{{Chembox | ImageFile = Pterostilbene.svg | ImageSize = | PIN = 4-[(''E'')-2-(3,5-Dimethoxyphenyl)ethen-1-yl]phenol | OtherNames = 3',5'-Dimethoxy-4-stilbenol<br>3,5-Dimethoxy-4'-hydroxy-''E''-stilbene<br>3',5'-Dimethoxy-resveratrol |Section1={{Chembox Identifiers | IUPHAR_ligand = 2681 | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4445042 | ChEMBL_Ref = {{ebicite|correct|EBI}} | 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+ | InChIKey = VLEUZFDZJKSGMX-ONEGZZNKBK | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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+ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VLEUZFDZJKSGMX-ONEGZZNKSA-N | InChIKey1 = VLEUZFDZJKSGMX-ONEGZZNKSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 537-42-8 | EINECS = | PubChem = 5281727 | SMILES = O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C | RTECS = | MeSHName = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 26R60S6A5I | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 8630 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | C=16 | H=16 | O=3 | Appearance = | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | HPhrases = | PPhrases = | GHS_ref = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} }} '''Pterostilbene''' ({{IPAc-en|ˌ|t|ɛr|ə|ˈ|s|t|ɪ|l|b|iː|n}}) (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol.<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 phytoalexin 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 found in almonds,<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 ''Vaccinium'' berries (including blueberries<ref>{{Cite web |url= https://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>), grape leaves and vines.<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> It is also encountered in the xylem, particularly in the heartwood of ''Pterocarpus marsupium''<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 }} {{Creative Commons text attribution notice|cc=by3}}</ref> as well as in other species of the ''Pterocarpus'' family, including Malay padauk, the Narra tree (''Pterocarpus indicus''), Muninga and African padauk (''Pterocarpus erinaceus''), thus contributing to the high natural durability as a known phytoalexin.<ref>{{cite book|title=Springer Handbooks|publisher=Springer International Publishing|isbn=978-3-030-81314-7|year=2023|chapter=Springer Handbook of Wood Science and Technology (Chapter 5. Wood Chemistry)|publication-place=Cham|page=263|issn=2522-8692|doi=10.1007/978-3-030-81315-4|s2cid=257902863}}</ref>
==Biosynthesis== The enzyme trans-resveratrol di-O-methyltransferase adds two methyl groups to resveratrol. They are transferred from the cofactor, S-adenosyl methionine (SAM). The enzyme was characterised from ''Vitis vinifera'' (grapevine).<ref>{{cite journal |vauthors = Schmidlin L, Poutaraud A, Claudel P, Mestre P, Prado E, Santos-Rosa M, Wiedemann-Merdinoglu S, Karst F, Merdinoglu D, Hugueney P |title = A stress-inducible resveratrol O-methyltransferase involved in the biosynthesis of pterostilbene in grapevine |journal = Plant Physiology |volume = 148 |issue = 3 |pages = 1630–9 |date = November 2008 |pmid = 18799660 |pmc = 2577258 |doi = 10.1104/pp.108.126003 }}</ref>
{{chemrxn|width=65%| {{chemrxn/cpd|resveratrol }} {{chemrxn/txt|+ 2 SAM }} {{chemrxn/arw| }} {{chemrxn/cpd|pterostilbene }} {{chemrxn/txt|+ 2 SAH }} }}
== 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.<ref name=pubchem/> 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.<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 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.<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 cardiovascular risk of pterostilbene supplementation in humans.<ref name=":2" />
Its chemical relative, resveratrol, 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 |archive-url=https://web.archive.org/web/20160424034643/http://www.accessdata.fda.gov/scripts/fdcc/index.cfm?set=GRASNotices&id=224 |url-status=dead |archive-date=April 24, 2016 |publisher=US Food and Drug Administration, Food Ingredient and Packaging Inventories |access-date=7 February 2019 |date=1 August 2007}}</ref> and approval of synthetic resveratrol as a safe compound by the European Food Safety Authority (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 methoxy groups which cause it to exhibit increased lipophilic and oral absorption.<ref name=PteroReview2013/>
== See also == * Piceatannol, a stilbenoid related to both resveratrol and pterostilbene
== References == {{reflist}} {{Stilbenes}}
Category:Nutrients Category:Stilbenoids Category:Phytoalexins