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Chrysin is under laboratory research for its potential effects on [[inflammation]].<ref name=Zeinali2017>{{cite journal | vauthors = Zeinali M, Rezaee SA, Hosseinzadeh H | title = An overview on immunoregulatory and anti-inflammatory properties of chrysin and flavonoids substances | journal = Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie | volume = 92 | issue = | pages = 998–1009 | year = 2017 | doi = 10.1016/j.biopha.2017.06.003 | pmid = 28609844 }}</ref> It displayed [[anti-inflammatory]] and antioxidant activity.<ref name=JaganathanMandal2009/> [[In vivo]] research indicates that orally administered chrysin does not have clinical activity as an [[aromatase]] inhibitor.<ref name="Saarinen2001">{{cite journal | vauthors = Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R | title = No evidence for the in vivo activity of aromatase-inhibiting flavonoids | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 78 | issue = 3 | pages = 231–9 | date = September 2001 | pmid = 11595503 | doi = 10.1016/S0960-0760(01)00098-X }}</ref><ref>{{cite journal | vauthors = Brown GA, Vukovich MD, Reifenrath TA, Uhl NL, Parsons KA, Sharp RL, King DS | title = Effects of anabolic precursors on serum testosterone concentrations and adaptations to resistance training in young men | journal = International Journal of Sport Nutrition and Exercise Metabolism | volume = 10 | issue = 3 | pages = 340–59 | date = September 2000 | pmid = 10997957 }}</ref>
Chrysin is under laboratory research for its potential effects on [[inflammation]].<ref name=Zeinali2017>{{cite journal | vauthors = Zeinali M, Rezaee SA, Hosseinzadeh H | title = An overview on immunoregulatory and anti-inflammatory properties of chrysin and flavonoids substances | journal = Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie | volume = 92 | issue = | pages = 998–1009 | year = 2017 | doi = 10.1016/j.biopha.2017.06.003 | pmid = 28609844 }}</ref> It displayed [[anti-inflammatory]] and antioxidant activity.<ref name=JaganathanMandal2009/> [[In vivo]] research indicates that orally administered chrysin does not have clinical activity as an [[aromatase]] inhibitor.<ref name="Saarinen2001">{{cite journal | vauthors = Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R | title = No evidence for the in vivo activity of aromatase-inhibiting flavonoids | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 78 | issue = 3 | pages = 231–9 | date = September 2001 | pmid = 11595503 | doi = 10.1016/S0960-0760(01)00098-X }}</ref><ref>{{cite journal | vauthors = Brown GA, Vukovich MD, Reifenrath TA, Uhl NL, Parsons KA, Sharp RL, King DS | title = Effects of anabolic precursors on serum testosterone concentrations and adaptations to resistance training in young men | journal = International Journal of Sport Nutrition and Exercise Metabolism | volume = 10 | issue = 3 | pages = 340–59 | date = September 2000 | pmid = 10997957 }}</ref>


