Sinapine is an

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

al amine found in some seeds, particularly

oil seeds Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed o ...

of plants in the

family Family (from ) is a Social group, group of people related either by consanguinity (by recognized birth) or Affinity (law), affinity (by marriage or other relationship). It forms the basis for social order. Ideally, families offer predictabili ...

Brassicaceae Brassicaceae () or (the older but equally valid) Cruciferae () is a medium-sized and economically important Family (biology), family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous pla ...

. It is the

choline Choline is a cation with the chemical formula . Choline forms various Salt (chemistry), salts, such as choline chloride and choline bitartrate. An essential nutrient for animals, it is a structural component of phospholipids and cell membrane ...

ester of

sinapic acid Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mas ...

. Sinapine was discovered by

Étienne-Ossian Henry Étienne-Ossian Henry (27 November 1798 in Paris – 26 August 1873) was a French chemist, son of Noël-Étienne Henry (1769–1832), and trained by his father, who was director of the Central Pharmacy of the Parisian hospitals and professor ...

in 1825.

Occurrence

Sinapine typically occurs in the outer seed coat of oil crops and is plentiful in some types of

press cake A press cake or oil cake is the solid matter remaining after Expeller pressing, pressing something to extract the liquids. Their most common use is in fodder, animal feed. Some foods whose processing creates press cakes are olives for olive o ...

leftover after vegetable oil extraction. Typical oil seed cake residues high in sinapine include ''

Brassica juncea ''Brassica juncea'', commonly mustard greens, brown mustard, Chinese mustard, Indian mustard, Korean green mustard, leaf mustard, Oriental mustard and vegetable mustard, is a species of mustard plant. Cultivar ''Brassica juncea'' cultivars c ...

'' (1.22% by mass), and

rapeseed Rapeseed (''Brassica napus'' subsp. ''napus''), also known as rape and oilseed rape and canola, is a bright-yellow flowering member of the family Brassicaceae (mustard or cabbage family), cultivated mainly for its oil-rich seed, which naturall ...

(0.39-1.06% by mass).

Isolation

The typical protocol for extracting Sinapine from seed cakes entails defatting the cake with

hexane Hexane () or ''n''-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14. Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately . It is widely used as ...

via a Soxhlet apparatus followed by extraction with 70% methanol held at 75 °C.

Metabolism

Sinapine esterase The enzyme sinapine esterase (EC 3.1.1.49) catalysis, catalyzes the reaction :sinapoylcholine + H2O \rightleftharpoons sinapate + choline This enzyme belongs to the family of hydrolases, specifically those acting on carboxylic ester bonds. The L ...

is an enzyme whose two substrates are sinapine and H₂O and whose two products are

and

Sinapoylglucose—choline O-sinapoyltransferase In enzymology, a sinapoylglucose---choline O-sinapoyltransferase () is an enzyme that catalyzes the chemical reaction :1-O-sinapoyl-beta-D-glucose + choline \rightleftharpoons D-glucose + sinapoylcholine Thus, the two substrates of this enzyme a ...

is an enzyme whose two substrates are 1-''O''-sinapoyl-β-D-glucose and

, whereas its two products are D-glucose and sinapine.

References

{{reflist Alkaloids Quaternary ammonium compounds Hydroxycinnamic acid esters O-methylated hydroxycinnamic acids Resorcinol ethers

Occurrence

Isolation

Metabolism

See also

References