Isolation, structure elucidation, and antibacterial evaluation of the metabolites produced by the marine-sourced Streptomyces sp. ZZ820

被引：23

作者：

Yi, Wenwen ^{[1
]}

Li, Qiao ^{[1
]}

Song, Tengfei ^{[1
]}

Chen, Lei ^{[1
]}

Li, Xing-Cong ^{[3
]}

Zhang, Zhizhen ^{[1
]}

Lian, Xiao-Yuan ^{[2
]}

机构：

[1] Zhejiang Univ, Ocean Coll, Zhoushan Campus, Zhoushan 316021, Peoples R China

[2] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China

[3] Univ Mississippi, Natl Ctr Nat Prod Res, Res Inst Pharmaceut Sci, Sch Pharm, University, MS 38677 USA

来源：

TETRAHEDRON | 2019年 / 75卷 / 09期

基金：

国家重点研发计划; 中国国家自然科学基金;

关键词：

Streptomyces sp. ZZ820; Marine actinomycetes; Streptoprenylindoles; Cyclooctatin analogues; Antibacterial activities; NATURAL-PRODUCTS; BETA-CARBOLINE; ALKALOIDS;

D O I：

10.1016/j.tet.2019.01.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New indole alkaloids streptoprenylindoles A-C (1-3) and diterpenoids 18-acetyl-cyclooctatin (8), 5,18-dedihydroxy-cyclooctatin (9), and 5-dehydroxy-cyclooctatin (10) were isolated from the culture of marine-derived Streptomyces sp. ZZ820, along with known 3-cyanomethyl-6-[3-methyl-2-butenyl]indole (4), N-(2-(1H-indol-3-yl)ethylacetamide (5), 1-acetyl-beta-carboline (6), indole-3-methylethanoate (7), cyclooctatin (11), and chromomycin A(3) (12). Their structures were elucidated by a combination of extensive spectroscopic analyses, ECD calculation, and the Mosher's method. Streptoprenylindoles A (1) and B (2) are enantiomers that were separated through the preparation of their Mosher esters. Three new diterpenoids (8-10) showed antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli with MIC values of 24.11-55.12 mu M, while chromomycin A(3) (12) showed potent antibacterial activities against MRSA (MIC: 0.59 mu M) and E. coli (MIC 0.04 mu M). (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：1186 / 1193

页数：8

共 27 条

[11] Antimalarial β-Carboline and Indolactam Alkaloids from Marinactinospora thermotolerans, a Deep Sea Isolate [J].

Huang, Hongbo ;

Yao, Yueliang ;

He, Zhengxiang ;

Yang, Tingting ;

Ma, Junying ;

Tian, Xinpeng ;

Li, Yayong ;

Huang, Caiguo ;

Chen, Xiaoping ;

Li, Wenjun ;

Zhang, Si ;

Zhang, Changsheng ;

Ju, Jianhua .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (10) :2122-2127

[12] Deep Sea Actinomycetes and Their Secondary Metabolites [J].

Kamjam, Manita ;

Sivalingam, Periyasamy ;

Deng, Zinxin ;

Hong, Kui .

FRONTIERS IN MICROBIOLOGY, 2017, 8

[13] 17-Hydroxycyclooctatin, a Fused 5-8-5 Ring Diterpene, from Streptomyces sp. MTE4a [J].

Kawamura, Akira ;

Iacovidou, Maria ;

Hirokawa, Emiri ;

Soll, Clifford E. ;

Trujillo, Monica .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (03) :492-495

[14] Indole alkaloids from a sponge Sarcotragus species [J].

Liu, YH ;

Jung, JH ;

Zhang, S .

BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2006, 34 (05) :453-456

[15] New cytotoxic indolic metabolites from a marine Streptomyces [J].

López, JMS ;

Insua, MM ;

Baz, JP ;

Puentes, JLF ;

Hernández, LMC .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (06) :863-864

[16] New anti-inflammatory metabolites produced by Streptomyces violaceoruber isolated from Equus burchelli feces [J].

Ma, Jian ;

Lei, Hui ;

Chen, Xiu ;

Bi, Xiaoxu ;

Jiang, Yi ;

Han, Li ;

Huang, Xueshi .

JOURNAL OF ANTIBIOTICS, 2017, 70 (10) :991-994

[17] Pharmaceutically active secondary metabolites of marine actinobacteria [J].

Manivasagan, Panchanathan ;

Venkatesan, Jayachandran ;

Sivakumar, Kannan ;

Kim, Se-Kwon .

MICROBIOLOGICAL RESEARCH, 2014, 169 (04) :262-278

[18] An Unusual Terpene Cyclization Mechanism Involving a Carbon-Carbon Bond Rearrangement [J].

Meguro, Ayuko ;

Motoyoshi, Yudai ;

Teramoto, Kazuya ;

Ueda, Shota ;

Totsuka, Yusuke ;

Ando, Yumi ;

Tomita, Takeo ;

Kim, Seung-Young ;

Kimura, Tomoyuki ;

Igarashi, Masayuki ;

Sawa, Ryuichi ;

Shinada, Tetsuro ;

Nishiyama, Makoto ;

Kuzuyama, Tomohisa .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (14) :4353-4356

[19] Chromomycins A2 and A3 from Marine Actinomycetes with TRAIL Resistance-Overcoming and Wnt Signal Inhibitory Activities [J].

Toume, Kazufumi ;

Tsukahara, Kentaro ;

Ito, Hanako ;

Arai, Midori A. ;

Ishibashi, Masami .

MARINE DRUGS, 2014, 12 (06) :3466-3476

[20]

Wang C., 2016, STUD MAR SIN, V51, P86

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