Chebulagic acid

Chebulagic acid is a benzopyran tannin and an antioxidant that has many potential uses in medicine.

Chebulagic acid
Identifiers
3D model (JSmol)
ChEMBL
PubChem CID
UNII
  • 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
    Key: HGJXAVROWQLCTP-YABCKIEDSA-N
SMILES
  • C1C2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7C8=C(C(=C(C=C8C(=O)O1)O)O)O)O)O)O
Properties
C41H30O27
Molar mass 954.66 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It has been found to be immunosuppressive, hepatoprotective, and a potent alpha-glucosidase inhibitor, a human gut enzyme useful in diabetic studies.

It has been shown to be active against Staphylococcus aureus and Candida albicans.

It is found in the plants Terminalia chebula, T. citrina and T. catappa.

It is formed from geraniin through a glutathione-mediated conversion.

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