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

[Image: see text] (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 revis...

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Autores principales: Lee, Ju Ryeong, Park, Kyoung Jin, Ham, Song Lim, Kim, Jonghwan, Kim, Chung Sub
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10116614/
https://www.ncbi.nlm.nih.gov/pubmed/37091423
http://dx.doi.org/10.1021/acsomega.3c00408
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author Lee, Ju Ryeong
Park, Kyoung Jin
Ham, Song Lim
Kim, Jonghwan
Kim, Chung Sub
author_facet Lee, Ju Ryeong
Park, Kyoung Jin
Ham, Song Lim
Kim, Jonghwan
Kim, Chung Sub
author_sort Lee, Ju Ryeong
collection PubMed
description [Image: see text] (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.
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spelling pubmed-101166142023-04-21 Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring Lee, Ju Ryeong Park, Kyoung Jin Ham, Song Lim Kim, Jonghwan Kim, Chung Sub ACS Omega [Image: see text] (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. American Chemical Society 2023-04-06 /pmc/articles/PMC10116614/ /pubmed/37091423 http://dx.doi.org/10.1021/acsomega.3c00408 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Lee, Ju Ryeong
Park, Kyoung Jin
Ham, Song Lim
Kim, Jonghwan
Kim, Chung Sub
Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring
title Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring
title_full Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring
title_fullStr Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring
title_full_unstemmed Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring
title_short Structure Revision of Anti-Inflammatory Indole Alkaloids with a 1,2-Benzisoxazole Ring
title_sort structure revision of anti-inflammatory indole alkaloids with a 1,2-benzisoxazole ring
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10116614/
https://www.ncbi.nlm.nih.gov/pubmed/37091423
http://dx.doi.org/10.1021/acsomega.3c00408
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