ABSTRACT
Pedalitin, isolated from the aerial part of Rabdosia japonica (Labiatae), inhibited soybean lipoxygenase-1 (EC 1.13.11.12, Type I) with an IC50 of 152.5 uM. The progress curves for an enzyme reaction, pedalitin inactivate the lipoxygenase-1 in a time dependent, irreversible manner, exhibiting kinetics with a kinact/KI of 59.6 +/- 10 mM-1min-1. In the pseudoperoxidase activity, pedalitin is very slowly oxidized by the soybean lipoxygenase-1 catalyzed decomposition of lipid hydroperoxides.
Pedalitina, aislada de las partes aereas de Rabdosia japonica inhibió a la lipooxigenasa-1 (EC 1.13.11.12 tipo I) con un IC50 de 152.5 uM. La curva de progreso para una acción enzimática, pedalitina inactivó a la lipooxigenasa-1 de una manera dependiente del tiempo, de una manera irreversible, exhibiendo una cinética con una kinact/KI de 59.6 +/- mM-1min-1. En la actividad pseudoperoxidasa, pedalitina es oxidada lentamente por la descomposición de la lípido hidroperóxido de la lipooxigenasa-1 de poroto de soya.
Subject(s)
Flavones/isolation & purification , Flavones/pharmacology , Isodon/chemistry , Lipoxygenase Inhibitors/pharmacology , Glycine max/enzymology , Kinetics , Lipoxygenase Inhibitors/isolation & purification , Time FactorsABSTRACT
Fifteen Isodon diterpenoids (1-15) were evaluated for their cytotoxic activity against HeLa and HL-60 human cancer cell lines, and against murine vincristine (VCR)-resistant P388 cells. Kamebanin (14) showed efficient cytotoxic activity against HeLa and HL-60 cells. In addition, although dihydroenmein (2) and trichorabdal B (7) were inactive against several tested cell types, they were found to have cytotoxic-enhancing activity of VCR against VCR-resistant P388 cells.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Isodon/chemistry , Animals , Cell Line , Humans , Mice , Molecular StructureABSTRACT
The effects of the four major ent-kaurene diterpenoids isolated from the aerial part of Rabdosia japonica (Labiatae) on murine B16-F10 melanoma cells were investigated. Among the compounds tested, oridonin and nodosin most significantly suppressed cellular melanin production when the cells were cultured with these diterpenoids. However, oridonin and nodosin exhibited cytotoxicity against the same melanoma cells with an IC(50) of 1.1 µM (0.40 µg/ml) and of 1.3 µM (0.47 µg/ml) and almost complete lethality was observed at 4.0 µM and at 8.0 µM, respectively, and therefore observed melanogenesis inhibition is mainly due to its melanocytotoxic effect. Morphological observation showed that oridonin or nodosin treated B16-F10 melanoma cells induced dendrite structure. Diterpenoids quickly formed adducts partly in Dulbecco's Modified Eagle's Medium (DMEM) containing 10% of fetal bovine serum (10% FBS-DMEM) before their application to the cells. Approximately 20% of oridonin formed adducts within the first 15 min. Notably, dihydronodosin exhibited inferior cytotoxicity (>85% cell viability at 100 µM) but still significantly suppressed melanogenesis (>55%) when murine B16-F10 melanoma cells were cultured with this diterpenoid derivatives. Hence, dihydronodosin can be a potential melanogenesis inhibitor.
Subject(s)
Diterpenes, Kaurane/pharmacology , Isodon/chemistry , Melanins/biosynthesis , Melanoma, Experimental/prevention & control , Plant Extracts/pharmacology , Animals , Cell Line, Tumor , Cell Survival/drug effects , Diterpenes/chemistry , Diterpenes/pharmacology , Diterpenes, Kaurane/chemistry , Inhibitory Concentration 50 , Melanins/analysis , Melanins/antagonists & inhibitors , Mice , Mice, Inbred C57BL , Plant Extracts/chemistryABSTRACT
We investigated antibacterial activities of ten compounds from Isodon species against five strains of Escherichia coli, Staphylococcus epidermidis, Serratia marcescens, Streptococcus mutans, and Helicobacter pylori. The compounds with the MIC values of 25 microg/ml were isodocarpin against Sta. epidermidis, Str. mutans, and H. pylori, nodosin against Sta. epidermidis and Str. mutans, oridonin against Ser. marcescens, and pedalitin against H. pylori.
