ABSTRACT
A new spiro heterocycle, decarboxyportentol acetate (1) was isolated from the barks of Laumoniera bruceadelpha Nooteboom (Simaroubaceae), together with 3,4-dehydrotheaspirone (2), and their structures were elucidated by 2D NMR analysis. 3,4-Dehydrotheaspirone (2) showed potent antiplasmodial activity against Plasmodium falciparum 3D7.
Subject(s)
Antimalarials/pharmacology , Simaroubaceae/chemistry , Spiro Compounds/pharmacology , Antimalarials/chemistry , Molecular Structure , Plasmodium falciparum/drug effects , Spiro Compounds/chemistryABSTRACT
Three new alkaloids, cassiarins C-E (1-3), and a new chromone, 10,11-dihydroanhydrobarakol (4), which showed moderate antiplasmodial activity against Plasmodium falciparum 3D7, were isolated from flowers of Cassia siamea, and the structures of 1-4 were elucidated by 2D NMR analysis and chemical transformation. Cassiarin D (2) was a dimeric compound consisting of 5-acetonyl-7-hydroxy-2-methylchromone and cassiarin C (1), and cassiarin E (3) was a dimer of cassiarins A and C (1).
Subject(s)
Alkaloids/isolation & purification , Alkaloids/pharmacology , Antimalarials/isolation & purification , Antimalarials/pharmacology , Cassia/chemistry , Heterocyclic Compounds, 3-Ring/isolation & purification , Heterocyclic Compounds, 3-Ring/pharmacology , Plasmodium falciparum/drug effects , Alkaloids/chemistry , Animals , Antimalarials/chemistry , Flowers/chemistry , Heterocyclic Compounds, 3-Ring/chemistry , Indonesia , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Parasitic Sensitivity TestsABSTRACT
New quassinoids, delaumonones A (1) and B (2) have been isolated from the bark of Laumoniera bruceadelpha NOOTEBOOM (Simaroubaceae) and the structures were elucidated by 2D NMR analysis and a chemical correlation. Delaumonones showed an antimalarial activity against Plasmodium falciparum.
Subject(s)
Antimalarials/isolation & purification , Antimalarials/pharmacology , Plasmodium falciparum/drug effects , Quassins/isolation & purification , Quassins/pharmacology , Simaroubaceae/chemistry , Animals , Antimalarials/chemistry , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Magnetic Resonance Spectroscopy/standards , Models, Molecular , Molecular Conformation , Parasitic Sensitivity Tests , Plant Bark/chemistry , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Quassins/chemistry , Reference Standards , StereoisomerismABSTRACT
A new bischromone, chrobisiamone A (1) with an antiplasmodial activity has been isolated from the leaves of Cassia siamea and the structure was elucidated by 2D NMR analysis. Cyclization of 5-acetonyl-7-hydroxy-2-methylchromone (2) in the presence of ammonium acetate resulted in generation of cassiarin A (3) with an unprecedented tricyclic skeleton, supporting a biogenetic pathway proposed for 3.
Subject(s)
Antimalarials/pharmacology , Cassia/metabolism , Chromones/chemistry , Heterocyclic Compounds, 3-Ring/chemistry , Plant Extracts/chemistry , Biomimetics , Chemistry, Pharmaceutical/methods , Chromones/chemical synthesis , Chromones/pharmacology , Drug Design , Magnetic Resonance Spectroscopy , Malaria/prevention & control , Models, Chemical , Models, Molecular , Plant Leaves/metabolismABSTRACT
From the fruits of Phaleria macrocarpa, icariside C(3) (1), phalerin (2), and mangiferin (3) were isolated and their structures were identified on the basis of spectroscopic data. Icariside C(3) (1) showed a slow vasorelaxant activity against noradrenaline-induced contraction of isolated rat aorta. The structure of phalerin (2) was revised as 2,4',6-trihydroxy-4-methoxybenzophenone-2-O-beta-D-glucoside.
Subject(s)
Benzophenones/isolation & purification , Fruit/chemistry , Glucosides/isolation & purification , Sesquiterpenes/isolation & purification , Thymelaeaceae/chemistry , Xanthones/isolation & purification , Animals , Aorta, Thoracic/drug effects , Aorta, Thoracic/physiology , Benzophenones/chemistry , Benzophenones/pharmacology , Glucosides/chemistry , Glucosides/pharmacology , In Vitro Techniques , Male , Muscle, Smooth, Vascular/drug effects , Muscle, Smooth, Vascular/physiology , Norepinephrine/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Rats , Rats, Wistar , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Vasoconstriction/drug effects , Vasodilation/drug effects , Vasodilator Agents/pharmacology , Xanthones/chemistry , Xanthones/pharmacologyABSTRACT
Two novel alkaloids with an unprecedented tricyclic skeleton, cassiarins A (1) and B (2), have been isolated from the leaves of Cassia siamea, and the structures were elucidated on the basis of spectroscopic data. Cassiarin A (1) showed a potent antiplasmodial activity.