Lambertianin C
Lambertianin C
Names
Systematic IUPAC name
(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 (310a R ,311 S ,312a R ,325a R ,325b S ,810a R ,811 R ,812a R ,825a R ,825b S )-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
Identifiers
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
[ 1] Key: JKDVHWQRXXBOIU-JRCJVTSXSA-N
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
Properties
C 123 H 80 O 78
Molar mass
2805 .915 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Lambertianin C is an ellagitannin .
Natural occurrence
Lambertianin C can be found in Rubus species such as Rubus lambertianus ,[ 2] in cloudberries (Rubus chamaemorus )[ 3] and in red raspberries (Rubus idaeus ).[ 4]
Chemistry
Lambertianin C is trimer of casuarictin linked by sanguisorbic acid ester groups between glucopyranose moieties.[ 2] It contributes to the in vitro antioxidant activity of raspberries.[ 5]
References
^ "Lambertianin C" . PubChem . 2017-07-29.
^ a b Tanaka, T.; Tachibana, H.; Nonaka, G.; Nishioka, I.; Hsu, F. L.; Kohda, H.; Tanaka, O. (1993). "Tannins and related compounds. CXXII. New dimeric, trimeric and tetrameric ellagitannins, lambertianins A-D, from Rubus lambertianus Seringe" . Chemical and Pharmaceutical Bulletin . 41 (7): 1214–1220. doi :10.1248/cpb.41.1214 . PMID 8374992 .
^ Kähkönen, M.; Kylli, P.; Ollilainen, V.; Salminen, J. P.; Heinonen, M. (2012). "Antioxidant Activity of Isolated Ellagitannins from Red Raspberries and Cloudberries". Journal of Agricultural and Food Chemistry . 60 (5): 1167–1174. doi :10.1021/jf203431g . PMID 22229937 .
^ Mullen, W.; Stewart, A. J.; Lean, M. E.; Gardner, P.; Duthie, G. G.; Crozier, A. (2002). "Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries". Journal of Agricultural and Food Chemistry . 50 (18): 5197–5201. doi :10.1021/jf020141f . PMID 12188629 .
^ Borges, G.; Degeneve, A.; Mullen, W.; Crozier, A. (2010). "Identification of Flavonoid and Phenolic Antioxidants in Black Currants, Blueberries, Raspberries, Red Currants, and Cranberries†". Journal of Agricultural and Food Chemistry . 58 (7): 3901–3909. doi :10.1021/jf902263n . PMID 20000747 .
External links
Moieties Lactones Monomers
Acetonyl geraniin
Alnusiin
Bicornin
Carlesiin
Casuarictin
Emblicanin A and B
Euscaphinin
Galloyl pedunculagin
Grandinin
Helioscopinin B
Jolkinin
Lagerstannin A , B and C
Macranganin
Myrobalanitannin
Nupharin A , B , C , D , E and F
Pedunculagin
Punicalagin
Punigluconin
Phyllanemblinin A , B , C , D , E and F
Punicalin
Roburin E
Rugosin E
Sanguiin H-5
Stenophyllanin A , B and C
Strictinin
Tellimagrandin I and II
Teracatain
Terchebulin
Terflavin A and B
Tergallic acid
Tergallic acid dilactone
Oligomers Other