Asiaticoside, 积雪草苷

Asiaticoside analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Asiaticoside, also known as blastoestimulina or centelase, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b, 19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Asiaticoside exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, asiaticoside is primarily located in the cytoplasm and membrane (predicted from logP). Outside of the human body, asiaticoside can be found in green vegetables and herbs and spices. This makes asiaticoside a potential biomarker for the consumption of these food products.

Asiaticoside is a natural compound that has been shown to have physiological effects on the skin. It has been found to have anti-cancer properties and can be used for the treatment of skin cancer. In vitro assays have shown that asiaticoside inhibits the growth of cervical cancer cells, which may be due to its ability to inhibit lipid peroxidation and scavenge reactive oxygen species. Asiaticoside also has anti-inflammatory properties and can be used in the treatment of acne vulgaris. Asiaticoside is a component of madecassol, which is an herbal medicine traditionally used in China for the relief of pain associated with arthritis. Madecassol contains various components, including asiaticoside, madecassic acid, and madecassoside. This herbal medicine is often taken orally or applied topically to relieve pain and inflammation associated with arthritis or rheumatism.

Title: Asiaticoside

CAS Registry Number: 16830-15-2

CAS Name: (2a,3b,4a)-2,3,23-Trihydroxyurs-12-en-28-oic acid O-6-deoxy-a-L-mannopyranosyl-(1®4)-O-b-D-glucopyranosyl-(1®6)-O-b-D-glucopyranosyl ester

Molecular Formula: C48H78O19

Molecular Weight: 959.12

Percent Composition: C 60.11%, H 8.20%, O 31.69%

Literature 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.

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

Melting point: mp 230-233°

Optical Rotation: [a]D20 -14° (alc)