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- Title
Asperindoles A–D and a p-Terphenyl Derivative from the Ascidian-Derived Fungus Aspergillus sp. KMM 4676.
- Authors
Ivanets, Elena V.; Yurchenko, Anton N.; Smetanina, Olga F.; Rasin, Anton B.; Zhuravleva, Olesya I.; Pivkin, Mikhail V.; Popov, Roman S.; von Amsberg, Gunhild; Afiyatullov, Shamil Sh.; Dyshlovoy, Sergey A.
- Abstract
Four new indole-diterpene alkaloids asperindoles A–D (<bold>1</bold>–<bold>4</bold>) and the known <italic>p</italic>-terphenyl derivative 3″-hydroxyterphenyllin (<bold>5</bold>) were isolated from the marine-derived strain of the fungus <italic>Aspergillus</italic> sp., associated with an unidentified colonial ascidian. The structures of <bold>1</bold>–<bold>5</bold> were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of <bold>1</bold>–<bold>4</bold> 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.
- Subjects
MARINE fungi; AQUATIC fungi; METABOLITES; INDOLE; DITERPENES
- Publication
Marine Drugs, 2018, Vol 16, Issue 7, p232
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md16070232