Ziziphin

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Ziziphin
Ziziphin.png
Names
IUPAC name
(23R)-3β-[α-L-Rhamnopyranosyl-(1→4)-α-L-arabinopyranosyloxy]-16β,23:16α,30-diepoxydammar-24-en-20-yl α-L-rhamnopyranoside 2,3-diacetate
Systematic IUPAC name
(12S,13R,14R,15S,16S,31S,33R,34aS,36aS,36bR,38aR,310S,312aR,312bR,314aR,314bS,52S,53R,54R,55S,72S,73R,74R,75R,76S)-15,53,54,73,74,75-Hexahydroxy-16,31,36b,39,39,312a,76-heptamethyl-33-(2-methylprop-1-en-1-yl)hexadecahydro-36H,38H-2,4,6-trioxa-3(1,10)-[4a,6a]methanophenanthro[2,1-d]pyrano[2,3-b]pyrana-1,7(2),5(2,5)-tris(oxana)heptaphane-13,14-diyl diacetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C51H80O18/c1-23(2)18-28-19-49(11,69-45-41(65-27(6)53)40(64-26(5)52)35(55)25(4)63-45)42-29-12-13-32-47(9)16-15-33(46(7,8)31(47)14-17-48(32,10)50(29)21-51(42,68-28)61-22-50)67-43-38(58)36(56)30(20-60-43)66-44-39(59)37(57)34(54)24(3)62-44/h18,24-25,28-45,54-59H,12-17,19-22H2,1-11H3/t24-,25-,28-,29+,30-,31-,32+,33-,34-,35-,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,47-,48+,49-,50-,51-/m0/s1
    Key: SPFBVQWRJFUDBB-FYBFSNJASA-N
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H]7[C@@](C[C@@H](O[C@@]78C[C@]6([C@@]5(CC[C@H]4C3(C)C)C)CO8)C=C(C)C)(C)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)OC(=O)C)OC(=O)C)C)O)O)O
Properties
C51H80O18
Molar mass 981.17 g/mol
Density 1.345 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ziziphin, a triterpene glycoside which exhibits taste-modifying properties, has been isolated from the leaves of Ziziphus jujuba ( Rhamnaceae ).

Among ziziphin's known homologues found in this plant, it is the most anti-sweet. However, its anti-sweet activity is less effective than gymnemic acid 1, another anti-sweet compound glycoside isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). [1]

Ziziphin reduces perceived sweetness of most of the carbohydrates (e.g. glucose, fructose), bulk sweeteners, intense sweeteners (natural: steviol glycoside – artificial: sodium saccharin and aspartame) and sweet amino acids (e.g. glycine). However, it has no effect on the perception of the other tastes, bitterness, sourness and saltiness. [2]

See also

References

  1. ↑ Kinghorn, A.D. and Compadre, C.M. Alternative Sweeteners: Third Edition, Revised and Expanded, Marcel Dekker ed., New York, 2001. ISBN   0-8247-0437-1
  2. ↑ Kurihara, Y. (1992). "Characteristics of antisweet substances, sweet proteins, and sweetness-inducing proteins". Crit. Rev. Food Sci. Nutr. 32 (3): 231–252. doi:10.1080/10408399209527598. PMID   1418601.
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