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Apiin - Wikipedia

From Wikipedia, the free encyclopedia

Apiin
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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15932^Y
ChEMBL	ChEMBL1535342^N
ChemSpider	4444321^Y
ECHA InfoCard	100.043.421
EC Number	247-780-0
KEGG	C04858
PubChem CID	5280746
UNII	6QU3EZE37U^Y
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^Y Key: NTDLXWMIWOECHG-YRCFQSNFSA-N^Y
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). N verify (what is ^YN ?) Infobox references

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]

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). Cell Press: e07250. 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 978-0080984209.
^ Advances in Carbohydrate Chemistry and Biochemistry. Vol. 31. Academic Press. 5 November 1975. p. 136. ISBN 0080562906.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide