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

[1] Conformational analysis and interpretation of ν(OH) bands in the IR spectrum of o-vinylphenol: a DFT study [J].

Berdyshev, D. V. ;

Glazunov, V. P. ;

Novikov, V. L. .

RUSSIAN CHEMICAL BULLETIN, 2008, 57 (03) :510-519

[2] Marine natural products [J].

Blunt, John W. ;

Carroll, Anthony R. ;

Copp, Brent R. ;

Davis, Rohan A. ;

Keyzers, Robert A. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2018, 35 (01) :8-53

[3] Marine natural products [J].

Blunt, John W. ;

Copp, Brent R. ;

Keyzers, Robert A. ;

Munro, Murray H. G. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2017, 34 (03) :235-294

[4]

Bruker, 2012, APEX2

[5] Bioactive Indole Alkaloids and Phenyl Ether Derivatives from a Marine-Derived Aspergillus sp Fungus [J].

Chen, Min ;

Shao, Chang-Lun ;

Fu, Xiu-Mei ;

Xu, Ru-Fang ;

Zheng, Juan-Juan ;

Zhao, Dong-Lin ;

She, Zhi-Gang ;

Wang, Chang-Yun .

JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :547-553

[6] The marine triterpene glycoside frondoside A exhibits activity in vitro and in vivo in prostate cancer [J].

Dyshlovoy, Sergey A. ;

Menchinskaya, Ekaterina S. ;

Venz, Simone ;

Rast, Stefanie ;

Amann, Kerstin ;

Hauschild, Jessica ;

Otte, Katharina ;

Kalinin, Vladimir I. ;

Silchenko, Alexandra S. ;

Avilov, Sergey A. ;

Alsdorf, Winfried ;

Madanchi, Ramin ;

Bokemeyer, Carsten ;

Schumacher, Udo ;

Walther, Reinhard ;

Aminin, Dmitry L. ;

Fedorov, Sergey N. ;

Shubina, Larisa K. ;

Stonik, Valentin A. ;

Balabanov, Stefan ;

Honecker, Friedemann ;

von Amsberg, Gunhild .

INTERNATIONAL JOURNAL OF CANCER, 2016, 138 (10) :2450-2465

[7] Marine alkaloid Monanchocidin a overcomes drug resistance by induction of autophagy and lysosomal membrane permeabilization [J].

Dyshlovoy, Sergey A. ;

Hauschild, Jessica ;

Amann, Kerstin ;

Tabakmakher, Ksenia M. ;

Venz, Simone ;

Walther, Reinhard ;

Guzii, Alla G. ;

Makarieva, Tatiana N. ;

Shubina, Larisa K. ;

Fedorov, Sergey N. ;

Stonik, Valentin A. ;

Bokemeyer, Carsten ;

Balabanov, Stefan ;

Honecker, Friedemann ;

Amsberg, Gunhild V. .

ONCOTARGET, 2015, 6 (19) :17328-17341

[8] Activity of aaptamine and two derivatives, demethyloxyaaptamine and isoaaptamine, in cisplatin-resistant germ cell cancer [J].

Dyshlovoy, Sergey A. ;

Venz, Simone ;

Shubina, Larisa K. ;

Fedorov, Sergey N. ;

Walther, Reinhard ;

Jacobsen, Christine ;

Stonik, Valentin A. ;

Bokemeyer, Carsten ;

Balabanov, Stefan ;

Honecker, Friedemann .

JOURNAL OF PROTEOMICS, 2014, 96 :223-239

[9] Notoamides A-D:: Prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. [J].

Kato, Hikaru ;

Yoshida, Takushi ;

Tokue, Takanori ;

Nojiri, Yuka ;

Hirota, Hiroshi ;

Ohta, Tomihisa ;

Williams, Robert M. ;

Tsukamoto, Sachiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2254-2256

[10] Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications [J].

Kato, Hikaru ;

Nakahara, Takashi ;

Sugimoto, Kayo ;

Matsuo, Kanae ;

Kagiyama, Ippei ;

Frisvad, Jens C. ;

Sherman, David H. ;

Williams, Robert M. ;

Tsukamoto, Sachiko .

ORGANIC LETTERS, 2015, 17 (03) :700-703

← 1 2 3 →