ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.

[Image: see text] Metabolites 1 and 2, isolated from cultures of the basidiomycete Resupinatus sp. BCC84615, collected in a tropical forest in northeastern Thailand, showed weak antibiotic activity against Bacillus subtilis and Staphylococcus aureus and cytotoxicity against cancer cell lines. Their...

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Autores principales: Harms, Karen, Paomephan, Pathompong, Boonpratuang, Thitiya, Choeyklin, Rattaket, Boonchird, Chuenchit, Surup, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10683060/
https://www.ncbi.nlm.nih.gov/pubmed/37931226
http://dx.doi.org/10.1021/acs.jnatprod.3c00174
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author Harms, Karen
Paomephan, Pathompong
Boonpratuang, Thitiya
Choeyklin, Rattaket
Boonchird, Chuenchit
Surup, Frank
author_facet Harms, Karen
Paomephan, Pathompong
Boonpratuang, Thitiya
Choeyklin, Rattaket
Boonchird, Chuenchit
Surup, Frank
author_sort Harms, Karen
collection PubMed
description [Image: see text] Metabolites 1 and 2, isolated from cultures of the basidiomycete Resupinatus sp. BCC84615, collected in a tropical forest in northeastern Thailand, showed weak antibiotic activity against Bacillus subtilis and Staphylococcus aureus and cytotoxicity against cancer cell lines. Their planar structures were elucidated by high-resolution electrospray ionization mass spectrometry and NMR spectroscopy as clavilactone J, known from the basidiomycete Ampulloclitocybe clavipes, and its new 1,4-benzoquinone derivative. A detailed analysis of the ROESY correlations in 1 confirmed the recent revision of the relative configuration of clavilactone J. However, specific rotation and Cotton effects observed by electronic circular dichroism were contrary to those of the clavilactones; thus, we assigned a rare antipodal absolute configuration.
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spelling pubmed-106830602023-11-30 ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp. Harms, Karen Paomephan, Pathompong Boonpratuang, Thitiya Choeyklin, Rattaket Boonchird, Chuenchit Surup, Frank J Nat Prod [Image: see text] Metabolites 1 and 2, isolated from cultures of the basidiomycete Resupinatus sp. BCC84615, collected in a tropical forest in northeastern Thailand, showed weak antibiotic activity against Bacillus subtilis and Staphylococcus aureus and cytotoxicity against cancer cell lines. Their planar structures were elucidated by high-resolution electrospray ionization mass spectrometry and NMR spectroscopy as clavilactone J, known from the basidiomycete Ampulloclitocybe clavipes, and its new 1,4-benzoquinone derivative. A detailed analysis of the ROESY correlations in 1 confirmed the recent revision of the relative configuration of clavilactone J. However, specific rotation and Cotton effects observed by electronic circular dichroism were contrary to those of the clavilactones; thus, we assigned a rare antipodal absolute configuration. American Chemical Society and American Society of Pharmacognosy 2023-11-06 /pmc/articles/PMC10683060/ /pubmed/37931226 http://dx.doi.org/10.1021/acs.jnatprod.3c00174 Text en © 2023 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 Harms, Karen
Paomephan, Pathompong
Boonpratuang, Thitiya
Choeyklin, Rattaket
Boonchird, Chuenchit
Surup, Frank
ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.
title ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.
title_full ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.
title_fullStr ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.
title_full_unstemmed ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.
title_short ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.
title_sort ent-clavilactone j and its quinone derivative, meroterpenoids from the fungus resupinatus sp.
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10683060/
https://www.ncbi.nlm.nih.gov/pubmed/37931226
http://dx.doi.org/10.1021/acs.jnatprod.3c00174
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