Tellimagrandin I

Tellimagrandin I
Names
	Systematic IUPAC name (11aR,13Ξ,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
CAS Number	79786-08-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9433;
ChEMBL	ChEMBL450376;
ChemSpider	391047;
KEGG	C10241;
PubChem CID	442690;
	InChI InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(47)55-28-27-18(53-34(51)29(28)56-31(48)9-3-14(37)22(42)15(38)4-9)7-52-32(49)10-5-16(39)23(43)25(45)19(10)20-11(33(50)54-27)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-46,51H,7H2/t18-,27-,28+,29-,34?/m1/s1 Key: YKDNTEQLKGYZHT-HTCCRONFSA-N;
	SMILES C1C2C(C(C(C(O2)O)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5C6=C(C(=C(C=C6C(=O)O1)O)O)O)O)O)O;
Properties
Chemical formula	C34H26O22
Molar mass	786.56 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Short description: Chemical compound

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]

References

↑ "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 32 (11): 1274–1280. 21 Jun 2017. doi:10.1080/14786419.2017.1343324. PMID 28637361. https://figshare.com/articles/journal_contribution/5135008.
↑ "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): 667–673. Jun 2009. doi:10.1016/j.tiv.2009.03.009. PMID 19328845.
↑ "Prooxidant action of chebulinic acid and tellimagrandin I: causing copper-dependent DNA strand breaks". Toxicology in Vitro 23 (3): 425–431. Apr 2009. doi:10.1016/j.tiv.2009.01.012. PMID 19344683.
↑ "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): 1727–1735. Sep 2016. doi:10.3109/13880209.2015.1125933. PMID 26731241.
↑ "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): 4444–4449. 25 Jun 2008. doi:10.1021/jf8002174. PMID 18494495.
↑ "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): 1786–1792. 11 Mar 2009. doi:10.1021/jf803441c. PMID 19256553.
↑ "Tellimagrandin I enhances gap junctional communication and attenuates the tumor phenotype of human cervical carcinoma HeLa cells in vitro". Cancer Lett 242 (1): 77–87. 8 Oct 2006. doi:10.1016/j.canlet.2005.10.044. PMID 16338066.
↑ "Chemical composition and anti-herpes simplex virus type 1 (HSV-1) activity of extracts from Cornus canadensis". BMC Complement Altern Med 17 (1): 123. 22 Feb 2017. doi:10.1186/s12906-017-1618-2. PMID 28228101.
↑ "Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos". Bioorg Med Chem Lett 20 (5): 1598–1600. 2010. doi:10.1016/j.bmcl.2010.01.084. PMID 20144544.

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Original source: https://en.wikipedia.org/wiki/Tellimagrandin I. Read more

[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". Nat Prod Res 32 (11): 1274–1280. 21 Jun 2017. doi:10.1080/14786419.2017.1343324. PMID 28637361. https://figshare.com/articles/journal_contribution/5135008.

[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)". Toxicol in Vitro 23 (4): 667–673. Jun 2009. doi:10.1016/j.tiv.2009.03.009. PMID 19328845.

[3] "Prooxidant action of chebulinic acid and tellimagrandin I: causing copper-dependent DNA strand breaks". Toxicology in Vitro 23 (3): 425–431. Apr 2009. doi:10.1016/j.tiv.2009.01.012. PMID 19344683.

[4] "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): 1727–1735. Sep 2016. doi:10.3109/13880209.2015.1125933. PMID 26731241.

[5] "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): 4444–4449. 25 Jun 2008. doi:10.1021/jf8002174. PMID 18494495.

[6] "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): 1786–1792. 11 Mar 2009. doi:10.1021/jf803441c. PMID 19256553.

[7] "Tellimagrandin I enhances gap junctional communication and attenuates the tumor phenotype of human cervical carcinoma HeLa cells in vitro". Cancer Lett 242 (1): 77–87. 8 Oct 2006. doi:10.1016/j.canlet.2005.10.044. PMID 16338066.

[8] "Chemical composition and anti-herpes simplex virus type 1 (HSV-1) activity of extracts from Cornus canadensis". BMC Complement Altern Med 17 (1): 123. 22 Feb 2017. doi:10.1186/s12906-017-1618-2. PMID 28228101.

[9] "Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos". Bioorg Med Chem Lett 20 (5): 1598–1600. 2010. doi:10.1016/j.bmcl.2010.01.084. PMID 20144544.

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Tellimagrandin I

Topic: Chemistry

See also

References