Combinatorial mutasynthesis of flavonoid analogues from acrylic acids in microorganisms

被引:48
作者
Chemler, Joseph A. [1 ]
Yan, Yajun [1 ]
Leonard, Effendi [1 ]
Koffas, Mattheos A. G. [1 ]
机构
[1] SUNY Buffalo, Dept Chem & Biol Engn, Buffalo, NY 14260 USA
关键词
CELL-SUSPENSION CULTURES; ESCHERICHIA-COLI; SUBSTRATE-SPECIFICITY; ENZYMATIC FORMATION; ALPHA-GLUCOSIDASE; CHALCONE SYNTHASE; NATURAL-PRODUCTS; GENE-CLUSTER; COA LIGASE; BIOSYNTHESIS;
D O I
10.1021/ol0703736
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Flavonoids are plant secondary metabolites often used as nutraceutical supplements, but a growing number of unnatural flavonoids are being investigated as therapeutic agents. Cultures of Saccharomyces cerevisiae expressing recombinant flavonoid enzymes, including 4-coumaroyl:CoA ligase (4CL), chalcone synthase (CHS), chalcone isomerase (CHI), and flavanone 3 beta-hydroxylase (FHT), produced novel flavanones and dihydroflavonols when fed with a number of aromatic acrylic acids. The flavonoid network also exhibited broad substrate specificity by converting muconic acid into a unique polypropanoid.
引用
收藏
页码:1855 / 1858
页数:4
相关论文
共 19 条
[1]   Substrate specificity of chalcone synthase: Enzymatic formation of unnatural polyketides from synthetic cinnamoyl-CoA analogues [J].
Abe, I ;
Morita, H ;
Nomura, A ;
Noguchi, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) :11242-11243
[2]   A gene cluster encoding malonyl-CoA decarboxylase (MatA), malonyl-CoA synthetase (MatB) and a putative dicarboxylate carrier protein (MatC) in Rhizobium trifolii -: Cloning, sequencing, and expression of the enzymes in Escherichia coli [J].
An, JH ;
Kim, YS .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1998, 257 (02) :395-402
[3]   Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster [J].
Hwang, EI ;
Kaneko, M ;
Ohnishi, Y ;
Horinouchi, S .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2003, 69 (05) :2699-2706
[4]   Glycosidase inhibitory flavonoids from Sophora flavescens [J].
Kim, JH ;
Ryu, YB ;
Kang, NS ;
Lee, BW ;
Heo, JS ;
Jeong, IY ;
Park, KH .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2006, 29 (02) :302-305
[5]   Inhibition of alpha-glucosidase and amylase by luteolin, a flavonoid [J].
Kim, JS ;
Kwon, CS ;
Son, KH .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (11) :2458-2461
[6]   4-COUMARATE - COA LIGASE FROM CELL-SUSPENSION CULTURES OF PETROSELINUM-HORTENSE-HOFFM - PARTIAL-PURIFICATION, SUBSTRATE-SPECIFICITY, AND FURTHER PROPERTIES [J].
KNOBLOCH, KH ;
HAHLBROCK, K .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1977, 184 (01) :237-248
[7]   ISOENZYMES OF PARA-COUMARATE - COA LIGASE FROM CELL-SUSPENSION CULTURES OF GLYCINE-MAX [J].
KNOBLOCH, KH ;
HAHLBROCK, K .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1975, 52 (02) :311-320
[8]   Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli [J].
Leonard, E ;
Yan, YJ ;
Koffas, MAG .
METABOLIC ENGINEERING, 2006, 8 (02) :172-181
[9]   Expression of a soluble flavone synthase allows the biosynthesis of phytoestrogen derivatives in Escherichia coli [J].
Leonard, E ;
Chemler, J ;
Lim, KH ;
Koffas, MAG .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2006, 70 (01) :85-91
[10]   PRIMARY STRUCTURES AND CATALYTIC PROPERTIES OF ISOENZYMES ENCODED BY THE 2 4-COUMARATE-COA LIGASE GENES IN PARSLEY [J].
LOZOYA, E ;
HOFFMANN, H ;
DOUGLAS, C ;
SCHULZ, W ;
SCHEEL, D ;
HAHLBROCK, K .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1988, 176 (03) :661-667