ABSTRACT
A new quassinoid, ailantinol H, was isolated from a methanol extract of the aerial parts of Ailanthus altissima collected in Taiwan. Its structure was established on the basis of 1D and 2D NMR and HREIMS spectroscopic methods.
Subject(s)
Ailanthus/chemistry , Plant Extracts/isolation & purification , Quassins , Mass Spectrometry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Optical Rotation , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Quassins/chemistry , Quassins/isolation & purification , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , TaiwanABSTRACT
A new quassinoid, ailantinol H, was isolated from the aerial parts of Ailanthus altissima. The structure was elucidated based on spectral evidence.
Subject(s)
Ailanthus/chemistry , Plant Extracts/isolation & purification , Quassins/isolation & purification , Mass Spectrometry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Optical Rotation , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Quassins/chemistry , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , TaiwanABSTRACT
Twenty-three quassinoids (1-23), which were isolated previously from Simaroubaceous plants, were evaluated for cytotoxicity against three multidrug-resistant cancer cell lines, KB-VIN, KB-7d, and KB-CPT. Nine compounds (2-7 and 9-11) showed significant cytotoxicity in all three cell lines. Compounds 1, 12-14, 17, and 20 demonstrated significant activity against the KB-7d and KB-CPT cell lines, and compounds 18, 19, and 23 revealed notable activity only against KB-7d cells. Structure-activity relationships were drawn based on these data. In addition, six quassinoid derivatives (24-29) and four canthin alkaloids (30-33), which were isolated from Brucea antidysenterica, were examined for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation as cancer chemopreventive agents. All of these compounds demonstrated significant inhibitory effects against EBV-EA activation.
Subject(s)
Alkaloids/pharmacology , Cytotoxins/pharmacology , Drug Resistance, Multiple/drug effects , Drug Resistance, Neoplasm/drug effects , Quassins/pharmacology , Alkaloids/chemistry , Alkaloids/isolation & purification , Cell Line, Tumor , Chemoprevention/methods , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Drug Resistance, Multiple/physiology , Drug Resistance, Neoplasm/physiology , Humans , Quassins/chemistry , Quassins/isolation & purificationABSTRACT
Three new quassinoids, ailantinol E (1), ailantinol F (2), and ailantinol G (3), and related compounds were isolated from Ailanthus altissima grown in Taiwan. Their structures were elucidated from spectral evidence. Each new quassinoid was evaluated for its antitumor promoting effects against Epstein-Barr virus early antigen activation introduced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The new quassinoids were found to show potent activity without showing any cytotoxicity. The screening for inhibitors against nitric oxide donor action was also conducted using the new quassinoids and some standard samples.
Subject(s)
Ailanthus , Antineoplastic Agents/isolation & purification , Quassins/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Herpesvirus 4, Human/drug effects , Humans , Plant Components, Aerial , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Stems , Quassins/chemistry , Quassins/pharmacology , Tumor Cells, CulturedABSTRACT
Twelve taxane diterpenes (1-12), which were isolated previously from the EtOH extract of the aerial parts of Taxus yunnanensis or Taxus chinensis, were evaluated for cytotoxicity against the multidrug resistant cancer cells KB-VIN and KB-7d. Compounds and showed significant cytotoxicity in these cell lines. Compounds and also demonstrated significant activity against KB-7d. The biflavonoid isolated from T. yunnanensis was only marginally cytotoxic against the A549 (lung) cell line, but a simple methoxylated analogue (14) was inactive.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Bridged-Ring Compounds/pharmacology , Diterpenes/pharmacology , Taxoids , Taxus/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Bridged-Ring Compounds/chemistry , Cell Survival/drug effects , Diterpenes/chemistry , Drug Resistance, Multiple , Drug Resistance, Neoplasm , Drug Screening Assays, Antitumor , Flavonoids/pharmacology , Humans , Magnetic Resonance Spectroscopy , Plant Epidermis/chemistry , Plant Leaves/chemistry , Tumor Cells, CulturedABSTRACT
A series of shinjulactone C (1) derivatives (2-8) were synthesized and evaluated for their anti-tumor promoting effects against Epstein-Barr virus early antigen activation introduced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The succinate and 3',3'-dimethylsuccinate derivatives of 1 exhibited higher inhibitory effects than 1. From the point of view of structure-activity relationships, the succinate derivatives (2, 4) demonstrated better potency than the glutarate derivatives (3, 5-8). As substituted moieties of 3'-position became bulky, the inhibitory effects of the glutarate derivatives (7, 8) significantly decreased.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Epstein-Barr Virus Infections/prevention & control , Herpesvirus 4, Human/drug effects , Lactones/pharmacology , Quassins/pharmacology , Virus Activation/drug effects , Antigens, Viral/metabolism , Antineoplastic Agents, Phytogenic/isolation & purification , Chemoprevention , Dose-Response Relationship, Drug , Herpesvirus 4, Human/physiology , Humans , Inhibitory Concentration 50 , Lactones/isolation & purification , Plant Bark/chemistry , Structure-Activity Relationship , Tetradecanoylphorbol Acetate/pharmacology , Tumor Cells, CulturedABSTRACT
Two new taxane diterpenes, dantaxusin C (1) and dantaxusin D (2), were isolated from an ethanol extract of the aerial parts of Taxus yunnanensis along with 14 known taxoids. All structures were established on the basis of 1D and 2D NMR and HREIMS spectroscopic methods.
