METABOLITES OF LACHNELLULA-FUSCOSANGUINEA (REHM) .1. THE ISOLATION, STRUCTURE DETERMINATION, AND SYNTHESIS OF LACHNELLULOIC ACID

被引:19
作者
AYER, WA [1 ]
VILLAR, JDF [1 ]
机构
[1] UNIV ALBERTA, DEPT CHEM, EDMONTON T6G 2G2, ALBERTA, CANADA
关键词
D O I
10.1139/v85-197
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The metabolites produced in liquid culture by the fungus L. fuscosanguinea (Rehm) Dennis have been examined and 2 antifungal agents, lachnelluloic acid and lachnellulone, have been isolated. The structure of lachnelluloic acid has been established as (-)-4-hydroxy-3-octanoyl-6-pentyl-5,6-dihydro-2-pyrone by chemical and spectroscopic methods. The total synthesis of racemic lachnelluloic acid, starting from 6,8-tridecanedione is reported. Lachnelluloic acid shows strong antifungal activity against Ceratocystis ulmi, the causative agent of Dutch elm disease.
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页码:1161 / 1165
页数:5
相关论文
共 10 条
[1]   ALTERNARIC ACID .3. STRUCTURE [J].
BARTELSKEITH, JR .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR) :1662-1665
[2]   HETEROCYCLIC SYNTHESES WITH MALONYL CHLORIDE .8. HYDROXYPYRONES FROM 1,3-DIKETONES [J].
BUTT, MA ;
ELVIDGE, JA .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (SEP) :4483-&
[3]  
Dharne C. G., 1965, Phytopathologische Zeitschrift, V53, P101
[4]  
GELIN S, 1968, B SOC CHIM FR, P288
[5]   A STUDY OF ACYLATION OF 4-HYDROXY-6-METHYL-2-PYRONE AND 4-HYDROXY-6-PHENYL-2-PYRONE [J].
MARCUS, E ;
STEPHEN, JF ;
CHAN, JK .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (01) :13-&
[6]   STUDIES ON PODOBLASTIN .1. PODOBLASTIN-A, PODOBLASTIN-B AND PODOBLASTIN-C - NEW ANTIFUNGAL 3-ACYL-4-HYDROXY-5,6-DIHYDRO-2-PYRONES OBTAINED FROM PODOPHYLLUM-PELTATUM L [J].
MIYAKADO, M ;
INOUE, S ;
TANABE, Y ;
WATANABE, K ;
OHNO, N ;
YOSHIOKA, H ;
MABRY, TJ .
CHEMISTRY LETTERS, 1982, (10) :1539-1542
[7]   METABOLITES OF ALTERNARIA-SOLANI .10. ALTERNARIC ACID - PROOF OF BIOSYNTHESIS VIA CONDENSATION OF 2 POLYKETIDE CHAINS - COMPLETE ASSIGNMENT OF THE H-1 AND C-13 MAGNETIC-RESONANCE SPECTRA BY 2D TECHNIQUES [J].
STOESSL, A ;
STOTHERS, JB .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (03) :549-553
[8]  
STOTHERS JB, 1972, CARBON 13 NMR SPECTR, P183
[9]   STUDIES ON PODOBLASTIN .2. A NEW 3-ACYL-4-HYDROXY-2-PYRONE SYNTHESIS AND ITS APPLICATION TO TOTAL SYNTHESIS OF (+/-) PODOBLASTIN-A, PODOBLASTIN-B AND PODOBLASTIN-C [J].
TANABE, Y ;
MIYAKADO, M ;
OHNO, N ;
YOSHIOKA, H .
CHEMISTRY LETTERS, 1982, (10) :1543-1546
[10]  
TSUNEDA A, 1982, FUNGAL MORPHOLOGY EC, P99