| 词条 | Pinoresinol |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 408179893 | Name = Pinoresinol | ImageFile = Pinoresinol.svg | ImageName = Chemical structure of pinoresinol | ImageAlt = Chemical structure of pinoresinol | IUPACName = (+) 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 | OtherNames = (+)-Pinoresinol (-)-Pinoresinol |Section1={{Chembox Identifiers | CASNo = 487-36-5 | CASNo_Ref = {{cascite|correct|??}}= | CASNoOther = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 487611 | PubChem = 73399 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 66116 | SMILES = COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O | 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 | InChIKey = HGXBRUKMWQGOIE-AFHBHXEDBE | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = HGXBRUKMWQGOIE-AFHBHXEDSA-N | MeSHName = }} |Section2={{Chembox Properties | Formula = C20H22O6 | MolarMass = 358.38 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }}Pinoresinol is a lignan found in Styrax sp.[1] and in Forsythia suspensa.[2] It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.[3] In food, it is found in sesame seed, in Brassica vegetables[4] and in olive oil.[5] BiosynthesisA first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers.[6] Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (-)-pinoresinol.[7] {{clear left}}{{clear left}}PharmacologyPinoresinol inhibits the enzyme α-glucosidase in vitro and may therefore act as a hypoglycemic agent.[8] 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.[9] Metabolism into enterolignansPinoresinol, along with other plant lignans, are converted into enterolignans by intestinal microflora in the human body.[10] See also
References1. ^Pastrorova et al. (1997){{full citation needed|date=October 2013}} {{lignan}}2. ^{{cite journal | doi = 10.1016/S0031-9422(00)97544-7 | title = On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol | year = 1992 | last1 = Davin | first1 = Laurence B. | last2 = Bedgar | first2 = Diana L. | last3 = Katayama | first3 = Takeshi | last4 = Lewis | first4 = Norman G. | journal = Phytochemistry | volume = 31 | issue = 11 | pages = 3869–74 | pmid = 11536515}} 3. ^{{cite journal | doi = 10.1073/pnas.0605921103 | title = Pinoresinol: A lignol of plant origin serving for defense in a caterpillar | year = 2006 | last1 = Schroeder | first1 = F. C. | last2 = Del Campo | first2 = M. L. | last3 = Grant | first3 = J. B. | last4 = Weibel | first4 = D. B. | last5 = Smedley | first5 = S. R. | last6 = Bolton | first6 = K. L. | last7 = Meinwald | first7 = J. | last8 = Eisner | first8 = T. | journal = Proceedings of the National Academy of Sciences | volume = 103 | issue = 42 | pages = 15497–501 | pmid=17030818 | pmc=1622851}} 4. ^{{cite journal | doi = 10.1079/BJN20051371 | title = Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol | year = 2007 | last1 = Milder | first1 = Ivon E. J. | last2 = Arts | first2 = Ilja C. W. | last3 = Putte | first3 = Betty van de | last4 = Venema | first4 = Dini P. | last5 = Hollman | first5 = Peter C. H. | journal = British Journal of Nutrition | volume = 93 | issue = 3 | pages = 393–402 | pmid=15877880}} 5. ^{{cite journal | doi = 10.1016/S0959-8049(00)00103-9 | title = The antioxidant/anticancer potential of phenolic compounds isolated from olive oil | year = 2000 | last1 = Owen | first1 = R.W | last2 = Giacosa | first2 = A | last3 = Hull | first3 = W.E | last4 = Haubner | first4 = R | last5 = Spiegelhalder | first5 = B | last6 = Bartsch | first6 = H | journal = European Journal of Cancer | volume = 36 | issue = 10 | pages = 1235–47 | pmid = 10882862}} 6. ^{{cite journal |vauthors=Davin LB, Wang HB, Crowell AL, etal |title=Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center |journal=Science |volume=275 |issue=5298 |pages=362–6 |year=1997 |pmid=8994027 |doi=10.1126/science.275.5298.362}} 7. ^{{cite journal|vauthors=Pickel B, Constantin MA, Pfannsteil J, Conrad J, Beifuss U, Schaffer A |title=An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols|journal=Angewandte Chemie|volume=53|issue=4|pages=273–284|date=March 2007|doi=10.1007/s10086-007-0892-x}} 8. ^{{cite journal | pmid = 22818971 | year = 2012 | last1 = Wikul | first1 = A | last2 = Damsud | first2 = T | last3 = Kataoka | first3 = K | last4 = Phuwapraisirisan | first4 = P | title = (+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase | volume = 22 | issue = 16 | pages = 5215–7 | doi = 10.1016/j.bmcl.2012.06.068 | journal = Bioorganic & Medicinal Chemistry Letters}} 9. ^{{cite journal | pmid = 17999988 | year = 2008 | last1 = Fini | first1 = L | last2 = Hotchkiss | first2 = E | last3 = Fogliano | first3 = V | last4 = Graziani | first4 = G | last5 = Romano | first5 = M | last6 = De Vol | first6 = EB | last7 = Qin | first7 = H | last8 = Selgrad | first8 = M | last9 = Boland | first9 = CR | last10 = Ricciardiello | first10 = L. | title = Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell lines | volume = 29 | issue = 1 | pages = 139–46 | doi = 10.1093/carcin/bgm255 | journal = Carcinogenesis| display-authors = 8 }} 10. ^{{cite journal | pmid = 15877880 | year = 2005 | last1 = Milder | first1 = IE | last2 = Arts | first2 = IC | last3 = Van De Putte | first3 = B | last4 = Venema | first4 = DP | last5 = Hollman | first5 = PC | title = Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol | volume = 93 | issue = 3 | pages = 393–402 | journal = The British Journal of Nutrition | doi=10.1079/BJN20051371}} 1 : Lignans |
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