Skip to main content
Log in

The biosynthetic pathway of the S-alk(en)yl-L-cysteine sulphoxides (flavour precursors) in species of Allium

  • Published:
Plant Cell, Tissue and Organ Culture Aims and scope Submit manuscript

Abstract

Pulse labelling experiments with 35SO4 2- fed for 24h to intact plants (shooted onion sets)of Allium cepa (onion) showed that >70% of the label appeared in the S-alkenyl-L-cysteine sulphoxides within 18h, reached a maximum at 48h and thereafter decreased. The amount of label detected in the γ-glutamyl peptide fractions was below 20% of the total label at any time. It is concluded that in intact plants (at the growth stage used) the γ-glutamyl peptides are not the immediate precursors of the S-alkenyl-L-cysteine sulphoxides. The major S-alkenyl-L-cysteine sulphoxide in onion was found to be compartmentalized mainly within the endoplasmatic reticulum.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

AllCysSO:

(+)-S-2-propenyl-L-cysteine sulphoxide

MeCysSO:

(+)-S-methyl-L-cysteine sulphoxide

PrenCysSO:

trans-(+)-S-1-propenyl-L-cysteine sulphoxide

ProCysSO:

(+)-S-propyl-L-cysteine sulphoxide

References

  • Cavallito CJ & Bailey JH (1944) Allicin the active principle of Allium sativum. I. Isolation, physical properties and antibacterial action. J. Am. Chem. Soc. 66: 1950–1951

    Google Scholar 

  • Collin HA, Musker D & Britton G (1989) Compartmentation of flavour precursor synthesis in the onion. In: Kurz WGW (Ed) Primary and secondary metabolism of plant cell cultures II (pp 125–132) Springer-Verlag, Berlin Heidelberg

    Google Scholar 

  • Edwards SJ, Musker D, Collin HA & Britton G (1994) The analysis of S-alk(en)yl-L-cysteine sulphoxides (flavour precursors) from species of Allium by HPLC. Phytochem. Anal. 5: 4–9

    Google Scholar 

  • Giovanelli J, Harvey Mudd S & Datko AH (1980) Sulfur amino acids in plants. In: Miflin BJ (Ed) The biochemistry of plants: a comprehensive treatise, Vol 5 (pp 453–505). Academic Press, New York

    Google Scholar 

  • Granroth B (1970) Biosynthesis and decomposition of cysteine derivatives in onion and other Allium species. Ann. Acad. Scient. Fenn. Ser. A. 2, 154: 1

    Google Scholar 

  • Kasai T & Larsen PO (1980) Chemistry and biochemistry of γ-glutamyl derivatives from plants including mushrooms (Basidiomycetes). In: Herz W, Grisebach H & Kirby GW (Eds) Progress in the chemistry of organic natural products, Vol 39. Springer New York

    Google Scholar 

  • Lancaster JE & Collin HA (1981) Presence of alliinase in isolated vacuoles and of alkyl cysteine sulphoxides in the cytoplasm of bulbs of onion (Allium cepa). Plant Sci. Lett. 22: 169–176

    Google Scholar 

  • Lancaster JE, McCallion BJ & Shaw ML (1984) The levels of S-alk(en)yl-L-cysteine sulphoxides during the growth of the onion (Allium cepa L.). J. Sci. Food Agric. 35: 415–420

    Google Scholar 

  • Lancaster JE, Reynolds PHS, Shaw M, Domisse EM & Munro J (1989) Intracellular localisation of the biosynthetic pathway to flavour precursors in onion. Phytochemistry 28: 461–464

    Google Scholar 

  • Lancaster JE & Shaw ML (1989) γ-Glutamyl peptides in the biosynthesis of s-alk(en)yl-L-cysteine sulphoxides (flavour precursors) in Allium. Phytochemistry 28: 455–460

    Google Scholar 

  • Lancaster JE & Shaw ML (1991) Metabolism of γ-glutamyl peptides during development, storage and sprouting of onion bulbs. Phytochemistry 30: 2857–2859

    Google Scholar 

  • Musker D (1988) Secondary Product Biosynthesis in Plant Cell Cultures Ph.D. Thesis, University of Liverpool

  • Naftalin L, Sexton M, Whitaker JE & Tracey D (1969) A routine procedure for estimating serum γ-glutamyl transpeptidase activity. Clin. Chim. Acta 26: 293

    Google Scholar 

  • Ohsumi C, Hayashi T & Sano K (1993) Formation of alliin in the culture tissues of Allium sativum. Oxidation of S-allyl-L-cysteine. Phytochemistry 33: 107–111

    Google Scholar 

  • Parry RJ & Lii F-L (1991) Investigations of the biosynthesis of trans-(+)-S-1-propenyl-L-cysteine sulfoxide. Elucidation of the stereochemistry of the oxidative decarboxylation process. J. Am. Chem. Soc. 113: 4704–4706

    Google Scholar 

  • Schneider A, Martini N & Rennenberg H (1992) Reduced glutathione (GSH) transport into cultured tobacco cells. Plant Physiol. Biochem. 30: 29–38

    Google Scholar 

  • Schwimmer S (1968) Enzymic conversion of trans-(+)-S-1-propenyl-L-cysteine sulphoxide to the bitter odor bearing component of onion. Phytochemistry 7: 401–404

    Google Scholar 

  • Stoll A & Seebeck E (1951) Chemical investigations on alliin the specific principle of garlic. Adv. Enzymol. 11: 377–400

    Google Scholar 

  • Sugii M, Nagasawa S & Suzuki (1963) Biosynthesis of S-Methyl-L-cysteine and S-Methyl-L-cysteine sulfoxide from methionine in Garlic. Chem. Pharm. Bull. 11: 135–136

    Google Scholar 

  • Suzuki T, Sugi M & Kakimoto T (1961) New γ-glutamyl peptides in garlic. Chem. Pharm. Bull. 9: 77–78

    Google Scholar 

  • Suzuki T, Sugii M & Kakimoto T (1962) Metabolic incorporation of L-valine (14C) into S-(2-carboxypropyl) glutathione and S-(2-carboxypropyl) cysteine in garlic. Chem. Pharm. Bull. 10: 328–331

    Google Scholar 

  • Turnbull A, Galpin IJ & Collin HA (1980) Comparison of the onion plant (Allium cepa) and onion tissue culture. III. Feeding of 14C labelled precursors of the flavour precursor compounds. New Phytol. 85: 483–487

    Google Scholar 

  • Virtanen AI (1965) Studies on organic sulphur compounds and other labile substances in plants. Phytochemistry 4: 207–228

    Google Scholar 

  • Virtanen AI & Spare C-G (1961) Isolation of the precursor of the lachrimatory factor in onion (Allium cepa). Suomen Kemistilehti 34: 72–74

    Google Scholar 

  • Whitaker RJ (1976) Development of flavour, odor and pungency in onion and garlic. Adv. Food. Res. 22: 73–133

    Google Scholar 

  • Wintermans JFGM & DeNots A (1965) Spectrophotometric characteristics of chlorophylls a and b and their pheophytins in ethanol. Biochim. Biophys. Acta. 109: 448–453

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Edwards, S.J., Britton, G. & Collin, H.A. The biosynthetic pathway of the S-alk(en)yl-L-cysteine sulphoxides (flavour precursors) in species of Allium . Plant Cell Tiss Organ Cult 38, 181–188 (1994). https://doi.org/10.1007/BF00033876

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00033876

Key words

Navigation