| Revision as of 10:45, 16 January 2011 edit79.69.228.14 (talk)No edit summary← Previous edit |
Latest revision as of 18:32, 29 January 2023 edit undoOAbot (talk | contribs)Bots440,440 editsm Open access bot: doi added to citation with #oabot. |
| (62 intermediate revisions by 31 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
|Verifiedfields = changed |
| ⚫ |
| Name = Pinoresinol |
|
|
|
|Watchedfields = changed |
| ⚫ |
| ImageFile = Pinoresinol.PNG |
|
|
|
|verifiedrevid = 408179893 |
|
| ImageSize = 200px |
|
|
⚫ |
|Name = Pinoresinol |
| ⚫ |
| ImageName = Chemical structure of pinoresinol |
|
|
⚫ |
|ImageFile = Pinoresinol.svg |
| ⚫ |
| ImageAlt = Chemical structure of pinoresinol |
|
|
⚫ |
|ImageName = Chemical structure of pinoresinol |
| ⚫ |
| IUPACName = 4-furan-3-yl]-2-methoxyphenol |
|
|
⚫ |
|ImageAlt = Chemical structure of pinoresinol |
| ⚫ |
| OtherNames = (+)-Pinoresinol<!-- <br> --> |
|
|
|
|IUPACNames = (+) form: |
| ⚫ |
|Section1= {{Chembox Identifiers |
|
|
⚫ |
* 4-furan-3-yl]-2-methoxyphenol |
| ⚫ |
| CASNo = 487-36-5 |
|
|
|
* (7α,7′α,8α,8′α)-3,3′-dimethoxy-7,9′:7′,9-diepoxylignane-4,4′-diol |
|
| CASNo_Ref = |
|
|
⚫ |
|OtherNames = (+)-Pinoresinol<br>(-)-Pinoresinol |
|
| CASOther = |
|
|
⚫ |
|Section1={{Chembox Identifiers |
| ⚫ |
| PubChem = 73399 |
|
|
⚫ |
|CASNo = 487-36-5 |
| ⚫ |
| SMILES = COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O |
|
|
|
|CASNo_Ref = {{cascite|correct|??}} |
|
| InChI = |
|
|
| MeSHName = |
|
|CASNoOther = |
|
|
|UNII_Ref = {{fdacite|correct|FDA}} |
|
|
|UNII = V4N1UDY811 |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
|
| KEGG = C05366 |
|
|
|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 |
|
}} |
|
}} |
|
|Section2= {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>20</sub>H<sub>22</sub>O<sub>6</sub> |
|
|Formula = C<sub>20</sub>H<sub>22</sub>O<sub>6</sub> |
|
| MolarMass = 358.38 g/mol |
|
|MolarMass = 358.38 g/mol |
|
| ExactMass = 358.141638 u |
|
|
| Appearance = |
|
|
| Density = |
|
|
| MeltingPt = <!-- °C --> |
|
|
| BoilingPt = <!-- °C --> |
|
|
| Solubility = |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
'''Pinoresinol''' is a ] found in ''] sp.''<ref>Pastrorova ''et al.'' (1997)</ref> and in '']''.<ref>On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, ]. Laurence B. Davin, Diana L. Bedgar, Takeshi Katayama and Norman G. Lewis, Phytochemistry, Volume 31, Issue 11, 1992, Pages 3869-3874, {{doi|10.1016/S0031-9422(00)97544-7}}</ref> It is also found in the caterpillar of the cabbage butterfly, '']'' where it serves as a defence against ants.<ref>Pinoresinol: A lignol of plant origin serving for defense in a caterpillar. Frank C. Schroeder, Marta L. del Campo, Jacqualine B. Grant, Douglas B. Weibel, Scott R. Smedley, Kelly L. Bolton, Jerrold Meinwald and Thomas Eisner, PNAS October 17, 2006 vol. 103 no. 42 15497-15501, {{doi|10.1073/pnas.0605921103}}</ref> |
|
'''Pinoresinol''' is a tetrahydrofuran ]<ref>{{Cite journal|last1=Páska|first1=Csilla|last2=Innocenti|first2=Gabbriella|last3=Ferlin|first3=Mariagrazia|last4=Kunvári|first4=Mónika|last5=László|first5=Miklós|date=January 2002|title=Pinoresinol from Ipomoea Cairica Cell Cultures|url=http://dx.doi.org/10.1080/1057530290033123|journal=Natural Product Letters|volume=16|issue=5|pages=359–363|doi=10.1080/1057530290033123|pmid=12434993 |s2cid=13015216 |issn=1057-5634}}</ref> found in ''] sp.'',<ref>Pastrorova ''et al.'' (1997){{full citation needed|date=October 2013}}</ref> ''], and in Forsythia koreana''.<ref>{{Cite journal|last1=Jung|first1=Hyo Won|last2=Mahesh|first2=Ramalingam|last3=Lee|first3=Jong Gu|last4=Lee|first4=Seung Ho|last5=Kim|first5=Young Shik|last6=Park|first6=Yong-Ki|date=August 2010|title=Pinoresinol from the fruits of Forsythia koreana inhibits inflammatory responses in LPS-activated microglia|url=http://dx.doi.org/10.1016/j.neulet.2010.06.043|journal=Neuroscience Letters|volume=480|issue=3|pages=215–220|doi=10.1016/j.neulet.2010.06.043|pmid=20600612 |s2cid=41511857 |issn=0304-3940}}</ref><ref>{{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}}</ref> It is also found in the caterpillar of the cabbage butterfly, '']'' where it serves as a defence against ants.<ref>{{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| bibcode = 2006PNAS..10315497S | doi-access = free}}</ref> |
