(-)-Pinoresinol

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
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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
  • COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
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).
☒N verify (what is checkY☒N ?)

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]

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]

(+)-Pinoresinol Biosynthesis
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[]

References[]

  1. ^ Páska, Csilla; Innocenti, Gabbriella; Ferlin, Mariagrazia; Kunvári, Mónika; László, Miklós (January 2002). "Pinoresinol from Ipomoea Cairica Cell Cultures". Natural Product Letters. 16 (5): 359–363. doi:10.1080/1057530290033123. ISSN 1057-5634.
  2. ^ Pastrorova et al. (1997)[full citation needed]
  3. ^ Jung, Hyo Won; Mahesh, Ramalingam; Lee, Jong Gu; Lee, Seung Ho; Kim, Young Shik; Park, Yong-Ki (August 2010). "Pinoresinol from the fruits of Forsythia koreana inhibits inflammatory responses in LPS-activated microglia". Neuroscience Letters. 480 (3): 215–220. doi:10.1016/j.neulet.2010.06.043. ISSN 0304-3940.
  4. ^ 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. PMID 11536515.
  5. ^ Schroeder, F. C.; Del Campo, M. L.; Grant, J. B.; Weibel, D. B.; Smedley, S. R.; Bolton, K. L.; Meinwald, J.; Eisner, T. (2006). "Pinoresinol: A lignol of plant origin serving for defense in a caterpillar". Proceedings of the National Academy of Sciences. 103 (42): 15497–501. Bibcode:2006PNAS..10315497S. doi:10.1073/pnas.0605921103. PMC 1622851. PMID 17030818.
  6. ^ Milder, Ivon E. J.; Arts, Ilja C. W.; Putte, Betty van de; Venema, Dini P.; Hollman, Peter C. H. (2007). "Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". British Journal of Nutrition. 93 (3): 393–402. doi:10.1079/BJN20051371. PMID 15877880.
  7. ^ Owen, R.W; Giacosa, A; Hull, W.E; Haubner, R; Spiegelhalder, B; Bartsch, H (2000). "The antioxidant/anticancer potential of phenolic compounds isolated from olive oil". European Journal of Cancer. 36 (10): 1235–47. doi:10.1016/S0959-8049(00)00103-9. PMID 10882862.
  8. ^ Cabral, M.M.O; Kelecom, A; Garcia, E.S (December 1999). "Effects of the lignan, pinoresinol on the moulting cycle of the bloodsucking bug Rhodnius prolixus and of the milkweed bug Oncopeltus fasciatus". Fitoterapia. 70 (6): 561–567. doi:10.1016/s0367-326x(99)00089-1. ISSN 0367-326X.
  9. ^ Lv, Yongkun; Cheng, Xiaozhong; Du, Guocheng; Zhou, Jingwen; Chen, Jian (2017-05-12). "Engineering of an H2 O2 auto-scavenging in vivo cascade for pinoresinol production". Biotechnology and Bioengineering. 114 (9): 2066–2074. doi:10.1002/bit.26319. ISSN 0006-3592.
  10. ^ 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. PMID 8994027. S2CID 41957412.
  11. ^ 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. S2CID 195313754.
  12. ^ 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. PMID 22818971.
  13. ^ Fini, L; Hotchkiss, E; Fogliano, V; Graziani, G; Romano, M; De Vol, EB; Qin, H; Selgrad, M; et al. (2008). "Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell lines". Carcinogenesis. 29 (1): 139–46. doi:10.1093/carcin/bgm255. PMID 17999988.
  14. ^ Goncalves, Aurélie; Margier, Marielle; Tagliaferri, Camille; Lebecque, Patrice; Georgé, Stéphane; Wittrant, Yohann; Coxam, Véronique; Amiot, Marie-Josèphe; Reboul, Emmanuelle (September 2016). "Pinoresinol of olive oil decreases vitamin D intestinal absorption". Food Chemistry. 206: 234–238. doi:10.1016/j.foodchem.2016.03.048. ISSN 0308-8146.
  15. ^ Milder, IE; Arts, IC; Van De Putte, B; Venema, DP; Hollman, PC (2005). "Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". The British Journal of Nutrition. 93 (3): 393–402. doi:10.1079/BJN20051371. PMID 15877880.