Two new pregnanone derivatives with strong cytotoxic activity from Pachysandra axillaris.
Two new, bioactive, pregnane-based natural products, pachysanonin (= 3beta,11alpha,12beta)-12-acetoxy-3-(dimethylamino)-11-[(3,4-dimethylpent-3-enoyl)oxy]pregnan-20-one; 1) and pachysanone (= (11alpha,12beta)-12-acetoxy-11-[(3,4-dimethylpent-3-enoyl)oxy]pregnan-3,20-dion; 2) have been isolated from Pachysandra axillaris. Their structures were determined by spectroscopic methods, and, in the case of 2, by single-crystal X-ray crystallography (Figure). Compound 2 showed significant antitumor activity against Lewis lung carcinoma (LCC) tumor cells, with an IC50 value of 0.020+/-0.006 microg/ml, which is equal or even lower than those of the well-known natural antitumor agents harringtonine (0.02), homoharringtonine (0.15), and adriamycin (0.06 microg/ml; positive control).
Qiu
Ming-Hua
MH
Laboratory of Phytochemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China. mhchiu@public.km.yn.cn
Nakamura
Norio
N
Min
Byung-Sun
BS
Hattori
Masao
M
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D031236:Pachysandra / Q000737:chemistry*; D011277:Pregnanediones / Q000737:chemistry* / Q000494:pharmacology*; D011280:Pregnanolone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
C516962:12-acetoxy-11-((3,4-dimethylpent-3-enoyl)oxy)pregnan-3,20-dione; C516961:12-acetoxy-3-(dimethylamino)-11-((3,4-dimethylpent-3-enoyl)oxy)pregnan-20-one; D000972:Antineoplastic Agents, Phytogenic; D011277:Pregnanediones; D011280:Pregnanolone