Tellimagrandin I
Names | |
---|---|
IUPAC name
(11aR,14R,15S,15aR)-2,3,4,5,6,7,13-Heptahydroxy-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-14,15-diyl bis(3,4,5-trihydroxybenzoate) | |
Other names
1-desgalloyleugeniin | |
Identifiers | |
3D model (JSmol) |
|
ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID |
|
| |
| |
Properties | |
C34H26O22 | |
Molar mass | 786.56 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 ยฐC [77 ยฐF], 100 kPa). | |
Infobox references | |
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
References
- โ Ganesan D, Al-Sayed E, Albert A, Paul E, Singab AN, Govindan Sadasivam S, Saso L (21 Jun 2017). "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". Nat Prod Res: 1โ7. PMID 28637361. doi:10.1080/14786419.2017.1343324.
- โ Yi ZC, Liu YZ, Li HX, Wang Z (Jun 2009). "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)". Toxicol in Vitro. 23 (4): 667โ673. PMID 19328845. doi:10.1016/j.tiv.2009.03.009.
- โ Yi ZC, Liu YZ, Li HX, Wang Z (Apr 2009). "Prooxidant action of chebulinic acid and tellimagrandin I: causing copper-dependent DNA strand breaks". Toxicology in vitro : an international journal published in association with BIBRA. 23 (3): 425โ431. PMID 19344683. doi:10.1016/j.tiv.2009.01.012.
- โ Al-Sayed E, Esmat A (Sep 2016). "Hepatoprotective and antioxidant effect of ellagitannins and galloyl esters isolated from Melaleuca styphelioides on carbon tetrachloride-induced hepatotoxicity in HepG2 cells". Pharm Biol. 54 (9): 1727โ1735. PMID 26731241. doi:10.3109/13880209.2015.1125933.
- โ Shimoda H, Tanaka J, Kikuchi M, Fukuda T, Ito H, Hatano T, Yoshida T (25 Jun 2008). "Walnut polyphenols prevent liver damage induced by carbon tetrachloride and d-galactosamine: hepatoprotective hydrolyzable tannins in the kernel pellicles of walnut". J Agric Food Chem. 56 (12): 4444โ4449. PMID 18494495. doi:10.1021/jf8002174.
- โ Shimoda H, Tanaka J, Kikuchi M, Fukuda T, Ito H, Hatano T, Yoshida T (11 Mar 2009). "Effect of polyphenol-rich extract from walnut on diet-induced hypertriglyceridemia in mice via enhancement of fatty acid oxidation in the liver". J Agric Food Chem. 57 (5): 1786โ1792. PMID 19256553. doi:10.1021/jf803441c.
- โ Yi ZC, Liu YZ, Li HX, Yin Y, Zhuang FY, Fan YB, Wang Z (8 Oct 2006). "Tellimagrandin I enhances gap junctional communication and attenuates the tumor phenotype of human cervical carcinoma HeLa cells in vitro". Cancer Lett. 242 (1): 77โ87. PMID 16338066. doi:10.1016/j.canlet.2005.10.044.
- โ Lavoie S, Cรดtรฉ I, Pichette A, Gauthier C, Ouellet M, Nagau-Lavoie F, Mshvildadze V, Legault J (22 Feb 2017). "Chemical composition and anti-herpes simplex virus type 1 (HSV-1) activity of extracts from Cornus canadensis". BMC Complement Altern Med. 17 (1): 123. PMC 5322616โฏ. PMID 28228101. doi:10.1186/s12906-017-1618-2.
- โ Tamura S, Yang GM, Yasueda N, Matsuura Y, Komoda Y, Murakami N (2010). "Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos". Bioorg Med Chem Lett. 20 (5): 1598โ1600. PMID 20144544. doi:10.1016/j.bmcl.2010.01.084.