ABSTRACT
Phytochemical investigation of the EtOAc soluble fraction from leaves of Trichilia dregeana Sond. (Meliaceae) afforded naturally rare four new pentacyclic triterpenoids (1-4), together with five known pentacyclic analogs (5-8, and 11) and two steroids (9 and 10). Their structures were elucidated by extensive spectroscopic techniques such as 1D and 2D NMR and HRESIMS data analyses. The absolute configuration of 1 was determined by using the single-crystal X-ray diffraction analysis. The nitric oxide (NO) production inhibitory assay indicated that the EtOAc fraction as well as 4 and 7 inhibited the NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with the IC50 values of 83.53 µg/mL and 81.31 and 85.71 µM, respectively. Compounds 1-4 are rare 19(10 â 9)abeo-euphane-type triterpenoids bearing a 3,10-ether bridge. To the best of our knowledge, this study is the first isolation of triterpenoids with the 3,10-ether bridge in their skeleton from the genus Trichilia, providing new insights into the chemodiversity of the terpenoids in T. dregeana.
Subject(s)
Meliaceae , Nitric Oxide , Phytochemicals , Plant Leaves , Triterpenes , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/metabolism , Nitric Oxide/biosynthesis , Plant Leaves/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacology , Triterpenes/chemistry , Mice , Animals , RAW 264.7 Cells , Meliaceae/chemistry , Molecular Structure , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , ChinaABSTRACT
Phytochemical investigation of the seeds of Salacia longipes var. camerunensis led to the isolation of four sesquiterpenoid derivatives, salaterpene A (1) (1α,2ß,8ß-triacetoxy-6ß,9ß-dibenzoyloxy-4ß-hydroxy-dihydro-ß-agarofuran), salaterpene B (2) (1α,2ß,8ß-triacetoxy-9ß-benzoyloxy-6ß-cinnamoyloxy-4ß-hydroxy-dihydro-ß-agarofuran), salaterpene C (3) (1α,2ß-diacetoxy-6ß,9ß-dibenzoyloxy-4ß-hydroxy-dihydro-ß-agarofuran) and salaterpene D (4) (2ß-acetoxy-1α,6ß-dibenzoyloxy-4ß-hydroxy-9ß-nicotinoyloxy-dihydro-ß-agarofuran) together with two known compounds (5 and 6). The structures of the compounds were established by means of NMR spectroscopy. Compounds 1-4 and 6 were tested in vitro for their antiplasmodial activity against Plasmodium falciparum chloroquine-resistant strain W2. All the tested compounds exhibited a moderate potency with IC50 below 2.7 µM.
Subject(s)
Chloroquine/pharmacology , Plasmodium falciparum/drug effects , Salacia/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Cameroon , Disease Resistance/drug effects , Erythrocytes/drug effects , Humans , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Seeds/chemistry , Sesquiterpenes/chemistryABSTRACT
Phytochemical investigation of the figs of Ficus mucuso led to the isolation of three new isoflavone dimer derivatives, mucusisoflavones A-C (1-3), together with 16 known compounds. Some of the isolates were tested in vitro for their inhibitory properties toward ß-glucuronidase and Plasmodium falciparum enoyl-ACP reductase (PfENR) enzymes. Compound 1 (IC50) 0.68 µM) showed inhibitory activity on ß-glucuronidase enzyme, while 3 (IC50) 7.69 µM) exhibited a weak inhibitory activity against P. falciparum enoyl-ACP reductase (PfENR).
