Tellimagrandin I Explained

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

Tellimagrandin I has been shown to restore antioxidant enzyme activity in glucose- and oxalate-challenged rat cells^[1] and affects Cu(II)- and Fe(II)-dependent DNA strand breaks.^{[2] [3]} It has hepatoprotective effects on carbon tetrachloride- and d-galactosamine-stressed HepG2 cells^{[4] [5]} and enhances peroxisomal fatty acid beta-oxidation in liver, increasing mRNA expression of PPAR alpha, ACOX1, and CPT1A.^[6] It enhances gap junction communication and reduces tumor phenotype in HeLa cells^[7] and inhibits invasion of HSV-1^[8] and HCV similar to eugeniin and casuarictin.^[9]

See also

• Ellagitannin
• Pedunculagin
• Punigluconin
• Tellimagrandin II

Notes and References

1. Antioxidant activity of phenolic compounds from extracts of Eucalyptus globulus and Melaleuca styphelioides and their protective role on D-glucose-induced hyperglycemic stress and oxalate stress in NRK-49Fcells. Ganesan D, Al-Sayed E, Albert A, Paul E, Singab AN, Govindan Sadasivam S, Saso L. 21 Jun 2017. Nat Prod Res. 32. 11. 1274–1280. 10.1080/14786419.2017.1343324. 28637361. 4705598.
2. Chebulinic acid and tellimagrandin I inhibit DNA strand breaks by hydroquinone/Cu(II) and H(2)O(2)/Cu(II), but potentiate DNA strand breaks by H(2)O(2)/Fe(II). Yi ZC, Liu YZ, Li HX, Wang Z. Jun 2009. Toxicol in Vitro. 23. 4. 667–673. 10.1016/j.tiv.2009.03.009. 19328845.
3. Prooxidant action of chebulinic acid and tellimagrandin I: causing copper-dependent DNA strand breaks. Toxicology in Vitro . Yi ZC, Liu YZ, Li HX, Wang Z. Apr 2009. 23. 3. 425–431. 10.1016/j.tiv.2009.01.012. 19344683.
4. Hepatoprotective and antioxidant effect of ellagitannins and galloyl esters isolated from Melaleuca styphelioides on carbon tetrachloride-induced hepatotoxicity in HepG2 cells. Al-Sayed E, Esmat A. Sep 2016. Pharm Biol. 54. 9. 1727–1735. 10.3109/13880209.2015.1125933. 26731241. free.
5. Walnut polyphenols prevent liver damage induced by carbon tetrachloride and d-galactosamine: hepatoprotective hydrolyzable tannins in the kernel pellicles of walnut. Shimoda H, Tanaka J, Kikuchi M, Fukuda T, Ito H, Hatano T, Yoshida T. 25 Jun 2008. J Agric Food Chem. 56. 12. 4444–4449. 10.1021/jf8002174. 18494495.
6. Effect of polyphenol-rich extract from walnut on diet-induced hypertriglyceridemia in mice via enhancement of fatty acid oxidation in the liver. Shimoda H, Tanaka J, Kikuchi M, Fukuda T, Ito H, Hatano T, Yoshida T. 11 Mar 2009. J Agric Food Chem. 57. 5. 1786–1792. 10.1021/jf803441c. 19256553.
7. Tellimagrandin I enhances gap junctional communication and attenuates the tumor phenotype of human cervical carcinoma HeLa cells in vitro. Yi ZC, Liu YZ, Li HX, Yin Y, Zhuang FY, Fan YB, Wang Z. Cancer Lett. 8 Oct 2006. 242. 1. 77–87. 10.1016/j.canlet.2005.10.044. 16338066.
8. Chemical composition and anti-herpes simplex virus type 1 (HSV-1) activity of extracts from Cornus canadensis. Lavoie S, Côté I, Pichette A, Gauthier C, Ouellet M, Nagau-Lavoie F, Mshvildadze V, Legault J. 22 Feb 2017. BMC Complement Altern Med. 17. 1. 123. 5322616. 10.1186/s12906-017-1618-2. 28228101. free.
9. Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos. Tamura S, Yang GM, Yasueda N, Matsuura Y, Komoda Y, Murakami N. Bioorg Med Chem Lett. 20. 5. 1598–1600. 10.1016/j.bmcl.2010.01.084. 20144544. 2010.