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Open AccessArticle

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

1
Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea
2
Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea
3
Nhatrang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, 02 Hung Vuong, Nha Trang 650000, Vietnam
4
Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Ha Noi 100000, Vietnam
5
Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(6), 346; https://doi.org/10.3390/md17060346
Received: 27 May 2019 / Revised: 6 June 2019 / Accepted: 6 June 2019 / Published: 11 June 2019
(This article belongs to the Special Issue Marine Microbial Diversity as Source of Bioactive Natural Products)
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 (69) 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 (19) 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 GI50 values ranging from 0.14 to 2.01 μM. View Full-Text
Keywords: ophiobolins; marine fungus; Aspergillus flocculosus; anti-proliferation ophiobolins; marine fungus; Aspergillus flocculosus; anti-proliferation
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Choi, B.-K.; Trinh, P.T.H.; Lee, H.-S.; Choi, B.-W.; Kang, J.S.; Ngoc, N.T.D.; Van, T.T.T.; Shin, H.J. New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells. Mar. Drugs 2019, 17, 346.

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