Robinetin

Type of a flavone
Robinetin
Names
IUPAC name
3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Other names
Norkanugin; 5-Hydroxyfisetin
Identifiers
CAS Number
  • 490-31-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:8876
ChEMBL
  • ChEMBL170405
ChemSpider
  • 4445009
ECHA InfoCard 100.007.009 Edit this at Wikidata
EC Number
  • 207-709-6
KEGG
  • C10177
PubChem CID
  • 5281692
UNII
  • KJ6DBC4U7E
CompTox Dashboard (EPA)
  • DTXSID30197654 Edit this at Wikidata
InChI
  • InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H
    Key: SOEDEYVDCDYMMH-UHFFFAOYSA-N
  • C1=CC2=C(C=C1O)OC(=C(C2=O)O)C3=CC(=C(C(=C3)O)O)O
Properties
Chemical formula
 C15H10O7
Molar mass 302.238 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Robinetin is an organic compound which belongs to flavones and has the molecular formula C15H10O7.

Chemically, robinetin is a pentahydroxyflavone that is a flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'. Its name originates from the botanical name of the genus, Robinia sp.

Natural role

It has a role as a plant metabolite and is a pentahydroxyflavone and a 7-hydroxyflavonol.[1] Robinetin is one of the basic chemical extracts of the species black locust, Robinia pseudoacacia and its wood, imparting a high biological resistance against several pathogens (fungi, insects).[2]

As flavonoid, robinetin has also been isolated from the heartwood of the African species, Millettia stuhlmannii.[3]

In plant systems, robinetin as flavonoids in general, help in combating oxidative stress and act as growth regulators.

Research

Recent research has focused on the health aspects of flavonoids for humans, particularly that of robinetin. It has been shown to possess a certain antioxidative activity, free radical scavenging capacity, coronary heart disease prevention, hepatoprotective, anti-inflammatory, and anticancer activities.[4]

Robinetin also can inhibit lipid peroxidation and protein glycosylation.

References

  1. ^ "Robinetin". PubChem. Retrieved 2024-08-30.
  2. ^ "Springer Handbook of Wood Science and Technology (Chapter 3. Wood Biology)". Springer Handbooks. Cham: Springer International Publishing. 2023. p. 107. doi:10.1007/978-3-030-81315-4. ISBN 978-3-030-81314-7. ISSN 2522-8692. S2CID 257902863.
  3. ^ ILDIS, International Legume Database and Information Service; CHCD, Chapman & Hall Chemical Database (1994). F.A. Bisby; J. Buckingham; J.B. Harborne (eds.). Phytochemical dictionary of the Leguminosae. compiler, I.W. Southon; chemical data, Chapman & Hall Chemical Database; phytochemical database, R.J. White; botanical data, J.L. Zarucchi (1st ed.). London: Chapman & Hall. ISBN 0412397706.
  4. ^ Kumar, Shashank; Pandey, Abhay K. (2013). "Chemistry and Biological Activities of Flavonoids: An Overview". The Scientific World Journal. 2013 (1). doi:10.1155/2013/162750. ISSN 2356-6140. PMC 3891543. PMID 24470791.
  • v
  • t
  • e
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
  • Hypolaetin 8-glucoside
  • Hypolaetin 8-glucuronide
of luteolin
Acetylated
  • Artocarpetin A
  • Artoindonesianin P
    • Sulfated glycosidesPolymersDrugs