Gymnemic acid

Gymnemic acids are a class of chemical compounds isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). 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
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

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
  1. Stoecklin, Walter (1969). "Chemistry and physiological properties of gymnemic acid, the antisaccharine principle of the leaves of Gymnema sylvestre". Journal of Agricultural and Food Chemistry. 17 (4): 704. doi:10.1021/jf60164a011.
  2. CID 10051937 from PubChem
  3. Sheng, Huaming; Sun, Hongbin (2011). "Synthesis, biology and clinical significance of pentacyclic triterpenes: A multi-target approach to prevention and treatment of metabolic and vascular diseases". Natural Product Reports. 28 (3): 543. doi:10.1039/C0NP00059K. PMID 21290067.
  4. AD kinghorn and CM Compadre (1991). L O'Brien Nabors (ed.). Less common high-potency sweeteners. Alternative Sweeteners (2nd ed.). New York: Marcel Dekker. ISBN 0-8247-8475-8.
  5. Kurihara, Yoshie (1992). "Characteristics of antisweet substances, sweet proteins, and sweetness‐inducing proteins". Critical Reviews in Food Science and Nutrition. 32 (3): 231–52. doi:10.1080/10408399209527598. PMID 1418601.
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