An ellagitannin with diverse biological activities
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Chebulinic Acid

Item No. 32554

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,6-tris(3,4,5-trihydroxybenzoate) cyclic 2→2:4→1-ester with (2S)-[(3R,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioic acid, β-D-glucopyranose
CAS Number
18942-26-2
Synonyms
  • Eutannin
  • NSC 69862
Molecular Formula
C41H32O27
Formula Weight
956.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: soluble
λmax
222, 283 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](COC(C5=CC(O)=C(O)C(O)=C5)=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)=C7)=O
InChi Code
InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30+,31+,33+,34+,41-/m0/s1
InChi Key
YGVHOSGNOYKRIH-IFPULTQJSA-N
Origin
Plant/Fructus Chebulae
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Chebulinic acid is an ellagitannin that has been found in T. chebula and has diverse biological activities.1,2,3,4,5 It is an inhibitor of protein tyrosine phosphatase non-receptor 9 (PTPN9) and PTPN11 (IC50s = 34 and 37 nM, respectively).2 Chebulinic acid (5 µM) increases glucose uptake in 3T3-L1 preadipocytes. It induces apoptosis of HL-60 and NB4 acute promyelocytic leukemia (APL), but not K562 chronic myelogenous leukemia (CML), cells (IC50s = 7.5, 5, and >60 µM, respectively).1 Chebulinic acid (25 µM) reduces the production of reactive oxygen species (ROS) induced by glyceraldehyde-related advanced glycation end products (glycer-AGEs) in human umbilical vein endothelial cells (HUVECs) and reduces glutamate-induced ROS production and cell death in HT22 mouse hippocampal cells.3,4 It inhibits H+/K+-ATPase activity (IC50 = 65.01 µg/ml) and reduces free and total gastric acidity, as well as increases gastric mucin secretion, in various rat models of gastric ulcer.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chhabra, S., Mishra, T., Kumar, Y., et al. Chebulinic acid isolated from the fruits of Terminalia chebula specifically induces apoptosis in acute myeloid leukemia cells. Phytother. Res. 31(12), 1849-1857 (2017).

    2. Yoon, S.-Y., Kang, H.J., Ahn, D., et al. Identification of chebulinic acid as a dual targeting inhibitor of protein tyrosine phosphatases relevant to insulin resistance. Bioorg. Chem. 90, 103087 (2019).

    3. Lee, H.-S., Koo, Y.-C., Suh, H.J., et al. Preventive effects of chebulic acid isolated from Terminalia chebula on advanced glycation endproduct-induced endothelial cell dysfunction. J. Ethnopharmacol. 131(3), 567-574 (2010).

    4. Song, J.H., Shin, M.-S., Hwang, G.S., et al. Chebulinic acid attenuates glutamate-induced HT22 cell death by inhibiting oxidative stress, calcium influx and MAPKs phosphorylation. Bioorg. Med. Chem. Lett. 28(3), 249-253 (2018).

    5. Mishra, V., Agrawal, M., Onasanwo, S.A., et al. Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Phytomedicine 20(6), 506-511 (2013).