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Sinapine
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| Names | |
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| Preferred IUPAC name
2-{[(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-N,N,N-trimethylethan-1-aminium | |
| Other names
Sinapoylcholine; Sinapic acid choline ester
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C16H24NO5 | |
| Molar mass | 310.370 g·mol−1 |
| Melting point | 178 °C (352 °F; 451 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae.[2] It is the choline ester of sinapic acid.
Sinapine was discovered by Étienne-Ossian Henry in 1825.[3]
Occurrence
[edit]Sinapine typically occurs in the outer seed coat of oil crops and is plentiful in some types of press cake leftover after vegetable oil extraction.[2] Typical oil seed cake residues high in sinapine include Brassica juncea (1.22% by mass),[4] and rapeseed (0.39-1.06% by mass).[5]
Isolation
[edit]The typical protocol for extracting sinapine from seed cakes entails defatting the cake with hexane via a Soxhlet apparatus followed by extraction with 70% methanol held at 75 °C.[5]
Biosynthesis and metabolism
[edit]The enzyme sinapoylglucose—choline O-sinapoyltransferase, characterised from radish and white mustard, converts 1-O-sinapoyl-beta-D-glucose and choline to sinapine.[6] The same transformation occurs in rapeseed.[7]
The enzyme sinapine esterase from radish can metabolise sinapine by hydrolysis to sinapinic acid and choline:[8]
See also
[edit]References
[edit]- ^ Gmelin, R; Bredenberg JB, son (February 1966). "[Studies on the constituents of various Erysimum varieties: a) identification of the bitter substance erysimupicrone as strophanthidin; b) glucosinolates in the seeds of Erysimum perofskianum Fisch et Mey., E. Allionii hort., E. crepidifolium Rohb. and E. cheiranthoides L]". Arzneimittel-Forschung (in German). 16 (2): 123–7. PMID 6014002.
- ^ a b Niciforovic, Neda; Abramovi, Helena (2014). "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity". Comprehensive Reviews in Food Science and Food Safety. 13 (1): 34–51. doi:10.1111/1541-4337.12041. PMID 33412688.
- ^ Tzagoloff, A. (1963). "Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline". Plant Physiology. 38 (2): 202–206. doi:10.1104/pp.38.2.202. PMC 549906. PMID 16655775.
- ^ Matthäus, B .; Zubr, J. (2000). "Variability of specific components in Camelina sativa oilseed cakes". Industrial Crops and Products. 12 (1): 9–18. doi:10.1016/S0926-6690(99)00040-0.
- ^ a b Vuorela, Satu (2005). Analysis, isolation, and bioactivities of rapeseed phenolics (PDF). Helsinki, Finland: University of Helsinki. pp. 19–20. ISBN 9789521027215. Retrieved 14 June 2014.
- ^ Gräwe, Walter; Strack, Dieter (1986). "Partial Purification and Some Properties of 1-Sinapoylglucose: Choline Sinapoyltransferase ("Sinapine Synthase") from Seeds of Raphanus sativus L. and Sinapis alba L". Zeitschrift für Naturforschung C. 41 (1–2): 28–33. doi:10.1515/znc-1986-1-206.
- ^ Vogt, T.; Aebershold, R.; Ellis, B. (1993). "Purification and Characterization of Sinapine Synthase from Seeds of Brassica napus". Archives of Biochemistry and Biophysics. 300 (2): 622–628. doi:10.1006/abbi.1993.1086. PMID 8382030.
- ^ Nurmann, Gerhild; Strack, Dieter (1979). "Sinapine Esterase I. Characterization of Sinapine Esterase from Cotyledons of Raphanus sativus". Zeitschrift für Naturforschung C. 34 (9–10): 715–720. doi:10.1515/znc-1979-9-1011.