Subject(s)
Escherichia coli/drug effects , Helicobacter pylori/drug effects , Isodon/chemistry , Plant Extracts/pharmacology , Serratia marcescens/drug effects , Staphylococcus epidermidis/drug effects , Streptococcus mutans/drug effects , Drug Resistance, Bacterial , Plant Extracts/chemistry , Plant Extracts/isolation & purificationABSTRACT
Pedalitin isolated from the aerial part of Rabdosia japonica (Labiatae), exhibited cytotoxicity against the murine B16-F10 melanoma cell line with an IC(50) of 30 microm (9.5 microg/mL). As the cells were cultured with this flavone, melanin production was not suppressed, but rather enhanced. Quercetin isolated from the same source exhibited similar activities, but rutin showed neither activity.
Subject(s)
Flavonols/pharmacology , Isodon/chemistry , Melanoma, Experimental/drug therapy , Phytotherapy , Animals , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Flavones/chemistry , Flavones/pharmacology , Flavonols/chemistry , Formazans/metabolism , Inhibitory Concentration 50 , Melanins/metabolism , Melanoma, Experimental/metabolism , Mice , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Quercetin/chemistry , Quercetin/pharmacology , Rutin/chemistry , Rutin/pharmacology , Tetrazolium Salts/metabolismABSTRACT
We studied the bioactivities of constituents from two tropical medicinal plants, Cunila spicata and Hyptis fasciculata. These plants found in Brazil belong to the Labiatae family. Four known compounds obtained from these herbs were identified as 3alpha, 24-dihydoxylurs-12-en-28-oic acid, betulinic acid, aurantiamide acetate, and aurantiamide benzoate by spectroscopic means. 3alpha, 24-Dihydoxylurs-12-en-28-oic acid has potent inhibitory activity against Streptococcus salivarius, Streptococcus pneumoniae, Streptococcus pyogenes, and Porphyromomas gingivalis. Aurantiamide benzoate exhibited moderate inhibitory activity against xanthine oxidase. It was clarified that herbs Cunila spicata and Hyptis fasciculata are effective against bronchitis and gout.
Subject(s)
Bacteria/drug effects , Dipeptides/isolation & purification , Dipeptides/pharmacology , Lamiaceae/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacology , Xanthine Oxidase/antagonists & inhibitors , Brazil , Bronchitis/drug therapy , Drug Resistance, Bacterial , Gout/drug therapy , Pentacyclic Triterpenes , Phytotherapy , Betulinic AcidABSTRACT
Two known flavonoids were isolated from a tropical medicinal plant, Hyptis fasciculata (Labiatae), found in Brazil. Flavonoids were identified as cirsilineol (1) and cirsimaritin (2) by spectroscopic means and were exhibited potent antibacterial activity against Helicobacter pylori, and cirsilineol (1) had weak antibacterial activity against Escherichia coli and Salmonella enteritidis. Following up on the relationship between anti-H. pylori activity and flavonoids with methoxy groups, several methoxy flavonoids were evaluated for proliferation of H. pylori.
Subject(s)
Flavones/pharmacology , Helicobacter pylori/drug effects , Hyptis/chemistry , Bacteria/drug effects , Brazil , Flavones/isolation & purification , Magnetic Resonance Spectroscopy , Mass Spectrometry , Microbial Sensitivity Tests , Plant Extracts/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
The antioxidant activities of phenolic compounds: pedalitin, quercetin, rutin, isoquercitrin, and rosmarinic acid, isolated from the dried leaves of Rabdosia japonica Hara (Labiatae) were elucidated. All the phenolics tested exhibited superoxide scavenging activity and an inhibitory effect on xanthine oxidase (EC 1.1.3.22), and pedalitin showed the most potent antioxidant activity. Pedalitin prevents the generation of superoxide radicals in part by inhibiting xanthine oxidase competitively. Both pedalitin and quercetin inhibited uric acid formation by xanthine oxidase, and the inhibition kinetics analysed by Lineweaver-Burk plots found both flavonoids to be competitive inhibitors. On the other hand, isoquercitrin, rutin and rosmarinic acid were effective in scavenging superoxide radicals generated by the xanthine-xanthine oxidase system without inhibiting the enzyme.
