Cargando…

Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample

[Image: see text] Polluxochrin (1) and dioschrin (2), two new dimers of sulochrin linked by thioether bonds, were purified from an Alternaria sp. isolate obtained from a Hawaiian soil sample. The structures of the two metabolites were established by NMR, mass spectrometry data, and X-ray analysis. M...

Descripción completa

Detalles Bibliográficos
Autores principales: Cai, Shengxin, King, Jarrod B., Du, Lin, Powell, Douglas R., Cichewicz, Robert H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4208674/
https://www.ncbi.nlm.nih.gov/pubmed/25265160
http://dx.doi.org/10.1021/np5005449
_version_ 1782341160780431360
author Cai, Shengxin
King, Jarrod B.
Du, Lin
Powell, Douglas R.
Cichewicz, Robert H.
author_facet Cai, Shengxin
King, Jarrod B.
Du, Lin
Powell, Douglas R.
Cichewicz, Robert H.
author_sort Cai, Shengxin
collection PubMed
description [Image: see text] Polluxochrin (1) and dioschrin (2), two new dimers of sulochrin linked by thioether bonds, were purified from an Alternaria sp. isolate obtained from a Hawaiian soil sample. The structures of the two metabolites were established by NMR, mass spectrometry data, and X-ray analysis. Metabolite 1 was determined to be susceptible to intramolecular cyclization under aqueous conditions, resulting in the generation of 2 as well as another dimeric compound, castochrin (3). An additional nine new metabolites were also obtained, including four new pyrenochaetic acid derivatives (8–11), one new asterric acid analogue (13), and four new secalonic acid analogues (14–17). Bioassay analysis of these compounds revealed 1–3 displayed antimicrobial and weak cytotoxic activities.
format Online
Article
Text
id pubmed-4208674
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society and American Society of Pharmacognosy
record_format MEDLINE/PubMed
spelling pubmed-42086742015-09-29 Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample Cai, Shengxin King, Jarrod B. Du, Lin Powell, Douglas R. Cichewicz, Robert H. J Nat Prod [Image: see text] Polluxochrin (1) and dioschrin (2), two new dimers of sulochrin linked by thioether bonds, were purified from an Alternaria sp. isolate obtained from a Hawaiian soil sample. The structures of the two metabolites were established by NMR, mass spectrometry data, and X-ray analysis. Metabolite 1 was determined to be susceptible to intramolecular cyclization under aqueous conditions, resulting in the generation of 2 as well as another dimeric compound, castochrin (3). An additional nine new metabolites were also obtained, including four new pyrenochaetic acid derivatives (8–11), one new asterric acid analogue (13), and four new secalonic acid analogues (14–17). Bioassay analysis of these compounds revealed 1–3 displayed antimicrobial and weak cytotoxic activities. American Chemical Society and American Society of Pharmacognosy 2014-09-29 2014-10-24 /pmc/articles/PMC4208674/ /pubmed/25265160 http://dx.doi.org/10.1021/np5005449 Text en Copyright © 2014 American Chemical Society and American Society of Pharmacognosy Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Cai, Shengxin
King, Jarrod B.
Du, Lin
Powell, Douglas R.
Cichewicz, Robert H.
Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample
title Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample
title_full Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample
title_fullStr Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample
title_full_unstemmed Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample
title_short Bioactive Sulfur-Containing Sulochrin Dimers and Other Metabolites from an Alternaria sp. Isolate from a Hawaiian Soil Sample
title_sort bioactive sulfur-containing sulochrin dimers and other metabolites from an alternaria sp. isolate from a hawaiian soil sample
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4208674/
https://www.ncbi.nlm.nih.gov/pubmed/25265160
http://dx.doi.org/10.1021/np5005449
work_keys_str_mv AT caishengxin bioactivesulfurcontainingsulochrindimersandothermetabolitesfromanalternariaspisolatefromahawaiiansoilsample
AT kingjarrodb bioactivesulfurcontainingsulochrindimersandothermetabolitesfromanalternariaspisolatefromahawaiiansoilsample
AT dulin bioactivesulfurcontainingsulochrindimersandothermetabolitesfromanalternariaspisolatefromahawaiiansoilsample
AT powelldouglasr bioactivesulfurcontainingsulochrindimersandothermetabolitesfromanalternariaspisolatefromahawaiiansoilsample
AT cichewiczroberth bioactivesulfurcontainingsulochrindimersandothermetabolitesfromanalternariaspisolatefromahawaiiansoilsample