A flavonoid glycoside with diverse biological activities
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Apiin

Item No. 34596

Technical Information
Formal Name
7-[(2-O-D-apio-β-D-furanosyl-β-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
26544-34-3
Synonyms
  • Apigenin 7-apisoylglucoside
  • Apigenin 7-O-apioglucoside
Molecular Formula
C26H28O14
Formula Weight
Purity
≥98%
A solid
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
269, 338 nm
SMILES
O=C1C2=C(O)C=C(O[C@H]3[C@H](O[C@@]4([H])[C@H](O)[C@](CO)(O)CO4)[C@@H](O)[C@H](O)[C@@H](CO)O3)C=C2OC(C5=CC=C(O)C=C5)=C1
InChi Code
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
InChi Key
NTDLXWMIWOECHG-YRCFQSNFSA-N
Origin
Plant/Apium graveolens
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Apiin is a polyketide synthase-derived flavonoid glycoside that has been found in A. graveolens and has diverse biological activities.1,2,3,4 It inhibits Aurora B kinase in a cell-free assay using the human enzyme (IC50 = 12.14 µM).2 Apiin (10 and 50 µg/ml) inhibits LPS-induced increases in nitric oxide (NO) release and inducible nitric oxide synthase (iNOS) levels in J774.A1 macrophages.3 It scavenges DPPH (Item No. 14805), superoxide, and hydroxyl radicals (IC50s = 68, 390, and 48 µg/ml, respectively), as well as increases the levels of superoxide dismutase (SOD) and catalase in mouse serum, brain, heart, liver, and kidney when administered at a dose of 50 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cheung, V.W.N., Xue, B., Hernandez-Valladares, M., et alIdentification of polyketide inhibitors targeting 3-dehydroquinate dehydratase in the shikimate pathway of Enterococcus faecalis. PLoS One 9(7), e103598 (2014).

    2. Jung, Y., Shin, S.Y., Yong, Y., et alPlant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chem. Biol. Drug Des. 85(5), 574-585 (2015).

    3. Mencherini, T., Cau, A., Bianco, G., et alAn extract of Apium graveolens var. dulce leaves: Structure of the major constituent, apiin, and its anti-inflammatory properties. J. Pharm. Pharmacol. 59(6), 891-897 (2007).

    4. Li, P., Jia, J., Zhang, D., et alIn vitro and in vivo antioxidant activities of a flavonoid isolated from celery (Apium graveolens L. var. dulce). Food Funct. 5(1), 50-56 (2014).