Chrysin

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Chrysin
Chrysin
Ball-and-stick model of chrysin
Names
IUPAC name
5,7-Dihydroxy-2-phenyl-4H-chromen-4-one
Other names
5,7-Dihydroxyflavone; NP-005901; Galangin flavanone
Identifiers
480-40-0 YesY
ChEBI CHEBI:75095 N
ChEMBL ChEMBL117 YesY
ChemSpider 4444926 YesY
Jmol interactive 3D Image
KEGG C10028 YesY
PubChem 5281607
UNII 3CN01F5ZJ5 YesY
Properties
C15H10O4
Molar mass 254.24 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Chrysin is a naturally occurring flavone, a type of flavonoid. It is found in the passion flowers Passiflora caerulea and Passiflora incarnata, and in Oroxylum indicum. It is also found in chamomile, in the mushroom Pleurotus ostreatus,[1] and in honeycomb.

Aromatase inhibition[edit]

Studies performed in vivo show that orally administered chrysin does not have clinical activity as an aromatase inhibitor.[2][3]

Chrysin is available as a bodybuilding supplement and it is taken with the hope of raising testosterone levels or stimulating testosterone production; however, there is no clinical evidence for this effect, as studies show that chrysin has no effect on testosterone levels in men.[4]

Inflammation[edit]

Chrysin is under laboratory research for its potential effects on inflammation,[5] but there is no evidence it has anti-inflammatory activity in humans.

Bioavailability[edit]

Following oral intake by humans, chrysin has negligible bioavailability, resulting from its extensive degradation during digestion and efflux of its metabolites back into the intestine for hydrolysis and rapid excretion.[6]

References[edit]

  1. ^ Anandhi R, Annadurai T, Anitha TS, Muralidharan AR, Najmunnisha K, Nachiappan V; et al. (2012). "Antihypercholesterolemic and antioxidative effects of an extract of the oyster mushroom, Pleurotus ostreatus, and its major constituent, chrysin, in Triton WR-1339-induced hypercholesterolemic rats.". J Physiol Biochem 69 (2): 313–323. doi:10.1007/s13105-012-0215-6. PMID 23104078. 
  2. ^ Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R. (2001). "No evidence for the in vivo activity of aromatase-inhibiting flavonoids". J Steroid Biochem Mol Biol. 78 (3): 231–9. doi:10.1016/S0960-0760(01)00098-X. PMID 11595503. 
  3. ^ Int J Sport Nutr Exerc Metab. (2000). "Effects of anabolic precursors on serum testosterone concentrations and adaptations to resistance training in young men". Int J Sport Nutr Exerc Metab. 10 (3): 340–59. PMID 10997957. 
  4. ^ Gambelunghe C, Rossi R, Sommavilla M, Ferranti C, Rossi R, Ciculi C, Gizzi S, Micheletti A, Rufini S (2003). "Effects of chrysin on urinary testosterone levels in human males". J Med Food 6 (4): 387–90. doi:10.1089/109662003772519967. PMID 14977449. 
  5. ^ Woo KJ, Jeong YJ, Inoue H, Park JW, Kwon TK (January 2005). "Chrysin suppresses lipopolysaccharide-induced cyclooxygenase-2 expression through the inhibition of nuclear factor for IL-6 (NF-IL6) DNA-binding activity". FEBS Lett. 579 (3): 705–11. doi:10.1016/j.febslet.2004.12.048. PMID 15670832. 
  6. ^ Walle T, Otake Y, Brubaker JA, Walle UK, Halushka PV (February 2001). "Disposition and metabolism of the flavonoid chrysin in normal volunteers". Br J Clin Pharmacol 51 (2): 143–6. doi:10.1111/j.1365-2125.2001.01317.x. PMC 2014445. PMID 11259985.