Grandinin

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Grandinin
Chemical structure of grandinin
Chemical structure of grandinin
Names
IUPAC name
(46R)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-46-[(3R,4S)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,18,21,41,43-pentaoxanonacyclo[27.13.3.138,42.02,20.05,10.011,16.023,28.033,45.034,39]hexatetraconta-5,7,9,11,13,15,23,25,27,29(45),30,32,34(39),35,37-pentadecaene-4,17,22,40,44-pentone
Identifiers
3D model (JSmol)
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  • InChI=1S/C46H34O30/c47-4-12-27(54)40(64)46(70,76-12)23-22-21-19(33(60)36(63)34(22)61)18-20-17(31(58)35(62)32(18)59)16-8(3-11(50)26(53)30(16)57)42(66)72-13-5-71-41(65)6-1-9(48)24(51)28(55)14(6)15-7(2-10(49)25(52)29(15)56)43(67)73-37(13)39(75-44(20)68)38(23)74-45(21)69/h1-3,12-13,23,27,37-40,47-64,70H,4-5H2/t12?,13?,23-,27-,37?,38?,39?,40-,46?/m1/s1
    Key: GCEXRPOQEVIITL-XJDSPLDHSA-N
  • C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)C8(C(C(C(O8)CO)O)O)O)OC(=O)C9=CC(=C(C(=C9C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O
Properties
C46H34O30
Molar mass 1066.748 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves[1] and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).[2] It shows antioxydant activity.[1] It is an astringent compound.[3] It is also found in wine, red[4] or white,[5] aged in oak barrels.

It is a castalagin glycoside[6] by binding of the pentose lyxose.[3] It contains a nonahydroxytriphenic acid moiety.

It suppresses the phosphorylation of the epidermal growth factor receptor in human colon carcinoma cells.[6]

See also

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References

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