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 (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
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	101196665;
	InChI 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 Key: JKDVHWQRXXBOIU-JRCJVTSXSA-N;
	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;
Properties
Chemical formula	C123H80O78
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). Infobox references

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

Lambertianin C at www.phenol-explorer.eu

[1] "Lambertianin C". PubChem. 2017-07-29.

[Tanaka-2] 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.

[Kahkonen-3] 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.

[4] 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.

[5] 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.

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