(2,4-cis)-asimicinone and (2,4-trans)-asimicinone: two novel bioactive ketolactone acetogenins from Asimina triloba (Annonaceae).
Two novel bioactive ketolactone Annonaceous acetogenins, (2,4-cis)-asimicinone (1) and (2,4-trans)-asimicinone (2), have been isolated from Asimina triloba (Annonaceae) by bioactivity directed fractionation. The separation of these two epimeric compounds was achieved by HPLC methods using a Si gel normal phase column eluted with acetone in hexane gradients. The assignments of cis or trans stereochemistry of the ketolactone moieties were made on the bases of 1H-1H COSY and NOESY experiments. 1 and 2 showed selective cytotoxicities against A-549 (human lung cancer) and MCF-7 (human breast cancer) cell lines with ED50 values as low as < 10(-7) micrograms/ml with 2 being the more active isomer.
Zhao
G X
GX
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
Chao
J F
JF
Zeng
L
L
McLaughlin
J L
JL
D000107:Acetylation; D000818:Animals; D001156:Artemia / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000633:toxicity; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008970:Molecular Weight; D018547:Plant Stems / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014118:Toxins, Biological / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity
D005663:Furans; D007783:Lactones; D014118:Toxins, Biological; C061021:bullatacinone