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Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring.

ABSTRACT: (R)- and (S)-2-(benzo[d]isoxazol-3-yl)-2-ethylindolin-3-one [(±)-1] were previously isolated from NIRAM, a natural blue dye from Polygonum tinctorium, and their structures were initially proposed to possess a 1,2-benzisoxazole ring. In this study, the structures of (±)-1 were revised to have an indole-anthranilic acid fused tetracyclic ring rather than the 1,2-benzisoxazole ring by reanalysis of one-dimensional (1D) and two-dimensional (2D) NMR followed by density functional theory (DFT) chemical shift calculation, DP4+ technique, and ECD simulation.

SUBMITTER: Lee JR

PROVIDER: S-EPMC10116614 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring.

Lee Ju Ryeong JR Park Kyoung Jin KJ Ham Song Lim SL Kim Jonghwan J Kim Chung Sub CS

ACS omega 20230406 15

(R)- and (S)-2-(benzo[d]isoxazol-3-yl)-2-ethylindolin-3-one [(±)-1] were previously isolated from NIRAM, a natural blue dye from Polygonum tinctorium, and their structures were initially proposed to possess a 1,2-benzisoxazole ring. In this study, the structures of (±)-1 were revised to have an indole-anthranilic acid fused tetracyclic ring rather than the 1,2-benzisoxazole ring by reanalysis of one-dimensional (1D) and two-dimensional (2D) NMR followed ...[more]

PMID: 37091423

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