Triterpenoid Saponins with Anti-Inflammatory Activity from Codonopsis lanceolata

Abstract

Six triterpenoid saponins, including a new compound named codonolaside III, were isolated from the roots of Codonopsis lanceolata. The spectral and chemical data revealed the structure of codonolaside III to be 3-O-[β-D-xylopyranosyl -(1→3)-β-D-glucuronopyranosyl]-3β,16α-dihydroxyolean-12-ene-28-oic acid 28-O-[β-D-xylopyranosyl-(1→4)-α-L-rhamnpyranosyl-(1→2)][β-D-glucopyranosyl -(1→4)]-α-L-arabinopyranosyl ester. The xylene-induced mouse ear edema inhibitory effect assay disclosed codonolaside and codonolasides I – III as the major anti-inflammatory constituents in this crude drug.

Key words

Codonopsis lanceolata Benth. et Hook. - Campanulaceae - triterpenoid saponins - anti-inflammatory activity

References

• 1 Jiangsu New Medical College. Dictionary of Chinese Materia Medica. Shanghai; Shanghai Science and Technology Publisher 1977: 1956
• 2 Li J P, Liang Z M, Yuan Z. Triterpenoid saponins and anti-inflammatory activity of Codonopsis lanceolata.  Pharmazie. 2007;  62 463-7
• 3 Yuan Z, Liang Z. A new triterpenoid saponin from Codonopsis lanceolata.  Chin Chem Lett. 2006;  17 1460-3
• 4 Ushijima M, Komoto N, Sugizono Y, Mizuno I, Sumhiro M, Ichikawa M. et al . Triterpene glycosides from the roots of Codonopsis lanceolata.  Chem Pharm Bull. 2008;  56 308-14
• 5 Lee K T, Choi J, Jun W T, Nam J H, Jung H J, Park H J. Structure of a new echinocystic acid bisdesmoside isolated from Codonopsis lanceolata roots and the cytotoxic activity of prosapogenins.  J Agric Food Chem. 2002;  50 4190-3
• 6 Han C J, Han L Z, Ye M, Li L J, Han Y. Experimental studies on the anti-mutagenic effect of the total saponin of Codonopsis lanceolata.  J Environ Occup Med. 2004;  21 397-401
• 7 Han L Z, Han C J, Ye M, Cui X S. Inhibitory effects of Codonopsis lanceolata saponins on micronuclei of bone marrow induced by cyclophosphamide in mice.  J Med Sci Yanbian Univ. 2003;  26 9-12
• 8 Lee K W, Jung H J, Park H J, Kim D G, Lee J Y, Lee K T. β-D-Xylopyranosyl-(1→3)-β-D-glucuronopyranosylechinocystic acid isolated from the roots of Codonopsis lanceolata induces caspase-dependent apoptosis in human acute promyelocytic leukemia HL-60 cells.  Biol Pharm Bull. 2005;  28 854-9
• 9 Zhang Z, Koike K, Jia Z, Nikaido T, Guo D, Zheng J. Triterpenoidal saponins acylated with two monoterpenic acids from Gleditsia sinensis.  Chem Pharm Bull. 1999;  47 388-93
• 10 Li W, Asada Y, Koike K, Furuya T, Yoshikawa T. Bellisosides A – F, six novel acylated triterpenoid saponins from Bellis perennis (Compositae).  Tetrahedron. 2005;  61 2921-9
• 11 Liang Z M, Lin Z, Yuan Z. Studies on chemical constituents of Codonopsis lanceolata. China J Chin Mater Med 2007: 1363-4
• 12 Gu K, Bi L, Zhao M. Toward the development of chemoprevention agents. Part II: Chemo-enzymatic synthesis and anti-inflammatory activities of a new class of 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes.  Bioorg Med Chem. 2007;  15 6273-90