Purification, partial amino acid sequence and structure of the product of raucaffricine-O-β-d-glucosidase from plant cell cultures of Rauwolfia serpentina

Warzecha, Heribert; Obitz, Peter; Stöckigt, Joachim

doi:10.1016/s0031-9422(98)00689-x

Cited by 23 publications

(16 citation statements)

References 29 publications

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“…Flavonols (Wollenweber 1986), monoterpenoids (Sefton et al 1994) and hydroxybenzoic acids (Klick and Herrmann 1988;Yazaki et al 1995) accumulate as both aglycones and glycosides, whilst alkaloids rarely accumulate as glycosides (Warzecha et al 1999). This pattern may re¯ect the varying stability or reactivity of secondary plant metabolite aglycones.…”

Section: Glycosylation As a Chemically Modifying Safety Netmentioning

confidence: 99%

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Glycosyltransferases in secondary plant metabolism: tranquilizers and stimulant controllers

Jones

Vogt

2001

Planta

374

244

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Plants are exposed to a wide range of toxic and bioactive low-molecular-weight molecules from both exogenous and endogenous sources. Glycosylation is one of the primary sedative mechanisms that plants utilise in order to maintain metabolic homeostasis. Recently, a range of glycosyltransferases has been characterized in detail with regard to substrate specificity. The next step in increasing our understanding of the biology of glycosylation will require information regarding the exact role of individual glycosyltransferases in planta, as well as an insight into their potential involvement in metabolon-complexes. Hopefully, this will answer how a large number of glycosyltransferases with broad, rather than narrow, substrate specificity can be constrained in order to avoid interfering with other pathways of primary and secondary metabolism. These and other topics are discussed.

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Section: Glycosylation As a Chemically Modifying Safety Netmentioning

confidence: 99%

“…It is important to remember that the hydrolysis of glycosides by beta-glucosidases is also a very important and a complementary part of glycoside metabolism that will not be covered here (Warzecha et al 1999;Cicek et al 2000).…”

Section: Introductionmentioning

confidence: 99%

Glycosyltransferases in secondary plant metabolism: tranquilizers and stimulant controllers

Jones

Vogt

2001

Planta

374

244

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“…The transport of secondary metabolites and/or xenobiotics across the vacuolar membrane is determined by the ligand to which they are conjugated. Polyphenolic acids (Regnault-Roger et al 2004), flavonols (Jones and Vogt 2001), monoterpenes (Sefton et al 1994), sesquiterpenes (Castillo et al 1999), flavonoids (Geibel 1995) and hydroxybenzoic acids (Klick and Herrmann 1988;Yazaki et al 1995) accumulate as both aglycones and glycosides, whilst alkaloids rarely accumulate as glycosides (Warzecha et al 1999). Szakiel and Janiszowska (2002) demonstrated that two endogenous oleanolic acid monoglycosides distinctly differed in their mechanism of transport to the vacuole in Calendula officinalis cells.…”

Section: Diversity Of Vacuolar Transportersmentioning

confidence: 99%

Role of vacuolar transporter proteins in plant secondary metabolism: Catharanthus roseus cell culture

Roytrakul

Verpoorte

2007

Phytochem Rev

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Here the current status of knowledge on some well-characterized transporters located in the vacuolar membrane is reviewed. As different cellular compartments and even different cells may be involved in certain steps of a biosynthetic pathway, the regulation of the flux is not only dependent on structural genes encoding enzymes catabolizing certain steps but also transport has a major regulatory function. The aim of the present review is to give an overview of the present knowledge of transport of secondary metabolites in plants, and to use this information in the context of our knowledge about Catharanthus roseus alkaloid biosynthesis. This should lead to further insight in the possible role of various transporters in the regulation of the biosynthesis of these alkaloids.

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“…This assignment is also supported by the strong deshielding of H‐5 of 21‐epi‐vomilenine (δ H =3.70 ppm), caused by the proximity of the C‐21 hydroxy group, in comparison to vomilenine (δ H =3.26 ppm; Table S1). A previous report showed that this slow equilibration can be accelerated by addition of water,23 thus suggesting that the epimerization could occur under physiologically relevant aqueous conditions. Given that plant CYPs in specialized metabolism typically catalyze highly specific reactions, it is most likely that VH catalyzes a regio‐ and stereoselective hydroxylation reaction that is followed by isomerization, although oxidation by VH through hydride abstraction to form the iminium moiety could also be possible.…”

mentioning

confidence: 94%

Dual Catalytic Activity of a Cytochrome P450 Controls Bifurcation at a Metabolic Branch Point of Alkaloid Biosynthesis in Rauwolfia serpentina

et al. 2017

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Plants create tremendous chemical diversity from a single biosynthetic intermediate. In plant‐derived ajmalan alkaloid pathways, the biosynthetic intermediate vomilenine can be transformed into the anti‐arrhythmic compound ajmaline, or alternatively, can isomerize to form perakine, an alkaloid with a structurally distinct scaffold. Here we report the discovery and characterization of vinorine hydroxylase, a cytochrome P450 enzyme that hydroxylates vinorine to form vomilenine, which was found to exist as a mixture of rapidly interconverting epimers. Surprisingly, this cytochrome P450 also catalyzes the non‐oxidative isomerization of the ajmaline precursor vomilenine to perakine. This unusual dual catalytic activity of vinorine hydroxylase thereby provides a control mechanism for the bifurcation of these alkaloid pathway branches. This discovery highlights the unusual catalytic functionality that has evolved in plant pathways.

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Purification, partial amino acid sequence and structure of the product of raucaffricine-O-β-d-glucosidase from plant cell cultures of Rauwolfia serpentina

Cited by 23 publications

References 29 publications

Glycosyltransferases in secondary plant metabolism: tranquilizers and stimulant controllers

Glycosyltransferases in secondary plant metabolism: tranquilizers and stimulant controllers

Role of vacuolar transporter proteins in plant secondary metabolism: Catharanthus roseus cell culture

Dual Catalytic Activity of a Cytochrome P450 Controls Bifurcation at a Metabolic Branch Point of Alkaloid Biosynthesis in Rauwolfia serpentina

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