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{{chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 455522964 | verifiedrevid = 464376256
| ImageFile = Pterostilbene.png | ImageFile = Pterostilbene.svg
| ImageSize = | ImageSize =
| IUPACName = 4-phenol | PIN = 4-phenol
| OtherNames = 3',5'-Dimethoxy-4-stilbenol<br>3,5-Dimethoxy-4'-hydroxy-''E''-stilbene | OtherNames = 3',5'-Dimethoxy-4-stilbenol<br>3,5-Dimethoxy-4'-hydroxy-''E''-stilbene<br>3',5'-Dimethoxy-resveratrol
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| IUPHAR_ligand = 2681
| Abbreviations = | Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4445042 | ChemSpiderID = 4445042
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 83527 | ChEMBL = 83527
| 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+ | 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+
Line 24: Line 26:
| PubChem = 5281727 | PubChem = 5281727
| SMILES = O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C | SMILES = O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C
| InChI =
| RTECS = | RTECS =
| MeSHName = | MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 26R60S6A5I
⚫ | ChEBI =
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | ChEBI = 8630
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
}}
| ATCCode_prefix =
⚫ |Section2={{Chembox Properties
| ATCCode_suffix =
| C=16 | H=16 | O=3
| ATC_Supplemental =}}
⚫ | Section2 = {{Chembox Properties
| Formula = C<sub>16</sub>H<sub>16</sub>O<sub>3</sub>
| MolarMass = 256.296 g/mol
| ExactMass = 256.109944
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| Melting_notes = | MeltingPt_notes =
| BoilingPt = | BoilingPt =
| Boiling_notes = | BoilingPt_notes =
| Solubility = | Solubility =
| SolubleOther = | SolubleOther =
| Solvent = | Solvent =
| pKa = | pKa =
| pKb = }} | pKb =
}}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| EUClass =
| EUIndex =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| RPhrases = | HPhrases =
| SPhrases = | PPhrases =
| RSPhrases = | GHS_ref =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| ExploLimits = | ExploLimits =
| PEL = }} | PEL =
}}
}} }}
'''Pterostilbene''' ({{IPAc-en|ˌ|t|ɛr|ə|ˈ|s|t|ɪ|l|b|iː|n}}) (trans-3,5-dimethoxy-4-hydroxystilbene) is a ] chemically related to ].<ref name="pubchem">{{cite web |title= Pterostilbene, CID 5281727 |publisher=PubChem, National Library of Medicine, US National Institutes of Health |url= https://pubchem.ncbi.nlm.nih.gov/compound/5281727 |date= 16 November 2019|access-date= 18 November 2019}}</ref> In plants, it serves a defensive ] role.<ref name="ex">{{cite journal |doi=10.1007/BF02124034 |title=A new class of phytoalexins from grapevines |year=1977 |last1=Langcake |first1=P. |last2=Pryce |first2=R. J. |journal=Experientia |volume=33 |issue=2 |pages=151–2 |pmid=844529|s2cid=34370048 }}</ref>


== Natural occurrence ==
'''Pterostilbene''' is a ] chemically related to ] and is found in ] and ]. It belongs to the group of ]s, agents produced by plants to fight infections.<ref>{{cite journal | author=Langcake P, Cornford CA, Pryce JR | title=Identification of pterostilbene as a phytoalexin from ''Vitis vinifera'' leaves. | journal=Experientia. 1977 Feb 15;33(2):151-2. | pmid=844529 | doi=10.1007/BF02124034 | volume=33 | issue=2 | year=1977 | month=February | pages=151–2}}</ref> Based on animal studies it is thought to exhibit anti-], anti-], anti-] properties, as well as fight off and reverse cognitive decline. It is believed that the compound also has anti-] properties, but so far very little has been studied on this issue.
Pterostilbene is found in ],<ref>{{cite journal |journal=Food Chem |year=2014 |issue=Apr 1 |volume=148 |pages=300–6 |doi= 10.1016/j.foodchem.2013.10.057 |title= Characterisation of stilbenes in California almonds (Prunus dulcis) by UHPLC-MS |vauthors= Xie L, Bolling BW |pmid=24262561}}</ref> various '']'' berries (including ]<ref>{{Cite web |url= http://agresearchmag.ars.usda.gov/2006/nov/health|title=Pterostilbene's healthy potential |publisher=US Department of Agriculture, Online Magazine, Vol. 54, No. 11|date=1 November 2006 |access-date=2016-03-21}}</ref><ref name=PteroReview2013/><ref>{{cite journal |journal=J Agric Food Chem |year=2004 |volume=52 |issue=15 |pages= 4713–9 |title= Resveratrol, pterostilbene, and piceatannol in vaccinium berries |vauthors= Rimando AM, Kalt W, Magee JB, Dewey J, Ballington JR |pmid=15264904 |doi= 10.1021/jf040095e}}</ref>), ] leaves and ]s,<ref name="ex" /><ref>{{cite journal |journal=Molecules |year=2014 |volume=2013 |issue=7 |pages=10587–600 |doi= 10.3390/molecules190710587 |title= MALDI mass spectrometry imaging for the simultaneous location of resveratrol, pterostilbene and viniferins on grapevine leaves |vauthors= Becker L, Carré V, Poutaraud A, Merdinoglu D, Chaimbault P |pmid=25050857|pmc=6271053 |doi-access=free }}</ref> and '']'' heartwood.<ref name="PteroReview2013">{{cite journal | last1=McCormack | first1=Denise | last2=McFadden | first2=David | title=A review of pterostilbene antioxidant activity and disease modification | journal=Oxidative Medicine and Cellular Longevity | volume=2013 | year=2013 | issn=1942-0900 | doi=10.1155/2013/575482 | pages=1–15|pmid=23691264| pmc=3649683 | doi-access=free }}</ref>


