Biosynthesis of Cyanogenic Glycosides

Overview

Journal Naturwissenschaften

Specialty Science

Date 1979 Jan 1

PMID 423994

Citations 9

Authors

E E Conn

Affiliations

Soon will be listed here.

Abstract

Cyanogenic glycosides are secondary plant compounds that occur widely in the plant kingdom. They are the source of HCN which can render the plant toxic if it is taken as food. The enzymes responsible for production of the HCN have long been known. More recent biosynthetic studies have established certain protein amino acids as precursors of the aglycones, and indicate N-hydroxyamino acids, aldoximes, nitriles and alpha-hydroxynitriles as intermediates. In sorghum the several biosynthetic enzymes catalyzing the flow of carbon atoms from L-tyrosine through such nitrogenous intermediates are located in a membrane fraction and may be capable of metabolic channeling.

Citing Articles

From sequence to function: a new workflow for nitrilase identification.

Egelkamp R, Friedrich I, Hertel R, Daniel R Appl Microbiol Biotechnol. 2020; 104(11):4957-4970.

PMID: 32291488 PMC: 7228900. DOI: 10.1007/s00253-020-10544-9.

Natural nitriles and their metabolism.

Legras J, Chuzel G, Arnaud A, Galzy P World J Microbiol Biotechnol. 2014; 6(2):83-108.

PMID: 24429979 DOI: 10.1007/BF01200927.

Cyanogenesis-a general phenomenon in the lepidoptera?.

Witthohn K, Naumann C J Chem Ecol. 2013; 13(8):1789-809.

PMID: 24302389 DOI: 10.1007/BF01013229.

Cyanide formation from glyoxylate and hydroxylamine catalysed by extracts of higher-plant leaves.

Hucklesby D, Dowling M, Hewitt E Planta. 2013; 156(6):487-91.

PMID: 24272725 DOI: 10.1007/BF00392769.

Effect of adaptation strategies when feeding fresh cassava foliage on intake and physiological responses of lambs.

Hue K, Thanh Van D, Sporndly E, Ledin I, Wredle E Trop Anim Health Prod. 2011; 44(2):267-76.

PMID: 22081316 DOI: 10.1007/s11250-011-0013-0.

References

Seely M, Criddle R, Conn E . The metabolism of aromatic compounds in higher plants. 8. On the requirement of hydroxynitrile lyase for flavin. J Biol Chem. 1966; 241(19):4457-62. View

Butler G, Conn E . BIOSYNTHESIS OF THE CYANOGENIC GLUCOSIDES LINAMARIN AND LOTAUSTRALIN. I. LABELING STUDIES IN VIVO WITH LINUM USITATISSIMUM. J Biol Chem. 1964; 239:1674-9. View

Hahlbrock K, Tapper B, Butler G, Conn E . Conversion of nitriles and alpha-hydroxynitriles to cyanogenic glucosides in flax seedlings and cherry laurel leaves. Arch Biochem Biophys. 1968; 125(3):1013-6. DOI: 10.1016/0003-9861(68)90538-9. View

Blum M, Woodring J . Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood). Science. 1962; 138(3539):512-3. DOI: 10.1126/science.138.3539.512. View

Reay P, Conn E . The purification and properties of a uridine diphosphate glucose: aldehyde cyanohydrin beta-glucosyltransferase from sorghum seedlings. J Biol Chem. 1974; 249(18):5826-30. View

Moller B, Conn E . Biological formation of N-hydroxyamino acids. Proc West Pharmacol Soc. 1977; 20:103-7. View

Eyjolfsson R . Recent advances in the chemistry of cyanogenic glycosides. Fortschr Chem Org Naturst. 1970; 28:74-108. DOI: 10.1007/978-3-7091-7123-3_2. View

Rosen M, Farnden K, Conn E . Stereochemical aspects of the biosynthesis of the epimeric cyanogenic glucosides dhurrin and taxiphyllin. J Biol Chem. 1975; 250(21):8302-8. View

Underhill E, Wetter L, Chisholm M . Biosynthesis of glucosinolates. Biochem Soc Symp. 1973; (38):303-326. View

10.

Gaertner F, Ericson M, Demoss J . Catalytic facilitation in vitro by two multienyzme complexes from Neurospora crassa. J Biol Chem. 1970; 245(3):595-600. View

11.

Saunders J, Conn E . Presence of the cyanogenic glucoside dhurrin in isolated vacuoles from sorghum. Plant Physiol. 1978; 61(2):154-7. PMC: 1091823. DOI: 10.1104/pp.61.2.154. View

12.

Czichi U, Kindl H . Phenylalanine ammonia lyase and cinnamic acid hydroxylases as assembled consecutive enzymes on microsomal membranes of cucumber cotyledons: Cooperation and subcellular distribution. Planta. 2014; 134(2):133-43. DOI: 10.1007/BF00384962. View

13.

Saunders J, Conn E . Subcellular localization of the cyanogenic glucoside of sorghum by autoradiography. Plant Physiol. 1977; 59(4):647-52. PMC: 542466. DOI: 10.1104/pp.59.4.647. View

14.

Macfarlane I, Lees E, Conn E . The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor. J Biol Chem. 1975; 250(12):4708-13. View

15.

Knowles C . Microorganisms and cyanide. Bacteriol Rev. 1976; 40(3):652-80. PMC: 413975. DOI: 10.1128/br.40.3.652-680.1976. View

16.

Lewis J . Laetrile. West J Med. 1977; 127(1):55-62. PMC: 1237697. View

17.

Koukol J, Miljanich P, CONNEE . The metabolism of aromatic compounds in higher plants. VI. Studies on the biosynthesis of dhurrin, the cyanogenic glucoside of Sorghum vulgare. J Biol Chem. 1962; 237:3223-8. View

18.

Zilg H, Tapper B, Conn E . The origin of the glucosidic linkage oxygen of the cyanogenic glucosides, linamarin and lotaustralin. J Biol Chem. 1972; 247(8):2384-6. View

19.

Conn E . Biosynthesis of cyanogenic glycosides. Biochem Soc Symp. 1973; (38):277-302. View

20.

Shimada M, Conn E . The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile. Arch Biochem Biophys. 1977; 180(1):199-207. DOI: 10.1016/0003-9861(77)90026-1. View