Microbial conversion of jasmonates-hydroxylations by Aspergillus niger

被引：25

作者：

Miersch, O ^{[1
]}

Porzel, A ^{[1
]}

Wasternack, C ^{[1
]}

机构：

[1] Inst Pflanzenbiochem, D-06120 Halle, Germany

来源：

PHYTOCHEMISTRY | 1999年 / 50卷 / 07期

关键词：

Aspergillus niger; Euascomycetidae; fungal hydroxylation; (-)-jasmonic acid; methyl (-)-jasmonate; (11S)-(-)-hydroxyjasmonic acid; (11R)-(-)-hydroxyjasmonic acid; (-)-11,12-didehydrojasmonic acid; (10E)-9-hydroxyjasmonic acid; (9E)-11-hydroxyjasmonic acid; (+/-)-9,10-dihydrojasmonic acid; (+/-)-11 xi-hydroxy-9,10-dihydrojasmonic acid;

D O I：

10.1016/S0031-9422(98)00698-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Aspergillus niger is able to hydroxylate the pentenyl side chain of(-)-jasmonic acid (JA) leading to (11S)-(-)-hydroxy-JA/(11 R)(-)-hydroxy-JA (2:1) and (-)-11,12-didehydro-JA. Methyl (-)-jasmonate (JA-Me) is converted upon hydrolysis. During prolonged cultivation or at non-optimized isolation procedures, the 11-hydroxy-(9Z)-pentenyl side chain may isomerize to (10E)-9-hydroxy-and (9E)-11-hydroxy-compounds by allylic rearrangement. The fungus hydroxylates (+/-)-9,10-dihydro-JA at position C-11 into 11 xi-hydroxy-9, 10-dihydro-JA. As JA-Me, the methyl dihydro-JA is hydroxylated only upon hydrolysis into the free acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1147 / 1152

页数：6

共 23 条

[1]

[Anonymous], 1993, Natural Product Letters

[2] ABSOLUTE CONFIGURATIONS OF SECONDARY ALCOHOLS - GAS-CHROMATOGRAPHIC MODIFICATION OF HOREAUS METHOD [J].

BROOKS, CJW ;

GILBERT, JD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (05) :194-195

[3] Biosynthesis and action of jasmonates in plants [J].

Creelman, RA ;

Mullet, JE .

ANNUAL REVIEW OF PLANT PHYSIOLOGY AND PLANT MOLECULAR BIOLOGY, 1997, 48 :355-381

[4] ENANTIOSELECTIVE HYDROLYSIS OF RACEMIC METHYL JASMONATE USING MICROORGANISMS AND ISOLATED-ENZYMES [J].

DART, RK ;

KERRY, S ;

MARPLES, BA .

ENZYME AND MICROBIAL TECHNOLOGY, 1992, 14 (12) :954-958

[5] JASMONIC ACID IS A SIGNAL TRANSDUCER IN ELICITOR-INDUCED PLANT-CELL CULTURES [J].

GUNDLACH, H ;

MULLER, MJ ;

KUTCHAN, TM ;

ZENK, MH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (06) :2389-2393

[6]

HELDER H, 1993, PHYSIOL PLANTARUM, V88, P647, DOI 10.1111/j.1399-3054.1993.tb01384.x

[7]

HOREAU A, 1961, TETRAHEDRON LETT, P506

[8]

KEHLEN A, 1991, THESIS U HALLE

[9] SYNTHESIS OF MEDIUM-CYCLIC AND MARCO-CYCLIC COMPOUNDS .3. SYNTHESIS OF JASMINE KETOLACTONE [J].

KITAHARA, T ;

IWAMOTO, M ;

TAKAGI, Y ;

MORI, K ;

MATSUI, M .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1984, 48 (07) :1731-1734

[10] POTATO TUBER-INDUCING ACTIVITIES OF JASMONIC ACID AND RELATED-COMPOUNDS [J].

KODA, Y ;

KIKUTA, Y ;

TAZAKI, H ;

TSUJINO, Y ;

SAKAMURA, S ;

YOSHIHARA, T .

PHYTOCHEMISTRY, 1991, 30 (05) :1435-1438

← 1 2 3 →