Chemistry:Pinoresinol

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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
KEGG
UNII
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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Infobox references

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. PMID 12434993. http://dx.doi.org/10.1080/1057530290033123. 
  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. PMID 20600612. http://dx.doi.org/10.1016/j.neulet.2010.06.043. 
  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. doi:10.1073/pnas.0605921103. PMID 17030818. Bibcode: 2006PNAS..10315497S. 
  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. http://dx.doi.org/10.1016/s0367-326x(99)00089-1. 
  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. PMID 28436004. http://dx.doi.org/10.1002/bit.26319. 
  10. ↑ "Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center". Science 275 (5298): 362–6. 1997. doi:10.1126/science.275.5298.362. PMID 8994027. 
  11. ↑ "An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols". Angewandte Chemie 53 (4): 273–284. March 2007. doi:10.1007/s10086-007-0892-x. 
  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 et al. (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. PMID 27041321. http://dx.doi.org/10.1016/j.foodchem.2016.03.048. 
  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. 



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