Prenylated indole alkaloids from co-culture of marine-derived fungi Aspergillus sulphureus and Isaria felina

被引：39

作者：

Afiyatullov, Shamil Sh. ^{[1
]}

Zhuravleva, Olesya I. ^{[1
,2
]}

Antonov, Alexandr S. ^{[1
]}

Berdyshev, Dmitrii V. ^{[1
]}

Pivkin, Mikhail V. ^{[1
]}

Denisenko, Vladimir A. ^{[1
]}

Popov, Roman S. ^{[1
]}

Gerasimenko, Andrey V. ^{[3
]}

von Amsberg, Gunhild ^{[4
]}

Dyshlovoy, Sergey A. ^{[1
,2
,4
]}

Leshchenko, Elena V. ^{[1
,2
]}

Yurchenko, Anton N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Far Eastern Branch, GB Elyakov Pacific Inst Bioorgan Chem, Vladivostok, Russia

[2] Far Eastern Fed Univ, Vladivostok, Russia

[3] Russian Acad Sci, Far Eastern Branch, Inst Chem, Vladivostok, Russia

[4] Univ Med Ctr Hamburg Eppendorf, Lab Expt Oncol, Dept Oncol Hematol & Bone Marrow Transplantat, Sect Pneumol,Hubertus Wald Tumorzentrum, Hamburg, Germany

来源：

JOURNAL OF ANTIBIOTICS | 2018年 / 71卷 / 10期

关键词：

PROSTATE-CANCER; NATURAL-PRODUCTS; F-K; POLYKETIDES; DERIVATIVES; RESISTANCE;

D O I：

10.1038/s41429-018-0072-9

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

Five new prenylated indole alkaloids, 17-hydroxynotoamide D (1), 17-O-ethylnotoamide M (2), 10-O-acetylsclerotiamide (3), 10-O-ethylsclerotiamide (4), and 10-O-ethylnotoamide R (5) were isolated from a co-culture of marine-derived fungi Aspergillus sulphureus KMM 4640 and Isaria felina KMM 4639. The structures of 1-5 were determined by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-5 were determined by time-dependent density functional theory (TD-DFT) calculations of ECD spectra. Compound 2 is able to inhibit the colony formation of human prostate cancer cells 22Rv1 at non-cytotoxic concentration of 10 mu M.

引用

页码：846 / 853

页数：8

共 27 条

[11] A new cyclopeptide with antifungal activity from the co-culture broth of two marine mangrove fungi [J].

Li, Chunyuan ;

Wang, Jinhua ;

Luo, Cuiping ;

Ding, Weijia ;

Cox, Daniel G. .

NATURAL PRODUCT RESEARCH, 2014, 28 (09) :616-621

[12] Niclosamide Inhibits Androgen Receptor Variants Expression and Overcomes Enzalutamide Resistance in Castration-Resistant Prostate Cancer [J].

Liu, Chengfei ;

Lou, Wei ;

Zhu, Yezi ;

Nadiminty, Nagalakshmi ;

Schwartz, Chad T. ;

Evans, Christopher P. ;

Gao, Allen C. .

CLINICAL CANCER RESEARCH, 2014, 20 (12) :3198-3210

[13] Citrifelins A and B, Citrinin Adducts with a Tetracyclic Framework from Cocultures of Marine-Derived Isolates of Penicillium citrinum and Beauveria felina [J].

Meng, Ling-Hong ;

Liu, Yang ;

Li, Xiao-Ming ;

Xu, Gang-Ming ;

Ji, Nai-Yun ;

Wang, Bin-Gui .

JOURNAL OF NATURAL PRODUCTS, 2015, 78 (09) :2301-2305

[14] INTRAMOLECULAR INTERACTION BETWEEN HYDROXYL GROUP AND PI-ELECTRONS .7. LIMITATION OF THE REACTION BY CHAIN LENGTH IN 2-(OMEGA-ALKENYL)-PHENOLS AND 2-(OMEGA-PHENYLALKYL)-PHENOLS [J].

OKI, M ;

IWAMURA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1960, 33 (05) :681-684

[15] Secondary metabolites of fungi from marine habitats [J].

Rateb, Mostafa E. ;

Ebel, Rainer .

NATURAL PRODUCT REPORTS, 2011, 28 (02) :290-344

[16]

Sheldrick GM, 2015, ACTA CRYSTALLOGR C, V71, P3, DOI [10.1107/S2053229614024218, 10.1107/S0108767307043930, 10.1107/S2053273314026370]

[17] Unique prostate cancer-toxic polyketides from marine sediment-derived fungus Isaria felina [J].

Smetanina, Olga F. ;

Yurchenko, Anton N. ;

Ivanets, Elena V. ;

Kalinovsky, Anatoly I. ;

Khudyakova, Yuliya V. ;

Dyshlovoy, Sergey A. ;

von Amsberg, Gunhild ;

Yurchenko, Ekaterina A. ;

Afiyatullov, Shamil Sh .

JOURNAL OF ANTIBIOTICS, 2017, 70 (07) :856-858

[18] Oxirapentyns B-D produced by a marine sediment-derived fungus Isaria felina (DC.) Fr [J].

Smetanina, Olga F. ;

Yurchenko, Anton N. ;

Afiyatullov, Shamil Sh. ;

Kalinovsky, Anatoly I. ;

Pushilin, Michael A. ;

Khudyakova, Yuliya V. ;

Slinkina, Natalya N. ;

Ermakova, Svetlana P. ;

Yurchenko, Ekaterina A. .

PHYTOCHEMISTRY LETTERS, 2012, 5 (01) :165-169

[19] Notoamide O, a Structurally Unprecedented Prenylated Indole Alkaloid, and Notoamides P-R from a Marine-Derived Fungus, Aspergillus sp. [J].

Tsukamoto, Sachiko ;

Umaoka, Hideharu ;

Yoshikawa, Kohei ;

Ikeda, Tsuyoshi ;

Hirota, Hiroshi .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (08) :1438-1440

[20] Notoamides F-K, Prenylated Indole Alkaloids Isolated from a Marine-Derived Aspergillus sp. [J].

Tsukamoto, Sachiko ;

Kato, Hikaru ;

Samizo, Masayuki ;

Nojiri, Yuka ;

Onuki, Hiroyuki ;

Hirota, Hiroshi ;

Ohta, Tomihisa .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (12) :2064-2067

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