ABSTRACT
The chemical constituents from the stems and leaves of Clausena excavata were isolated and purified by column chromatography with silica gel, ODS, Sephadex LH-20 and RP-HPLC. The chemical structures of the isolated compounds were identified on the basis of physicochemical properties, spectroscopic analysis, as well as the comparisons with the data reported in literature. Nineteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. excavata, which were identified as methyl orsellinate(1), syringaresinol(2), lenisin A(3), scopoletin(4), osthenol(5), N-benzoyltyrarnine methyl ether(6), N-p-coumaroyltyramine(7), aurantiamide acetate(8), 1H-indole-3-carboxaldehyde(9), furostifoline(10), clausenalansine E(11), 3-formylcarbazole(12), clausine L(13), clausine E(14), methyl carbazole-3-carboxylate(15), glycosinin(16), murrayafoline A(17), clausine H(18) and 2,7-dihydroxy-3-formyl-1-(3'-methyl-2'-butenyl)carbazole(19). Among these isolated compounds, compounds 1-11 were isolated from C. excavata for the first time, and compounds 1, 2 and 10 were isolated from the genus Clausena for the first time. In addition, this study evaluated the anti-rheumatoid arthritis activities of compounds 1-19 by measuring their anti-proliferative effects on synoviocytes in vitro according to MTS method. Compounds 10-19 displayed remarkable anti-rheumatoid arthritis activities, which exhibited the inhibitory effects on the proliferation of MH7 A synovial fibroblast cells with the IC_(50) values ranging from(27.63±0.18) to(235.67±2.16) μmol·L~(-1).
Subject(s)
Cell Proliferation , Chromatography, Reverse-Phase , Clausena , Plant Leaves , SynoviocytesABSTRACT
The chemical constituents from the stems and leaves of Clausena emarginata were separated and purified by column chromatographies on silica gel,ODS,Sephadex LH-20,and PR-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. emarginata,which were identified as siamenol( 1),murrastanine A( 2),3-formyl-1,6-dimethoxycarbazole( 3),3-methoxymethylcarbazole( 4),3-methylcarbazole( 5),murrayafoline A( 6),3-formylcarbazole( 7),3-formyl-1-hydroxycarbazole( 8),3-formyl-6-methoxycarbazole( 9),murrayanine( 10),murrayacine( 11),girinimbine( 12),nordentatin( 13),chalepin( 14),8-hydroxy-6-methoxy-3-pentylisocoumarin( 15) and ethyl orsellinate( 16). Compounds 1-4,14-16 were isolated from C. emarginata for the first time. Among them,compounds 1,2,15 and 16 were isolated from the genus Clausena for the first time. All isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines: HL-60,SMMC-7721,A-549,MCF-7 and SW480 in vitro. Compounds 12 and 14 showed significant inhibitory effects against various human cancer cell lines with IC_(50) values comparable to those of doxorubicin.
Subject(s)
Humans , Antineoplastic Agents, Phytogenic , Pharmacology , Cell Line, Tumor , Clausena , Chemistry , Doxorubicin , Phytochemicals , Pharmacology , Plant Leaves , Chemistry , Plant Stems , ChemistryABSTRACT
The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC values ranging from 8.67 to 98.89 μmol·L.
Subject(s)
Humans , A549 Cells , Alkaloids , Chemistry , Toxicity , Antineoplastic Agents , Chemistry , Toxicity , Carbazoles , Chemistry , Toxicity , Cell Line, Tumor , Cell Survival , Clausena , Chemistry , HeLa Cells , Molecular Structure , Plant Extracts , Chemistry , Toxicity , Plant Leaves , Chemistry , Plant Stems , Chemistry , Plants, Medicinal , ChemistryABSTRACT
The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC values ranging from 8.67 to 98.89 μmol·L.
