Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

被引:10
作者
Sharma, Amit Raj [1 ,2 ]
Harunari, Enjuro [1 ,2 ]
Zhou, Tao [1 ,2 ]
Trianto, Agus [3 ]
Igarashi, Yasuhiro [1 ,2 ]
机构
[1] Toyama Prefectural Univ, Biotechnol Res Ctr, 5180 Kurokawa, Imizu, Toyama 9390398, Japan
[2] Toyama Prefectural Univ, Dept Biotechnol, 5180 Kurokawa, Imizu, Toyama 9390398, Japan
[3] Diponegoro Univ, Fac Fisheries & Marine Sci, Tembalang Campus, Semarang 50275, Central Java, Indonesia
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷
关键词
biosynthesis; fatty acid; marine bacteria; methylation; Microbulbifer; SP NOV; MARINE; PSEUDOALTEROMONE; METHIONINE; SEA;
D O I
10.3762/bjoc.15.225
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2Z,4E)-3-Methyl-2,4-decadienoic acid (1) was identified as a major metabolite from a culture extract of a marine bacterium Microbulbifer which was collected from a stony coral Porites sp. NMR-based spectroscopic analysis revealed that 1 is an unsaturated fatty acid in which a methyl group is located in an uncommon position as a natural product. Feeding experiments of C-13-labeled precursors clarified that L-methionine-derived methylation takes place at the carbon which is derived from the carbonyl carbon of acetate. Compound 1 showed weak growth inhibition against Saccharomyces cerevisiae.
引用
收藏
页码:2327 / 2332
页数:6
相关论文
共 22 条
[1]  
[Anonymous], 2009, MED NATURAL PRODUCTS
[2]   Biosynthetic Studies of 13-Desmethylspirolide C Produced by Alexandrium ostenfeldii (= A. peruvianum): Rationalization of the Biosynthetic Pathway Following Incorporation of 13C-Labeled Methionine and Application of the Odd-Even Rule of Methylation [J].
Anttila, Matthew ;
Strangman, Wendy ;
York, Robert ;
Tomas, Carmelo ;
Wright, Jeffrey L. C. .
JOURNAL OF NATURAL PRODUCTS, 2016, 79 (03) :484-489
[3]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Keyzers, Robert A. ;
Munro, Murray H. G. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2016, 33 (03) :382-431
[4]   An Overview on Marine Sponge-Symbiotic Bacteria as Unexhausted Sources for Natural Product Discovery [J].
Brinkmann, Candice M. ;
Marker, Amberlee ;
Kurtboeke, D. Ipek .
DIVERSITY-BASEL, 2017, 9 (04)
[5]   Exotic biomodification of fatty acids [J].
Buist, Peter H. .
NATURAL PRODUCT REPORTS, 2007, 24 (05) :1110-1127
[6]  
CAMPBELL IM, 1969, J LIPID RES, V10, P593
[7]   Pseudoalteromone B: A Novel 15C Compound from a Marine Bacterium Pseudoalteromonas sp CGH2XX [J].
Chen, Yu-Hsin ;
Kuo, Jimmy ;
Su, Jui-Hsin ;
Hwang, Tsong-Long ;
Chen, Yung-Husan ;
Lee, Chia-Hung ;
Weng, Ching-Feng ;
Sung, Ping-Jyun .
MARINE DRUGS, 2012, 10 (07) :1566-1571
[8]   Pseudoalteromone A: a novel bioactive ubiquinone from a marine bacterium Pseudoalteromonas sp. CGH2XX (Pseudoalteromonadaceae) [J].
Chen, Yu-Hsin ;
Lu, Mei-Chin ;
Chang, Yu-Chia ;
Hwang, Tsong-Long ;
Wang, Wei-Hsien ;
Weng, Ching-Feng ;
Kuo, Jimmy ;
Sung, Ping-Jyun .
TETRAHEDRON LETTERS, 2012, 53 (13) :1675-1677
[9]   Antibacterial and antilarval compounds from marine gorgonian-associated bacterium Bacillus amyloliquefaciens SCSIO 00856 [J].
Gao, Cheng-Hai ;
Tian, Xin-Peng ;
Qi, Shu-Hua ;
Luo, Xiong-Ming ;
Wang, Ping ;
Zhang, Si .
JOURNAL OF ANTIBIOTICS, 2010, 63 (04) :191-193
[10]   Sagittula stellata gen. nov, sp. nov, a lignin-transforming bacterium from a coastal environment [J].
Gonzalez, JM ;
Mayer, F ;
Moran, MA ;
Hodson, RE ;
Whitman, WB .
INTERNATIONAL JOURNAL OF SYSTEMATIC BACTERIOLOGY, 1997, 47 (03) :773-780