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Pinoresinol information


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
CAS Number
  • 487-36-5 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL487611 ☒N
ChemSpider
  • 66116 ☒N
KEGG
  • C05366 checkY
PubChem CID
  • 73399
UNII
  • V4N1UDY811 checkY
CompTox Dashboard (EPA)
  • DTXSID20964099 Edit this at Wikidata
InChI
  • 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
SMILES
  • COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
Properties
Chemical formula
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 ?)
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]

  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.

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Pinoresinol

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Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the...

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Lignan

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9'-dihydroxydibenzylbutane motif Justicidin A, illustrating the arylnaphthalene motif Pinoresinol, illustrating the furanofuran motif Steganacin, illustrating the...

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Sesame

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United States. Sesame seeds contain the lignans sesamolin, sesamin, pinoresinol, and lariciresinol. Contamination by Salmonella, E.coli, pesticides,...

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Forsythia suspensa

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herbs used in traditional Chinese medicine. It contains the lignans Pinoresinol and phillyrin. "Forsythia suspensa". Germplasm Resources Information...

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Stereoselectivity

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the bulky t-butyl group resulting in high facial diastereoselectivity: Pinoresinol biosynthesis involved a protein called a dirigent protein. The first...

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Capsaicin

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Wood

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phenolic constituents are stilbenes (e.g. pinosylvin), lignans (e.g. pinoresinol, conidendrin, plicatic acid, hydroxymatairesinol), norlignans (e.g. nyasol...

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Coniferyl alcohol

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protein was found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol. Recently, a second, enantiocomplementary dirigent...

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Betel

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alkaloids (piperine, pellitorine, piperdardine, guineensine etc.), lignan (pinoresinol) and other components. Some of them are oleanolic acid, dehydropipernonaline...

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Dietary fiber

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Dirigent protein

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protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers: Lignan biosynthesis is catalysed by...

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Podophyllotoxin

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converted to (+)-pinoresinol in the presence of a one-electron oxidant through dimerization of stereospecific radical intermediate. Pinoresinol is subsequently...

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Olive oil

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elenolic acid. Other phenolic constituents include flavonoids, lignans and pinoresinol. Olive oil is 100% fat, containing no carbohydrates, dietary fiber, protein...

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Flavonoid

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Allamanda

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plumierdin, plumeridoid C, and allamandicin did not have activity. The lignan pinoresinol and coumarins such as scopoletin and scoparone have been isolated from...

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Phenylpropanoid

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Phenolic acid

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Abies alba

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lariciresinol, hydroxymatairesinol, isolariciresinol, matairesinol and pinoresinol). The extract from the trunk was shown to prevent atherosclerosis in...

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Lariciresinol

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"Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". British Journal of Nutrition...

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Anthraquinones

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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List of phytochemicals in food

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strawberries, blueberries, cranberries, zucchini, blackcurrant, carrots. Pinoresinol and lariciresinol sesame seed, Brassica vegetables. Resveratrol grape...

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Styrax

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resin; other less well known secondary compounds such as lignans like pinoresinol are likely significant too. Several species of storax are popular ornamental...

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Enterolactone

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precursors, such as secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, and sesamin, can be metabolized by gut microbes to enterolactone. In...

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Phytochemical

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Polyphenol

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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C20H22O6

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u) may refer to: Matairesinol, a lignan Miroestrol, a phytoestrogen Pinoresinol, a lignan This set index page lists chemical structure articles associated...

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Cycas beddomei

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3"-tetrahydroamentoflavone, 2,3-dihydro-4"'-0-methyl-amentoflavone, and pinoresinol can be isolated from C. beddomei. The male cones of the plant are used...

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Saponin

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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Xanthonoid

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Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin...

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