|
|
|
|
|
|
In food, it is found in ] seed, in '']'' vegetables<ref>{{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| doi-access = free }}</ref> and in ].<ref>{{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}}</ref> 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.<ref>{{Cite journal|last1=Cabral|first1=M.M.O|last2=Kelecom|first2=A|last3=Garcia|first3=E.S|date=December 1999|title=Effects of the lignan, pinoresinol on the moulting cycle of the bloodsucking bug Rhodnius prolixus and of the milkweed bug Oncopeltus fasciatus|url=http://dx.doi.org/10.1016/s0367-326x(99)00089-1|journal=Fitoterapia|volume=70|issue=6|pages=561–567|doi=10.1016/s0367-326x(99)00089-1|issn=0367-326X}}</ref> |
|
In food, it is found in ] seed and in '']'' vegetables.<ref>Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Ivon E. J. Milder, Ilja C. W. Arts, Betty van de Putte, Dini P. Venema and Peter C. H. Hollman, British Journal of Nutrition (2005), 93: 393-402, {{doi|10.1079/BJN20051371}}</ref> |
|
|
|
|
|
|
|
Currently, pinoresinol is isolated from plants with low efficiency and low yield.<ref>{{Cite journal|last1=Lv|first1=Yongkun|last2=Cheng|first2=Xiaozhong|last3=Du|first3=Guocheng|last4=Zhou|first4=Jingwen|last5=Chen|first5=Jian|date=2017-05-12|title=Engineering of an H2 O2 auto-scavenging in vivo cascade for pinoresinol production|url=http://dx.doi.org/10.1002/bit.26319|journal=Biotechnology and Bioengineering|volume=114|issue=9|pages=2066–2074|doi=10.1002/bit.26319|pmid=28436004 |s2cid=3289052 |issn=0006-3592}}</ref> |
| ⚫ |
==See also== |
|
|
|
|
|
|
== Biosynthesis == |
|
|
A first ] was discovered in '']''. This protein has been found to direct the ] of (+)-pinoresinol from ] monomers.<ref>{{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|s2cid=41957412}}</ref> Recently, a second, enantiocomplementary ] was identified in '']'', which directs enantioselective synthesis of (-)-pinoresinol.<ref>{{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|s2cid=195313754|doi-access=free}}</ref> |
|
|
|
|
|
]{{clear left}} |
|
|
|
|
|
]{{clear left}} |
|
|
|
|
|
==Pharmacology== |
|
|
Pinoresinol inhibits the enzyme ] '']'' and may therefore act as a ] agent.<ref>{{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}}</ref> A study involving ] showed that pinoresinol possess ''in vitro'' chemoprevention properties. Increased apoptosis and cellular arrest at the G2/M stage in p53-proficient cells occurred.<ref>{{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 | doi-access = free }}</ref> Pinoresinol of olive oil decreases vitamin D intestinal absorption.<ref>{{Cite journal|last1=Goncalves|first1=Aurélie|last2=Margier|first2=Marielle|last3=Tagliaferri|first3=Camille|last4=Lebecque|first4=Patrice|last5=Georgé|first5=Stéphane|last6=Wittrant|first6=Yohann|last7=Coxam|first7=Véronique|last8=Amiot|first8=Marie-Josèphe|last9=Reboul|first9=Emmanuelle|date=September 2016|title=Pinoresinol of olive oil decreases vitamin D intestinal absorption|url=http://dx.doi.org/10.1016/j.foodchem.2016.03.048|journal=Food Chemistry|volume=206|pages=234–238|doi=10.1016/j.foodchem.2016.03.048|pmid=27041321 |issn=0308-8146}}</ref> |
|
|
|
|
|
==Metabolism into enterolignans== |
|
|
Pinoresinol, along with other plant lignans, are converted into ]s by intestinal microflora in the human body.<ref>{{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| doi-access = free }}</ref> |
|
|
|
|
⚫ |
== See also == |
|
* ] |
|
* ] |
|
|
|
|
|
==References== |
|
== References == |
|
{{reflist}} |
|
{{reflist}} |
|
|
|
|
{{lignan}} |
|
{{lignan}} |
|
|
|
|
|
] |
|
] |
|
|
|
|
{{polyphenol-stub}} |
|