-CYCLIC, TRI-CYCLIC, AND TETRA-CYCLIC SESQUITERPENES RELATED TO CARYOPHYLLENE, FROM THE FUNGUS PORONIA-PUNCTATA (LINNAEUS, FRIES) FRIES [J].

ANDERSON, JR ;

EDWARDS, RL ;

POYSER, JP ;

WHALLEY, AJS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (04) :823-831

[2]

BARRERO FA, 1995, TETRAHEDRON, V51, P3813

[3] METABOLITES OF THE HIGHER FUNGI .25. PUNCTAPORONIN-G FROM THE FUNGUS PORONIA-PUNCTATA (LINNAEUS, FRIES) FRIES [J].

EDWARDS, RL ;

MAITLAND, DJ ;

POYSER, JP ;

WHALLEY, AJS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :1939-1941

[4] GRADIENT-ENHANCED PROTON-DETECTED HETERONUCLEAR MULTIPLE-QUANTUM COHERENCE SPECTROSCOPY [J].

HURD, RE ;

JOHN, BK .

JOURNAL OF MAGNETIC RESONANCE, 1991, 91 (03) :648-653

[5] GRADIENT-ENHANCED SPECTROSCOPY [J].

HURD, RE .

JOURNAL OF MAGNETIC RESONANCE, 1990, 87 (02) :422-428

[6] TOTAL SYNTHESIS OF (+/-)-PUNCTAPORONIN-B [J].

KENDE, AS ;

KALDOR, I ;

ASLANIAN, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6265-6266

[7] CONFORMATIONAL ASPECTS OF CARYOPHYLLENE - POPULATION OF STABLE CONFORMERS AND RING INVERSION BARRIER OF TRANS CYCLONONENE RING PORTION [J].

SHIRAHAMA, H ;

OSAWA, E ;

CHHABRA, BR ;

SHIMOKAWA, T ;

YOKONO, T ;

KANAIWA, T ;

AMIYA, T ;

MATSUMOTO, T .

TETRAHEDRON LETTERS, 1981, 22 (16) :1527-1528

[8] TAXOL AND TAXANE PRODUCTION BY TAXOMYCES-ANDREANAE, AN ENDOPHYTIC FUNGUS OF PACIFIC YEW [J].

STIERLE, A ;

STROBEL, G ;

STIERLE, D .

SCIENCE, 1993, 260 (5105) :214-216

[9]

SUFFNESS M, 1993, ANNU REP MED CHEM, V28, P305

[10] PLANT ANTITUMOR AGENTS .6. ISOLATION AND STRUCTURE OF TAXOL, A NOVEL ANTILEUKEMIC AND ANTITUMOR AGENT FROM TAXUS-BREVIFOLIA [J].

WANI, MC ;

TAYLOR, HL ;

WALL, ME ;

COGGON, P ;

MCPHAIL, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (09) :2325-&