Chebulagic acid
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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). ![]() ![]() ![]() 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,[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. S2CID 10233899.
- ^ "Medicinal Plants of Myanmar". Archived from the original on 2008-12-06. Retrieved 2008-10-25.
- ^ 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.
- ^ 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.
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Types of ellagitannins
- Diphenolic acid : Hexahydroxydiphenic acid (HHDP)
- Triphenolic acids : Nonahydroxytriphenic acid
- Sanguisorbic acid
- Valoneic acid
- Tetraphenolic acids : Isoterchebulic acid
- Terchebulinic acid
- Ellagic acid
- Gallagic acid
- Gallagic acid dilactone
- Luteic acid
- Sanguisorbic acid dilactone
- Valoneic acid dilactone
- Acetonyl geraniin
- Alnusiin
- Bicornin
- Carlesiin
- Casuarictin
- Emblicanin A and B
- Euscaphinin
- Galloyl pedunculagin
- Grandinin
- Helioscopinin B
- Jolkinin
- Lagerstannin A, B and C
- Macranganin
- Myrobalanitannin
- Nupharin A, B, C, D, E and F
- Pedunculagin
- Punicalagin
- Punigluconin
- Phyllanemblinin A, B, C, D, E and F
- Punicalin
- Roburin E
- Rugosin E
- Sanguiin H-5
- Stenophyllanin A, B and C
- Strictinin
- Tellimagrandin I and II
- Teracatain
- Terchebulin
- Terflavin A and B
- Tergallic acid
- Tergallic acid dilactone
C-glycosidic ellagitannins |
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Dehydroellagitannins (molecules with dehydrohexahydroxydiphenic acid (DHHDP) |
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Transformed ellagitannins |
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- 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
- Flavono-ellagitannins (hybrid type)
- Urolithins (metabolites)
- Pomegranate ellagitannins
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