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" Cyanogenic glycosides: physiology and regulation of synthesis "

Determination of cyanide and cyanogenic compounds in biological systems.

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Cyanogenic glycosides and cyanohydrins in plant tissues.

Transgenic tobacco and Arabidopsis plants expressing the two multifunctional sorghum cytochrome P450 enzymes, CYP79A1 and CYP71E1, are cyanogenic and accumulate metabolites derived from intermediates in dhurrin biosynthesis.

Biosynthesis of cyanogenic glycosides.

The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates.

Investigations on cyanogenic plants.

The glycoside is usually a monoglycoside, although there are a number of diglycosides and one triglycoside Chemically, cyanogenic glycosides are defined as glycosides of alpha-hydroxynitriles; plants store these compounds in vacuoles.

Most of the plant families producing cyanogenic glycosides belong to the Angyospermatophyta and the remaining to the Dicotyledonopsida and Monocotyledonopsida.

Why are so many food plants cyanogenic?

Several important crop plants such as sorghum (Sorghum bicolor), cassava (Manihot esculenta), and barley (Hordium vulgare) are among others which essentially biosynthesize and accumulate cyanogenic glycosides.

Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin.

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  • Cyanogenesis and the role of cyanogenic compounds in insects.

    Cyanogenic glycosides are secondary plant compounds that occur widely inthe plant kingdom.

  • The biology of the cyanogenic glycosides: new developments.

    Frequency and distribution of cyanogenic glycosides in Eucalyptus L'Hérit.

  • Localization and catabolism of cyanogenic glycosides.

    Fate in humans of dietary intake of cyanogenic glycosides from roots of sweet cassava consumed in Cuba.

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Biosynthesis of cyanogenic glycosides.

cyanogenic glycoside biosynthetic pathway in plants:

(i) precursor amino acid --> aldoxime (N-hydroxylation by cytochrome-P450 enzyme)
(ii) aldoxime --> cyanohydrin (another cytochrome-P450 enzyme)
(iii) cyanohydrins get glycosylated (soluble enzyme UDP-glucosyltransferase) Degradation of cyanogenic glycosides is a two-step process.

Biosynthesis of the Cyanogenic Glucosides Linamarin …

thaliana plants expressing both CYP79A1 and CYP71E1, but not sbHMNGT, accumulate glucosides of benzoic acid, a product of p-hydroxymandelonitrile decomposition.

CYP79A1 gene expression --> production of p-hydroxybenzylglucosinolate (metabolic cross talk between cyanogenic glucoside and glucosinolate synthesis).

Biosynthesis of cyanogenic glycosides | SpringerLink

Galactinol is synthesized by the formation of a glycoside betweenUDP-D-galactose and myoinsitol by UDP-D-glactose:myoinositolgalactosyltransferase:

STRUCTURE AND BIOSYNTHESIS OF CYANOGENIC GLYCOSIDES

nemorum, demonstrating that cyanogenic glucosides can promote plant defense.

with this technology at hand, installment of natural products for plant defense in food crops is possible.

Biosynthesis of cyanogenic glycosides

Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.

Convergent evolution in biosynthesis of cyanogenic …

Cloning and expression of cytochrome P450 enzymes catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of cyanogenic glucosides in Triglochin maritima.

Cyanogenic glycosides: physiology and regulation of …

Since plant hormone ethylene is produced by all plants, andcyanide is a co-product of ethylene biosynthesis, it is not surprising thatL-3-cyanoalanine synthase is not confined to cyanogenic plants but occurswidely throughout the plant kingdom. A major source of cyanide is from thehydrolysis of cyanogenic glycosides in those plant species which accumulatethem. For those plant tissues which do not accumulate cyanogenic glycosides,but produce ethylene at a high rate, ethylene biosynthesis can be the majorsource of HCN (Wurtele et al., 1985). Hence, when the ethylene production rateand the capability to detoxify HCN in a tissue are known, it is possible toestimate the steady state [HCN] level within the tissue. The overall reactionis shown below:

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