In other laboratory studies, chrysin displayed toxic effects on isolated cancer cells, indicating its potential in anticancer research.<ref name=FDA2016/><ref name=Sak2014>{{cite journal | vauthors = Sak K | title = Cytotoxicity of dietary flavonoids on different human cancer types | journal = Pharmacognosy Reviews | volume = 8 | issue = 16 | pages = 122–46 | year = 2014 | pmid = 25125885 | pmc = 4127821 | doi = 10.4103/0973-7847.134247 }}</ref> It also showed [[cytostasis|antiproliferative]] effects in vitro.<ref name=FDA2016/><ref name=JaganathanMandal2009>{{cite journal | vauthors = Jaganathan SK, Mandal M | title = Antiproliferative Effects of Honey and of Its Polyphenols: A Review | journal = Journal of Biomedicine & Biotechnology | volume = 2009 | issue = | pages = 830616 | year = 2009 | pmid = 19636435 | pmc = 2712839 | doi = 10.1155/2009/830616 | url = }}{{CC-notice|cc=by3|url=https://www.hindawi.com/journals/bmri/2009/830616/|authors=Saravana Kumar Jaganathan and Mahitosh Mandal}}</ref> There is no evidence for chrysin in clinical applications and its use for compounding of therapeutic agents is not recommended.<ref name=FDA2016/>
In other laboratory studies, chrysin displayed toxic effects on isolated cancer cells, indicating its potential in anticancer research.<ref name=FDA2016/><ref name=Sak2014>{{cite journal | vauthors = Sak K | title = Cytotoxicity of dietary flavonoids on different human cancer types | journal = Pharmacognosy Reviews | volume = 8 | issue = 16 | pages = 122–46 | year = 2014 | pmid = 25125885 | pmc = 4127821 | doi = 10.4103/0973-7847.134247 }}</ref> It also showed [[cytostasis|antiproliferative]] effects in vitro.<ref name=FDA2016/><ref name=JaganathanMandal2009>{{cite journal | vauthors = Jaganathan SK, Mandal M | title = Antiproliferative Effects of Honey and of Its Polyphenols: A Review | journal = Journal of Biomedicine & Biotechnology | volume = 2009 | issue = | pages = 830616 | year = 2009 | pmid = 19636435 | pmc = 2712839 | doi = 10.1155/2009/830616 | url = }}{{CC-notice|cc=by3|url=https://www.hindawi.com/journals/bmri/2009/830616/|authors=Saravana Kumar Jaganathan and Mahitosh Mandal}}</ref> There is no evidence for chrysin in clinical applications and its use for compounding of therapeutic agents is not recommended.<ref name=FDA2016/> It has been used in nanoformulations to determine its suitability as an anticancer agent.<ref name=Davatgaran-TaghipourMasoomzadeh2017/> Nanoformulations of polyphenols including chrysin are made using various of methods that use carriers such as liposomes and nanocapsules.<ref name=Davatgaran-TaghipourMasoomzadeh2017>{{cite journal|last1=Davatgaran-Taghipour|first1=Yasamin|last2=Masoomzadeh|first2=Salar|last3=Farzaei|first3=Mohammad Hosein|last4=Bahramsoltani|first4=Roodabeh|last5=Karimi-Soureh|first5=Zahra|last6=Rahimi|first6=Roja|last7=Abdollahi|first7=Mohammad|title=Polyphenol nanoformulations for cancer therapy: experimental evidence and clinical perspective|journal=International Journal of Nanomedicine|volume=Volume 12|year=2017|pages=2689–2702|issn=1178-2013|doi=10.2147/IJN.S131973|pmc=5388197|pmid=28435252}}</ref>


== References ==
== References ==

Revision as of 14:40, 29 October 2017

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.864 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H checkY
    Key: RTIXKCRFFJGDFG-UHFFFAOYSA-N checkY
  • InChI=1/C15H10O4/c16-10-6-11(17)15-12(18)8-13 (19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
    Key: RTIXKCRFFJGDFG-UHFFFAOYAO
  • O=C\1c3c(O/C(=C/1)c2ccccc2)cc(O)cc3O
Properties
C15H10O4
Molar mass 254.241 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 checkY☒N ?)

Chrysin is a flavone found in honey, propolis, the passion flowers, Passiflora caerulea and Passiflora incarnata, and in Oroxylum indicum.[1] It is an ingredient in dietary supplements.[2] and is under basic research for its potential biological effects.[3]

Occurrence

Chrysin is a naturally occurring flavone, a type of flavonoid.[4] It is primarily found in honey, propolis, and the passion flowers, Passiflora caerulea and Passiflora incarnata, and in Oroxylum indicum.[1] It is also found in chamomile and in the mushroom, Pleurotus ostreatus.[5]

The amount of chrysin in honey is about 0.2 mg per 100 g of honey.[6] Chrysin is typically found at higher amounts in propolis than in honey.[7]

Bioavailability

Following oral intake by humans, chrysin has low bioavailability and rapid excretion.[8][9]

Supplement

Although chrysin is an ingredient in dietary supplements and topical medications intended to improve physical performance or treat various clinical conditions, its safety, efficacy, and history for use in compounding remain undefined.[2]

Safety

Preliminary determinations of safety in oral consumption of chrysin indicate a daily amount of 0.5 to 3 g,[4] although other reviews describe that its safety is not yet adequately evaluated.[2] It is not recommended for use as an ingredient in topical medications.[2]

Research

Chrysin is under laboratory research for its potential effects on inflammation.[3] It displayed anti-inflammatory and antioxidant activity.[10] In vivo research indicates that orally administered chrysin does not have clinical activity as an aromatase inhibitor.[11][12]

In other laboratory studies, chrysin displayed toxic effects on isolated cancer cells, indicating its potential in anticancer research.[2][13] It also showed antiproliferative effects in vitro.[2][10] There is no evidence for chrysin in clinical applications and its use for compounding of therapeutic agents is not recommended.[2] It has been used in nanoformulations to determine its suitability as an anticancer agent.[14] Nanoformulations of polyphenols including chrysin are made using various of methods that use carriers such as liposomes and nanocapsules.[14]

