title: Elegaphenone and 7-epi-clusianone, the major cytotoxic constituents of Hypericum elegans.
abstract: Two cytotoxic constituents, namely elegaphenone and 7-epi-clusianone, were isolated from the aerial parts of Hypericum elegans Stepan ex Willd. Elegaphenone was identified as (E)-(2-(3,7-dimethylocta-2,6-dienyloxy)-4,6-dihydroxyphenyl)(phenyl)methanone by means of spectral evidence. Both compounds showed prominent cytotoxicity on HD-MY-Z, K-562 and KE-37 tumour cell lines. The IC(50) values for elegaphenone were 15.9 (HD-MY-Z), 13.9 (K-562) and 16.9 (KE-37) µmol while those of 7-epi-clusianone were 9.8 (HD-MY-Z), 11.8 (K-562) and 13.6 (KE-37) µmol. The established oligonucleosomal deoxyribonucleic acid (DNA) fragmentation of genomic DNA following short-term (6 h) or long-term (24 h) exposure to the tested compounds clearly indicates that the induction of apoptotic cell death is an important component for their cytotoxic mode of action.
authors.affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Medical University of Sofia, Sofia, Bulgaria. pnedialkov@gmail.com
authors.forename: Paraskev T
authors.initials: PT
authors.lastname: Nedialkov
authors.forename: Dimitrina
authors.initials: D
authors.lastname: Zheleva-Dimitrova
authors.forename: Georgi
authors.initials: G
authors.lastname: Momekov
authors.forename: Kaloyan
authors.initials: K
authors.lastname: Karlov
authors.forename: Ulrich
authors.initials: U
authors.lastname: Girreser
authors.forename: Gerassim M
authors.initials: GM
authors.lastname: Kitanov
mesh_terms: D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology; D053938:DNA Fragmentation / Q000187:drug effects; D006801:Humans; D020902:Hypericum / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008752:Methylene Chloride; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry*; D010936:Plant Extracts / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013997:Time Factors
chemical_list: C118110:7-epiclusianone; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds; D003603:Cytotoxins; D010936:Plant Extracts; D008752:Methylene Chloride