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Names | |
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IUPAC names
(+) form:
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Other names
(+)-Pinoresinol
(-)-Pinoresinol | |
Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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).
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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]
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]
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]
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]
Pinoresinol, along with other plant lignans, are converted into enterolignans by intestinal microflora in the human body.[15]