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Allium discoloration: the precursor and formation of the red pigment in giant onion (Allium giganteum Regel) and some other subgenus Melanocrommyum species
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SYSNO ASEP 0358482 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Allium discoloration: the precursor and formation of the red pigment in giant onion (Allium giganteum Regel) and some other subgenus Melanocrommyum species Author(s) Kučerová, P. (CZ)
Kubec, R. (CZ)
Šimek, Petr (BC-A) RID, ORCID
Václavík, P. (CZ)
Schraml, Jan (UCHP-M) RID, ORCID, SAINumber of authors 5 Source Title Journal of Agricultural and Food Chemistry. - : American Chemical Society - ISSN 0021-8561
Roč. 59, č. 5 (2011), s. 1821-1828Number of pages 8 s. Language eng - English Country US - United States Keywords S-(2-pyrrolyl)cysteine S-oxide ; S-(3-pyrrolyl)cysteine S-oxide ; giant onion Subject RIV CE - Biochemistry R&D Projects IAA400720706 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z50070508 - ENTU-I, BC-A (2005-2011) AV0Z40720504 - UCHP-M (2005-2011) UT WOS 000287824400044 DOI 10.1021/jf104195k Annotation The precursor of the orange-red pigment formed upon wounding the bulbs of Allium giganteum (Allium subg. Mclanocrommyum) was isolated and shown to be S-(2-pyrroly)cysteine S-oxide. In addition, two other pyrrolylsulfinyl derivatives were found in an extract from the bulbs, namely, 3-(2-pyrrolylsulfinyl)lactic acid and S-(3-pyrrolyl)c-ysteine S-oxide. Contrary to a previous report, the latter compound was shown not to serve as the precursor of the pigment, being in fact only an artifact formed du:ring isolation. The formation of pyrrolyl-containing compounds following disruption of A. giganteum bulbs was studied by a combination of LC-MS, LC-NMR and DART-MS. It was found that S-(2-pyrroly)cysteine S-oxide is cleaved by a C-S lyase (alliinase) to yield 2-pyrrolesulfenic acid. Two molecules of the latter compound give rise to highly reactive S-(2-pyrrolyl) 2-pyrrolethiosulfinate which in turn converts into red 2,2'-epidithio-3,3'-dipyrrole (dipyrrolo[2,3-d:2',3'-e]-1,2-dithiin). Workplace Biology Centre (since 2006) Contact Dana Hypšová, eje@eje.cz, Tel.: 387 775 214 Year of Publishing 2012
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