Lambertianin C

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Lambertianin C
Lambertianin C.png
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)
PubChem CID
  • 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
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).

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]

Contents

Chemistry

Lambertianin C is trimer of casuarictin linked by sanguisorbic acid ester groups between glucopyranose moieties. [2] It contributes to the antioxidant capacity of raspberries. [5]

Related Research Articles

<i>Rubus chamaemorus</i> Species of flowering plant in the rose family Rosaceae

Rubus chamaemorus is a species of flowering plant in the rose family Rosaceae, native to cool temperate regions, alpine and arctic tundra and boreal forest. This herbaceous perennial produces amber-colored edible fruit similar to the blackberry. English common names include cloudberry, nordic berry, bakeapple, knotberry and knoutberry, aqpik or low-bush salmonberry, and averin or evron.

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<i>Rubus idaeus</i> Red raspberry

Rubus idaeus is a red-fruited species of Rubus native to Europe and northern Asia and commonly cultivated in other temperate regions.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Procyanidin C2</span> Chemical compound

Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.

<span class="mw-page-title-main">Antirrhinin</span> Chemical compound

Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

<span class="mw-page-title-main">Grandinin</span> Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

<span class="mw-page-title-main">Phenolic content in tea</span> Natural plant compounds

The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel of tea. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Ethyl protocatechuate</span> Chemical compound

Ethyl protocatechuate is a phenolic compound. It can be found in the peanut seed testa. It is also present in wine. It is the ethylic ester of protocatechuic acid.

<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

<span class="mw-page-title-main">Sanguiin H-6</span> Chemical compound

Sanguiin H-6 is an ellagitannin.

Rubus lambertianus is a flowering plant species in the genus Rubus found in Southern China, Taiwan, Japan, and Thailand. Its ploidy is 2n = 4X (tetraploid). The ellagitannins lambertianin A, B, C and D can be found in R. lambertianus.

<span class="mw-page-title-main">Lambertianin D</span> Chemical compound

Lambertianin D is an ellagitannin found in Rubus lambertianus.

<span class="mw-page-title-main">Sanguisorbic acid</span> Chemical compound

Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid.

<span class="mw-page-title-main">Urolithin A</span> Chemical compound

Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, walnuts, and others.

<span class="mw-page-title-main">Urolithin B</span> Chemical compound

Urolithin B (UB) is an urolithin, a type of phenolic compounds produced in the human gut after absorption of ellagitannins-containing food such as pomegranate, strawberries, red raspberries, walnuts or oak-aged red wine. Urolithin B is found in the urine in the form of urolithin B glucuronide.

References

  1. ↑ "Lambertianin C". PubChem. 2017-07-29.
  2. 1 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.
  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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