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Chebulagic acid

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Chebulagic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • 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/s1Key: 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
Chemical formula C41H30O27
Molar mass 954.66 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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.

References

  1. HAMADA, Shin-ichi; KATAOKA, Takao; WOO, Je-Tae; YAMADA, Atsushi; YOSHIDA, Takashi; NISHIMURA, Toshio; OTAKE, Noboru; NAGAI, Kazuo (1997). "Immunosuppressive Effects of Gallic Acid and Chebulagic Acid on CTL-Mediated Cytotoxicity". Biological & Pharmaceutical Bulletin. 20 (9): 1017–1019. doi:10.1248/bpb.20.1017. PMID 9331989.
  2. Kinoshita, S.; Inoue, Y.; Nakama, S.; Ichiba, T.; Aniya, Y. (November 2007). "Antioxidant and hepatoprotective actions of medicinal herb, Terminalia catappa L. from Okinawa Island and its tannin corilagin". Phytomedicine. 14 (11): 755–762. doi:10.1016/j.phymed.2006.12.012. PMID 17293097.
  3. Sasidharan, I; Sundaresan, A; Nisha, VM; Kirishna, MS; Raghu, KG; Jayamurthy, P (2012). "Inhibitory effect of Terminalia chebula Retz. fruit extracts on digestive enzyme related to diabetes and oxidative stress". J Enzyme Inhib Med Chem. 27 (4): 578–86. doi:10.3109/14756366.2011.603130. PMID 22512724.
  4. Pham, AT; Malterud, KE; Paulsen, BS; Diallo, D; Wangensteen, H (2014). "α-Glucosidase inhibition, 15-lipoxygenase inhibition, and brine shrimp toxicity of extracts and isolated compounds from Terminalia macroptera leaves". Pharm Biol. 52 (9): 1166–9. doi:10.3109/13880209.2014.880486. PMID 24635511. S2CID 10233899.
  5. "Medicinal Plants of Myanmar". Archived from the original on 2008-12-06. Retrieved 2008-10-25.
  6. Chen, Pin-Shern; Li, Jih-Heng (5 May 2006). "Chemopreventive effect of punicalagin, a novel tannin component isolated from Terminalia catappa, on H-ras-transformed NIH3T3 cells". Toxicology Letters. 163 (1): 44–53. doi:10.1016/j.toxlet.2005.09.026. PMID 16242868.
  7. Tanaka, Takashi; Kouno, Isao; Nonaka, Gen-Ichiro (1996). "Glutathione-Mediated Conversion of the Ellagitannin Geraniin into Chebulagic Acid". Chemical and Pharmaceutical Bulletin. 44: 34–40. doi:10.1248/cpb.44.34. INIST 3003361.
Types of ellagitannins
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A, B, C and D
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other


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