Chebulagic acid

Chebulagic acid
Identifiers
CAS Number	23094-71-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL525240 ;
PubChem CID	12400;
UNII	JW8L3F5IW9 ;
	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/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
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 [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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

It has been found to be immunosuppressive,[1] hepatoprotective,[2] and a potent alpha-glucosidase inhibitor,[3][4] a human gut enzyme useful in diabetic studies.

It has been shown to be active against Staphylococcus aureus and Candida albicans.[5]

It is found in the plants Terminalia chebula, T. citrina and T. catappa.[6]

It is formed from geraniin through a glutathione-mediated conversion.[7]

References

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.
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.
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.
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.
"Archived copy". Archived from the original on 2008-12-06. Retrieved 2008-10-25.CS1 maint: archived copy as title (link)
Chemopreventive effect of punicalagin, a novel tannin component isolated from Terminalia catappa, on H-ras-transformed NIH3T3 cells. Pin-Shern Chen and Jih-Heng Li, Toxicology Letters, Volume 163, Issue 1, 5 May 2006, Pages 44-53
Glutathione-mediated conversion of the ellagitannin geraniin into chebulagic acid. Tanaka T, Kouno I and Nonaka G.I, Chemical and pharmaceutical bulletin, 1996, volume 44, no 1, pages 34-40, INIST:3003361

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[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.

[5] "Archived copy". Archived from the original on 2008-12-06. Retrieved 2008-10-25.CS1 maint: archived copy as title (link)

[6] Chemopreventive effect of punicalagin, a novel tannin component isolated from Terminalia catappa, on H-ras-transformed NIH3T3 cells. Pin-Shern Chen and Jih-Heng Li, Toxicology Letters, Volume 163, Issue 1, 5 May 2006, Pages 44-53

[7] Glutathione-mediated conversion of the ellagitannin geraniin into chebulagic acid. Tanaka T, Kouno I and Nonaka G.I, Chemical and pharmaceutical bulletin, 1996, volume 44, no 1, pages 34-40, INIST:3003361