Cytotoxic Constituents from Aquilegia ecalcarata

Abstract

A new alkaloid, 7-hydroxy-4-(5′-hydroxymethylfuran-2′-yl)-2-quinolone (1), and a new nitrile derivative, 3α,4β-dihydroxy-6-oxo-1-cyclohexene-1-acetonitrile (2), together with three known oxoaporphine alkaloids, were isolated from the whole plant of Aquilegia ecalcarata. Their structures were established on the basis of spectral evidence. Their in vitro cytotoxicity against different classes of cancer cell lines, including GLC-82 and HCT were determined. The new alkaloid 1 [IC₅₀ (GLC-82) 8.8 ± 0.2 μM, IC₅₀ (HCT) 10.1 ± 0.3 μM] and hernandonine (3) [IC₅₀ (GLC-82) 7.6 ± 0.5 μM, IC₅₀ (HCT) 8.2 ± 0.5 μM] exhibited cytotoxicity towards the cancer cell lines.

References

• 1 Wu Z Y, Zhou T Y, Xiao P G. Xin Hua Compendium of Materia Medica (I). Shanghai; Shanghai Science & Technology Press 1998: p. 113
• 2 Chen S B, Gao G Y, Leung H Y, Yeung H W, Yang J S, Xiao P G. Aquiledine and isoaquiledine, novel flavonoid alkaloids from Aquilegia ecalcarata .  J. Nat. Prod.. 2001;  64 85-7
• 3 Yu D Q, Yang J S, Handbook of Analytical Chemistry: Analysis of Nuclear Magnetic Resonance S pectra. Beijing; Chemical Industry Press 1999: p. 109-13, 88-91
• 4 Coppola G M, Kahle A D, Shapiro M J. Carbon-13 NMR investigation of some hetero-ring-substituted 2- and 4-quinolone systems.  Org. Magn. Reson.. 1981;  17 242-5
• 5 Cava M P, Stern P, Wakisaka K. An improved photochemical aporphine synthesis: new syntheses of dicentrine and cassameridine.  Tetrahedron. 1973;  29 2245-9
• 6 Sonnet P E, Jacobson M. Tumor inhibitors. II. Cytotoxic alkaloids from Annona purpurea .  J. Pharm. Sci.. 1971;  60 1254-6
• 7 Harrigan G G, Gunatilaka A AL, Kingston D GI, Chan G W, Johnson R K. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea .  J. Nat. Prod.. 1994;  57 68-73
• 8 Scudiero D A, Shoemaker R H, Paull K D, Monks A, Tierney S, Nofziger H ,. et al . Evaluation of a soluble tetrazolium/formazan assay for cell growth and sensitivity in culture using human and other tumor cell lines.  Cancer Research. 1988;  48 4827-33