:Sanguiin H-6
{{chembox
| Verifiedfields =
| verifiedrevid =
| Name = Sanguiin H-6
| ImageFile = Sanguiin H-6.PNG
| ImageName = Chemical structure of sanguiin H-6
| SystematicName = (10aR,11S,12aR,25aR,25bS)-2,3,4,5,6,7,17,18,19,20,21,22-Dodecahydroxy-9,15,24,27-tetraoxo-9,10a,11,12a,13,15,24,25a,25b,27-decahydrodibenzo[g,i]dibenzo[6′,7′:8′,9′][1,4]dioxecino[2′,3′:4,5]pyrano[3,2-b][1,5]dioxacycloundecin-11-yl 3-({(10aR,11R,12aR,25aR,25bS)-2,3,4,5,6,7,17,18,19,20,21-hendecahydroxy-9,15,24,27-tetraoxo-11-[(3,4,5-trihydroxybenzoyl)oxy]-9,10a,11,12a,13,15,24,25a,25b,27-decahydrodibenzo[g,i]dibenzo[6′,7′:8′,9′][1,4]dioxecino[2′,3′:4,5]pyrano[3,2-b][1,5]dioxacycloundecin-22-yl}oxy)-4,5-dihydroxybenzoate
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 82978-00-5
| CASNo_Ref =
| ChemSpiderID = 17287615
| PubChem = 16130897
| ChEMBL_Ref =
| ChEMBL = 508647
| MeSHName =
| StdInChI = 1S/C82H54O52/c83-23-1-14(2-24(84)45(23)93)71(112)133-81-70-68(130-77(118)20-9-30(90)50(98)57(105)39(20)41-22(79(120)132-70)11-32(92)52(100)59(41)107)65-35(126-81)13-123-74(115)17-6-27(87)53(101)60(108)42(17)43-44(80(121)128-65)66(63(111)62(110)61(43)109)124-33-4-15(3-25(85)46(33)94)72(113)134-82-69-67(129-76(117)19-8-29(89)49(97)56(104)38(19)40-21(78(119)131-69)10-31(91)51(99)58(40)106)64-34(125-82)12-122-73(114)16-5-26(86)47(95)54(102)36(16)37-18(75(116)127-64)7-28(88)48(96)55(37)103/h1-11,34-35,64-65,67-70,81-111H,12-13H2/t34-,35-,64-,65-,67+,68+,69-,70-,81-,82+/m1/s1
| StdInChIKey = FFZOOOCGCNFHAQ-GWOIDVGPSA-N
| SMILES = C1[C@@H]2[C@H]([C@H]3[C@H]([C@@H](O2)OC(=O)C4=CC(=C(C(=C4)OC5=C(C(=C(C6=C5C(=O)O[C@@H]7[C@@H](COC(=O)C8=CC(=C(C(=C86)O)O)O)O[C@@H]([C@H]9[C@H]7OC(=O)C2=CC(=C(C(=C2C2=C(C(=C(C=C2C(=O)O9)O)O)O)O)O)O)OC(=O)C2=CC(=C(C(=C2)O)O)O)O)O)O)O)O)OC(=O)C2=CC(=C(C(=C2C2=C(C(=C(C=C2C(=O)O3)O)O)O)O)O)O)OC(=O)C2=CC(=C(C(=C2C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O
}}
|Section2={{Chembox Properties
| C=82
| H=54
| O=52
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
}}
Sanguiin H-6 is an ellagitannin.
Natural occurrence
Sanguiin H-6 can be found in Rosaceae such as the great burnet (Sanguisorba officinalis),{{Cite journal | last1 = Bastow | first1 = K. | last2 = Bori | first2 = I. | last3 = Fukushima | first3 = Y. | last4 = Kashiwada | first4 = Y. | last5 = Tanaka | first5 = T. | last6 = Nonaka | first6 = G. | last7 = Nishioka | first7 = I. | last8 = Lee | first8 = K. -H. | doi = 10.1055/s-2006-959659 | title = Inhibition of DNA Topoisomerases by Sanguiin H-6, a Cytotoxic Dimeric Ellagitannin fromSanguisorba officinalis1 | journal = Planta Medica | volume = 59 | issue = 3 | pages = 240–245 | year = 2007 | pmid = 8391144| s2cid = 260281189 }} in strawberries (Fragaria × ananassa){{Cite journal | last1 = Seeram | first1 = N. P. | last2 = Lee | first2 = R. | last3 = Scheuller | first3 = H. S. | last4 = Heber | first4 = D. | title = Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy | doi = 10.1016/j.foodchem.2005.02.047 | journal = Food Chemistry | volume = 97 | pages = 1–11 | year = 2006 | s2cid = 73532960 | url = https://cloudfront.escholarship.org/dist/prd/content/qt6526f1m8/qt6526f1m8.pdf }} and in Rubus species such as red raspberries (Rubus idaeus){{Cite journal
| last1 = Mullen | first1 = W.
| last2 = Stewart | first2 = A. J.
| last3 = Lean | first3 = M. E.
| last4 = Gardner | first4 = P.
| last5 = Duthie | first5 = G. G.
| last6 = Crozier | first6 = A.
| title = Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries
| journal = Journal of Agricultural and Food Chemistry
| volume = 50
| issue = 18
| pages = 5197–5201
| year = 2002
| pmid = 12188629 | doi=10.1021/jf020141f
}}{{Cite journal | last1 = Kähkönen | first1 = M. | last2 = Kylli | first2 = P. | last3 = Ollilainen | first3 = V. | last4 = Salminen | first4 = J. P. | last5 = Heinonen | first5 = M. | title = Antioxidant Activity of Isolated Ellagitannins from Red Raspberries and Cloudberries | doi = 10.1021/jf203431g | journal = Journal of Agricultural and Food Chemistry | volume = 60 | issue = 5 | pages = 1167–1174 | year = 2012 | pmid = 22229937}} or cloudberries (Rubus chamaemorus).
Chemistry
Sanguiin H-6 is dimer of casuarictin linked by a bond between the gallic acid residue and one of the hexahydroxydiphenic acid units. It has sanguisorbic acid ester groups as linking units between glucopyranose moieties.{{Cite journal | last1 = Vrhovsek | first1 = U. | last2 = Guella | first2 = G. | last3 = Gasperotti | first3 = M. | last4 = Pojer | first4 = E. | last5 = Zancato | first5 = M. | last6 = Mattivi | first6 = F. | doi = 10.1021/jf2052256 | title = Clarifying the Identity of the Main Ellagitannin in the Fruit of the Strawberry, Fragaria vesca and Fragaria ananassa Duch | journal = Journal of Agricultural and Food Chemistry | volume = 60 | issue = 10 | pages = 2507–2516 | year = 2012 | pmid = 22339338}} Sanguiin H-6 contributes to the in vitro antioxidant activity of raspberries.{{Cite journal | last1 = Borges | first1 = G. | last2 = Degeneve | first2 = A. | last3 = Mullen | first3 = W. | last4 = Crozier | first4 = A. | title = Identification of Flavonoid and Phenolic Antioxidants in Black Currants, Blueberries, Raspberries, Red Currants, and Cranberries† | doi = 10.1021/jf902263n | journal = Journal of Agricultural and Food Chemistry | volume = 58 | issue = 7 | pages = 3901–3909 | year = 2010 | pmid = 20000747}}
References
{{Reflist}}
External links
- [http://www.phenol-explorer.eu/compounds/446 Sanguiin H-6 on www.phenol-explorer.eu]
{{Ellagitannin}}