Sinapine

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
Chemical structure of sinapine
Names
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
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1 ☒N
    Key: HUJXHFRXWWGYQH-UHFFFAOYSA-O ☒N
  • InChI=1/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
    Key: HUJXHFRXWWGYQH-IKLDFBCSAX
  • O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCC[N+](C)(C)C
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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Infobox references

Sinapine was discovered by Etienne Ossian Henry in 1825.[3]

Occurrence

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

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.[6]

Metabolism

Sinapine esterase is an enzyme whose two substrates are sinapine and H2O and whose two products are sinapic acid and choline.

Sinapoylglucose—choline O-sinapoyltransferase is an enzyme whose two substrates are 1-O-sinapoyl-β-D-glucose and choline, whereas its two products are D-glucose and sinapine.

See also

References
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
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