Asperindoles A⁻D and a -Terphenyl Derivative from the Ascidian-Derived Fungus sp. KMM 4676
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Asperindoles A⁻D and a -Terphenyl Derivative from the Ascidian-Derived Fungus sp. KMM 4676. / 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.
in: MAR DRUGS, Jahrgang 16, Nr. 7, 09.07.2018, S. 232.Publikationen: SCORING: Beitrag in Fachzeitschrift/Zeitung › SCORING: Zeitschriftenaufsatz › Forschung › Begutachtung
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T1 - Asperindoles A⁻D and a -Terphenyl Derivative from the Ascidian-Derived Fungus sp. KMM 4676
AU - Ivanets, Elena V
AU - Yurchenko, Anton N
AU - Smetanina, Olga F
AU - Rasin, Anton B
AU - Zhuravleva, Olesya I
AU - Pivkin, Mikhail V
AU - Popov, Roman S
AU - von Amsberg, Gunhild
AU - Afiyatullov, Shamil Sh
AU - Dyshlovoy, Sergey A
PY - 2018/7/9
Y1 - 2018/7/9
N2 - 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.
AB - 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.
KW - Animals
KW - Antineoplastic Agents
KW - Apoptosis
KW - Aquatic Organisms
KW - Aspergillus
KW - Cell Line, Tumor
KW - Diterpenes
KW - Docetaxel
KW - Drug Screening Assays, Antitumor
KW - Humans
KW - Indole Alkaloids
KW - Molecular Structure
KW - Stereoisomerism
KW - Taxoids
KW - Urochordata
KW - Journal Article
U2 - 10.3390/md16070232
DO - 10.3390/md16070232
M3 - SCORING: Journal article
C2 - 29987238
VL - 16
SP - 232
JO - MAR DRUGS
JF - MAR DRUGS
SN - 1660-3397
IS - 7
ER -