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New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells

Five new sesterterpenes, 14,15-dehydro-6-epi-ophiobolin K (1), 14,15-dehydro- ophiobolin K (2), 14,15-dehydro-6-epi-ophiobolin G (3), 14,15-dehydro-ophiobolin G (4) and 14,15-dehydro-(Z)-14-ophiobolin G (5), together with four known ophiobolins (6–9) were isolated from the marine fungus Aspergillus...

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Autores principales: Choi, Byeoung-Kyu, Trinh, Phan Thi Hoai, Lee, Hwa-Sun, Choi, Byeong-Woo, Kang, Jong Soon, Ngoc, Ngo Thi Duy, Van, Tran Thi Thanh, Shin, Hee Jae
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6628216/
https://www.ncbi.nlm.nih.gov/pubmed/31212583
http://dx.doi.org/10.3390/md17060346
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author Choi, Byeoung-Kyu
Trinh, Phan Thi Hoai
Lee, Hwa-Sun
Choi, Byeong-Woo
Kang, Jong Soon
Ngoc, Ngo Thi Duy
Van, Tran Thi Thanh
Shin, Hee Jae
author_facet Choi, Byeoung-Kyu
Trinh, Phan Thi Hoai
Lee, Hwa-Sun
Choi, Byeong-Woo
Kang, Jong Soon
Ngoc, Ngo Thi Duy
Van, Tran Thi Thanh
Shin, Hee Jae
author_sort Choi, Byeoung-Kyu
collection PubMed
description Five new sesterterpenes, 14,15-dehydro-6-epi-ophiobolin K (1), 14,15-dehydro- ophiobolin K (2), 14,15-dehydro-6-epi-ophiobolin G (3), 14,15-dehydro-ophiobolin G (4) and 14,15-dehydro-(Z)-14-ophiobolin G (5), together with four known ophiobolins (6–9) were isolated from the marine fungus Aspergillus flocculosus derived from the seaweed Padina sp. collected in Vietnam. The five new ophiobolins were first isolated as ophiobolin derivatives consisting of a fully unsaturated side chain. Their structures were elucidated via spectroscopic methods including 1D, 2D NMR and HR-ESIMS. The absolute configurations were determined by the comparison of chemical shifts and optical rotation values with those of known ophiobolins. All compounds (1–9) were then evaluated for their cytotoxicity against six cancer cell lines, HCT-15, NUGC-3, NCI-H23, ACHN, PC-3 and MDA-MB-231. All the compounds showed potent cytotoxicity with GI(50) values ranging from 0.14 to 2.01 μM.
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spelling pubmed-66282162019-07-23 New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells Choi, Byeoung-Kyu Trinh, Phan Thi Hoai Lee, Hwa-Sun Choi, Byeong-Woo Kang, Jong Soon Ngoc, Ngo Thi Duy Van, Tran Thi Thanh Shin, Hee Jae Mar Drugs Article Five new sesterterpenes, 14,15-dehydro-6-epi-ophiobolin K (1), 14,15-dehydro- ophiobolin K (2), 14,15-dehydro-6-epi-ophiobolin G (3), 14,15-dehydro-ophiobolin G (4) and 14,15-dehydro-(Z)-14-ophiobolin G (5), together with four known ophiobolins (6–9) were isolated from the marine fungus Aspergillus flocculosus derived from the seaweed Padina sp. collected in Vietnam. The five new ophiobolins were first isolated as ophiobolin derivatives consisting of a fully unsaturated side chain. Their structures were elucidated via spectroscopic methods including 1D, 2D NMR and HR-ESIMS. The absolute configurations were determined by the comparison of chemical shifts and optical rotation values with those of known ophiobolins. All compounds (1–9) were then evaluated for their cytotoxicity against six cancer cell lines, HCT-15, NUGC-3, NCI-H23, ACHN, PC-3 and MDA-MB-231. All the compounds showed potent cytotoxicity with GI(50) values ranging from 0.14 to 2.01 μM. MDPI 2019-06-11 /pmc/articles/PMC6628216/ /pubmed/31212583 http://dx.doi.org/10.3390/md17060346 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Choi, Byeoung-Kyu
Trinh, Phan Thi Hoai
Lee, Hwa-Sun
Choi, Byeong-Woo
Kang, Jong Soon
Ngoc, Ngo Thi Duy
Van, Tran Thi Thanh
Shin, Hee Jae
New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
title New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
title_full New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
title_fullStr New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
title_full_unstemmed New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
title_short New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells
title_sort new ophiobolin derivatives from the marine fungus aspergillus flocculosus and their cytotoxicities against cancer cells
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6628216/
https://www.ncbi.nlm.nih.gov/pubmed/31212583
http://dx.doi.org/10.3390/md17060346
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