Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum

Spirocitrinols A (1) and B (2), two new citrinin-derived metabolites possessing a spiro[chromane-2,3′-isochromane] skeleton, were isolated from cultures of Penicillium citrinum. Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2 were assigned by ele...

Descripción completa

Detalles Bibliográficos
Autores principales: Tong, Junjie, Zhang, Yang, Xu, Yang, Han, Yangyang, Li, Chuan, Zhuang, Wenying, Che, Yongsheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9940459/
https://www.ncbi.nlm.nih.gov/pubmed/36814878
http://dx.doi.org/10.1039/d3ra00665d
_version_ 1784891082108043264
author Tong, Junjie
Zhang, Yang
Xu, Yang
Han, Yangyang
Li, Chuan
Zhuang, Wenying
Che, Yongsheng
author_facet Tong, Junjie
Zhang, Yang
Xu, Yang
Han, Yangyang
Li, Chuan
Zhuang, Wenying
Che, Yongsheng
author_sort Tong, Junjie
collection PubMed
description Spirocitrinols A (1) and B (2), two new citrinin-derived metabolites possessing a spiro[chromane-2,3′-isochromane] skeleton, were isolated from cultures of Penicillium citrinum. Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2 were assigned by electronic circular dichroism calculations. Compound 2 is the first naturally occurring trimeric citrinin derivative with a spiro[chromane-2,3′-isochromane] core. Compound 1 showed modest cytotoxicity against A549 human tumor cells.
format Online
Article
Text
id pubmed-9940459
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-99404592023-02-21 Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum Tong, Junjie Zhang, Yang Xu, Yang Han, Yangyang Li, Chuan Zhuang, Wenying Che, Yongsheng RSC Adv Chemistry Spirocitrinols A (1) and B (2), two new citrinin-derived metabolites possessing a spiro[chromane-2,3′-isochromane] skeleton, were isolated from cultures of Penicillium citrinum. Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2 were assigned by electronic circular dichroism calculations. Compound 2 is the first naturally occurring trimeric citrinin derivative with a spiro[chromane-2,3′-isochromane] core. Compound 1 showed modest cytotoxicity against A549 human tumor cells. The Royal Society of Chemistry 2023-02-20 /pmc/articles/PMC9940459/ /pubmed/36814878 http://dx.doi.org/10.1039/d3ra00665d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Tong, Junjie
Zhang, Yang
Xu, Yang
Han, Yangyang
Li, Chuan
Zhuang, Wenying
Che, Yongsheng
Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum
title Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum
title_full Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum
title_fullStr Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum
title_full_unstemmed Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum
title_short Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum
title_sort spirocitrinols a and b, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from penicillium citrinum
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9940459/
https://www.ncbi.nlm.nih.gov/pubmed/36814878
http://dx.doi.org/10.1039/d3ra00665d
work_keys_str_mv AT tongjunjie spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum
AT zhangyang spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum
AT xuyang spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum
AT hanyangyang spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum
AT lichuan spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum
AT zhuangwenying spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum
AT cheyongsheng spirocitrinolsaandbcitrininderivativeswithaspirochromane23isochromaneskeletonfrompenicilliumcitrinum

Ejemplares similares