Identification of a Pentaketide Stilbene Produced by a Type III Polyketide Synthase from Pinus sylvestris and Characterisation of Free Coenzyme A Intermediates

被引:11
作者
Li, Tsung-Lin [1 ]
Spiteller, Dieter [2 ]
Spencer, Jonathan B. [3 ]
机构
[1] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan
[2] Max Planck Inst Chem Ecol, D-07745 Jena, Germany
[3] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England
基金
英国生物技术与生命科学研究理事会;
关键词
biosynthesis; malonylresveratrol; polyketide intermediates; polyketides; stilbene synthase; CHALCONE SYNTHASE; BIOSYNTHESIS; PATHWAY; COA;
D O I
10.1002/cbic.200800840
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The stilbene synthase (STS) from Scots pine (Pinus sylvestris), which is a type III polyketide synthase, produces the well known tetraketide resveratrol from coumaroyl-CoA and three molecules of malonyl-CoA. The same stilbene synthase, however, also generates the previously unknown pentaketide 2-malonylresveratrol from coumaroyl-CoA and four molecules of malonyl-CoA; this indicates that the enzyme does not precisely control the number of condensations leading to diverse products. Tetraketide- and pentaketide-CoA intermediates of the STS were identified by LC-MS/MS; this suggests that CoA-bound polyketide intermediates are involved in the product formation of type III polyketide synthases.
引用
收藏
页码:896 / 901
页数:6
相关论文
共 24 条
[1]   Engineered biosynthesis of plant polyketides: Chain length control in an octaketide-producing plant type III polyketide synthase [J].
Abe, I ;
Oguro, S ;
Utsumi, Y ;
Sano, Y ;
Noguchi, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12709-12716
[2]   A plant type III polyketide synthase that produces pentaketide chromone [J].
Abe, I ;
Utsumi, Y ;
Oguro, S ;
Morita, H ;
Sano, Y ;
Noguchi, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1362-1363
[3]   The first plant type III polyketide synthase that catalyzes formation of aromatic heptaketide [J].
Abe, I ;
Utsumi, Y ;
Oguro, S ;
Noguchi, H .
FEBS LETTERS, 2004, 562 (1-3) :171-176
[4]   Enzymatic formation of unnatural novel polyketides from alternate starter and nonphysiological extension substrate by chalcone synthase [J].
Abe, I ;
Takahashi, Y ;
Lou, WW ;
Noguchi, H .
ORGANIC LETTERS, 2003, 5 (08) :1277-1280
[5]   An aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases [J].
Austin, MB ;
Bowman, ME ;
Ferrer, JL ;
Schröder, J ;
Noel, JP .
CHEMISTRY & BIOLOGY, 2004, 11 (09) :1179-1194
[6]   The chalcone synthase superfamily of type III polyketide synthases [J].
Austin, MB ;
Noel, JP .
NATURAL PRODUCT REPORTS, 2003, 20 (01) :79-110
[7]   Iso-coenzyme A [J].
Burns, KL ;
Gelbaum, LT ;
Sullards, MC ;
Bostwick, DE ;
May, SW .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (17) :16550-16558
[8]   Novell stilbenes isolated from the root bark of Ekebergia benguelensis [J].
Chávez, D ;
Chai, HB ;
Chagwedera, TE ;
Gao, Q ;
Farnsworth, NR ;
Cordell, GA ;
Pezzuto, JM ;
Kinghorn, AD .
TETRAHEDRON LETTERS, 2001, 42 (22) :3685-3688
[9]   Structure of the CoA transferase from pig heart to 1.7 Å resolution [J].
Coros, AM ;
Swenson, L ;
Wolodko, WT ;
Fraser, ME .
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 2004, 60 :1717-1725
[10]   New pathway to polyketides in plants [J].
Eckermann, S ;
Schröder, G ;
Schmidt, J ;
Strack, D ;
Edrada, RA ;
Helariutta, Y ;
Elomaa, P ;
Kotilainen, M ;
Kilpeläinen, I ;
Proksch, P ;
Teeri, TH ;
Schröder, J .
NATURE, 1998, 396 (6709) :387-390