†State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
§School of Pharmacy, Nanjing Medical University, Nanjing 210029, China.
Org Lett. 2015 Jun 5;17(11):2610-3. doi: 10.1021/acs.orglett.5b00882. Epub 2015 May 18.
Dalesindole, an antibacterial and anti-inflammatory indole alkaloid with an undescribed carbon skeleton, was stereoselectively constructed by Daldinia eschscholzii through class II aldolase catalyzed Michael addition of fungal chromone with 3,3'-diindolylmethane (DIM) formed in situ from indole-3-carbinol (I3C) under catalyses of monooxygenase and 8-amino-7-oxononanoate synthase (AONS). Dalesindole isomerizes via a retro-Michael reaction to give stereoisomers with bioactivities. The work provides an access to new bioactive hybrids of fungal oligoketide with microbially decorated exogenous chemistry.
达灵多辛，一种具有未描述碳骨架的抗菌和抗炎吲哚生物碱，由 Daldinia eschscholzii 通过 II 类醛缩酶催化真菌色酮与 3,3'-二吲哚基甲烷（DIM）的迈克尔加成反应立体选择性构建，该反应是由吲哚-3-甲醇（I3C）原位形成的，在单加氧酶和 8-氨基-7-氧代壬酸合酶（AONS）的催化下。达灵多辛通过逆向迈克尔反应异构化，得到具有生物活性的立体异构体。这项工作为具有微生物修饰外源性化学的真菌寡肽的新型生物活性杂合提供了一种途径。
