Ziziphin

Ziziphin
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
CAS Number	73667-51-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	390526 ;
PubChem CID	441957;
CompTox Dashboard (EPA)	DTXSID00905122 ;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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]

References

^ 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
^ 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.

[Kinghorn-book3-1] 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

[crfsn-32-231-2] 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.

[1]

[2]

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,3^4aS,3^6aS,3^6bR,3^8aR,3¹⁰S,3^12aR,3^12bR,3^14aR,3^14bS,5²S,5³R,5⁴R,5⁵S,7²S,7³R,7⁴R,7⁵R,7⁶S)-1⁵,5³,5⁴,7³,7⁴,7⁵-Hexahydroxy-1⁶,3¹,3^6b,3⁹,3⁹,3^12a,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
CAS Number	73667-51-3^Y
3D model (JSmol)	Interactive image
ChemSpider	390526^N
PubChem CID	441957
CompTox Dashboard (EPA)	DTXSID00905122
SMILES 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
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Ziziphin

See also

References