Chebulinic Acid

Cas：18942-26-2

Product Information：

Chebulinic acid is a potent natural inhibitor of M. tuberculosis DNA gyrase, also can inhibit SMAD-3 phosphorylation, inhibit H+ K+-ATPase activity.

Chemical Formula: C41H32O27

Exact Mass: 956.1131

Molecular Weight: 956.68

Elemental Analysis: C, 51.47; H, 3.37; O, 45.15

Chemical Name: 2-((3S,3aS,4S,7R,8R,10S,11R,17S)-3,15,16-Trihydroxy-2,5,13-trioxo-10,17-bis((3,4,5-trihydroxybenzoyl)oxy)-8-(((3,4,5-trihydroxybenzoyl)oxy)methyl)-2,3,3a,4,5,7,8,10,11,13-decahydro-7,11-methano[1,4,7]trioxacyclotridecino[11,10,9-de]chromen-4-yl)acetic acid

InChi Key:

YGVHOSGNOYKRIH-FJPMMHPYSA-N

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

Smiles Code:

O=C(O)C[C@@H]([C@](C1=C(O2)C(O)=C(O)C=C1C3=O)([H])[C@H](O)C2=O)C(O[C@]([C@@H]4OC(C5=CC(O)=C(O)C(O)=C5)=O)([H])[C@@H](COC(C6=CC(O)=C(O)C(O)=C6)=O)O[C@@H](OC(C7=CC(O)=C(O)C(O)=C7)=O)[C@]4([H])O3)=O

Technical Data：

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

In Vitro：

In vitro: binding of Chebulinic acid causes displacement of catalytic Tyr129 away from its target DNA-phosphate molecule. Chebulinic acid reduce the expression and activity of MMP-2 at an ED50 value of 100 μM. EMT (Epithelial to Mesenchymal Transition) is found to be induced in ARPE-19 cells, through SMAD-3 phosphorylation and it is inhibited by CA. chebulinic acid significantly inhibited H+ K+-ATPase activity in vitrowith IC50 of 65.01 μg/ml.

References：

1: Song JH, Shin MS, Hwang GS, Oh ST, Hwang JJ, Kang KS. Chebulinic acid attenuates glutamate-induced HT22 cell death by inhibiting oxidative stress, calcium influx and MAPKs phosphorylation. Bioorg Med Chem Lett. 2017 Dec 29. pii: S0960-894X(17)31236-2. doi: 10.1016/j.bmcl.2017.12.062. [Epub ahead of print] PubMed PMID: 29317168.

2: Lopez HL, Habowski SM, Sandrock JE, Raub B, Kedia A, Bruno EJ, Ziegenfuss TN. Effects of dietary supplementation with a standardized aqueous extract of Terminalia chebula fruit (AyuFlex(®)) on joint mobility, comfort, and functional capacity in healthy overweight subjects: a randomized placebo-controlled clinical trial. BMC Complement Altern Med. 2017 Oct 2;17(1):475. doi: 10.1186/s12906-017-1977-8. PubMed PMID: 28969626; PubMed Central PMCID: PMC5625793.

3: Song IS, Jeong YJ, Park JH, Shim S, Jang SW. Chebulinic acid inhibits smooth muscle cell migration by suppressing PDGF-Rβ phosphorylation and inhibiting matrix metalloproteinase-2 expression. Sci Rep. 2017 Sep 18;7(1):11797. doi: 10.1038/s41598-017-12221-w. PubMed PMID: 28924208; PubMed Central PMCID: PMC5603554.

4: Chhabra S, Mishra T, Kumar Y, Thacker G, Kanojiya S, Chattopadhyay N, Narender T, Trivedi AK. Chebulinic Acid Isolated From the Fruits of Terminalia chebula Specifically Induces Apoptosis in Acute Myeloid Leukemia Cells. Phytother Res. 2017 Dec;31(12):1849-1857. doi: 10.1002/ptr.5927. Epub 2017 Sep 18. PubMed PMID: 28921713.

5: Vu TT, Kim H, Tran VK, Vu HD, Hoang TX, Han JW, Choi YH, Jang KS, Choi GJ, Kim JC. Antibacterial activity of tannins isolated from Sapium baccatum extract and use for control of tomato bacterial wilt. PLoS One. 2017 Jul 25;12(7):e0181499. doi: 10.1371/journal.pone.0181499. eCollection 2017. PubMed PMID: 28742863; PubMed Central PMCID: PMC5526539.

Products are for research use only. Not for human use.