Studies on organic sulphur compounds and other labile substances in plants

Virtanen, Artturi I.

doi:10.1016/s0031-9422(00)86168-3

Cited by 230 publications

(117 citation statements)

References 52 publications

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“…Plants of the Allium genus (Alliaceae), such as the leek Allium porrum (L.), produce nonprotein sulfur amino acids derived from cystein, i.e., alk(en)ylcysteine sulfoxides (Virtanen, 1965;Block, 1992). These amino acids are considered precursors of sulfur volatiles because their contact with the enzyme alliinase produced after the rupture of plant tissue cells leads to the formation of sulfur volatiles mainly in the form of thiosulfinates that subsequently break down and rearrange into disulfides and trisulfides (Auger et al, 1989;Jaillais et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Increased Sulfur Precursors and Volatiles Production by the Leek Allium porrum in Response to Specialist Insect Attack

et al. 2005

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Abstract-To defend themselves against herbivory, plants use a variety of direct and indirect strategies involving induced increases in secondary substances. Species of the Allium genus (Alliaceae), such as the leek Allium porrum (L.), produce nonprotein sulfur amino acids derived from cysteine, i.e., alk(en)yl-cysteine sulfoxides that are precursors of volatile thiosulfinates and disulfides. These defend most species including the specialist leek moth, Acrolepiopsis assectella. We determined by measuring the increase in the sulfur precursor propyl-cysteine sulfoxide (PCSO) if production of this precursor is induced in response to moth attack and mechanical wounding. The concentration of PCSO was determined by HPLC in 2-or 6-mo-old leeks after attacks of various intensity either by the specialist leek moth or by a generalist moth, Agrotis ipsilon. Injury-induced release of sulfur volatiles was measured by GC/MS after the attacks. Results showed an increase in the production of sulfur compounds in both the precursor and volatile form, occurring only in association with intensive attacks by leek moths. The increase in sulfur precursors also led to an increase in the release of sulfur volatiles. This induced response may provide an effective defense strategy against the plant's main natural enemy, both directly and indirectly by attracting entomophagous insects.

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Section: Introductionmentioning

confidence: 99%

Increased Sulfur Precursors and Volatiles Production by the Leek Allium porrum in Response to Specialist Insect Attack

et al. 2005

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“…(10). The garlic and onion enzymes are specific for S-alkyl-L-cysteine sulfoxides, however the Brassica preparations studied to date (1,6,11,12) S-Alkyl-L-cysteines and their sulfoxides are prominent constituents of the nonprotein amino acid pool in a number of species of the Amaryllidaceae, Cruciferae, and Leguminosae (4,18). Many of these plants are of considerable economic importance as vegetables.…”

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confidence: 99%

The C-S Lyases of Higher Plants

Hamamoto¹,

Mazelis²

1986

Plant Physiol.

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Cystine lyase degrades L-cystine by a al-elimination to form cysteine persulide, pyruvate, and ammonia. This enzyme is common in Brassica sp. and has been purified to homogeneity from extracts of broccoli (Brassica okeracea var botrytis) buds. Two isozymes were separated on DEAE-Fractogel columns and the first peak, cystine lyase I further purified to homogeneity. The purified enzyme had a narrow range of substrate specificity with L-cystine and S-alkyl-L-cysteine sulfoxides being the primary substrates. The K,. for L-cystine was 1.9 millimolar and for S-ethyl-L-cysteine sulfoxide was 15.6 millimolar, suggesting that L-cystine would be prefeffed in vivo. Using gel filtration and sodium dodecyl sulfate-polyacrylamide gel electrophoresis the molecular weight of the holoenzyme was estimated as 152,000 composed of subunits of approximately 49,000. This strongly suggests the native enzyme is a trimer. The presence of carbohydrate in the native enzyme was detected at the level of 5.8% on a weight basis. Except for the ability to utilize Lcystine as a substrate there are many similarities between cystine lyase I and the alliin lyase of onion (Allium cepa).This enzyme has been purified to homogeneity from garlic (8,14) and onion (17) and found in a number of Brassica sp. (10). The garlic and onion enzymes are specific for S-alkyl-L-cysteine sulfoxides, however the Brassica preparations studied to date (1,6,11,12) also can cleave L-cystine according to reaction 2: S -s H2C +

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“…The other diastereoisomer, which has the same mobility on HVE as that of natural 5 and considered to be (2S,4R)-5 (Lerythro) was eluted in fractions 24"" 28 and obtained as a crystalline evaporation residue. It seems reasonable to presume that two diastereoisomers of 5 show the same behavior on HVE as those of 1,7) that is, the erythro form has a higher mobility than the threo form. It has been reported that the three configurations A, B, and C shown below all give positive Cotton effects at about 200 nm and the contributions of the assymmetric centers C-2 and C-4 of 4-substituted glutamic .acid derivatives are approximately additive.…”

Section: (S Ih) Fdms M/z: 116 (M+ + 1 100%)mentioning

confidence: 99%

“…1 ) The plants belonging to Tulipa of the same family are famous for containing a variety of 4-substituted glutamic acid derivatives. 2 -4) We have isolated four acidic cysteine derivatives and several acidic peptides from Asparagus officinalis of the same family.5) This report deals with non-protein amino acids and small peptides in tubers of Smilax china (sarutori-ibara), bulbs of Lilium maximowiczii, Tulipa gesneriana, A. cepa, and A. sativum including the isolation of two new amino acids and one peptide, that is, 4-hydroxymethylglutamic acid and 4-ethyl-4-hydroxyglutamic acid from T. gesneriana and S-(2-carboxy-npropyl)cysteinylglycine from A. cepa.…”

mentioning

confidence: 99%