Subject(s)
Antioxidants/chemistry , Flavonols/chemistry , Isodon/chemistry , Plant Extracts/chemistry , Antioxidants/isolation & purification , Antioxidants/pharmacology , Biphenyl Compounds , Cinnamates/chemistry , Cinnamates/isolation & purification , Cinnamates/pharmacology , Depsides , Flavones/chemistry , Flavones/isolation & purification , Flavones/pharmacology , Flavonoids/metabolism , Flavonols/isolation & purification , Flavonols/pharmacology , Inhibitory Concentration 50 , Picrates/metabolism , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves/chemistry , Superoxides/chemical synthesis , Uric Acid/metabolism , Xanthine Oxidase/antagonists & inhibitors , Xanthine Oxidase/metabolism , Rosmarinic AcidABSTRACT
Two new labdane diterpenoids, 15beta-methoxyfaciculatin (1) and 15alpha-methoxyfaciculatin B (2), together with the previously known methoxynepetaefolin (3), were isolated from a methanol extract of the dried aerial parts of a Brazilian medicinal plant, Hyptis faciculata. Their structures were elucidated by analysis of spectroscopic data. Plausible biogenetic correlation between faciculatins and nepetaefolin is briefly discussed.
Subject(s)
Diterpenes/chemistry , Hyptis/chemistry , Brazil , Carbohydrate Conformation , Carbohydrate Sequence , Magnetic Resonance Spectroscopy , Methanol , Molecular Sequence Data , Plant Extracts/analysis , Solvents , Spectrometry, Mass, Electrospray IonizationABSTRACT
Three flavonoids, quercetin 3- O-glucoside-2''-gallate (QGG), quercetin 3- O-rhamnoside-2''-gallate (QRG) and kaempferol 3- O-glucoside-2''-gallate (KGG) were isolated from Japanese Polygonum species. The effect of these flavonoids on stimulus-induced superoxide generation in human neutrophils was assayed by measuring the reduction of cytochrome c. The tyrosyl or serine/threonine phosphorylation of neutrophil proteins and the translocation of p4(phox) and p67(phox) to the cell membrane were detected using specific monoclonal antibodies. The flavonoids used in this experiment significantly suppressed stimulus-induced superoxide generation in a concentration-dependent manner. FMLP-induced tyrosyl phosphorylation or PMA-induced serine/threonine phosphorylation and the translocation of the cytosolic proteins p47(phox) and p67(phox) to the cell membrane were suppressed in parallel to the suppression of the stimulus-induced superoxide generation.
Subject(s)
Caryophyllaceae , Neutrophils/drug effects , Phytotherapy , Plant Extracts/pharmacology , Superoxides/metabolism , Cell Membrane/metabolism , Dose-Response Relationship, Drug , Flavonoids/administration & dosage , Flavonoids/pharmacology , Flavonoids/therapeutic use , Humans , Japan , Medicine, Traditional , Neutrophils/metabolism , Phosphorylation , Plant Extracts/administration & dosage , Plant Extracts/therapeutic use , Protein Transport/drug effectsABSTRACT
Four known compounds have been isolated from the aerial parts of the Brazilian medicinal plant Pariparoba (Pothomorphe umbellata). They were an alkaloid, a flavone, a dihydrocalcone, and a steroid. The chemical structures were established to be N-benzoylmescaline, wogonin, uvangoletin, and beta-sitosterol glucoside using spectral methods. Among these compounds, the main component N-benzoylmescaline showed significant antibacterial activity against Helicobacter pylori.