References

  1. ^ a b Morissette, Marc; Litim, Nadhir; Di Paolo, Thérèse (18 May 2017). "Chapter 2 – Natural Phytoestrogens: A Class of Promising Neuroprotective Agents for Parkinson Disease". In Brahmachari, Goutam (ed.). Discovery and Development of Neuroprotective Agents from Natural Products. Elsevier Science. p. 32. doi:10.1016/B978-0-12-809593-5.00002-1. ISBN 978-0-12-809769-4. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  2. ^ a b c d e f g Brave, Michael (23 June 2016). "Chrysin" (PDF). Pharmacy Compounding Advisory Committee, Division of Oncology Products, US Food and Drug Administration. Retrieved 28 October 2017. {{cite web}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ a b Zeinali M, Rezaee SA, Hosseinzadeh H (2017). "An overview on immunoregulatory and anti-inflammatory properties of chrysin and flavonoids substances". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 92: 998–1009. doi:10.1016/j.biopha.2017.06.003. PMID 28609844.
  4. ^ a b Samarghandian S, Farkhondeh T, Azimi-Nezhad M (2017). "Protective Effects of Chrysin Against Drugs and Toxic Agents". Dose-response : a Publication of International Hormesis Society. 15 (2): 1559325817711782. doi:10.1177/1559325817711782. PMC 5484430. PMID 28694744.
  5. ^ Anandhi R, Annadurai T, Anitha TS, Muralidharan AR, Najmunnisha K, Nachiappan V, Thomas PA, Geraldine P (June 2013). "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". Journal of Physiology and Biochemistry. 69 (2): 313–23. doi:10.1007/s13105-012-0215-6. PMID 23104078.
  6. ^ Istasse T, Jacquet N, Berchem T, Haubruge E, Nguyen BK, Richel A (2016). "Extraction of Honey Polyphenols: Method Development and Evidence of Cis Isomerization". Analytical Chemistry Insights. 11: 49–57. doi:10.4137/ACI.S39739. PMC 4981221. PMID 27547032.
  7. ^ Premratanachai P, Chanchao C (2014). "Review of the anticancer activities of bee products". Asian Pacific Journal of Tropical Biomedicine. 4 (5): 337–44. doi:10.12980/APJTB.4.2014C1262. PMC 3985046. PMID 25182716.
  8. ^ Walle T, Otake Y, Brubaker JA, Walle UK, Halushka PV (February 2001). "Disposition and metabolism of the flavonoid chrysin in normal volunteers". British Journal of Clinical Pharmacology. 51 (2): 143–6. doi:10.1111/j.1365-2125.2001.01317.x. PMC 2014445. PMID 11259985.
  9. ^ Nabavi SF, Braidy N, Habtemariam S, Orhan IE, Daglia M, Manayi A, Gortzi O, Nabavi SM (2015). "Neuroprotective effects of chrysin: From chemistry to medicine". Neurochemistry International. 90: 224–31. doi:10.1016/j.neuint.2015.09.006. PMID 26386393.
  10. ^ a b Jaganathan SK, Mandal M (2009). "Antiproliferative Effects of Honey and of Its Polyphenols: A Review". Journal of Biomedicine & Biotechnology. 2009: 830616. doi:10.1155/2009/830616. PMC 2712839. PMID 19636435.{{cite journal}}: CS1 maint: unflagged free DOI (link) This article incorporates text available under the CC BY 3.0 license.
  11. ^ Saarinen N, Joshi SC, Ahotupa M, Li X, Ammälä J, Mäkelä S, Santti R (September 2001). "No evidence for the in vivo activity of aromatase-inhibiting flavonoids". The Journal of Steroid Biochemistry and Molecular Biology. 78 (3): 231–9. doi:10.1016/S0960-0760(01)00098-X. PMID 11595503.
  12. ^ Brown GA, Vukovich MD, Reifenrath TA, Uhl NL, Parsons KA, Sharp RL, King DS (September 2000). "Effects of anabolic precursors on serum testosterone concentrations and adaptations to resistance training in young men". International Journal of Sport Nutrition and Exercise Metabolism. 10 (3): 340–59. PMID 10997957.
  13. ^ Sak K (2014). "Cytotoxicity of dietary flavonoids on different human cancer types". Pharmacognosy Reviews. 8 (16): 122–46. doi:10.4103/0973-7847.134247. PMC 4127821. PMID 25125885.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  14. ^ a b Davatgaran-Taghipour, Yasamin; Masoomzadeh, Salar; Farzaei, Mohammad Hosein; Bahramsoltani, Roodabeh; Karimi-Soureh, Zahra; Rahimi, Roja; Abdollahi, Mohammad (2017). "Polyphenol nanoformulations for cancer therapy: experimental evidence and clinical perspective". International Journal of Nanomedicine. Volume 12: 2689–2702. doi:10.2147/IJN.S131973. ISSN 1178-2013. PMC 5388197. PMID 28435252. {{cite journal}}: |volume= has extra text (help)CS1 maint: unflagged free DOI (link)

Further reading


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