Pinoresinol

Pinoresinol

Names
IUPAC name 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
Other names (+)-Pinoresinol (-)-Pinoresinol
Identifiers
CAS Number	487-36-5 Y=
3D model (Jmol)	Interactive image
ChemSpider	66116 N
PubChem CID	73399
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  (what is YN ?)
Infobox references

Pinoresinol is a lignan found in Styrax sp. and in Forsythia suspensa. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

In food, it is found in sesame seed, in Brassica vegetables and in olive oil.

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. Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (-)-pinoresinol.

Pinoresinol inhibits the enzyme α-glucosidase in vitro and may therefore act as a hypoglycemic agent. 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.

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