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Pterostilbene

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Pterostilbene
Names
IUPAC name 4-phenol
Other names 3',5'-Dimethoxy-4-stilbenol
3,5-Dimethoxy-4'-hydroxy-E-stilbene
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.122.141 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+Key: VLEUZFDZJKSGMX-ONEGZZNKSA-N
  • Key: VLEUZFDZJKSGMX-ONEGZZNKBK
  • Key: VLEUZFDZJKSGMX-ONEGZZNKSA-N
SMILES
  • O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C
Properties
Chemical formula C16H16O3
Molar mass 256.296 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Pterostilbene is a stilbenoid chemically related to resveratrol and is found in blueberries and grapes. It belongs to the group of phytoalexins, agents produced by plants to fight infections. Based on animal studies it is thought to exhibit anti-cancer, anti-hypercholesterolemia, anti-hypertriglyceridemia properties, as well as fight off and reverse cognitive decline. It is believed that the compound also has anti-diabetic properties, but so far very little has been studied on this issue.

Pharmacokinetics

Pterostilbene is a double-methylated version of resveratrol exhibiting a higher bioavailability as it is more easily transported into the cell and more resistant to degradation and elimination. In rats, pterostilbene's oral availability is 67%-94%, and its half-life has been published to be between 78 minutes and 104 minutes.

Pterostilbene has anti -inflammatory, antineoplastic, and antioxidant actions via modulations of gene expression and enzyme activity. In plants the substance displays antifungal and antiviral activities.

Focus of studies has been generally on the trans isomer of pterostilbene.

Animal studies

Lowering blood lipids and cholesterol

Studies that used animals fed on blueberry based diets found significant reduction in blood lipid count and cholesterol count. While lipids and cholesterol stored in the cells do not pose much harm, elevated lipid and cholesterol levels in the blood have been linked to heart disease and stroke. In the mentioned study blueberries were found to be more effective than ciprofibrate, a cholesterol-lowering drug predominantly used outside the United States. According to the study pterostilbene binds to PPARs, breaking down the cholesterol.

Diabetes

Similar to what has been discovered with the drug metformin, pterostilbene has been shown to lower blood glucose levels in rats by as much as 56 percent, while simultaneously raising insulin and hemoglobin levels to near normal levels.

Cognitive decline

In a study of 40 19-month-old rats fed either a normal diet or a diet containing blueberry, strawberry, or spinach extracts, the rats that were fed blueberry extracts had a significant reversal in motor-skill decline due to aging as well as other cognitive impairments. All of the diets above, except the normal one, resulted in some reversal or reduction of cognitive decline but none greater than the blueberry group. Even when animal based studies yield positive results, the effects on humans may not be the same.

Possible anti-cancer effects

In 2002, Rimando and UIC collaborators found in experiments using rat mammary glands that pterostilbene possessed potent anti-oxidant characteristics and possible cancer-fighting properties at concentrations similar to resveratrol.

Additional work by Rimando and collaborators revealed a possible mechanism for pterostilbene's purported anti-cancer properties. Using mice cells, they demonstrated that pterostilbene, as well as other analogs of resveratrol, potently inhibits an enzyme called cytochrome P450. (Cytochromes are found within the cells of animals, plants, bacteria, and other microorganisms that transport electrons. They’re also a factor in people’s varying response to drugs and toxins entering their bodies. Cytochrome P450 enzymes activate a variety of compounds known as ”procarcinogens,” which can turn substances such as cigarette smoke and pesticides into carcinogens.)

According to Rimando, Pterostilbene showed strong inhibitory activity, much more than resveratrol, against a particular form of cytochrome P450 in a mouse mammary gland culture assay.

Human studies

No randomized human studies have been completed, however the first human clinical trial on the effect of pterostilbene on cholesterol and blood pressure should run from Dec 2010 to Jan 2013 at the University of Mississippi. Effect upon human health is an extrapolation of animal data. The data collected from rat studies suggest a dose of 50–100 mg of pterostilbene 2x/day, similar to the dosage of resveratrol.

In wine

While resveratrol has been touted for its heart healthy benefits, pterostilbene is not found in wine despite darker grapes having the highest concentrations among the fruit. The reason believed is that it is unstable in light and air.

Toxicity

Pterostilbene is not known to be toxic to humans.

See also

References

  1. Langcake P, Cornford CA, Pryce JR (1977). "Identification of pterostilbene as a phytoalexin from Vitis vinifera leaves". Experientia. 1977 Feb 15;33(2):151-2. 33 (2): 151–2. doi:10.1007/BF02124034. PMID 844529. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Alternative Medicine Review (AMR). "Pterostilbene Monograph". AMR, 2010, Vol. 15, Number 2, pages 159-163.
  3. IM Kapetanovic; et al. (2010). "Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats". Cancer Chemother Pharmacol, 2010. 68 (3): 593–601. doi:10.1007/s00280-010-1525-4. PMC 3090701. PMID 21116625. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)
  4. CM Remsberg; et al. (2008). "Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, antiinflammatory, antioxidant and analgesic activity". Phytother Res, 2008 Feb;22(2):169-79,. 22 (2): 169–79. doi:10.1002/ptr.2277. PMID 17726731. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: extra punctuation (link)
  5. P Ferrer; et al. (2005). "Association between Pterostilbene and Quercetin Inhibits Metastatic Activity of B16 Melanoma". Neoplasia, 2005 Jan;7(1):37-47,. 7 (1): 37–47. PMC 1490314. PMID 15736313. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: extra punctuation (link)
  6. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11982391, please use {{cite journal}} with |pmid=11982391 instead.
  7. Gastaminza P, Whitten-Bauer C, Chisari FV (2010). "Unbiased probing of the entire hepatitis C virus life cycle identifies clinical compounds that target multiple aspects of the infection". Proc Natl Acad Sci U S A. 2010 Jan 5;107(1):291-6. Epub 2009 Dec 7. 107 (1): 291–6. Bibcode:2010PNAS..107..291G. doi:10.1073/pnas.0912966107. PMC 2806752. PMID 19995961. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. WebMD.com
  9. Cholesterol.about.com
  10. ^ Pari L, Satheesh MA (2006). "Effect of pterostilbene on hepatic key enzymes of glucose metabolism in streptozotocin- and nicotinamide-induced diabetic rats". Life Sciences. 79 (7): 641–5. doi:10.1016/j.lfs.2006.02.036. PMID 16616938. {{cite journal}}: Unknown parameter |month= ignored (help)
  11. Braslavsky, Andrea, "Blueberries May Be King of the Hill for Those Over the Hill," WebMD Medical News, Sept. 16, 1999, retrieved December 29, 2006.
  12. Ars.usda.gov/main/main
  13. http://clinicaltrials.gov/ct2/show/NCT01267227 Effect of Pterostilbene on Cholesterol, Blood Pressure and Oxidative Stress
  14. Reagan-Shaw S, Nihal M, Ahmad N (2008). "Dose translation from animal to human studies revisited". The FASEB Journal. 22 (3): 659–61. doi:10.1096/fj.07-9574LSF. PMID 17942826. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)

External links

Type of stilbenoids (molecules with a C6-C2-C6 backbone)
Types
Categories: