Pterostilbene

From Wikipedia, the free encyclopedia
Pterostilbene
Pterostilbene.png
Names
Preferred IUPAC name
4-[(E)-2-(3,5-Dimethoxyphenyl)ethen-1-yl]phenol
Other names
3',5'-Dimethoxy-4-stilbenol
3,5-Dimethoxy-4'-hydroxy-E-stilbene
3',5'-Dimethoxy-resveratrol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.122.141 Edit this at Wikidata
IUPHAR/BPS
UNII
  • 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+ checkY
    Key: VLEUZFDZJKSGMX-ONEGZZNKSA-N checkY
  • 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
  • O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C
Properties
C16H16O3
Molar mass 256.301 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pterostilbene (/ˌtɛrəˈstɪlbiːn/) (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol.[1] In plants, it serves a defensive phytoalexin role.[2]

Natural occurrence[]

Pterostilbene is found in almonds,[3] various Vaccinium berries (including blueberries[4][5][6]), grape leaves and vines,[2][7] and Pterocarpus marsupium heartwood.[5]

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.[1] A randomized, double-blind, placebo-controlled 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.[8]

Its chemical relative, resveratrol, received FDA GRAS status in 2007,[9] and approval of synthetic resveratrol as a safe compound by the European Food Safety Authority (EFSA) in 2016.[10] 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.[5]

Research[]

Pterostilbene is being studied in laboratory and preliminary clinical research.[1]

See also[]

  • Piceatannol, a stilbenoid related to both resveratrol and pterostilbene

References[]

  1. ^ a b c "Pterostilbene, CID 5281727". PubChem, National Library of Medicine, US National Institutes of Health. 16 November 2019. Retrieved 18 November 2019.
  2. ^ a b Langcake, P.; Pryce, R. J. (1977). "A new class of phytoalexins from grapevines". Experientia. 33 (2): 151–2. doi:10.1007/BF02124034. PMID 844529.
  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. ^ a b c 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.
  9. ^ "GRAS Notice GRN 224: Resveratrol". US Food and Drug Administration, Food Ingredient and Packaging Inventories. 1 August 2007. Retrieved 7 February 2019.
  10. ^ "Safety of synthetic trans‐resveratrol as a novel food pursuant to Regulation (EC) No 258/97". EFSA Journal. European Food Safety Authority, EFSA Panel on Dietetic Products, Nutrition and Allergies. 14 (1): 4368. 12 January 2016. doi:10.2903/j.efsa.2016.4368.
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