Chebulagic acid explained

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]

Notes and References

1. HAMADA. Shin-ichi. KATAOKA. Takao. WOO. Je-Tae. YAMADA. Atsushi. YOSHIDA. Takashi. NISHIMURA. Toshio. OTAKE. Noboru. NAGAI. Kazuo. Immunosuppressive Effects of Gallic Acid and Chebulagic Acid on CTL-Mediated Cytotoxicity.. Biological & Pharmaceutical Bulletin. 1997. 20. 9. 1017–1019. 10.1248/bpb.20.1017. 9331989. free.
2. Kinoshita. S.. Inoue. Y.. Nakama. S.. Ichiba. T.. Aniya. Y.. Antioxidant and hepatoprotective actions of medicinal herb, Terminalia catappa L. from Okinawa Island and its tannin corilagin. Phytomedicine. November 2007. 14. 11. 755–762. 10.1016/j.phymed.2006.12.012. 17293097.
3. 22512724 . 10.3109/14756366.2011.603130 . 27 . 4 . Inhibitory effect of Terminalia chebula Retz. fruit extracts on digestive enzyme related to diabetes and oxidative stress . 2012 . J Enzyme Inhib Med Chem . 578–86 . Sasidharan . I . Sundaresan . A . Nisha . VM . Kirishna . MS . Raghu . KG . Jayamurthy . P. free .
4. 24635511 . 10.3109/13880209.2014.880486 . 52 . 9 . α-Glucosidase inhibition, 15-lipoxygenase inhibition, and brine shrimp toxicity of extracts and isolated compounds from Terminalia macroptera leaves . 2014 . Pharm Biol . 1166–9 . Pham . AT . Malterud . KE . Paulsen . BS . Diallo . D . Wangensteen . H. 10233899 . free .
5. Web site: Medicinal Plants of Myanmar . 2008-10-25 . dead . https://web.archive.org/web/20081206115257/http://www.tuninst.net/MyanMedPlants/TIL/famC/Combretaceae.htm#Terminalia-citrina . 2008-12-06 .
6. https://archive.today/20120909153035/http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TCR-4HCDJS0-2&_user=4296857&_rdoc=1&_fmt=&_orig=search&_sort=d&_docanchor=&view=c&_acct=C000012518&_version=1&_urlVersion=0&_userid=4296857&md5=ba49ce34c6a6ef6943e0f1befed82776 Chemopreventive effect of punicalagin, a novel tannin component isolated from Terminalia catappa, on H-ras-transformed NIH3T3 cells.
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,