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Pterostilbene

Pterostilbene
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
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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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 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.[8]

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.[9] 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.[9]

Its chemical relative, resveratrol, received FDA GRAS status in 2007,[10] and approval of synthetic resveratrol as a safe compound by the European Food Safety Authority (EFSA) in 2016.[11] 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. 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. ^ 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. S2CID 2649118.
  9. ^ a b 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.
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