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Mar. Drugs 2018, 16(7), 232; https://doi.org/10.3390/md16070232

Asperindoles A–D and a p-Terphenyl Derivative from the Ascidian-Derived Fungus Aspergillus sp. KMM 4676

1
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia
2
School of Natural Science, Far Eastern Federal University, Sukhanova St., 8, Vladivostok 690000, Russia
3
Laboratory of Experimental Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, Germany
*
Author to whom correspondence should be addressed.
Received: 7 June 2018 / Revised: 2 July 2018 / Accepted: 3 July 2018 / Published: 9 July 2018
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Abstract

Four new indole-diterpene alkaloids asperindoles A–D (14) and the known p-terphenyl derivative 3″-hydroxyterphenyllin (5) were isolated from the marine-derived strain of the fungus Aspergillus sp., associated with an unidentified colonial ascidian. The structures of 15 were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of 14 were determined by the combination of ROESY data, coupling constants analysis, and biogenetic considerations. Asperindoles C and D contain a 2-hydroxyisobutyric acid (2-HIBA) residue, rarely found in natural compounds. Asperindole A exhibits cytotoxic activity against hormone therapy-resistant PC-3 and 22Rv1, as well as hormone therapy-sensitive human prostate cancer cells, and induces apoptosis in these cells at low-micromolar concentrations. View Full-Text
Keywords: marine-derived fungi; secondary metabolites; indole-diterpenoids; cytotoxicity marine-derived fungi; secondary metabolites; indole-diterpenoids; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ivanets, E.V.; Yurchenko, A.N.; Smetanina, O.F.; Rasin, A.B.; Zhuravleva, O.I.; Pivkin, M.V.; Popov, R.S.; von Amsberg, G.; Afiyatullov, S.S.; Dyshlovoy, S.A. Asperindoles A–D and a p-Terphenyl Derivative from the Ascidian-Derived Fungus Aspergillus sp. KMM 4676. Mar. Drugs 2018, 16, 232.

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