Subject(s)
Humans , A549 Cells , Alkaloids , Chemistry , Toxicity , Antineoplastic Agents , Chemistry , Toxicity , Carbazoles , Chemistry , Toxicity , Cell Line, Tumor , Cell Survival , Clausena , Chemistry , HeLa Cells , Molecular Structure , Plant Extracts , Chemistry , Toxicity , Plant Leaves , Chemistry , Plant Stems , Chemistry , Plants, Medicinal , ChemistryABSTRACT
Pharmaceutical research has focused on the discovery and development of anticancer drugs. Clinical application of chemotherapy drugs is limited due to their severe side effects. In this regard, new naturally occurring anticancer drugs have gained increasing attention because of their potential effectiveness and safety. Fruits and vegetables are promising sources of anticancer remedy. Clausena (family Rutaceae) is a genus of flowering plants and includes several kinds of edible fruits and vegetables. Phytochemical and pharmacological studies show that carbazole alkaloids and coumarins from Clausena plants exhibit anticancer activity. This review summarizes research progresses made in the anticancer properties of plants belonging to Clausena; in particular, compounds with direct cytotoxicity, cell cycle arrest, apoptosis induction, and immune potentiation effects are discussed. This review reveals the potential use of plants from Clausena in preventing and treating cancer and provides a basis for development of relevant therapeutic agents.
Subject(s)
Humans , Alkaloids , Chemistry , Pharmacology , Therapeutic Uses , Antineoplastic Agents , Chemistry , Pharmacology , Therapeutic Uses , Apoptosis , Carbazoles , Chemistry , Pharmacology , Therapeutic Uses , Cell Cycle Checkpoints , Clausena , Chemistry , Coumarins , Chemistry , Pharmacology , Therapeutic Uses , Drugs, Chinese Herbal , Chemistry , Pharmacology , Therapeutic Uses , Plants, Medicinal , ChemistryABSTRACT
The first study on chemical constituents and biological activities of Clausena lansium (Lour.) Skeels (Rutaceae) growing in Vietnam has been done. Phytochemical investigation of n-hexane extract led to the isolation of five compounds: dihydroindicolactone (1), 8-geranyloxy psoralen (2), imperatorin (3), heraclenol (4) and indicolactone (5), in which this is the first report on the presence of dihydroindicolactone (1). Their structures were elucidated based on LC/MS/NMR hyphenated techniques as well as comparison with those of literature data. The n-hexane extract and its subfractions, ethanol 95% extract and several isolated compounds were evaluated for antifungal activity.
Subject(s)
Clausena , Ethanol , Ficusin , VietnamABSTRACT
A new phenethanol, (2'R)-4-(2', 3'-dihydroxy-3'-methyl-butanoxy)-phenethanol (1), along with other eleven known benzene derivatives (2-12) were isolated from the roots, stems and leaves of Clausena excavata (Rutaceae). Compounds 3 and 4 are new natural products, and compounds 5-8, 10-12 were isolated from C. excavata for the first time. Their structures were elucidated on the basis of MS, 1D and 2D NMR spectroscopic analyses including HSQC, COSY and HMBC experiments. 1 was tested for its cytotoxicities against A549, HeLa and BGC-823 cancer cell lines, and antimicrobial activities against Candida albicans and Staphylococcus aureus. The results showed that 1 did not exhibit cytotoxic and antimicrobial activities.
Subject(s)
Humans , Benzene Derivatives , Chemistry , Candida albicans , Cell Line, Tumor , Clausena , Chemistry , HeLa Cells , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Leaves , Chemistry , Plant Roots , Chemistry , Plant Stems , Chemistry , Staphylococcus aureusABSTRACT
To investigate monoterpenes and sesquiterpenes of the stems and leaves of Clausena excavata, an AcOEt fraction of the methanol extract was subjected on column chromatographies including silica gel and RP-18, as well as preparative HPLC. The structures of compounds isolated were identified on the basis of spectroscopic data as excamonoterpene (1), (6R, 9S)-9, 10-dihydroxy-4-megastigmen-3-one (2), (3R, 6R, 7E) -3-hydroxy-4, 7-megastigmadien-9-one (3), (3S) -3-hydroxy-7, 8-dihydro-beta-ionone (4), (3S, 5R, 6S) -3-hydroxy-5,6-epoxy-beta-ionone (5), (6R, 9R) -9-hydroxy-4-megastigmen-3-one (6), (3S, SR) -dihydroxy-6, 7-megstigmadien-9-one(7), (-)-loliolide(8), caryolane-1, 9alpha-diol(9) and 2, 6-dihydroxyhumula-3 (12), 7 (13), 9(E)-triene (10), were isolated from the stems and leaves of C. excavata. Compound 1 is a new monoterpene, named as excamonoterpene. Compounds 2-10 were isolated from this plant for the first time.
