Grandinin

{{short description|Chemical compound}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 441141120

| Name = Grandinin

| ImageFile = Grandinin.PNG

| ImageName = Chemical structure of grandinin

| IUPACName = (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[27.13.3.1^38,42.0^2,20.0^5,10.0^11,16.0^23,28.0^33,45.0^34,39]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

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 115166-32-0

| PubChem = 492392

| SMILES = 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

| StdInChI=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

| StdInChIKey = GCEXRPOQEVIITL-XJDSPLDHSA-N

}}

|Section2={{Chembox Properties

| C=46 | H=34 | O=30

| Appearance =

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Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves{{cite journal | doi = 10.1002/ptr.1214 | title = Polyphenols of Melaleuca quinquenervia leaves – pharmacological studies of grandinin | date = 2003 | last1 = Moharram | first1 = F. A. | last2 = Marzouk | first2 = M. S. | last3 = El-Toumy | first3 = S. A. A. | last4 = Ahmed | first4 = A. A. E. | last5 = Aboutabl | first5 = E. A. | journal = Phytotherapy Research | volume = 17 | issue = 7 | pages = 767–773 | pmid = 12916075 }} and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).{{Cite journal | last1 = Mämmelä | first1 = P. | last2 = Savolainen | first2 = H. | last3 = Lindroos | first3 = L. | last4 = Kangas | first4 = J. | last5 = Vartiainen | first5 = T. | title = Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry | doi = 10.1016/S0021-9673(00)00624-5 | journal = Journal of Chromatography A | volume = 891 | issue = 1 | pages = 75–83 | year = 2000 | pmid = 10999626}} It shows antioxydant activity. It is an astringent compound. It is also found in wine, red{{Cite journal

| last1 = García-Estévez | first1 = I.

| last2 = Escribano-Bailón | first2 = M. T.

| last3 = Rivas-Gonzalo | first3 = J. N. C.

| last4 = Alcalde-Eon | first4 = C.

| title = Development of a fractionation method for the detection and identification of oak ellagitannins in red wines

| doi = 10.1016/j.aca.2009.10.020

| journal = Analytica Chimica Acta

| volume = 660

| issue = 1–2

| pages = 171–176

| year = 2010

| pmid = 20103159

| bibcode = 2010AcAC..660..171G

| hdl = 10366/141103

| hdl-access = free

}} or white,{{Cite journal | last1 = Marinov | first1 = M. G. | last2 = Dimitrova | first2 = E. D. | last3 = Puech | first3 = J. -L. | title = Kinetics of ellagitannin extraction from oak wood using white wine | doi = 10.1080/09571269708718095 | journal = Journal of Wine Research | volume = 8 | pages = 29–40 | year = 1997 }} aged in oak barrels.

It is a castalagin glycoside{{Cite journal | last1 = Fridrich | first1 = D. | last2 = Glabasnia | first2 = A. | last3 = Fritz | first3 = J. | last4 = Esselen | first4 = M. | last5 = Pahlke | first5 = G. | last6 = Hofmann | first6 = T. | last7 = Marko | first7 = D. | doi = 10.1021/jf073427z | title = Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells | journal = Journal of Agricultural and Food Chemistry | volume = 56 | issue = 9 | pages = 3010–3015 | year = 2008 | pmid = 18419129}}, {{INIST|20325664}} by binding of the pentose lyxose.{{Cite journal | last1 = Hofmann | first1 = T. | last2 = Glabasnia | first2 = A. | last3 = Schwarz | first3 = B. | last4 = Wisman | first4 = K. N. | last5 = Gangwer | first5 = K. A. | last6 = Hagerman | first6 = A. E. | doi = 10.1021/jf062272c | title = Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-d-glucopyranose, Castalagin, and Grandinin | journal = Journal of Agricultural and Food Chemistry | volume = 54 | issue = 25 | pages = 9503–9509 | year = 2006 | pmid = 17147439| pmc =2597504 }} It contains a nonahydroxytriphenic acid moiety.

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