Sinapine

Sinapine
Chemical structure of 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 checkY
    Key: HUJXHFRXWWGYQH-UHFFFAOYSA-O checkY
  • 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae. It is the choline ester of sinapic acid.

Sinapine was discovered by Étienne-Ossian Henry in 1825.

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. Typical oil seed cake residues high in sinapine include Brassica juncea (1.22% by mass), and rapeseed (0.39-1.06% by mass).

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.

Biosynthesis and metabolism

The enzyme sinapoylglucose—choline O-sinapoyltransferase, characterised from radish and white mustard, converts 1-O-sinapoyl-beta-D-glucose and choline to sinapine. The same transformation occurs in rapeseed.

2D representation of the chemical structure of Q27101966.
1-O-sinapoyl-beta-D-glucose
+
 
2D representation of the chemical structure of choline.
choline
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of sinapine .
sinapine
+
 
2D representation of the chemical structure of Q23905964.
D-glucose

The enzyme sinapine esterase from radish can metabolise sinapine by hydrolysis to sinapinic acid and choline:

2D representation of the chemical structure of sinapine.
sinapine
 
H2O
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of sinapinic acid .
sinapinic acid
+
 
2D representation of the chemical structure of choline.
choline

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. 1 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. PMID 33412688.
  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. 1 2 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. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.