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]
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-glucosidasein 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]
^Davin, Laurence B.; Bedgar, Diana L.; Katayama, Takeshi; Lewis, Norman G. (1992). "On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol". Phytochemistry. 31 (11): 3869–74. doi:10.1016/S0031-9422(00)97544-7. PMID11536515.
^Davin LB, Wang HB, Crowell AL, et al. (1997). "Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center". Science. 275 (5298): 362–6. doi:10.1126/science.275.5298.362. PMID8994027. S2CID41957412.
^Pickel B, Constantin MA, Pfannsteil J, Conrad J, Beifuss U, Schaffer A (March 2007). "An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols". Angewandte Chemie. 53 (4): 273–284. doi:10.1007/s10086-007-0892-x. S2CID195313754.
^Wikul, A; Damsud, T; Kataoka, K; Phuwapraisirisan, P (2012). "(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase". Bioorganic & Medicinal Chemistry Letters. 22 (16): 5215–7. doi:10.1016/j.bmcl.2012.06.068. PMID22818971.