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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
ChEMBL
ChemSpider
KEGG
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
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
COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
Properties
C20 H22 O6
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).
Chemical compound
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]
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
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
^ 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 .
^ Pastrorova et al. (1997)[
full citation needed ]
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .