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Apiin

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Apiin
Apigenin
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.043.421 Edit this at Wikidata
EC Number
  • 247-780-0
KEGG
UNII
  • 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 checkY
    Key: NTDLXWMIWOECHG-YRCFQSNFSA-N checkY
  • 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
C26H28O14
Molar mass 564.496 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley[1] and celery,[2] and in banana leaf.[3] 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.[4] The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.[5]

Biosynthesis

[edit]

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:[6][7]

2D representation of the chemical structure of naringenin chalcone .
naringenin chalcone
Synthase
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of naringenin .
naringenin
Oxidase
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of apigenin .
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:[6][8]

apigenin + UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of apigetrin .
apigetrin


Finally, apigetrin is converted to apiin when a second apiose sugar is added by the enzyme flavone apiosyltransferase:[7]

apigetrin + UDP-apiose
 
 
 
UDP
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of apiin .
apiin


References

[edit]
  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.
  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.
  6. ^ a b 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.
  7. ^ a b 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.