Gymnemic acid

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Gymnemic acids are a class of chemical compounds isolated from the leaves of Gymnema sylvestre (Apocynaceae). They are anti-sweet compounds, or sweetness inhibitors.[1] After chewing the leaves, solutions sweetened with sugar taste like water.

Chemically, gymnemic acids are triterpenoid glycosides. The central structure is the aglycone gymnemagenin (C30H50O6).[2] This is adorned with a sugar such as glucuronic acid and with various ester groups. These variations give rise to the different gymnemic acids.[3] More than 20 homologs of gymnemic acid are known.[4]

Gymnemic acid I has the highest anti-sweet properties. It suppresses the sweetness of most of the sweeteners including intense artificial sweeteners such as aspartame and natural sweeteners such as thaumatin, a sweet protein. The anti-sweet activity is reversible, but sweetness recovery on the tongue can take more than 10 minutes.[5]

Example chemical structures

More information Chemical structure, Name ...
Gymnemic acids[5]
Chemical structure
NameGymnemic acid IGymnemic acid IIGymnemic acid IIIGymnemic acid IV
R1tigloyl2-methylbutanoyl2-methylbutanoyltigloyl
R2acetylacetylHH
CAS Number122168-40-5122144-48-3122074-65-1121903-96-6
PubChem ID11953919916178721426406614264063
Chemical formulaC43H66O14C43H68O14C41H66O13C41H64O13
Molar mass (g/mol)806.98809.00766.97764.95
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See also

Other anti-sweeteners:

  • Hodulcine, a dammarane-type triterpene glycoside from the leaves of Hovenia dulcis
  • Lactisole, sodium 2-(4-methoxyphenoxy)propanoate
  • Ziziphin, a triterpene glycoside, C51H80O18
  • Gurmarin

References

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