鉴定averantin为黄曲霉毒素B1前体：确定其在生物合成途径中的位置。
Identification of averantin as an aflatoxin B1 precursor: placement in the biosynthetic pathway.
作者信息
Bennett J W, Lee L S, Shoss S M, Boudreaux G H
出版信息
Appl Environ Microbiol. 1980 Apr;39(4):835-9. doi: 10.1128/aem.39.4.835-839.1980.
Abstract
A new blocked mutant of Aspergillus parasiticus produces no detectable aflatoxin B1, but accumulates several polyhydroxyanthraquinones. One of these pigments was identified as averantin. This is the first report of its formation by A. parasiticus. Radiotracer studies with [14C]averantin showed that 15.3% of label from averantin was incorporated into aflatoxin B1. This incorporation was blocked by dichlorvos. With radiotracers and other mutants, averantin was placed after norsolorinic acid and before averufin in the biosynthetic pathway in which the general steps are norsolorinic acid leads to averantin leads to averufin leads to versiconal hemiacetal acetate leads to versicolorin A leads to sterigmatocystin leads to aflatoxin B1.
摘要
一种新的寄生曲霉阻断突变体不产生可检测到的黄曲霉毒素B1，但积累了几种多羟基蒽醌。其中一种色素被鉴定为阿弗菌素。这是关于寄生曲霉形成阿弗菌素的首次报道。用[14C]阿弗菌素进行的放射性示踪研究表明，阿弗菌素中15.3%的标记物被整合到黄曲霉毒素B1中。敌敌畏可阻断这种整合。利用放射性示踪剂和其他突变体，在生物合成途径中，阿弗菌素位于诺索尔菌素酸之后、阿弗鲁芬之前，其一般步骤为诺索尔菌素酸生成阿弗菌素，阿弗菌素生成阿弗鲁芬，阿弗鲁芬生成Versiconal半缩醛乙酸酯，Versiconal半缩醛乙酸酯生成Versicolorin A，Versicolorin A生成柄曲霉素，柄曲霉素生成黄曲霉毒素B1。
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本文引用的文献
1
INCORPORATION OF LABELLED COMPOUNDS INTO AFLATOXINS.
Biochim Biophys Acta. 1964 May 11;86:418-20. doi: 10.1016/0304-4165(64)90077-7.
2
Studies in mycological chemistry. XIX. "Product B" (averantin) [1,3,6,8-tetrahydroxy-2-(1-hydroxyhexyl)anthraquinone], a pigment from Aspergillus versicolor (Vuillemin) Tiraboschi.
J Chem Soc Perkin 1. 1966;9:855-7. doi: 10.1039/j39660000855.
3
Enrichment of auxotrophic mutants of Aspergillus flavus by tritium suicide.
J Bacteriol. 1968 Nov;96(5):1551-5. doi: 10.1128/jb.96.5.1551-1555.1968.
4
Norsolorinic acid from a mutant strain of Aspergillus parasiticus.
J Am Oil Chem Soc. 1971 Feb;48(2):93-4. doi: 10.1007/BF02635696.
5
Isolation of averufin from a mutant of Aspergillus parasiticus impaired in aflatoxin biosynthesis.
Biochem Biophys Res Commun. 1972 Jun 9;47(5):1051-5. doi: 10.1016/0006-291x(72)90939-4.
6
Step of dichlorvos inhibition in the pathway of aflatoxin biosynthesis.
Appl Microbiol. 1974 Jul;28(1):52-7. doi: 10.1128/am.28.1.52-57.1974.
7
Conversion of averufin into aflatoxins by Aspergillus parasiticus.
Biochemistry. 1973 Dec 4;12(25):5167-71. doi: 10.1021/bi00749a023.
8
Aflatoxin and anthraquinone biosynthesis by nitrosoguanidine-derived mutants of Aspergillus parasiticus.
Can J Microbiol. 1973 Nov;19(11):1373-8. doi: 10.1139/m73-221.
9
Conversion of sterigmatocystin to aflatoxin B 1 by Aspergillus parasiticus.
Biochem Biophys Res Commun. 1973 Jun 8;52(3):992-7. doi: 10.1016/0006-291x(73)91035-8.
10
Averufin in the biosynthesis of aflatoxin B.
J Am Chem Soc. 1973 Mar 7;95(5):1668-9. doi: 10.1021/ja00786a056.
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