Chemistry:Daphnetin
Daphnetin is a chemical compound with the molecular formula C
9H
6O
4. It has been isolated from plants of the genus Daphne.[1][2] It has also been found in Matricaria chamomilla (chamomile).[3]
It a crystalline solid with a melting point of 256 °C.[4] It is soluble in boiling water.[4]
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-dihydroxy coumarin 7-O-glucosyltransferase.[5][6]
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.[3]
References
- ↑ Ueno, K.; Saito, N. (1976). "Daphnetin, isolated from Daphne odora". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 32 (3): 946–948. doi:10.1107/S0567740876004275. Bibcode: 1976AcCrB..32..946U.
- ↑ 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.
- ↑ 3.0 3.1 Petruľová-Poracká, Veronika; Repčák, Miroslav; Vilková, Mária; Imrich, Ján (2013-11-01). "Coumarins of Matricaria chamomilla L.: Aglycones and glycosides" (in en). Food Chemistry 141 (1): 54–59. doi:10.1016/j.foodchem.2013.03.004. ISSN 0308-8146. PMID 23768326. https://www.sciencedirect.com/science/article/pii/S0308814613003051.
- ↑ 4.0 4.1 Cite error: Invalid
<ref>tag; no text was provided for refs namedMerck - ↑ Ibrahim, Ragai K.; Boulay, Bernard (1980-05-01). "Purification and some properties of UDP-glucose:o-dihydroxycoumarin7-O-glucosyltransferase from tobacco cell cultures" (in en). 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" (in en). BioMed Research International 2016. doi:10.1155/2016/2816056. ISSN 2314-6133. PMID 28119924.
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