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. 2018 Dec 8;4(12):e00997.
doi: 10.1016/j.heliyon.2018.e00997. eCollection 2018 Dec.

Isolation of allithiamine from Hungarian red sweet pepper seed (Capsicum annuum L.)

Attila Biro  1 , Ferenc Gál  2 , Csaba Hegedűs  3 , Gyula Batta  4 , Zoltán Cziáky  5 , Barna Peitl  3 , László Stündl  1 , Gyöngyi Gyémánt  6 , Judit Remenyik  1
Affiliations

Isolation of allithiamine from Hungarian red sweet pepper seed (Capsicum annuum L.)

Attila Biro et al. Heliyon. .

Abstract

A natural fat-soluble thiamine derivative, namely N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(2E)-5-hydroxy-3-(prop-2-en-1-yldisulfanyl)pent-2-en-2-yl]formamide (allithiamine) has been identified only in garlic (Allium sativum) until now. Hungarian red sweet pepper (Capsicum annuum) was found as a new source of allithiamine. Extraction procedure and analytical method were developed for the isolation of allithiamine and a chemical synthesis of the compound was also developed. First solid-liquid extraction was performed with 96 % ethanol to isolate allithiamine from pepper seeds. Thereafter, solid phase extraction was applied from ethanolic extract using C18 cartridge to concentrate and purify samples for further analysis. The structure of the synthesized and the isolated compounds was verified by reverse phase HPLC, HPLC-MS, MALD-TOF MS and NMR. Furthermore, effect of allithiamine was investigated on streptozotocin-induced diabetic mice with neuropathy. The results show that neuropathic pain sensation is improved by allithiamine treatment similarly to benfothiamine.

Keywords: Analytical chemistry; Food science.

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Figures

Fig. 1
Fig. 1
HPLC chromatogram of a synthetic mixture.
Fig. 2
Fig. 2
MALDI-TOF spectrum of purified allithiamine.
Fig. 3
Fig. 3
13C-NMR spectrum of purified allithiamine.
Fig. 4
Fig. 4
HPLC chromatogram of purified pepper seed oil.
Fig. 5
Fig. 5
MS2 spectrum of allithiamine.
Fig. 6
Fig. 6
Effect of allithiamine and benfothiamine on latency time of experimental. * indicates significant difference in tail flick latency between pre-treatment and post treatment STZ-C group. + indicates significant difference in tail flick latency between posttreatment STZ-C and HC, STZ-B, STZ-A groups.
Fig. 7
Fig. 7
Schematic illustration of chemical synthesis of allithiamine.
Fig. 8
Fig. 8
Schematic diagram of sample preparation.
Fragmentaton pathways of allithiamine
Fragmentaton pathways of allithiamine
See this image and copyright information in PMC

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