Stilbene biosynthesis

Stilbene synthase shows similarity to chalcone synthase, which is not surprising given that stilbenes (3.97) also originate from the condensation of 

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Rupprich N, Hildebrand H, Kindi H. 1980. Substrate specificity in vivo and in vitro in the formation of stilbenes. Biosynthesis of rhaponticin. Arch Biochem Biophys 200 72-78. 

The irreversible condensation reaction between a starter hydroxycinnamoyl-CoA molecule and three acetate extender units derived from malonyl-CoA constitute the first committed step of flavonoid and stilbene biosynthesis [Springob et al., 2003] (Fig. 21.2). The reactions catalyzed by two type III... 

In recent years great endeavor has been devoted to the biosynthesis of stilbene. Biosynthesis of simple stilbenes has been well characterized [4], and it only specifically requires the presence of stilbene synthase (STS) [366, 367]. There exists a balance between the stilbenoid and flavonoid biosyntheses [368]. The related research such as function of related gene sequences, molecular regulation of the biosynthesis process etc. could be referred to the literatures [369-371]. 

Some groups applied C NMR to study the stilbene biosynthesis pathway [18,372], for example mulberrosides A [373] and D (32) [18]. The type III PKS stilbene synthase (STS) was also employed to investigate the potential of a nonhydrolyzable malonyl-coenzyme A analog to trap intermediates of polyketide biosynthesis [374],... 

Pyrones and Styrylpyrones Biosynthesis Systematic usefulness Biological activity Stilbenes Biosynthesis Biological activity... 

The next major enzyme in the series, p-coumarate CoA ligase, was first isolated from illuminated cell suspension cultures of Petroselinum crispum (syn. P. hortense) and shown to be specifically related to flavonoid and stilbene biosynthesis. The enzyme requires p-coumaric acid, CoASH, ATP, and Mg for activity (Hahlbrock, 1981 Hutchinson, 1986). Three malonyl-CoA units are added and cyclized via a Claisen condensation (see Chapter 5) to produce a chalcone intermediate (9). Condensation of the same intermediates via an aldol condensation yields pyrones and... 

Saigne-Soulard et al. [32] analyzed the influence of Phe on stilbene biosynthesis in V. vinifera cv Camay Freaux cell cultures, observing that the treatment of the cells with 1 mM Phe resulted in an enrichment in stilbenes (62 mg L ), the maximal stilbene levels being reached when Phe was completely metabolized by the cells. Aumont et al. [33] also studied the effect of the administration of 3 mM Phe to V. vinifera cv Camay Freaux cell cultures. Their results pointed out an increase in the... 

Sparvoli F, Martin C, Scienza A, Gavazzi G, Tonelli C (1994) Cloning and molecular analysis of structural genes involved in flavonoid and stilbene biosynthesis in grape (Vitis vinifera L.). Plant Mol Biol 24 743-755... 

Watts, K. T., R C. Lee et al. (2006). Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. BMC Biotechnol. 6 22. 

Recently, a new polyketide biosynthetic pathway in bacteria that parallels the well studied plant PKSs has been discovered that can assemble small aromatic metabolites.8,9 These type III PKSs10 are members of the chalcone synthase (CHS) and stilbene synthase (STS) family of PKSs previously thought to be restricted to plants.11 The best studied type III PKS is CHS. Physiologically, CHS catalyzes the biosynthesis of 4,2, 4, 6 -tetrahydroxychalcone (chalcone). Moreover, in some organisms CHS works in concert with chalcone reductase (CHR) to produce 4,2 ,4 -trihydroxychalcone (deoxychalcone) (Fig. 12.1). Both natural products constitute plant secondary metabolites that are used as precursors for the biosynthesis of anthocyanin pigments, anti-microbial phytoalexins, and chemical inducers of Rhizobium nodulation genes.12... 

Biotin metabolism Folate biosynthesis One carbon pool by folate Retinol metabolism Porphyrin and chlorophyll metabolism Terpenoid biosynthesis Xenobiotics metabolism Ubiquinone biosynthesis Flavonoids, stilbene, and lignin biosynthesis... 

Figure 3-15. Biosynthesis of stilbene from p-coumaroyl-CoA with three molecules malonyl-CoA, catalyzed by the enzyme stilbene synthase (a E.C. 2.3.1.95).

The biosynthesis of flavonoids, stilbenes, hydroxycinnamates, and phenolic acids involves a complex network of routes based principally on the shikimate, phenyl-propanoid, and flavonoid pathways (Figs. 1.35 and 1.36). These biosynthetic pathways constitute a complex biological regulatory network that has evolved in vascular plants during their successful transition on land and that ultimately is essential for their growth, development, and survival [Costa et al., 2003]. 

Kodan A, Kuroda H, Sakai F. 2002. Stilbene synthase from Japanese red pine (Pinus densiflora) implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis. Proc Natl Acad Sci USA 99 3335-3339. 

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