Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants

被引:261
作者
Frey, Monika [1 ]
Schullehner, Katrin [1 ]
Dick, Regina [1 ]
Fiesselmann, Andreas [1 ]
Gierl, Alfons [1 ]
机构
[1] Tech Univ Munich, Lehrstuhl Genet, D-85350 Freising Weihenstephan, Germany
关键词
Hydroxamic acids; Cytochrome P450 monooxygenase; DIBOA; DIMBOA; Evolution of secondary metabolism; Functional gene cluster; Glucosyltransferase; O-methyltransferase; 2-Oxoglutarate dependent dioxygenase; Tryptophan synthase; CYCLIC HYDROXAMIC ACIDS; TRYPTOPHAN SYNTHASE; ALPHA-SUBUNIT; MOLECULAR CHARACTERIZATION; CYTOCHROME-P450; GENES; ALKALOID BIOSYNTHESIS; DIMBOA; RESISTANCE; WHEAT; ARABIDOPSIS;
D O I
10.1016/j.phytochem.2009.05.012
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
Benzoxazinoids are secondary metabolites that are effective in defence and allelopathy. They are synthesised in two subfamilies of the Poaceae and sporadically found in single species of the dicots. The biosynthesis is fully elucidated in maize; here the genes encoding the enzymes of the pathway are in physical proximity. This "biosynthetic cluster" might facilitate coordinated gene regulation. Data from Zea mays, Triticum aestivum and Hordeum lechleri suggest that the pathway is of monophyletic origin in the Poaceae. The branchpoint from the primary metabolism (Bx1 gene) can be traced back to duplication and functionalisation of the alpha-subunit of tryptophan synthase (TSA). Modification of the intermediates by consecutive hydroxylation is catalysed by members of a cytochrome P450 enzyme subfamily (Bx2-Bx5). Glucosylation by an UDP-glucosyltransferase (UGT, W, Bx9) is essential for the reduction of autotoxicity of the benzoxazinoids. In some species 2,4-dihydroxy-1,4-benzoxazin-3-one-glucoside (DIBOA-glc) is further modified by the 2-oxoglutarate-dependent dioxygenase BX6 and the O-methyltransferase BX7. In the dicots Aphelandra squarrosa, Consolida orientalis, and Lamium galeobdolon, benzoxazinoid biosynthesis is analogously organised: The branchpoint is established by a homolog of TSA, P450 enzymes catalyse hydroxylations and at least the first hydroxylation reaction is identical in dicots and Poaceae, the toxic aglucon is glucosylated by an UGT. Functionally, TSA and BX1 are indole-glycerolphosphate lyases (IGLs). Igl genes seem to be generally duplicated in angiosperms. Modelling and biochemical characterisation of IGLs reveal that the catalytic properties of the enzyme can easily be modified by mutation. Independent evolution can be assumed for the BX1 function in dicots and Poaceae. (C) 2009 Elsevier Ltd. All rights reserved.
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页码:1645 / 1651
页数:7
相关论文
共 53 条
[1]   Benzoxazinoids and iridoid glucosides from four Lamium species [J].
Alipieva, KI ;
Taskova, RM ;
Evstatieva, LN ;
Handjieva, NV ;
Popov, SS .
PHYTOCHEMISTRY, 2003, 64 (08) :1413-1417
[2]   ROLE OF BENZOXAZINONES IN ALLELOPATHY BY RYE (SECALE-CEREALE L) [J].
BARNES, JP ;
PUTNAM, AR .
JOURNAL OF CHEMICAL ECOLOGY, 1987, 13 (04) :889-906
[3]   Benzoxazinoids-cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae) [J].
Baumeler, A ;
Hesse, M ;
Werner, C .
PHYTOCHEMISTRY, 2000, 53 (02) :213-222
[4]  
Copaja SV, 2006, Z NATURFORSCH C, V61, P670
[5]   REACTION OF DIMBOA, A RESISTANCE FACTOR FROM CEREALS, WITH ALPHA-CHYMOTRYPSIN [J].
CUEVAS, L ;
NIEMEYER, HM ;
PEREZ, FJ .
PHYTOCHEMISTRY, 1990, 29 (05) :1429-1432
[6]   EFFECT OF HYDROXAMIC ACIDS FROM CEREALS ON APHID CHOLINESTERASES [J].
CUEVAS, L ;
NIEMEYER, HM .
PHYTOCHEMISTRY, 1993, 34 (04) :983-985
[7]   Natural products and plant disease resistance [J].
Dixon, RA .
NATURE, 2001, 411 (6839) :843-847
[8]   Metabolic diversification - Independent assembly of operon-like gene clusters in different plants [J].
Field, Ben ;
Osbourn, Anne E. .
SCIENCE, 2008, 320 (5875) :543-547
[9]   EXPRESSION OF A CYTOCHROME-P450 GENE FAMILY IN MAIZE [J].
FREY, M ;
KLIEM, R ;
SAEDLER, H ;
GIERL, A .
MOLECULAR & GENERAL GENETICS, 1995, 246 (01) :100-109
[10]   A 2-oxoglutarate-dependent dioxygenase is integrated in DIMBOA-biosynthesis [J].
Frey, M ;
Huber, K ;
Park, WJ ;
Sicker, D ;
Lindberg, P ;
Meeley, RB ;
Simmons, CR ;
Yalpani, N ;
Gierl, A .
PHYTOCHEMISTRY, 2003, 62 (03) :371-376