lambertianin C
{{chembox
| Verifiedfields =
| verifiedrevid =
| Name = Lambertianin C
| ImageFile = Lambertianin C.png
| ImageName = Chemical structure of lambertianin C
| 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 (310aR,311S,312aR,325aR,325bS,810aR,811R,812aR,825aR,825bS)-15,16,32,33,34,35,36,37,317,318,319,320,321,322,64,65,82,83,84,85,86,87,817,818,819,820,821,822,113,114,115-hentriacontahydroxy-39,315,324,327,5,89,815,824,827,10-decaoxo-39,310a,311,312a,313,315,324,325a,325b,327,89,810a,811,812a,813,815,824,825a,825b,827-icosahydro-2,4,7,9-tetraoxa-3,8(22,11)-bis(dibenzo[g,i]dibenzo[6′,7′:8′,9′][1,4]dioxecino[2′,3′:4,5]pyrano[3,2-b][1,5]dioxacycloundecina)-1,11(1),6(1,3)-tribenzenaundecaphane-13-carboxylate
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo =
| CASNo_Ref =
| CASNoOther =
| PubChem = 101196665
| ChEMBL_Ref =
| ChEMBL =
| SMILES = C1C2C(C3C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5C6=C(C(=C(C=C6C(=O)O3)O)O)O)O)O)O)OC7=C(C8=C(C(=C(C=C8O1)O)O)O)C(=C(C(=C7OC9=CC(=CC(=C9O)O)C(=O)OC1C2C(C3C(O1)COC(=O)C1=CC(=C(C(=C1C1=C(C(=C(C(=C1O)O)O)OC1=CC(=CC(=C1O)O)C(=O)OC1C4C(C5C(O1)COC(=O)C1=CC(=C(C(=C1C1=C(C(=C(C=C1C(=O)O5)O)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1C1=C(C(=C(C=C1C(=O)O4)O)O)O)O)O)O)C(=O)O3)O)O)O)OC(=O)C1=CC(=C(C(=C1C1=C(C(=C(C=C1C(=O)O2)O)O)O)O)O)O)O)O)O
| InChIKey = JKDVHWQRXXBOIU-JRCJVTSXSA-N
| InChI = 1S/C121H80O76/c122-32-1-20(2-33(123)65(32)136)106(165)195-119-103-100(189-112(171)26-10-39(129)70(141)80(151)54(26)57-29(115(174)192-103)13-42(132)73(144)83(57)154)94-49(183-119)17-178-46-16-45(135)77(148)87(158)61(46)63-89(160)91(162)93(164)99(98(63)186-94)182-48-6-22(4-35(125)67(48)138)108(167)197-121-105-102(191-114(173)28-12-41(131)72(143)82(153)56(28)59-31(117(176)194-105)15-44(134)75(146)85(59)156)96-51(185-121)19-180-110(169)24-8-37(127)76(147)86(157)60(24)62-64(118(177)188-96)97(92(163)90(161)88(62)159)181-47-5-21(3-34(124)66(47)137)107(166)196-120-104-101(190-113(172)27-11-40(130)71(142)81(152)55(27)58-30(116(175)193-104)14-43(133)74(145)84(58)155)95-50(184-120)18-179-109(168)23-7-36(126)68(139)78(149)52(23)53-25(111(170)187-95)9-38(128)69(140)79(53)150/h1-16,49-51,94-96,100-105,119-164H,17-19H2/t49-,50-,51-,94-,95-,96-,100+,101+,102+,103-,104-,105-,119-,120+,121+/m1/s1{{cite web| title=Lambertianin C| date=2017-07-29| website=PubChem| url=https://pubchem.ncbi.nlm.nih.gov/compound/101196665}}
| MeSHName =
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|Section2={{Chembox Properties
| C=123
| H=80
| O=78
| Appearance =
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Lambertianin C is an ellagitannin.
Natural occurrence
Lambertianin C can be found in Rubus species such as Rubus lambertianus,{{Cite journal
| last1 = Tanaka | first1 = T.
| last2 = Tachibana | first2 = H.
| last3 = Nonaka | first3 = G.
| last4 = Nishioka | first4 = I.
| last5 = Hsu | first5 = F. L.
| last6 = Kohda | first6 = H.
| last7 = Tanaka | first7 = O.
| title = Tannins and related compounds. CXXII. New dimeric, trimeric and tetrameric ellagitannins, lambertianins A-D, from Rubus lambertianus Seringe
| journal = Chemical and Pharmaceutical Bulletin
| volume = 41
| issue = 7
| pages = 1214–1220
| year = 1993
| pmid = 8374992 | doi=10.1248/cpb.41.1214
| doi-access = free
}} in cloudberries (Rubus chamaemorus){{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| bibcode = 2012JAFC...60.1167K }} and in 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
| bibcode = 2002JAFC...50.5197M
}}
Chemistry
Lambertianin C is trimer of casuarictin linked by sanguisorbic acid ester groups between glucopyranose moieties. It 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| bibcode = 2010JAFC...58.3901B }}
References
{{Reflist}}
External links
- [http://www.phenol-explorer.eu/compounds/445 Lambertianin C at www.phenol-explorer.eu]
{{Ellagitannin}}