Apiin

Apiin
	Apigenin
Names
	IUPAC name 4′,5-Dihydroxy-7-[3-C-(hydroxymethyl)-β-D-erythrofuranosyl-(1→2)-β-D-glucopyranosyloxy]flavone
	Systematic IUPAC name 7-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
	Other names Apioside; Apigenin-7-apioglucoside; Apigenin-7-O-apioglucoside
Identifiers
CAS Number	26544-34-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15932 ;
ChEMBL	ChEMBL1535342 ;
ChemSpider	4444321 ;
ECHA InfoCard	100.043.421
EC Number	247-780-0;
KEGG	C04858;
PubChem CID	5280746;
UNII	6QU3EZE37U ;
CompTox Dashboard (EPA)	DTXSID90949393 ;
	InChI InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1 Key: NTDLXWMIWOECHG-YRCFQSNFSA-N ;
	SMILES O=C\4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]1OC[C@](O)(CO)[C@H]1O)cc5O/C(c3ccc(O)cc3)=C/4;
Properties
Chemical formula	C26H28O14
Molar mass	564.496 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley and celery, and in banana leaf. The glycoside moiety at carbon-7 of apigenin, O-β-D-apiofuranosyl(→)2-β-D-glucosyl, is carried by several other flavones in parsley plant and seed. The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.

Biosynthesis

Apiin is a diglycoside 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:

naringenin chalcone

Synthase

naringenin

Oxidase

apigenin

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

apigenin + UDP-glucose

UDP

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

apigetrin

Finally, apigetrin is converted to apiin when a second apiose sugar is added by the enzyme flavone apiosyltransferase:

apigetrin + UDP-apiose

UDP

apiin

References

↑ H. Meyer; A. Bolarinwa; G. Wolfram; J. Linseisen (2006). "Bioavailability of Apigenin from Apiin-Rich Parsley in Humans". Ann Nutr Metab. 50 (3): 167–172. doi:10.1159/000090736. PMID 16407641. S2CID 8223136.
↑ S. R. Gupta (1952). "A study of apiin from the parsley seeds and plant". Proceedings of the Indian Academy of Sciences, Section A. 35 (5). doi:10.1007/BF03172503. S2CID 91953908.
↑ Sayadi, Khali; Akbarzadeh, Fatemeh; Pourmardan, Vahid; Saravani-Aval, Mehdi; Sayadi, Jalis; Chauhan, Narendra Pal Singh; Sargazi, Ghasem (2021). "Methods of green synthesis of Au NCs with emphasis on their morphology: A mini-review". Heliyon. 7 (6) e07250. Cell Press. Bibcode:2021Heliy...707250S. doi:10.1016/j.heliyon.2021.e07250. ISSN 2405-8440. PMC 8220187. PMID 34189304.
↑ "Methods in plant biochemistry". Carbohydrates. Vol. 2. Academic Press. 2 December 2012. p. 245. ISBN 978-0-08-098420-9.
↑ Advances in Carbohydrate Chemistry and Biochemistry. Vol. 31. Academic Press. 5 November 1975. p. 136. ISBN 0-08-056290-6.
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] H. Meyer; A. Bolarinwa; G. Wolfram; J. Linseisen (2006). "Bioavailability of Apigenin from Apiin-Rich Parsley in Humans". Ann Nutr Metab. 50 (3): 167–172. doi:10.1159/000090736. PMID 16407641. S2CID 8223136.

[2] S. R. Gupta (1952). "A study of apiin from the parsley seeds and plant". Proceedings of the Indian Academy of Sciences, Section A. 35 (5). doi:10.1007/BF03172503. S2CID 91953908.

[Sayadi-et-al-2021-3] Sayadi, Khali; Akbarzadeh, Fatemeh; Pourmardan, Vahid; Saravani-Aval, Mehdi; Sayadi, Jalis; Chauhan, Narendra Pal Singh; Sargazi, Ghasem (2021). "Methods of green synthesis of Au NCs with emphasis on their morphology: A mini-review". Heliyon. 7 (6) e07250. Cell Press. Bibcode:2021Heliy...707250S. doi:10.1016/j.heliyon.2021.e07250. ISSN 2405-8440. PMC 8220187. PMID 34189304.

[4] "Methods in plant biochemistry". Carbohydrates. Vol. 2. Academic Press. 2 December 2012. p. 245. ISBN 978-0-08-098420-9.

[5] Advances in Carbohydrate Chemistry and Biochemistry. Vol. 31. Academic Press. 5 November 1975. p. 136. ISBN 0-08-056290-6.

[Ververidis-6] 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-7] 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.

[8] 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.