A polyphenol with diverse biological activities
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Chebulagic Acid

Item No. 25203

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
β-D-glucopyranose, cyclic 3,6-[(1R)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate] 1-(3,4,5-trihydroxybenzoate), cyclic 2→2:4→1-ester with (2S)-2-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioic acid
CAS Number
23094-71-5
Molecular Formula
C41H30O27
Formula Weight
954.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 m/gmlDMSO: 20 m/gmlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/mlEthanol: 5 mg/ml
λmax
226, 278 nm
SMILES
O=C([C@H]([C@]1([H])[C@H](O)C(OC2=C1C3=CC(O)=C2O)=O)CC(O)=O)O[C@@H]4[C@@H](COC5=O)O[C@@H](OC(C6=CC(O)=C(O)C(O)=C6)=O)[C@H](OC3=O)[C@H]4OC(C7=CC(O)=C(O)C(O)=C7C8=C(O)C(O)=C(O)C=C85)=O
InChi Code
InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)/t12-,18+,22-,30-,31+,33-,34+,41-/m0/s1
InChi Key
HGJXAVROWQLCTP-YABCKIEDSA-N
Origin
Plant/Chebulae Fructus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $129

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    5 mg

    $510

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    10 mg

    $953

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    Product Description

    Chebulagic acid is a polyphenol and tannin that has been found in T. chebula and has diverse biological activities.1,2,3,4,5 It is an inhibitor of COX-1, COX-2, and 5-lipoxygenase (5-LO; IC50s = 15, 0.92, and 2.1 μM, respectively) as well as α-glucosidase and 15-LO (IC50s = 0.05 and 24.9 μM, respectively).1,2 Chebulagic acid inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS), COX-1, COX-2, and 5-LO protein levels, production of NO, prostaglandin E2 (PGE2), and reactive oxygen species (ROS), and nuclear translocation of NF-κB in RAW 264.7 macrophages in a concentration-dependent manner.3 It inhibits the growth of HCT15, COLO 205, MDA-MB-231, DU145, and K562 cancer cells (GI50s = 20.3, 18, 26.2, 28.54, and 30.66 μM, respectively).1 Chebulagic acid increases insulin-stimulated glucose uptake in 3T3-L1 adipocytes by 10.2-, 13.8-, and 16.6-fold when used at concentrations of 10, 50, and 100 μM, respectively.4 It also scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 1.4 μM) and exhibits antiviral activity against cytomegalovirus, hepatitis C virus, dengue virus, measles virus, and respiratory syncytial virus in vitro (EC50s = 25.5, 12.16, 13.11, 34.42, and 0.38 μM, respectively).1,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Reddy, D.B., Reddy, T.C., Jyotsna, G., et al. Chebulagic acid, a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula retz., induces apoptosis in COLO-205 cell line. J. Ethnopharmacol. 124(3), 506-512 (2009).

    2. Pham, A.T., Malterud, K.E., Paulsen, B.S., et al. α-Glucosidase inhibition, 15-lipoxygenase inhibition, and brine shrimp toxicity of extracts and isolated compounds from Terminalia macroptera leaves. Pharm. Biol. 52(9), 1166-1169 (2014).

    3. Reddy, D.B., and Reddanna, P. Chebulagic acid (CA) attenuates LPS-induced inflammation by suppressing NF-κB and MAPK activation in RAW 264.7 macrophages. Biochem. Biophys. Res. Commun. 381(1), 112-117 (2009).

    4. Shyni, G.L., Kavitha, S., Indu, S., et al. Chebulagic acid from Terminalia chebula enhances insulin mediated glucose uptake in 3T3-L1 adipocytes via PPARγ signaling pathway. Biofactors 40(6), 646-657 (2014).

    5. Lin, L.T., Chen, T.Y., Lin, S.C., et al. Broad-spectrum antiviral activity of chebulagic acid and punicalagin against viruses that use glycosaminoglycans for entry. BMC Microbiol. 13, 187 (2013).