Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina

[Image: see text] Two diarylheptanoid heterodimers, zosterabisphenones A (1) and B (2), were isolated from the seagrass Zostera marina. They feature unprecedented catechol keto tautomers, stable because of steric constraints. Their structure elucidation was based on extensive low-temperature NMR stu...

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Autores principales: Li, Yan, Grauso, Laura, Scarpato, Silvia, Cacciola, Nunzio Antonio, Borrelli, Francesca, Zidorn, Christian, Mangoni, Alfonso
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453622/
https://www.ncbi.nlm.nih.gov/pubmed/34491069
http://dx.doi.org/10.1021/acs.orglett.1c02537
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author Li, Yan
Grauso, Laura
Scarpato, Silvia
Cacciola, Nunzio Antonio
Borrelli, Francesca
Zidorn, Christian
Mangoni, Alfonso
author_facet Li, Yan
Grauso, Laura
Scarpato, Silvia
Cacciola, Nunzio Antonio
Borrelli, Francesca
Zidorn, Christian
Mangoni, Alfonso
author_sort Li, Yan
collection PubMed
description [Image: see text] Two diarylheptanoid heterodimers, zosterabisphenones A (1) and B (2), were isolated from the seagrass Zostera marina. They feature unprecedented catechol keto tautomers, stable because of steric constraints. Their structure elucidation was based on extensive low-temperature NMR studies and ECD and MS data, with the essential aid of DFT prediction of NMR and ECD spectra. Zosterabisphenone B (2) was selectively cytotoxic against the adenocarcinoma colon cancer cell line HCT116 with IC(50) 3.6 ± 1.1 μM at 48 h.
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spelling pubmed-84536222021-09-22 Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina Li, Yan Grauso, Laura Scarpato, Silvia Cacciola, Nunzio Antonio Borrelli, Francesca Zidorn, Christian Mangoni, Alfonso Org Lett [Image: see text] Two diarylheptanoid heterodimers, zosterabisphenones A (1) and B (2), were isolated from the seagrass Zostera marina. They feature unprecedented catechol keto tautomers, stable because of steric constraints. Their structure elucidation was based on extensive low-temperature NMR studies and ECD and MS data, with the essential aid of DFT prediction of NMR and ECD spectra. Zosterabisphenone B (2) was selectively cytotoxic against the adenocarcinoma colon cancer cell line HCT116 with IC(50) 3.6 ± 1.1 μM at 48 h. American Chemical Society 2021-09-07 2021-09-17 /pmc/articles/PMC8453622/ /pubmed/34491069 http://dx.doi.org/10.1021/acs.orglett.1c02537 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Li, Yan
Grauso, Laura
Scarpato, Silvia
Cacciola, Nunzio Antonio
Borrelli, Francesca
Zidorn, Christian
Mangoni, Alfonso
Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
title Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
title_full Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
title_fullStr Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
title_full_unstemmed Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
title_short Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
title_sort stable catechol keto tautomers in cytotoxic heterodimeric cyclic diarylheptanoids from the seagrass zostera marina
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453622/
https://www.ncbi.nlm.nih.gov/pubmed/34491069
http://dx.doi.org/10.1021/acs.orglett.1c02537
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