Daphnetin

Daphnetin
	source ↗
Names
	IUPAC name 7,8-Dihydroxy-2H-chromen-2-one
	Other names 7,8-Dihydroxycoumarin
Identifiers
CAS Number	486-35-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17313;
ChEMBL	ChEMBL244948;
ChemSpider	4444191;
ECHA InfoCard	100.006.939
EC Number	207-632-8;
KEGG	C03093;
PubChem CID	5280569;
UNII	XC84571RD2;
CompTox Dashboard (EPA)	DTXSID00197560 ;
	InChI InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H Key: ATEFPOUAMCWAQS-UHFFFAOYSA-N;
	SMILES C1=CC(=C(C2=C1C=CC(=O)O2)O)O;
Properties
Chemical formula	C9H6O4
Molar mass	178.143 g·mol−1
Melting point	256 °C (493 °F; 529 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Daphnetin is a chemical compound with the molecular formula C₉H₆O₄. It has been isolated from plants of the genus Daphne.²³ It has also been found in Matricaria chamomilla (chamomile).⁴

It a crystalline solid with a melting point of 256 °C.¹ It is soluble in boiling water.¹

Daphnetin can undergo enzymatic glycosylation to yield its 7-O-glucoside which is called daphnin (daphnetin 7-β-D-glucopyranoside). The reaction is catalyzed by the enzyme O-dihydroxycoumarin 7-O-glucosyltransferase. The glucose unit is transferred from UDP-glucose, with uridine diphosphate (UDP) as byproduct.⁵⁶

daphnetin

+ UDP-glucose

UDP

Rightward reaction arrow with minor product(s) to top right

daphnin

Daphnetin shows several neuroprotective and anti-inflammatory effects on the inhibition of the TLR4/NF-κB mediated inflammatory signaling pathway. They also could inhibit the IKKs/IkBa/NF-κB, AKT, and the Src/FAK/ERK1/2 multi-target medication signaling pathway for anti-angiogenesis and cancer.⁷

Daphnetin has been reported to be a strong sensitizer, which means that this compound and its glycosidic derivatives (e.g. daphnin) can be a cause of allergic reactions.⁴

References

Merck Index (11th ed.). p. 2818. 2816. Daphnetin.
Ueno, K.; Saito, N. (1976). "Daphnetin, isolated from Daphne odora". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 32 (3): 946–948. Bibcode:1976AcCrB..32..946U. doi:10.1107/S0567740876004275.
Brown, Stewart A. (1986). "Biosynthesis of Daphnetin in Daphne mezereum L". Zeitschrift für Naturforschung C. 41 (3): 247–252. doi:10.1515/znc-1986-0301.
Petruľová-Poracká, Veronika; Repčák, Miroslav; Vilková, Mária; Imrich, Ján (2013-11-01). "Coumarins of Matricaria chamomilla L.: Aglycones and glycosides". Food Chemistry. 141 (1): 54–59. doi:10.1016/j.foodchem.2013.03.004. ISSN 0308-8146. PMID 23768326.
Ibrahim, Ragai K.; Boulay, Bernard (1980-05-01). "Purification and some properties of UDP-glucose:o-dihydroxycoumarin7-O-glucosyltransferase from tobacco cell cultures". Plant Science Letters. 18 (2): 177–184. doi:10.1016/0304-4211(80)90048-6. ISSN 0304-4211.
Ueno, Katsuhiko; Sato, Mitsuhiko; Saito, Norio (1983-06-01). "The Crystal and Molecular Structure of Daphnin Dihydrate: 7-(β-D-Glucopyranosyloxy)-8-hydroxycoumarin Dihydrate". Bulletin of the Chemical Society of Japan. 56 (6): 1577–1580. doi:10.1246/bcsj.56.1577. ISSN 0009-2673.
Liu, Jia; Chen, Qianxue; Jian, Zhihong; Xiong, Xiaoxing; Shao, Lingmin; Jin, Tong; Zhu, Xiqun; Wang, Lei (2016-12-29). "Daphnetin Protects against Cerebral Ischemia/Reperfusion Injury in Mice via Inhibition of TLR4/NF-κB Signaling Pathway". BioMed Research International. 2016 e2816056. doi:10.1155/2016/2816056. ISSN 2314-6133. PMC 5227117. PMID 28119924.

[Merck-1] Merck Index (11th ed.). p. 2818. 2816. Daphnetin.

[2] Ueno, K.; Saito, N. (1976). "Daphnetin, isolated from Daphne odora". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 32 (3): 946–948. Bibcode:1976AcCrB..32..946U. doi:10.1107/S0567740876004275.

[3] Brown, Stewart A. (1986). "Biosynthesis of Daphnetin in Daphne mezereum L". Zeitschrift für Naturforschung C. 41 (3): 247–252. doi:10.1515/znc-1986-0301.

[:0-4] Petruľová-Poracká, Veronika; Repčák, Miroslav; Vilková, Mária; Imrich, Ján (2013-11-01). "Coumarins of Matricaria chamomilla L.: Aglycones and glycosides". Food Chemistry. 141 (1): 54–59. doi:10.1016/j.foodchem.2013.03.004. ISSN 0308-8146. PMID 23768326.

[5] Ibrahim, Ragai K.; Boulay, Bernard (1980-05-01). "Purification and some properties of UDP-glucose:o-dihydroxycoumarin7-O-glucosyltransferase from tobacco cell cultures". Plant Science Letters. 18 (2): 177–184. doi:10.1016/0304-4211(80)90048-6. ISSN 0304-4211.

[6] Ueno, Katsuhiko; Sato, Mitsuhiko; Saito, Norio (1983-06-01). "The Crystal and Molecular Structure of Daphnin Dihydrate: 7-(β-D-Glucopyranosyloxy)-8-hydroxycoumarin Dihydrate". Bulletin of the Chemical Society of Japan. 56 (6): 1577–1580. doi:10.1246/bcsj.56.1577. ISSN 0009-2673.

[7] Liu, Jia; Chen, Qianxue; Jian, Zhihong; Xiong, Xiaoxing; Shao, Lingmin; Jin, Tong; Zhu, Xiqun; Wang, Lei (2016-12-29). "Daphnetin Protects against Cerebral Ischemia/Reperfusion Injury in Mice via Inhibition of TLR4/NF-κB Signaling Pathway". BioMed Research International. 2016 e2816056. doi:10.1155/2016/2816056. ISSN 2314-6133. PMC 5227117. PMID 28119924.

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