Pinoresinol

Last updated
Pinoresinol
Chemical structure of pinoresinol Pinoresinol.svg
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
PubChem CID
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 X mark.svgN
    Key: HGXBRUKMWQGOIE-AFHBHXEDSA-N X mark.svgN
  • 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).
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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]

Contents

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]

Reaction of monolignol radicals in the presence of dirigent protein to form (+)-pinoresinol (+)-Pinoresinol Biosynthesis.svg
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. Activity of Dirigent protein.png
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. S2CID   13015216.
  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. S2CID   41511857.
  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. PMID   28436004. S2CID   3289052.
  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. PMID   27041321.
  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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