Pinoresinol

Pinoresinol is a tetrahydrofuran lignan^[1] found in Styrax sp.,^[2] Forsythia suspensa, and in Forsythia koreana.^[3][4] It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.^[5]

Pinoresinol

Chemical structure of pinoresinol
Names
IUPAC names (+) form: 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol (7α,7′α,8α,8′α)-3,3′-dimethoxy-7,9′:7′,9-diepoxylignane-4,4′-diol
Other names (+)-Pinoresinol (-)-Pinoresinol
Identifiers
CAS Number	487-36-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL487611 N
ChemSpider	66116 N
KEGG	C05366 Y
PubChem CID	73399
UNII	V4N1UDY811 Y
CompTox Dashboard (EPA)	DTXSID20964099
InChI InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1 N Key: HGXBRUKMWQGOIE-AFHBHXEDSA-N N InChI=1/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1 Key: HGXBRUKMWQGOIE-AFHBHXEDBE
SMILES COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
Properties
Chemical formula	C20H22O6
Molar mass	358.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

In food, it is found in sesame seed, in Brassica vegetables^[6] and in olive oil.^[7] Pinoresinol has also been found to be toxic to larvae of the milkweed bug Oncopeltus fasciatus and of the haematophagous insect Rhodnius prolixus, which is a vector of chagas disease.^[8]

Currently, pinoresinol is isolated from plants with low efficiency and low yield.^[9]

Biosynthesis

A first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers.^[10] Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (-)-pinoresinol.^[11]

Reaction of monolignol radicals in the presence of dirigent protein to form (+)-pinoresinol

In the presence of dirigent protein from Forsythia intermedia, production of (+)-pinoresinol is greatly enriched while production of other products of dimerization is inhibited.

Pharmacology

Pinoresinol inhibits the enzyme α-glucosidase in vitro and may therefore act as a hypoglycemic agent.^[12] A study involving extra virgin olive oil showed that pinoresinol possess in vitro chemoprevention properties. Increased apoptosis and cellular arrest at the G2/M stage in p53-proficient cells occurred.^[13] Pinoresinol of olive oil decreases vitamin D intestinal absorption.^[14]

Metabolism into enterolignans

Pinoresinol, along with other plant lignans, are converted into enterolignans by intestinal microflora in the human body.^[15]

See also

• List of phytochemicals in food