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Biosynthesis of resveratrol derivatives and evaluation of their anti-inflammatory activity
Applied Biological Chemistry ( IF 3.2 ) Pub Date : 2021-04-02 , DOI: 10.1186/s13765-021-00607-4
Yoojin Chong , Hye Lim Lee , Jihyeon Song , Youngshim Lee , Bong-Gyu Kim , Hyejung Mok , Joong-Hoon Ahn

Resveratrol is a typical plant phenolic compound whose derivatives are synthesized through hydroxylation, O-methylation, prenylation, and oligomerization. Resveratrol and its derivatives exhibit anti-neurodegenerative, anti-rheumatoid, and anti-inflammatory effects. Owing to the diverse biological activities of these compounds and their importance in human health, this study attempted to synthesize five resveratrol derivatives (isorhapontigenin, pterostilbene, 4-methoxyresveratrol, piceatannol, and rhapontigenin) using Escherichia coli. Two-culture system was used to improve the final yield of resveratrol derivatives. Resveratrol was synthesized in the first E. coli cell that harbored genes for resveratrol biosynthesis including TAL (tyrosine ammonia lyase), 4CL (4-coumaroyl CoA ligase), STS (stilbene synthase) and genes for tyrosine biosynthesis such as aroG (deoxyphosphoheptonate aldolase) and tyrA (prephenate dehydrogenase). Thereafter, culture filtrate from the first cell was used for the modification reaction carried out using the second E. coli harboring hydroxylase and/or O-methyltransferase. Approximately, 89.8 mg/L of resveratrol was synthesized and using the same, five derivatives were prepared with a conversion rate of 88.2% to 22.9%. Using these synthesized resveratrol derivatives, we evaluated their anti-inflammatory activity. 4-Methoxyresveratrol, pterostilbene and isorhapontigenin showed the anti-inflammatory effects without any toxicity. In addition, pterostilbene exhibited the enhanced anti-inflammatory effects for macrophages compared to resveratrol.

中文翻译:

白藜芦醇衍生物的生物合成及其抗炎活性的评价

白藜芦醇是一种典型的植物酚类化合物,其衍生物是通过羟基化,O-甲基化,异戊烯基化和低聚反应合成的。白藜芦醇及其衍生物具有抗神经变性,抗类风湿和抗炎作用。由于这些化合物的多种生物活性及其在人类健康中的重要性,本研究尝试使用大肠杆菌合成五种白藜芦醇衍生物(异佛手皂甙元,紫檀骨素,4-甲氧基白藜芦醇,苦味酚和菜黄素)。两次培养系统用于提高白藜芦醇衍生物的最终收率。白藜芦醇是在第一个具有白藜芦醇生物合成基因的大肠杆菌细胞中合成的,包括TAL(酪氨酸氨裂合酶),4CL(4-香豆酰CoA连接酶),STS(苯乙烯合成酶)和酪氨酸生物合成基因,例如aroG(脱氧磷酸庚酯醛缩酶)和tyrA(苯甲酸酯脱氢酶)。之后,将来自第一个细胞的培养滤液用于使用带有羟化酶和/或O-甲基转移酶的第二个大肠杆菌进行的修饰反应。大约合成了89.8 mg / L的白藜芦醇,并使用白藜芦醇制备了五种衍生物,转化率为88.2%至22.9%。使用这些合成的白藜芦醇衍生物,我们评估了它们的抗炎活性。4-甲氧基白藜芦醇,萜烯和异皂甙元显示抗炎作用,无任何毒性。此外,与白藜芦醇相比,紫檀二烯对巨噬细胞具有增强的抗炎作用。
更新日期:2021-04-04
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