ABSTRACT
A new limonoid, swietemacrophin (1), was isolated from the seeds of Swietenia macrophylla, together with five known compounds 2-6. The structure of 1 was determined through extensive 1D/2D-NMR and mass-spectrometric analyses. Swietemacrophin (1), humilinolide F (2), 3,6-O,O-diacetylswietenolide (3), 3-O-tigloylswietenolide (4), and swietemahonin E (5) exhibited inhibition (IC50 values≤45.44 µM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP). Compounds 1, 4, 5, and swietenine (6) showed potent inhibition with IC50 values≤36.32 µM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Limonins/isolation & purification , Meliaceae/chemistry , Seeds/chemistry , Triterpenes/isolation & purification , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Humans , Inhibitory Concentration 50 , Limonins/chemistry , Limonins/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , N-Formylmethionine Leucyl-Phenylalanine/analogs & derivatives , N-Formylmethionine Leucyl-Phenylalanine/antagonists & inhibitors , N-Formylmethionine Leucyl-Phenylalanine/pharmacology , Neutrophils/cytology , Neutrophils/drug effects , Neutrophils/metabolism , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Plant Extracts/chemistry , Primary Cell Culture , Structure-Activity Relationship , Superoxides/antagonists & inhibitors , Triterpenes/chemistry , Triterpenes/pharmacologyABSTRACT
Two new biphenyl-type neolignan derivatives, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1) and 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), were isolated from the twigs of Magnolia denudata, together with six known compounds (3-8). The structures of 1 and 2 were determined through extensive 1D- and 2D-NMR and mass-spectrometric analyses. Magnolol (6) and honokiol (7) exhibited potent inhibition (IC50 values=4.4±0.2 and 0.71±0.13â µg/ml, resp.) of O$\rm{{_{2}^{{^\cdot} -}}}$ generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). In addition, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1), 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), magnolol (6), and vanillic acid (8) inhibited fMLP/CB-induced elastase release with IC50 values=6.4±1.5, 2.4±0.4, 1.5±0.2, and 4.8±0.5â µg/ml, respectively.
Subject(s)
Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Biphenyl Compounds/chemistry , Biphenyl Compounds/pharmacology , Lignans/chemistry , Lignans/pharmacology , Magnolia/chemistry , Adult , Anti-Inflammatory Agents/isolation & purification , Biphenyl Compounds/isolation & purification , Humans , Lignans/isolation & purification , Neutrophils/drug effects , Neutrophils/immunology , Superoxides/immunology , Young AdultABSTRACT
Three new coumarin derivatives, 8-formylalloxanthoxyletin (1), avicennone (2), and (Z)-avicennone (3), have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae), together with 15 known compounds (4-18). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4, 9, 12, and 15 exhibited inhibition (half maximal inhibitory concentration (IC50) values ≤7.65 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, 4, 8 and 9 inhibited fMLP/CB-induced elastase release with IC50 values ≤8.17 µg/mL. This investigation reveals bioactive isolates (especially 1, 2, 4, 8, 9, 12 and 15) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.
Subject(s)
Coumarins/pharmacology , Inflammation/pathology , Neutrophils/immunology , Plant Bark/chemistry , Plant Stems/chemistry , Zanthoxylum/chemistry , Adult , Coumarins/chemistry , Coumarins/isolation & purification , Cytochalasin B/pharmacology , Humans , Magnetic Resonance Spectroscopy , N-Formylmethionine Leucyl-Phenylalanine/analogs & derivatives , N-Formylmethionine Leucyl-Phenylalanine/pharmacology , Neutrophils/drug effects , Superoxides/metabolism , Young AdultABSTRACT
Muntingia calabura (Tiliaceae) is commercially used in healthcare for the improvement of hypertension, myocardial infarction, spasm, and inflammatory conditions. Its fruits can be processed into jam and the leaves can be used for making tea. In the work reported herein a new biflavan, (M),(2S),(2''S)-,(P),(2S),(2''S)-7,8,3',4',5',7'',8'',3''',4''',5'''-decamethoxy-5,5'' biflavan (1), a new flavone, 4'-hydroxy-7,8,3',5'-tetramethoxyflavone (2), and a new dihydrochalcone, (R)-2',ß-dihydroxy-3',4'-dimethoxydihydrochalcone (3), have been isolated from the stem wood of M. calabura, together with 12 known compounds (4-15). The structures of these new compounds were elucidated by the interpretations of extensive spectroscopic data. Among the isolated compounds, 5-hydroxy-7-methoxyflavone (5), quercetin (6), and (2S)-7-hydroxyflavanone (10) exhibited potent inhibition of fMLP-induced superoxide anion generation by human neutrophils, with IC50 values of 1.77 ± 0.70, 3.82 ± 0.46, and 4.92 ± 1.71 µM, respectively.
ABSTRACT
Two new thymol (=5-methyl-2-(1-methylethyl)phenol) derivatives, 8,10-didehydro-9-(3-methylbutanoyl)thymol 3-O-tiglate (1) and 9-O-angeloyl-8-methoxythymol 3-O-isobutyrate (2), were isolated from the root of Eupatorium cannabinum ssp. asiaticum, together with six known compounds, 3-8. The structures of 1 and 2 were determined through extensive 1D/2D-NMR and MS analyses. Among the isolates, 9-acetoxy-8,10-epoxythymol 3-O-tiglate (3) was the most cytotoxic, with IC50 values of 0.02±0.01, 1.02±0.07, and 1.36±0.12â µg/ml, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines. In addition, 10-acetoxy-9-O-angeloyl-8-hydroxythymol (4) and eupatobenzofuran (6) exhibited cytotoxicities, with IC50 values of 1.14±0.16 and 2.63±0.22, and 7.63±0.94 and 2.31±0.14â µg/ml, respectively, against DLD-1 and CCRF-CEM cell lines.