== Safety and regulation ==
==Pharmacokinetics==
Pterostilbene is considered to be a ], is dangerous upon exposure to the eyes, and is an environmental ], especially to ].<ref name=pubchem/>
Pterostilbene is a double-methylated version of resveratrol exhibiting a higher ] as it is more easily transported into the cell and more resistant to degradation and elimination.<ref name=amr>{{cite journal | url=http://www.altmedrev.com/sobi2.html?sobi2Task=sobi2Details&catid=294&sobi2Id=22794 | author=Alternative Medicine Review (AMR)|title=Pterostilbene Monograph | journal=AMR, 2010, Vol. 15, Number 2, pages 159-163 | pmid= }}</ref> In rats, pterostilbene's oral availability is 67%-94%, and its half-life has been published to be between 78 minutes and 104 minutes.<ref name=ccp>{{cite journal | author=IM Kapetanovic et al|title=Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats| journal=Cancer Chemother Pharmacol, 2010| pmid= 21116625| doi=10.1007/s00280-010-1525-4| year=2010| month=November | volume=68 | issue=3 | pages=593–601 | pmc=3090701}}</ref><ref name=pr>{{cite journal | author=CM Remsberg et al|title=Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, antiinflammatory, antioxidant and analgesic activity| journal=Phytother Res, 2008 Feb;22(2):169-79, | pmid= 17726731| doi=10.1002/ptr.2277| volume=22| issue=2| year=2008| month=February| pages=169–79}}</ref><ref name=neo>{{cite journal | author= P Ferrer et al|title=Association between Pterostilbene and Quercetin Inhibits Metastatic Activity of B16 Melanoma | journal=Neoplasia, 2005 Jan;7(1):37-47, | pmid= 15736313 | volume=7 | issue=1 | pmc=1490314 | year=2005 | month=January | pages=37–47}}</ref>
A preliminary study of healthy human subjects given pterostilbene for 6–8 weeks, showed pterostilbene to be safe for human use at dosages up to 250&nbsp;mg per day, although this study did not assess metabolic effects on the lipid profile.<ref name="pmid29315886">{{cite journal | vauthors=Wang P, Sang S | title=Metabolism and pharmacokinetics of resveratrol and pterostilbene | journal=BioFactors | volume=44 | issue=1 | pages=16–25 | year=2018 | doi = 10.1002/biof.1410 | pmid=29315886| s2cid=2649118 | doi-access=free }}</ref>


Other studies have reported dose-based elevations of ] (LDL-C, "]") and decreased ] cholesterol (HDL-C, "]") within 4 to 8 weeks of daily dosing.<ref name=":2">{{cite journal |last1=Brenner |first1=C |last2=Boileau |first2=AC |title=Pterostilbene raises low density lipoprotein cholesterol in people |journal=Clinical Nutrition |date=October 13, 2018 |volume=38 |issue=1 |pages=480–481 |doi=10.1016/j.clnu.2018.10.007 |pmid=30482564 |doi-access=free }}</ref> The elevation of LDL-C may move previously normal ranges into borderline high or high reference range and has raised questions about the longterm ] of pterostilbene supplementation in humans.<ref name=":2" />
Pterostilbene has anti -inflammatory, antineoplastic, and antioxidant actions via modulations of gene expression and enzyme activity.<ref name=amr/> In plants the substance displays antifungal<ref>{{cite pmid|11982391}}</ref> and antiviral activities.<ref>{{cite journal |journal=Proc Natl Acad Sci U S A. 2010 Jan 5;107(1):291-6. Epub 2009 Dec 7 |title=Unbiased probing of the entire hepatitis C virus life cycle identifies clinical compounds that target multiple aspects of the infection |author=Gastaminza P, Whitten-Bauer C, Chisari FV |pmid=19995961 |doi=10.1073/pnas.0912966107 |volume=107 |issue=1 |year=2010 |month=January |pages=291–6 |pmc=2806752 |bibcode=2010PNAS..107..291G}}</ref>


Its chemical relative, ], received FDA GRAS status in 2007,<ref>{{cite web |title=GRAS Notice GRN 224: Resveratrol |url=https://www.accessdata.fda.gov/scripts/fdcc/index.cfm?set=GRASNotices&id=224 |publisher=US Food and Drug Administration, Food Ingredient and Packaging Inventories |access-date=7 February 2019 |date=1 August 2007}}</ref> and approval of ] resveratrol as a safe compound by the ] (EFSA) in 2016.<ref name="efsa">{{cite journal |title=Safety of synthetic trans‐resveratrol as a novel food pursuant to Regulation (EC) No 258/97 |journal=EFSA Journal |date=12 January 2016 |volume=14 |issue=1 |pages=4368 |doi=10.2903/j.efsa.2016.4368 |publisher=European Food Safety Authority, EFSA Panel on Dietetic Products, Nutrition and Allergies|doi-access=free }}</ref> Pterostilbene differs from resveratrol by exhibiting increased bioavailability (80% compared to 20% in resveratrol) due to the presence of two ]s which cause it to exhibit increased ] and oral absorption.<ref name=PteroReview2013/>
Focus of studies has been generally on the ] of pterostilbene.<ref name=amr/>


==Animal studies== ==Research==
Pterostilbene is being studied in laboratory and preliminary ].<ref name=pubchem/>
===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 ], a cholesterol-lowering drug predominantly used outside the United States.<ref>
</ref>
According to the study pterostilbene binds to ], breaking down the cholesterol.<ref></ref>

===Diabetes===
Similar to what has been discovered with the drug ], 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.<ref name="Pari L, Satheesh MA 2006 641–5">{{cite journal |author=Pari L, Satheesh MA |title=Effect of pterostilbene on hepatic key enzymes of glucose metabolism in streptozotocin- and nicotinamide-induced diabetic rats |journal=Life Sciences |volume=79 |issue=7 |pages=641–5 |year=2006 |month=July |pmid=16616938 |doi=10.1016/j.lfs.2006.02.036}}</ref>

===Cognitive decline===
In a study of 40 19-month-old rats fed either a normal diet or a diet containing blueberry, ], or ] 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.<ref name="webmd"></ref> 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 ] that pterostilbene possessed potent anti-oxidant characteristics and possible cancer-fighting properties at concentrations similar to resveratrol.<ref></ref>

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 ].{{Citation needed|date=October 2011}} (] 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 ”],” which can turn substances such as ] and ] into ].)

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.<ref>http://clinicaltrials.gov/ct2/show/NCT01267227 Effect of Pterostilbene on Cholesterol, Blood Pressure and Oxidative Stress</ref> Effect upon human health is an extrapolation of animal data. The data collected from rat studies suggest a dose of 50–100&nbsp;mg of pterostilbene 2x/day, similar to the dosage of resveratrol.<ref name="Pari L, Satheesh MA 2006 641–5"/><ref>{{cite journal |author=Reagan-Shaw S, Nihal M, Ahmad N |title=Dose translation from animal to human studies revisited |journal=The FASEB Journal |volume=22 |issue=3 |pages=659–61 |year=2008 |month=March |pmid=17942826 |doi=10.1096/fj.07-9574LSF}}</ref>

==In wine==
While ] 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.<ref name=amr/>


== See also == == See also ==
⚫ * ], a stilbenoid related to both resveratrol and pterostilbene
* ]
* ]
* ]
⚫ * ], a ] related to both resveratrol and pterostilbene.
* ]


== References == == References ==
{{reflist}} {{reflist}}
{{Stilbenes}}

== External links ==
*
*
*

{{Stilbenoids}}


] ]
] ]
]

]

Latest revision as of 21:16, 15 October 2023

Pterostilbene
Names
Preferred IUPAC name 4-phenol
Other names 3',5'-Dimethoxy-4-stilbenol
3,5-Dimethoxy-4'-hydroxy-E-stilbene
3',5'-Dimethoxy-resveratrol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.122.141 Edit this at Wikidata
IUPHAR/BPS
PubChem CID
UNII
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
  • 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-ONEGZZNKBK
  • Key: VLEUZFDZJKSGMX-ONEGZZNKSA-N
SMILES
  • O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C
Properties
Chemical formula C16H16O3
Molar mass 256.301 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 (/ˌtɛrəˈstɪlbiːn/) (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role.

