Tellimagrandin I

Last updated
Tellimagrandin I
Tellimagrandin I.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
  • 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
  • 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
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).

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

Related Research Articles

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<i>Citrus depressa</i> Species of fruit and plant

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<i>Eucalyptus globulus</i> Species of tree endemic to southeastern Australia

Eucalyptus globulus, commonly known as southern blue gum or blue gum, is a species of flowering plant in the family Myrtaceae. It is a tall, evergreen tree endemic to southeastern Australia. This Eucalyptus species has mostly smooth bark, juvenile leaves that are whitish and waxy on the lower surface, glossy green, lance-shaped adult leaves, glaucous, ribbed flower buds arranged singly or in groups of three or seven in leaf axils, white flowers and woody fruit.

<span class="mw-page-title-main">Myricetin</span> Chemical compound

Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties. Common dietary sources include vegetables, fruits, nuts, berries, tea, and red wine. Myricetin is structurally similar to fisetin, luteolin, and quercetin and is reported to have many of the same functions as these other members of the flavonol class of flavonoids. Reported average intake of myricetin per day varies depending on diet, but has been shown in the Netherlands to average 23 mg/day.

<span class="mw-page-title-main">Galactosamine</span> Chemical compound

Galactosamine is a hexosamine derived from galactose with the molecular formula C6H13NO5. This amino sugar is a constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH).

<span class="mw-page-title-main">Cystamine</span> Chemical compound

Cystamine (2,2'-dithiobisethanamine) is an organic disulfide. It is formed when cystine is heated, the result of decarboxylation. Cystamine is an unstable liquid and is generally handled as the dihydrochloride salt, C4H12N2S2·2HCl, which is stable to 203-214 °C at which point it decomposes. Cystamine is toxic if swallowed or inhaled and potentially harmful by contact.

<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

<i>Cornus officinalis</i> Species of flowering plant

Cornus officinalis, the Japanese cornel or Japanese cornelian cherry, is a species of flowering plant in the dogwood family Cornaceae. Despite its name, it is native to China and Korea as well as Japan. It is not to be confused with C. mas, which is also known as the Cornelian cherry. It is not closely related to the true cherries of the genus Prunus.

<span class="mw-page-title-main">Chebulagic acid</span> Chemical compound

Chebulagic acid is a benzopyran tannin and an antioxidant that has many potential uses in medicine.

<span class="mw-page-title-main">Castalagin</span> Chemical compound

Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides.

The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

<span class="mw-page-title-main">Grandinin</span> Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

<span class="mw-page-title-main">Tellimagrandin II</span> Chemical compound

Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum (clove).

<span class="mw-page-title-main">1,2,3,4,6-Pentagalloyl glucose</span> Chemical compound

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

<span class="mw-page-title-main">Punicalin</span> Chemical compound

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis. It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.

<span class="mw-page-title-main">Punicafolin</span> Chemical compound

Punicafolin is an ellagitannin from the leaves of Punica granatum (pomegranate) and in Phyllanthus emblica.

<span class="mw-page-title-main">Pomegranate ellagitannin</span> Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of pomegranates.

<span class="mw-page-title-main">Casuarinin</span> Chemical compound

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana.

<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

<span class="mw-page-title-main">Urolithin B</span> Chemical compound

Urolithin B (UB) is an urolithin, a type of phenolic compounds produced in the human gut after absorption of ellagitannins-containing food such as pomegranate, strawberries, red raspberries, walnuts or oak-aged red wine. Urolithin B is found in the urine in the form of urolithin B glucuronide.

References

  1. 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. 32 (11): 1274–1280. doi:10.1080/14786419.2017.1343324. PMID   28637361. S2CID   4705598.
  2. 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): 667–673. doi:10.1016/j.tiv.2009.03.009. PMID   19328845.
  3. 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. 23 (3): 425–431. doi:10.1016/j.tiv.2009.01.012. PMID   19344683.
  4. 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): 1727–1735. doi: 10.3109/13880209.2015.1125933 . PMID   26731241.
  5. 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): 4444–4449. doi:10.1021/jf8002174. PMID   18494495.
  6. 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): 1786–1792. doi:10.1021/jf803441c. PMID   19256553.
  7. 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): 77–87. doi:10.1016/j.canlet.2005.10.044. PMID   16338066.
  8. Lavoie S, Côté 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. doi:10.1186/s12906-017-1618-2. PMC   5322616 . PMID   28228101.
  9. 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): 1598–1600. doi:10.1016/j.bmcl.2010.01.084. PMID   20144544.