Sinapine is an

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

al amine found in some seeds, particularly

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

of plants in the

family Family (from la, familia) is a Social group, group of people related either by consanguinity (by recognized birth) or Affinity (law), affinity (by marriage or other relationship). The purpose of the family is to maintain the well-being of its ...

Brassicaceae Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The le ...

. It is the

choline Choline is an essential nutrient for humans and many other animals. Choline occurs as a cation that forms various salts (X− in the depicted formula is an undefined counteranion). Humans are capable of some ''de novo synthesis'' of choline but re ...

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 mass ...

. Sinapine was discovered by Etienne 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 A press cake or oil cake is the solids remaining after pressing something to extract the liquids. Their most common use is in animal feed. Some foods whose processing creates press cakes are olives for olive oil (''pomace''), peanuts for ...

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

Brassica juncea ''Brassica juncea'', commonly brown mustard, Chinese mustard, Indian mustard, leaf mustard, Oriental mustard and vegetable mustard, is a species of mustard plant. Cultivar ''Brassica juncea'' cultivars can be divided into four major subgroup ...

'' (1.22% by mass), and

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

(0.39-1.06% by mass).

Isolation

The typical protocol for extracting Sinapine from seed cakes entails

defatting Degreasing, often called defatting or fat trimming, is the removal of fatty acids from an object. In culinary science, degreasing is done with the intention of reducing the fat content of a meal. Degreasing food Degreasing is often used by diet ...

the cake with

hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...

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) catalyzes the reaction :sinapoylcholine + H2O \rightleftharpoons sinapate + choline This enzyme belongs to the family of hydrolases, specifically those acting on carboxylic ester bonds. The systematic ...

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 catalysis, catalyzes the chemical reaction :1-O-sinapoyl-beta-D-glucose + choline \rightleftharpoons D-glucose + sinapoylcholine Thus, the two substrate (bioche ...

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 Vinylogous carboxylic acids Resorcinol ethers

Occurrence

Isolation

Metabolism

See also

References