ABSTRACT
Several prenylflavonoids have been synthesised and tested against human tumour cell lines. The prenyl unit has been geranyl or a labdane diterpene. These labdane-flavonoids have been synthesised for the first time. The antitumour activity increase with the prenylation at C-8 position. Twenty-three C and O-prenylated acylphloroglucinols have been synthesised as well. In this case the C-alkylation products have resulted, in general, more active.
Subject(s)
Acetophenones/chemical synthesis , Acetophenones/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Flavonoids/chemical synthesis , Flavonoids/pharmacology , Acetophenones/chemistry , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Flavonoids/chemistry , Humans , Inhibitory Concentration 50 , Spectrum AnalysisABSTRACT
Several sesterterpenolides analogues of dysidiolide have been synthesized and their in vitro antitumoural activity against human HeLa, A549, HT-29 and HL-60 carcinoma cells is presented. The proliferation inhibition data showed a significant antitumour activity of the compounds 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5, inhibiting proliferation of distinct cancer cell types with an IC(50) in the low micromolar range.
Subject(s)
4-Butyrolactone/analogs & derivatives , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Terpenes/chemistry , 4-Butyrolactone/chemical synthesis , 4-Butyrolactone/chemistry , 4-Butyrolactone/pharmacology , Aldehydes/chemistry , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Hydroxylation , Ketones/chemistry , Models, Molecular , Molecular Structure , Sesterterpenes , Stereoisomerism , Structure-Activity RelationshipABSTRACT
[Reaction: see text]. The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, was obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.
Subject(s)
Porifera/chemistry , Sesquiterpenes/chemical synthesis , Terpenes/chemical synthesis , Aldehydes/chemistry , Animals , Diterpenes/chemistry , Molecular Conformation , Molecular Structure , Oxidation-Reduction , Photochemistry , Stereoisomerism , Terpenes/chemistryABSTRACT
Incubation of sclareol with Rhizopus stolonifer affords in high yield a mixture of triols with 18-hydroxy-sclareol as the main component.
Subject(s)
Diterpenes/metabolism , Rhizopus/metabolism , Diterpenes/chemistry , HydroxylationABSTRACT
A new route for the degradation of the saturated side chain of dihydrozamoranic acid has been devised, giving an advanced intermediate, compound 14, useful for the synthesis of insect antifeedants such as warburganal and polygodial.
Subject(s)
Diphosphonates/chemistry , Diterpenes/chemistry , Imidazoles/chemistry , Sesquiterpenes/chemistry , Hydrolysis , Models, Chemical , Molecular Structure , Polycyclic Sesquiterpenes , Zoledronic AcidABSTRACT
The bioactive sesterterpenoid gamma-hydroxybutenolides 15,18-bisepi-ent-Cladocoran A and B, 1 and 2, and 15-epi-ent-Cladocoran A and B, 57 and 55, were synthesized from ent-halimic acid. The synthesized sesterterpenolids 2, 55, 57, and 59 inhibited cellular proliferation (IC(50) congruent with 2 micro M) of a number of human leukaemic and solid tumor cell lines.
Subject(s)
Antineoplastic Agents/chemical synthesis , Terpenes/chemical synthesis , Terpenes/pharmacology , 4-Butyrolactone/analogs & derivatives , 4-Butyrolactone/chemistry , 4-Butyrolactone/pharmacology , Antineoplastic Agents/pharmacology , Cell Division/drug effects , Cell Line, Tumor , Humans , Inhibitory Concentration 50 , Protein Tyrosine Phosphatases/antagonists & inhibitors , Sesterterpenes , Stereoisomerism , Structure-Activity RelationshipABSTRACT
Two new diterpenic acids with an ent-halimane skeleton have been isolated from the aerial parts of Halimium viscosum (Villarino de los Aires chemotype) and separated as methyl esters. These diterpenes were 13-oxo-14, 15-dinor-1(10),11E-ent-halimadien-18-oic acid and 15-hydroxy-1(10),13Z-ent-halimadien-18-oic acid.
Subject(s)
Cistaceae/chemistry , Diterpenes/isolation & purification , Plants, Medicinal/chemistry , Diterpenes/chemistry , Esters/chemistry , Nuclear Magnetic Resonance, Biomolecular , Plant Stems/chemistry , Spain , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , StereoisomerismABSTRACT
The benzene extract from the roots of FERULA COMMUNIS afforded the coumarin ferulenol ( 1) and the structurally related acetylenes named ferulinolone [3-(1,2-dihydrofalcarinolonyl)-ferulenol] ( 4) and decarboxyferulinolone [2-nor-3-(1,2-dihydrofal-carinolonyl-ferulenol] ( 7). The structures of these substances were deduced from their spectral data and those of their derivatives, mainly from the (1)H- and (13)C-NMR 1D and 2D spectra (one bond and long-range correlations). Methoxylatifolone ( 10) was also isolated from this extract.
