833. Asiaticoside

Nomenclature

CAS number: 16830-15-2
(2α,3β,4α)-2,3,23-Trihydroxyurs-12-en-28-oic acid O-6-deoxy-α-l-mannopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester.
C48H78O19; mol wt 959.12.
C 60.11%, H 8.20%, O 31.69%.

Description and references

Active principle of Centella asiatica (L.) Urban, Umbelliferae. Trisaccharide moiety linked to the aglycone: asiatic acid. Isoln: J.-E. Bontems, Bull. Sci. Pharmacol. 49, 186 (1941), C.A. 38, 4094 (1944); idem, Gaz. Med. Madagascar 5, 29 (1942). Structure of asiatic acid: J. Polonsky, Bull. Soc. Chim. Fr. 1953, 173. Structure of asiaticoside: P. Boiteau et al., Nature 163, 258 (1949); J. Polonsky et al., Bull. Soc. Chim. Fr. 1959, 880. Metabolism: L. F. Chasseaud et al., Arzneim.-Forsch. 21, 1379 (1971). Wound healing properties: H. Rosen et al., Proc. Soc. Exp. Biol. Med. 125, 279 (1967). Clinical study: J.-P. Bosse et al., Ann. Plast. Surg. 3, 13 (1979). Review on asiatic acid: J. L. Simonsen, W. C. J. Ross, The Terpenes vol. 5 (University Press, Cambridge, 1957) pp 58-67.

Chemical structure

Properties

Minute needles from 60% methanol, mp 230-233°. Insol in water. Sol in alcohol, pyridine. [α]D20 14° (alc).