(Peer-Reviewed) Post-ingestion conversion of dietary indoles into anticancer agents
Li Ping Lin ¹ ², Dan Liu 刘丹 ², Jia Cheng Qian ², Liang Wu ², Quan Zhao 赵权 ¹, Ren Xiang Tan 谭仁祥 ¹ ²
¹ State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210023, China 南京大学 功能生物分子研究所 医药生物技术国家重点实验室
² State Key Laboratory Cultivation Base for TCM Quality and Efficacy, Nanjing University of Chinese Medicine, Nanjing 210023, China 南京中医药大学 中药品质与效能国家重点实验室培育点
National Science Review, 2021-08-13

Human health benefits from consuming cruciferous vegetables that release indole-3-carbinol (I3C), but the in vivo transformation of I3C-related indoles remains underinvestigated. Here we present the post-ingestion conversion of I3C into antitumor agents, 2-(indol-3-ylmethyl)-3,3′-diindolylmethane (LTr1) and 3,3′-diindolylmethane (DIM), by conceptualizing and materializing the reaction flux derailing (RFD) approach as a means of unraveling these stepwise transformations to be non-enzymatic but pH-dependent and gut microbe-sensitive.

In the upper (or acidic) gastrointestine, LTr1 generates through the Michael addition of 3-methyleneindolium (3MI, derived in situ from I3C) to DIM producing from I3C via the formaldehyde-releasing (major) and CO2-liberating (minor) pathways. In the large intestine, 'endogenous' I3C and DIM can form respectively from couplings of formaldehyde with one and two molecules of indole (a tryptophan catabolite). Acid-producing gut bacteria such as Lactobacillus acidophilus facilitate the H+-promotable steps. The work updates the understanding on the merits of I3C consumptions and identifies LTr1 as a drug candidate.
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