A flavone glycoside with diverse biological activities
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Isomer(s)
33747Kaempferol 3-O-galactoside
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Orientin

Item No. 25143

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(3,4-dihydroxyphenyl)-8-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one
CAS Number
28608-75-5
Molecular Formula
C21H20O11
Formula Weight
448.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
λmax
258, 351 nm
SMILES
OC1=CC(O)=C(C(C=C(C2=CC=C(O)C(O)=C2)O3)=O)C3=C1[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4
InChi Code
InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
InChi Key
PLAPMLGJVGLZOV-VPRICQMDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $68

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    50 mg

    $105

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    100 mg

    $182

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    250 mg

    $387

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    Cayman Chemical
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    Product Description

    Orientin is a flavone glycoside originally isolated from P. orientale that has diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties.1,2,3,4 Orientin scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH; Item No. 14805) radicals with an IC50 value of 316.21 µg/ml.2 It also decreases the cytopathic effects of parainfluenza type 3 virus with an IC50 value of 11.7 µg/ml and a cytotoxic concentration (CC50) value of 375 µg/ml in Hep-2 cells.3 Orientin (5-40 µM) inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs).4 It also prolongs survival in a mouse model of LPS-induced lethal endotoxemia when administered at a dose of 36 µg/animal 12 hours after LPS administration.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Horhammer, L., Wagner, H., and Gloggengiesser, F. A new glycoside type of flavone series. I. Isolation of luteolin & apigenine glycosides from Polygonum orientale. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 291/63(3), 126-137 (1958).

    2. Wu, N., Fu, K., Fu, Y.J., et al. Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves. Molecules 14(3), 1032-1043 (2009).

    3. Li, Y.L., Ma, S.C., Yang, Y.T., et al. Antiviral activities of flavonoids and organic acid from Trollius chinensis Bunge. J. Ethnaopharmacol. 79(3), 365-368 (2002).

    4. Lee, W., Ku, S.K., and Bae, J.S. Vascular barrier protective effects of orientin and isoorientin in LPS-induced inflammation in vitro and in vivo. Vascul. Pharmacol. 62(1), 3-14 (2014).