Pinoresinol

Last updated
Pinoresinol
Pinoresinol.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Related Research Articles

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<span class="mw-page-title-main">Secoisolariciresinol diglucoside</span> Antioxidant phytoestrogen

Secoisolariciresinol diglucoside (SDG) is an antioxidant phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed. It is a precursor of mammal lignans which are produced in the colon from chemicals in foods.

In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in steric and electronic effects in the mechanistic pathways leading to the different products. Stereoselectivity can vary in degree but it can never be total since the activation energy difference between the two pathways is finite. Both products are at least possible and merely differ in amount. However, in favorable cases, the minor stereoisomer may not be detectable by the analytic methods used.

The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores.

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<span class="mw-page-title-main">Secoisolariciresinol</span> Chemical compound

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<span class="mw-page-title-main">Coniferyl alcohol</span> Chemical compound

Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferin is a glucoside of coniferyl alcohol. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters. It is found in both gymnosperm and angiosperm plants. Sinapyl alcohol and paracoumaryl alcohol, the other two lignin monomers, are found in angiosperm plants and grasses.

<span class="mw-page-title-main">Dirigent protein</span>

Dirigent proteins are members of a class of proteins which dictate the stereochemistry of a compound synthesized by other enzymes. The first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers:

<i>Rhodnius prolixus</i> Kissing bug, vector of Chagas disease

Rhodnius prolixus is the principal triatomine vector of the Chagas parasite due to both its sylvatic and domestic populations in northern South America as well as to its exclusively domestic populations in Central America. It has a wide range of ecotopes, mainly savanna and foothills with an altitude of between 500 to 1,500 metres above sea level and temperatures of 16 to 28 °C. Sylvatic R. prolixus, as virtually all Rhodnius spp., is primarily associated with palm tree habitats and has a wide range of hosts including birds, rodents, marsupials, sloths, and reptiles.

<span class="mw-page-title-main">Matairesinol</span> Chemical compound

Matairesinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, e.g. rye, and together with Secoisolariciresinol, has attracted much attention for its beneficial nutritional effects.

<i>Forsythia suspensa</i> Species of flowering plant in the olive family Oleaceae

Forsythia suspensa, commonly known as weeping forsythia or golden-bell, is a species of flowering plant in the family Oleaceae, it is native to China.

<i>Forsythia <span style="font-style:normal;">×</span> intermedia</i> Hybrid flowering plant in the olive family Oleaceae

Forsythia × intermedia, or border forsythia, is an ornamental deciduous shrub of garden origin.

<span class="mw-page-title-main">Lariciresinol</span> Chemical compound

Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora. Enterolignans are of interest because they are speculated to exhibit beneficial medicinal properties.

<span class="mw-page-title-main">Enterolactone</span> Chemical compound

Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

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<span class="mw-page-title-main">Phillyrin</span> Chemical compound

Phillyrin is an endophytic fungal isolate with anti-obesity activity. It can be produced by Colletotrichum gloeosporioides, an endophytic fungus isolated from Forsythia suspensa. It can also be prepared directly from Forsythia suspensa.

<span class="mw-page-title-main">Hydroxymatairesinol</span> Chemical compound

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce. It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro.

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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