Apiin

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]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.043.421
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).
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Infobox references

See also

References
  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. Cell Press. 7 (6): e07250. doi:10.1016/j.heliyon.2021.e07250. ISSN 2405-8440. PMC 8220187. PMID 34189304.
  4. page 245 "Methods in plant biochemistry" volume 2: "Carbohydrates", ISBN 0080984207
  5. page 136 "Advances in Carbohydrate Chemistry and Biochemistry", Volume 31, ISBN 0080562906



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