Burapan Supawadee, Kim Mihyang, Han Jaehong
Metalloenzyme Research Group and Department of Integrative Plant Science, Chung-Ang University , Anseong 17546, Korea.
J Agric Food Chem. 2017 Apr 26;65(16):3305-3310. doi: 10.1021/acs.jafc.7b00943. Epub 2017 Apr 14.
Curcumin and other curcuminoids from Curcuma longa are important bioactive compounds exhibiting various pharmacological activities. In addition to the known reductive metabolism of curcuminoids, an alternative biotransformation of curcuminoids by human gut microbiota is reported herein. A curcuminoid mixture, composed of curcumin (1), demethoxycurcumin (2), and bisdemethoxycurcumin (3), was metabolized by the human intestinal bacterium Blautia sp. MRG-PMF1. 1 and 2 were converted to new metabolites by the methyl aryl ether cleavage reaction. Two metabolites, demethylcurcumin (4) and bisdemethylcurcumin (5), were sequentially produced from 1, and demethyldemethoxycurcumin (6) was produced from 2. Until now, sequential reduction of the heptadienone backbone of curcuminoids was the only known metabolism to occur in the human intestine. In this study, a new intestinal metabolism of curcuminoids was discovered. Demethylation of curcuminoids produced three new colonic metabolites that were already known as promising synthetic curcumin analogues. The results could explain the observed beneficial effects of turmeric.
姜黄素及姜黄中的其他姜黄素类化合物是具有多种药理活性的重要生物活性化合物。除了已知的姜黄素类化合物的还原代谢外，本文还报道了人类肠道微生物群对姜黄素类化合物的另一种生物转化。由姜黄素（1）、去甲氧基姜黄素（2）和双去甲氧基姜黄素（3）组成的姜黄素类混合物被人类肠道细菌Blautia sp. MRG-PMF1代谢。1和2通过甲基芳基醚裂解反应转化为新的代谢产物。两种代谢产物，去甲基姜黄素（4）和双去甲基姜黄素（5）依次由1产生，去甲基去甲氧基姜黄素（6）由2产生。到目前为止，姜黄素类化合物庚二烯酮骨架的顺序还原是人类肠道中唯一已知的代谢方式。在本研究中，发现了姜黄素类化合物一种新的肠道代谢。姜黄素类化合物的去甲基化产生了三种新的结肠代谢产物，这些产物已被认为是有前景的合成姜黄素类似物。这些结果可以解释姜黄所观察到的有益效果。