Natural occurrence

Pterostilbene is found in almonds, various Vaccinium berries (including blueberries), grape leaves and vines, and Pterocarpus marsupium heartwood.

Safety and regulation

Pterostilbene is considered to be a corrosive substance, is dangerous upon exposure to the eyes, and is an environmental toxin, especially to aquatic life. A preliminary study of healthy human subjects given pterostilbene for 6–8 weeks, showed pterostilbene to be safe for human use at dosages up to 250 mg per day, although this study did not assess metabolic effects on the lipid profile.

Other studies have reported dose-based elevations of low density lipoprotein cholesterol (LDL-C, "bad cholesterol") and decreased high density lipoprotein cholesterol (HDL-C, "good cholesterol") within 4 to 8 weeks of daily dosing. The elevation of LDL-C may move previously normal ranges into borderline high or high reference range and has raised questions about the longterm cardiovascular risk of pterostilbene supplementation in humans.

Its chemical relative, resveratrol, received FDA GRAS status in 2007, and approval of synthetic resveratrol as a safe compound by the European Food Safety Authority (EFSA) in 2016. Pterostilbene differs from resveratrol by exhibiting increased bioavailability (80% compared to 20% in resveratrol) due to the presence of two methoxy groups which cause it to exhibit increased lipophilic and oral absorption.

Research

Pterostilbene is being studied in laboratory and preliminary clinical research.

See also

  • Piceatannol, a stilbenoid related to both resveratrol and pterostilbene

References

  1. ^ "Pterostilbene, CID 5281727". PubChem, National Library of Medicine, US National Institutes of Health. 16 November 2019. Retrieved 18 November 2019.
  2. ^ Langcake, P.; Pryce, R. J. (1977). "A new class of phytoalexins from grapevines". Experientia. 33 (2): 151–2. doi:10.1007/BF02124034. PMID 844529. S2CID 34370048.
  3. Xie L, Bolling BW (2014). "Characterisation of stilbenes in California almonds (Prunus dulcis) by UHPLC-MS". Food Chem. 148 (Apr 1): 300–6. doi:10.1016/j.foodchem.2013.10.057. PMID 24262561.
  4. "Pterostilbene's healthy potential". US Department of Agriculture, Online Magazine, Vol. 54, No. 11. 1 November 2006. Retrieved 2016-03-21.
  5. ^ McCormack, Denise; McFadden, David (2013). "A review of pterostilbene antioxidant activity and disease modification". Oxidative Medicine and Cellular Longevity. 2013: 1–15. doi:10.1155/2013/575482. ISSN 1942-0900. PMC 3649683. PMID 23691264.
  6. Rimando AM, Kalt W, Magee JB, Dewey J, Ballington JR (2004). "Resveratrol, pterostilbene, and piceatannol in vaccinium berries". J Agric Food Chem. 52 (15): 4713–9. doi:10.1021/jf040095e. PMID 15264904.
  7. Becker L, Carré V, Poutaraud A, Merdinoglu D, Chaimbault P (2014). "MALDI mass spectrometry imaging for the simultaneous location of resveratrol, pterostilbene and viniferins on grapevine leaves". Molecules. 2013 (7): 10587–600. doi:10.3390/molecules190710587. PMC 6271053. PMID 25050857.
  8. Wang P, Sang S (2018). "Metabolism and pharmacokinetics of resveratrol and pterostilbene". BioFactors. 44 (1): 16–25. doi:10.1002/biof.1410. PMID 29315886. S2CID 2649118.
  9. ^ Brenner, C; Boileau, AC (October 13, 2018). "Pterostilbene raises low density lipoprotein cholesterol in people". Clinical Nutrition. 38 (1): 480–481. doi:10.1016/j.clnu.2018.10.007. PMID 30482564.
  10. "GRAS Notice GRN 224: Resveratrol". US Food and Drug Administration, Food Ingredient and Packaging Inventories. 1 August 2007. Retrieved 7 February 2019.
  11. "Safety of synthetic trans‐resveratrol as a novel food pursuant to Regulation (EC) No 258/97". EFSA Journal. 14 (1). European Food Safety Authority, EFSA Panel on Dietetic Products, Nutrition and Allergies: 4368. 12 January 2016. doi:10.2903/j.efsa.2016.4368.
Hydroxystilbenes and their glycosides (monomeric forms)
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
Combretastatins
carboxylated
other acylations
Glycosides
of resveratrol
of rhapontigenin
Oligomeric formsoligostilbenoids
Categories: