A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina

[Image: see text] The widespread seagrass Zostera marina contains a new diarylheptanoid heterodimer, zosterabisphenone C (1), featuring an unprecedented rearrangement of one of its benzene rings to a cyclopentenecarbonyl unit. The planar structure and absolute configuration of zosterabisphenone C we...

Descripción completa

Detalles Bibliográficos
Autores principales: Grauso, Laura, Li, Yan, Scarpato, Silvia, Cacciola, Nunzio Antonio, De Cicco, Paola, Zidorn, Christian, Mangoni, Alfonso
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9623580/
https://www.ncbi.nlm.nih.gov/pubmed/36261887
http://dx.doi.org/10.1021/acs.jnatprod.2c00796
_version_ 1784822031718547456
author Grauso, Laura
Li, Yan
Scarpato, Silvia
Cacciola, Nunzio Antonio
De Cicco, Paola
Zidorn, Christian
Mangoni, Alfonso
author_facet Grauso, Laura
Li, Yan
Scarpato, Silvia
Cacciola, Nunzio Antonio
De Cicco, Paola
Zidorn, Christian
Mangoni, Alfonso
author_sort Grauso, Laura
collection PubMed
description [Image: see text] The widespread seagrass Zostera marina contains a new diarylheptanoid heterodimer, zosterabisphenone C (1), featuring an unprecedented rearrangement of one of its benzene rings to a cyclopentenecarbonyl unit. The planar structure and absolute configuration of zosterabisphenone C were elucidated by a combination of spectroscopic (MS, ECD, and low-temperature NMR) and computational (DFT-NMR and DFT-ECD) evidence. Consistent with the previously isolated zosterabisphenones, compound 1 was selectively cytotoxic against HCT 116 adenocarcinoma colon cancer cells, reducing their viability by 73% at 10 μM (IC(50) of 7.6 ± 1.1 μM). The biosynthetic origin of zosterabisphenone C (1) from an oxidative rearrangement of zosterabisphenone A (4) is proposed.
format Online
Article
Text
id pubmed-9623580
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society and American Society of Pharmacognosy
record_format MEDLINE/PubMed
spelling pubmed-96235802022-11-02 A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina Grauso, Laura Li, Yan Scarpato, Silvia Cacciola, Nunzio Antonio De Cicco, Paola Zidorn, Christian Mangoni, Alfonso J Nat Prod [Image: see text] The widespread seagrass Zostera marina contains a new diarylheptanoid heterodimer, zosterabisphenone C (1), featuring an unprecedented rearrangement of one of its benzene rings to a cyclopentenecarbonyl unit. The planar structure and absolute configuration of zosterabisphenone C were elucidated by a combination of spectroscopic (MS, ECD, and low-temperature NMR) and computational (DFT-NMR and DFT-ECD) evidence. Consistent with the previously isolated zosterabisphenones, compound 1 was selectively cytotoxic against HCT 116 adenocarcinoma colon cancer cells, reducing their viability by 73% at 10 μM (IC(50) of 7.6 ± 1.1 μM). The biosynthetic origin of zosterabisphenone C (1) from an oxidative rearrangement of zosterabisphenone A (4) is proposed. American Chemical Society and American Society of Pharmacognosy 2022-10-20 2022-10-28 /pmc/articles/PMC9623580/ /pubmed/36261887 http://dx.doi.org/10.1021/acs.jnatprod.2c00796 Text en © 2022 The Authors. Published by American Chemical Society and American Society of Pharmacognosy 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 Grauso, Laura
Li, Yan
Scarpato, Silvia
Cacciola, Nunzio Antonio
De Cicco, Paola
Zidorn, Christian
Mangoni, Alfonso
A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina
title A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina
title_full A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina
title_fullStr A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina
title_full_unstemmed A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina
title_short A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina
title_sort cytotoxic heterodimeric cyclic diarylheptanoid with a rearranged benzene ring from the seagrass zostera marina
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9623580/
https://www.ncbi.nlm.nih.gov/pubmed/36261887
http://dx.doi.org/10.1021/acs.jnatprod.2c00796
work_keys_str_mv AT grausolaura acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT liyan acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT scarpatosilvia acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT cacciolanunzioantonio acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT deciccopaola acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT zidornchristian acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT mangonialfonso acytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT grausolaura cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT liyan cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT scarpatosilvia cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT cacciolanunzioantonio cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT deciccopaola cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT zidornchristian cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina
AT mangonialfonso cytotoxicheterodimericcyclicdiarylheptanoidwitharearrangedbenzeneringfromtheseagrasszosteramarina

Ejemplares similares