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
Name Gymnemic acid I Gymnemic acid II Gymnemic acid III Gymnemic acid IV
R1 tigloyl 2-methylbutanoyl 2-methylbutanoyl tigloyl
R2 acetyl acetyl H H
CAS Number 122168-40-5 122144-48-3 122074-65-1 121903-96-6
PubChem ID 11953919 91617872 14264066 14264063
Chemical formula C43H66O14 C43H68O14 C41H66O13 C41H64O13
Molar mass (g/mol) 806.98 809.00 766.97 764.95

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): 704–708. 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): 543–593. doi:10.1039/C0NP00059K. PMID 21290067.
  4. ^ A. Douglas Kinghorn and Cesar M. Compadre (1991). Lyn O'Brien Nabors and Robert C. Gelardi (ed.). Less common high-potency sweeteners (2nd ed.). New York: Marcel Dekker. ISBN 0-8247-8475-8. {{cite book}}: |work= ignored (help)
  5. ^ a b 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.