Isoalliin-Derived Thiolanes Formed in Homogenized Onion

0509099 - MBÚ 2020 RIV US eng J - Článek v odborném periodiku
Štefanová, I. - Zápal, Jakub - Moos, Martin - Kuzma, Marek - Kubec, R.
Isoalliin-Derived Thiolanes Formed in Homogenized Onion.
Journal of Agricultural and Food Chemistry. Roč. 67, č. 35 (2019), s. 9895-9906. ISSN 0021-8561. E-ISSN 1520-5118
Grant CEP: GA ČR(CZ) GA17-22276S; GA MŠMT(CZ) LO1509
Institucionální podpora: RVO:61388971 ; RVO:60077344
Klíčová slova: ajothiolane * allithiolane * Allium cepa
Obor OECD: Microbiology; Biochemistry and molecular biology (BC-A)
Impakt faktor: 4.192, rok: 2019
Způsob publikování: Omezený přístup
https://pubs.acs.org/doi/10.1021/acs.jafc.9b01384

Several families of 3,4-dimethylthiolane-based compounds spontaneously formed upon cutting of onion (Allium cepa) were studied. We report the isolation of the first known example of a naturally occurring dithiolactone, 5-hydroxy-3,4-dimethylthiolane-2-thione (cepadithiolactone A, C6H10OS2). Furthermore, on the basis of conceivable spectroscopic evidence (MS, NMR, IR), we could disprove the structure previously proposed for onionin A (C9H16O2S2), which is shown to be in fact (E)-3,4-dimethyl-5-(1-propenylsulfinyl)thiolane-2-ol. The identification of hitherto unknown methyl and propyl homologues of onionin A (dubbed onionins B and C, respectively) is also reported. Furthermore, the existence of the methyl and propyl homologues of cepathiolanes A (C9H16O2S3), trivially named cepathiolanes B and C, respectively, has been newly revealed. The organoleptic properties of these 3,4-dimethylthiolanes and their role in the formation of the pink discoloration of processed onion were also evaluated.
Trvalý link: http://hdl.handle.net/11104/0299890