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Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.

[Image: see text] Fourteen new resorcylic acid lactones (1–14) were isolated from an organic extract of a culture of a freshwater aquatic fungus Halenospora sp. originating from a stream in North Carolina. The structures were elucidated using a set of spectroscopic and spectrometric techniques. The...

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Autores principales: El-Elimat, Tamam, Raja, Huzefa A., Day, Cynthia S., Chen, Wei-Lun, Swanson, Steven M., Oberlies, Nicholas 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/PMC4176394/
https://www.ncbi.nlm.nih.gov/pubmed/25093280
http://dx.doi.org/10.1021/np500497r
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author El-Elimat, Tamam
Raja, Huzefa A.
Day, Cynthia S.
Chen, Wei-Lun
Swanson, Steven M.
Oberlies, Nicholas H.
author_facet El-Elimat, Tamam
Raja, Huzefa A.
Day, Cynthia S.
Chen, Wei-Lun
Swanson, Steven M.
Oberlies, Nicholas H.
author_sort El-Elimat, Tamam
collection PubMed
description [Image: see text] Fourteen new resorcylic acid lactones (1–14) were isolated from an organic extract of a culture of a freshwater aquatic fungus Halenospora sp. originating from a stream in North Carolina. The structures were elucidated using a set of spectroscopic and spectrometric techniques. The absolute configuration of one representative member of the compounds (7) was assigned using X-ray crystallography of an analogue that incorporated a heavy atom, whereas for compounds 8–11, a modified Mosher’s ester method was utilized. The relative configurations of compounds 12–14 were determined on the basis of NOE data. Compounds 12–14 were proposed as artifacts produced by intramolecular cycloetherification of the ε-hydroxy-α,β-unsaturated ketone moieties of the parent compounds during the purification processes. The isolated compounds, except for 8 and 12, were tested against the MDA-MB-435 (melanoma) and HT-29 (colon) cancer cell lines. Compound 5 was the most potent, with IC(50) values of 2.9 and 7.5 μM, respectively. The compounds were evaluated as TAK1–TAB1 inhibitors but were found to be inactive.
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spelling pubmed-41763942015-08-05 Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp. El-Elimat, Tamam Raja, Huzefa A. Day, Cynthia S. Chen, Wei-Lun Swanson, Steven M. Oberlies, Nicholas H. J Nat Prod [Image: see text] Fourteen new resorcylic acid lactones (1–14) were isolated from an organic extract of a culture of a freshwater aquatic fungus Halenospora sp. originating from a stream in North Carolina. The structures were elucidated using a set of spectroscopic and spectrometric techniques. The absolute configuration of one representative member of the compounds (7) was assigned using X-ray crystallography of an analogue that incorporated a heavy atom, whereas for compounds 8–11, a modified Mosher’s ester method was utilized. The relative configurations of compounds 12–14 were determined on the basis of NOE data. Compounds 12–14 were proposed as artifacts produced by intramolecular cycloetherification of the ε-hydroxy-α,β-unsaturated ketone moieties of the parent compounds during the purification processes. The isolated compounds, except for 8 and 12, were tested against the MDA-MB-435 (melanoma) and HT-29 (colon) cancer cell lines. Compound 5 was the most potent, with IC(50) values of 2.9 and 7.5 μM, respectively. The compounds were evaluated as TAK1–TAB1 inhibitors but were found to be inactive. American Chemical Society and American Society of Pharmacognosy 2014-08-05 2014-09-26 /pmc/articles/PMC4176394/ /pubmed/25093280 http://dx.doi.org/10.1021/np500497r 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 El-Elimat, Tamam
Raja, Huzefa A.
Day, Cynthia S.
Chen, Wei-Lun
Swanson, Steven M.
Oberlies, Nicholas H.
Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.
title Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.
title_full Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.
title_fullStr Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.
title_full_unstemmed Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.
title_short Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.
title_sort greensporones: resorcylic acid lactones from an aquatic halenospora sp.
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4176394/
https://www.ncbi.nlm.nih.gov/pubmed/25093280
http://dx.doi.org/10.1021/np500497r
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