Subject(s)
Eupatorium/chemistry , Plant Roots/chemistry , Thymol/isolation & purification , Cell Line , Drug Screening Assays, Antitumor , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Thymol/chemistry , Thymol/pharmacologyABSTRACT
A new dihydroagarofuran-based sesquiterpene, microjaponin (1), was isolated from the stem of Microtropis japonica. Its structure was determined by in-depth spectroscopic and mass-spectrometric analyses. Microjaponin (1) exhibited potent in vitro antituberculosis activity, with an MIC value of 12.5 µg/ml against Mycobacterium tuberculosis H37 Rv.
Subject(s)
Antitubercular Agents/chemistry , Antitubercular Agents/pharmacology , Benzoates/chemistry , Benzoates/pharmacology , Celastraceae/chemistry , Sesquiterpenes, Eudesmane/chemistry , Sesquiterpenes, Eudesmane/pharmacology , Antitubercular Agents/isolation & purification , Benzoates/isolation & purification , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Mycobacterium tuberculosis/drug effects , Plant Stems/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes, Eudesmane/isolation & purification , Spectrometry, Mass, Electrospray IonizationABSTRACT
The fruit of Cnidium monnieri is commercially used as healthcare products for the improvement of impotence and skin diseases. Three new coumarins, 3'-O-methylmurraol (1), rel-(1'S,2'S)-1'-O-methylphlojodicarpin (2), and (1'S,2'S)-1'-O-methylvaginol (3), have been isolated from the fruits of C. monnieri, together with 14 known compounds (4-17). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4-12, and 14-17 exhibited inhibition (IC50 ≤ 7.31 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7, 9-11, 15, and 17 inhibited fMLP/CB-induced elastase release with IC50 values ≤7.83 µg/mL. This investigation reveals that bioactive isolates (especially 6, 7, 14, and 17) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.
Subject(s)
Anti-Inflammatory Agents/chemistry , Cnidium/chemistry , Coumarins/chemistry , Fruit/chemistry , Adult , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Cell Degranulation/drug effects , Coumarins/isolation & purification , Coumarins/pharmacology , Humans , Neutrophils/drug effects , Neutrophils/immunology , Neutrophils/physiology , Pancreatic Elastase/immunology , Superoxides/immunology , Young AdultABSTRACT
A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known compounds (4-14). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, decarine (4), (-)-syringaresinol (6), (+)-episesamin (8), glaberide I (9), (-)-dihydrocubebin (10), and xanthyletin (11) exhibited potent inhibition (IC50 values ≤ 4.79 µg/mL) of superoxide anion generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 4, 8, and 11 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 5.48 µg/mL.
Subject(s)
Benzoates/chemistry , Benzophenanthridines/pharmacology , Cinnamates/chemistry , Hydroxybutyrates/chemistry , Neutrophils/drug effects , Zanthoxylum/chemistry , Benzophenanthridines/chemistry , Benzophenanthridines/isolation & purification , Humans , Superoxides/antagonists & inhibitorsABSTRACT
Reactive oxygen species (ROS) and granule proteases produced by human neutrophils contribute to the pathogenesis of inflammatory diseases. The MeOH extract of the stem bark of Magnolia officinalis showed potent inhibitory effects on superoxide anion generation and elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Five biphenyl-type neolignan derivatives, 5-allyl-5'-(1â³-hydroxyallyloxy)biphenyl-2,2'-diol, 5,5'-diallyl-2'-(allyloxy)biphenyl-2-ol, 5,5'-diallyl-2'-(3-methylbut-2-enyloxy)biphenyl-2-ol, (E)-5-allyl-3'-(prop-1-enyl)biphenyl-2,4'-diol, and 4-allyl-2-(2'-methylbenzofuran-5'-yl)phenol, have been isolated from the stem bark of M. officinalis, together with 12 known compounds. Several exhibited inhibition (IC50) values ≤10.7 µM) of superoxide anion generation by human neutrophils in response to fMLP/CB. Others inhibited fMLP/CB-induced elastase release with IC50) values ≤8.76 µM.
Subject(s)
Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Lignans/chemistry , Lignans/pharmacology , Magnolia/chemistry , Adult , Cells, Cultured , Humans , Molecular Structure , Young AdultABSTRACT
Six aporphine alkaloids, (+)-(S)-N-butyrylcaaverine (1), (+)-(S)-N-propionylcaaverine (2), (+)-(S)-N-acetylcaaverine (3), (+)-(6aR,7R)-N-butyrylnorushinsunine (4), (+)-(6aR,7R,E)-N-(but-2-enoyl)norushinsunine (5), and N-formyldehydrocaaverine (6) were isolated from the roots of Illigera luzonensis, together with 16 known compounds. Their structures were determined through spectroscopic and MS analyses. Among the isolates, (-)-deoxypodophyllotoxin (13) was the most cytotoxic, with IC(50) values of 0.0057, 0.0067, 0.00004, and 0.0035µg/mL, respectively, against DLD-1, CCRF-CEM, HL-60, and IMR-32 cell lines. In addition, (-)-yatein (12) exhibited cytotoxic effects, with IC(50) values of 0.81, 0.20, and 0.59µg/mL, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines.