BIOSYNTHESIS OF CYANOGENIC GLUCOSIDES IN THE LEPIDOPTERA - INCORPORATION OF [U-C-14]-2-METHYLPROPANEALDOXIME, 2S-[U-C-14]-METHYLBUTANEALDOXIME AND D,L-[U-C-14]-N-HYDROXYISOLEUCINE INTO LINAMARIN AND LOTAUSTRALIN BY THE LARVAE OF ZYGAENA-TRIFOLII

被引:16
作者
HOLZKAMP, G [1 ]
NAHRSTEDT, A [1 ]
机构
[1] WESTFAL WILHELMS UNIV, INST PHARMAZEUT BIOL & PHYTOCHEM, D-48149 MUNSTER, GERMANY
关键词
ZYGAENA TRIFOLII; ZYGAENIDAE; LEPIDOPTERA; CYANOGENIC GLUCOSIDES; LINAMARIN; LOTAUSTRALIN; BIOSYNTHESIS; ALDOXIME; INTERMEDIATES; N-HYDROXYAMINO ACID INTERMEDIATES; 2-METHYLPROPANEALDOXIME; 2S-METHYLBUTANEALDOXIME; D; L-N-HYDROXYISOLEUCINE;
D O I
10.1016/0965-1748(94)90082-5
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
[U-C-14]-2-methylpropanealdoxime was incorporated into the cyanogenic glucoside linamarin (1-cyano-1-methylethyl-beta-D-glucopyraraoside) and D,L-[U-C-14]-N-hydroxyisoleucine and 2S-[U-C-14]-methylbutanealdoxime were incorporated into the cyanogenic glucoside lotaustralin (R-1-cyano-1-methylpropyl-beta-D-glucopyranoside) after injection into the haemocoele of larvae of Zygaena trifolii. The incorporation rates of the aldoximes were 17-22% and of the N-hydroxyamino acid 4-5%. The results indicate that both aldoximes and N-hydroxyamino acids are intermediates in the biosynthesis of linamarin and lotaustralin by the larvae by Zygaena trifolii.
引用
收藏
页码:161 / 165
页数:5
相关论文
共 21 条
[1]   EVIDENCE THAT LINAMARIN AND LOTAUSTRALIN, THE 2 CYANOGENIC GLUCOSIDES OF TRIFOLIUM-REPENS L ARE SYNTHESIZED BY A SINGLE SET OF MICROSOMAL-ENZYMES CONTROLLED BY THE AC/AC LOCUS [J].
COLLINGE, DB ;
HUGHES, MA .
PLANT SCIENCE LETTERS, 1984, 34 (1-2) :119-125
[2]   THE METABOLISM OF A NATURAL PRODUCT - LESSONS LEARNED FROM CYANOGENIC GLYCOSIDES [J].
CONN, EE .
PLANTA MEDICA, 1991, 57 :S1-S9
[3]  
CUTLER AJ, 1981, J BIOL CHEM, V256, P4253
[4]   THE BIOSYNTHESIS OF CYANOGENIC GLUCOSIDES IN LINUM-USITATISSIMUM (LINEN FLAX) INVITRO [J].
CUTLER, AJ ;
CONN, EE .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1981, 212 (02) :468-474
[5]   BIOSYNTHESIS OF CYANOGENIC GLUCOSIDES IN BUTTERFLIES AND MOTHS - EFFECTIVE INCORPORATION OF 2-METHYLPROPANENITRILE AND 2-METHYLBUTANENITRILE INTO LINAMARIN AND LOTAUSTRALIN BY ZYGAENA AND HELICONIUS SPECIES (LEPIDOPTERA) [J].
DAVIS, RH ;
NAHRSTEDT, A .
INSECT BIOCHEMISTRY, 1987, 17 (05) :689-693
[6]  
Davis RH, 1985, COMPREHENSIVE INSECT, V11, P635, DOI DOI 10.1016/B978-0-08-030812-8.50020-4
[7]  
DAVIS RH, 1986, Z NATURFORSCH C, V41, P928
[8]   2-NITRO-3-(PARA-HYDROXYPHENYL)PROPIONATE AND ACI-1-NITRO-2-(PARA-HYDROXYPHENYL)ETHANE, 2 INTERMEDIATES IN THE BIOSYNTHESIS OF THE CYANOGENIC GLUCOSIDE DHURRIN IN SORGHUM-BICOLOR (L) MOENCH [J].
HALKIER, BA ;
LYKKESFELDT, J ;
MOLLER, BL .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (02) :487-491
[9]  
MCFARLANE IJ, 1975, J BIOL CHEM, V250, P4708
[10]   CHEMICAL SYNTHESIS OF LABELED INTERMEDIATES IN CYANOGENIC GLUCOSIDE BIOSYNTHESIS [J].
MOLLER, BL .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1978, 14 (05) :663-671