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

Five new sesterterpenes, 14,15-dehydro-6- -ophiobolin K ( ), 14,15-dehydro- ophiobolin K ( ), 14,15-dehydro-6- -ophiobolin G ( ), 14,15-dehydro-ophiobolin G ( ) and 14,15-dehydro-( )-14-ophiobolin G ( ), together with four known ophiobolins ( - ) were isolated from the marine fungus derived from the...

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Bibliographic Details
Published in:Marine drugs 2019-06, Vol.17 (6), p.346
Main Authors: 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
Format: Article
Language:English
Subjects:
Algae
anti-proliferation
Aquatic Organisms - chemistry
Aspergillus
Aspergillus - chemistry
Aspergillus flocculosus
Cancer
Carbon
Cell Line, Tumor
Cell lines
Cytotoxicity
Derivatives
Drugs
Fungi
Fungi - chemistry
Humans
marine fungus
Metabolites
Microorganisms
Natural products
NMR
Nuclear magnetic resonance
ophiobolins
Optical properties
Optical rotation
Organic chemistry
PC-3 Cells
Science
Seaweed - microbiology
Seaweeds
Sesterterpenes - chemistry
Sesterterpenes - pharmacology
Toxicity
Tumor cell lines
Vietnam
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Summary:Five new sesterterpenes, 14,15-dehydro-6- -ophiobolin K ( ), 14,15-dehydro- ophiobolin K ( ), 14,15-dehydro-6- -ophiobolin G ( ), 14,15-dehydro-ophiobolin G ( ) and 14,15-dehydro-( )-14-ophiobolin G ( ), together with four known ophiobolins ( - ) were isolated from the marine fungus derived from the seaweed 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 ( - ) 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 values ranging from 0.14 to 2.01 μM.
ISSN:1660-3397
1660-3397
DOI:10.3390/md17060346