（-）-异长叶烯微生物转化产物对化学诱变剂诱导 SOS 活性的抑制作用。

Suppression of SOS-inducing activity of chemical mutagens by metabolites from microbial transformation of (-)-isolongifolene.

机构信息

Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosakashi, Osaka 577-8502, Japan.

出版信息

J Agric Food Chem. 2010 Feb 24;58(4):2164-7. doi: 10.1021/jf903651c.

DOI:10.1021/jf903651c

PMID:20108941

Abstract

In this study, biotransformation of (-)-isolongifolene (1) by Glomerella cingulata and suppressive effect on umuC gene expression by chemical mutagens 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide) and aflatoxin B(1) (AFB(1)) of the SOS response in Salmonella typhimurium TA1535/pSK1002 were investigated. Initially, 1 was carried out the microbial transformation by G. cingulata. The result found that 1 was converted into (-)-isolongifolen-9-one (2), (-)-(2S)-13-hydroxy-isolongifolen-9-one (3), and (-)-(4R)-4-hydroxy-isolongifolen-9-one (4) by G. cingulata, and their conversion rates were 60, 25, and 15%, respectively. The metabolites suppressed the SOS-inducing activity of furylfuramid and AFB(1) in the umu test. Comound 2 showed gene expression by chemical mutagens furylfuramide and AFB(1) was suppressed 54 and 50% at <0.5 mM, respectively. Compound 2 is the most effective compound in this experiment.

摘要

在这项研究中，我们研究了胶孢炭疽菌对 (-)-异长叶烯（1）的生物转化作用，以及化学诱变剂 2-(2-呋喃基)-3-(5-硝基-2-呋喃基)丙烯酰胺（呋喃呋喃酰胺）和黄曲霉毒素 B(1)（AFB(1)）对鼠伤寒沙门氏菌 TA1535/pSK1002 的 SOS 反应中 umuC 基因表达的抑制作用。首先，我们用胶孢炭疽菌对 1 进行了微生物转化。结果发现，1 被胶孢炭疽菌转化为 (-)-异长叶烯-9-酮（2）、(-)-(2S)-13-羟基-异长叶烯-9-酮（3）和 (-)-(4R)-4-羟基-异长叶烯-9-酮（4），转化率分别为 60%、25%和 15%。代谢产物抑制了 furylfuramide 和 AFB(1)在 umu 试验中的 SOS 诱导活性。化合物 2 对化学诱变剂 furylfuramide 和 AFB(1)的基因表达抑制率分别为 54%和 50%，在<0.5mM 时。化合物 2 是本实验中最有效的化合物。