Apigetrin

Apigetrin
Names
	IUPAC name 7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyflavone
	Systematic IUPAC name 5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
	Other names Apigetrin; Cosmosiine; Cosmetin; Cosmosiin; Cosmosioside; Thalictiin; Cosmosin; Apigenin 7-glucoside; Apigenin 7-O-glucoside
Identifiers
CAS Number	578-74-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16778 ;
ChEMBL	ChEMBL487017 ;
ChemSpider	4444290 ;
ECHA InfoCard	100.008.574
KEGG	C04608 ;
PubChem CID	5280704;
UNII	7OF2S66PCH ;
CompTox Dashboard (EPA)	DTXSID401028774 ;
	InChI InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1 Key: KMOUJOKENFFTPU-QNDFHXLGSA-N ; InChI=1/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1;
	SMILES O=C\3c4c(O)cc(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)cc4O/C(c2ccc(O)cc2)=C/3;
Properties
Chemical formula	C21H20O10
Molar mass	432.381 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

Apigetrin is a chemical compound that can be found in dandelion coffee and in Teucrium gnaphalodes.^[1]

Biosynthesis and metabolism

Apigetrin is a glycoside of the flavone, apigenin. Its biosynthesis in plants involves a sequence of enzymes, with chalcone synthase being the one that forms the ring system of the natural product naringenin. Naringenin is then oxidised to apigenin:^[2]^[3]

naringenin chalcone

Synthase

naringenin

Oxidase

apigenin

Next, the enzyme flavone 7-O-beta-glucosyltransferase transfers the glucose sugar fragment from UDP-glucose, giving apigetrin, with uridine diphosphate (UDP) as byproduct:^[2]^[4]

apigenin + UDP-glucose

UDP

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

apigetrin

Apigetrin is further metabolised to apiin when a second apiose sugar is added by the enzyme flavone apiosyltransferase:^[3]

apigetrin + UDP-apiose

UDP

apiin

References

↑ Barberán, F. A. T.; Gil, M. I.; Tomás, F.; Ferreres, F.; Arques, A. (1985). "Flavonoid Aglycones and Glycosides from Teucrium gnaphalodes". Journal of Natural Products. 48 (5): 859. doi:10.1021/np50041a040.
1 2 Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal. 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
1 2 Hădărugă, Daniel-Ioan; Hădărugă, Nicoleta-Gabriela (2023). "Flavones: Structure, Properties, Sources and Food Applications". Handbook of Food Bioactive Ingredients. pp. 111–158. doi:10.1007/978-3-031-28109-9_4. ISBN 978-3-031-28108-2.
↑ Sutter, Arne; Ortmann, Rainer; Grisebach, Hans (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the transfer of d-glucose from UDP-d-glucose to flavonoids". Biochimica et Biophysica Acta (BBA) - Enzymology. 258 (1): 71–87. doi:10.1016/0005-2744(72)90967-9. PMID 5058406.

[1] Barberán, F. A. T.; Gil, M. I.; Tomás, F.; Ferreres, F.; Arques, A. (1985). "Flavonoid Aglycones and Glycosides from Teucrium gnaphalodes". Journal of Natural Products. 48 (5): 859. doi:10.1021/np50041a040.

[Ververidis-2] 1 2 Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal. 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.

[Handbook-3] 1 2 Hădărugă, Daniel-Ioan; Hădărugă, Nicoleta-Gabriela (2023). "Flavones: Structure, Properties, Sources and Food Applications". Handbook of Food Bioactive Ingredients. pp. 111–158. doi:10.1007/978-3-031-28109-9_4. ISBN 978-3-031-28108-2.

[4] Sutter, Arne; Ortmann, Rainer; Grisebach, Hans (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the transfer of d-glucose from UDP-d-glucose to flavonoids". Biochimica et Biophysica Acta (BBA) - Enzymology. 258 (1): 71–87. doi:10.1016/0005-2744(72)90967-9. PMID 5058406.

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[2]

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Biosynthesis and metabolism

References