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

ABSTRACT: Four new indole-diterpene alkaloids asperindoles A?D (1?4) 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 1?5 were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of 1?4 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.

SUBMITTER: Ivanets EV 

PROVIDER: S-EPMC6070833 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Asperindoles A⁻D and a <i>p</i>-Terphenyl Derivative from the Ascidian-Derived Fungus <i>Aspergillus</i> sp. KMM 4676.

Ivanets Elena V EV   Yurchenko Anton N AN   Smetanina Olga F OF   Rasin Anton B AB   Zhuravleva Olesya I OI   Pivkin Mikhail V MV   Popov Roman S RS   von Amsberg Gunhild G   Afiyatullov Shamil Sh SS   Dyshlovoy Sergey A SA  

Marine drugs 20180709 7

Four new indole-diterpene alkaloids asperindoles A⁻D (<b>1</b>⁻<b>4</b>) and the known <i>p</i>-terphenyl derivative 3&Prime;-hydroxyterphenyllin (<b>5</b>) were isolated from the marine-derived strain of the fungus <i>Aspergillus</i> sp., associated with an unidentified colonial ascidian. The structures of <b>1</b>⁻<b>5</b> were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of <b>1</b>⁻<b>4</b> were determined by the combination of ROESY data, coupling  ...[more]

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