Subject(s)
Chromatography, High Pressure Liquid , Methods , Clausena , Chemistry , Magnetic Resonance Spectroscopy , Methanol , Chemistry , Molecular Structure , Monoterpenes , Chemistry , Plant Leaves , Chemistry , Plant Stems , Chemistry , Sesquiterpenes , Chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
Background & objectives: Conventional insecticides are generally used as larvicides to control Culex quinquefasciatus, vector of lymphatic filariasis. This study was undertaken to evaluate the larvicidal activity of some potential larvicidal plants leaf extracts against Cx. quinquefasciatus larvae. Methods: The toxic effects of petroleum ether leaf extracts of plants viz., Argemone mexicana (Mexican prickly poppy), Clausena dentata (Dentate), Cipadessa baccifera (Rana bili), Dodonaea angustifolia (Hop bush) and Melia dubia (Pride of India) were evaluated under laboratory conditions in individual and in combination against 3rd - 4th instar larvae of Cx. quinquefasciatus. Results: The results indicated that among the selected plants, A. mexicana showed maximum larvicidal activity with an LC50 value of 48.89 ppm. Its toxicity was enhanced when the extract was mixed (1:1) with that of C. dentata as the LC50 value became 28.60 ppm indicating synergistic action of A. mexicana. Interpretation & conclusions: Our results showed high larvicidal potential in A. mexicana leaf extract, and it also showed additive effect when mixed with C. dentata extract.
Subject(s)
Animals , Clausena/chemistry , Culex/drug effects , Culex/parasitology , Elephantiasis, Filarial/parasitology , Elephantiasis, Filarial/prevention & control , Elephantiasis, Filarial/transmission , Insect Vectors/drug effects , Insect Vectors/parasitology , Larva/drug effects , Larva/parasitology , Plant Extracts/pharmacology , Plant Leaves/chemistryABSTRACT
OBJECTIVE@#Antiplasmodial and analgesic activities of the leaf extract and fractions of Clausena anisata (C. anisata) were evaluated for antimalarial and analgesic activities.@*METHODS@#The crude leaf extract (39-117 mg/kg) and fractions (chloroform and acqeous; 78 mg/kg) of C. anisata were investigated for antiplasmodial activity against chloroquine-sensitive Plasmodium berghei (P. berghei) infections in mice using suppressive, prophylactic and curative models and analgesic activity against acetic acid, formalin and heat-induced pains. Artesunate, 5 mg/kg and pyrimethamine, 1.2 mg/kg were used as positive controls. Thin films made from tail blood of each mouse were used to assess the level of parasitaemia of the mice.@*RESULTS@#The extract and its fractions dose-dependently reduced parasitaemia induced by chloroquine-sensitive P. berghei in prophylactic, suppressive and curative models in mice. These reductions were statistically significant (P<0.001). They also improved the mean survival time (MST) from 17 to 21 days relative to control (P<0.01 - 0.001). On chemically and thermally-induced pains, the extract inhibited acetic acid and formalin-induced inflammation as well as hot plate-induced pain in mice. These inhibitions were statistically significant (P<0.001) and in a dose-dependent fashion.@*CONCLUSIONS@#The antiplasmodial and analgesic effects of this plant may in part be mediated through its chemical constituents and it can be concluded that the C. anisata possess significant antimalarial and analgesic properties.
Subject(s)
Animals , Mice , Analgesics , Pharmacology , Antimalarials , Pharmacology , Clausena , Chemistry , Malaria , Drug Therapy , Musculoskeletal Pain , Parasitemia , Drug Therapy , Phytotherapy , Plant Extracts , Pharmacology , Plant Leaves , Chemistry , Plasmodium bergheiABSTRACT
From the stem bark of Clausena heptaphylla, the limonoid clausenolide-1-methyl ether (1) was isolated. The structure of the compound was elucidated by extensive spectroscopic studies, including 2D NMR and MS measurements and by comparison with spectroscopic and physical data from the literature. This is the first report of occurrence of clausenolide-1-methyl ether (1) in Clausena heptaphylla.
El limonoíde clausenolido-1-metil eter (1) fue aislado de corteza de Clausena heptaphylla. La estructura del compuesto fue determinada por metodos espectroscópicos, incluyendo 2D RMN, espectrometría de masas (EM) y comparación de los datos espectroscópicos y constantes físicas con los publicados en la literatura. Este es el primer informe del aislamiento de clausenolido-1-metil eter (1) de Clausena heptaphylla.
Subject(s)
Clausena/chemistry , Plant Bark/chemistry , Spectrum AnalysisABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of the leaf of Clausena lansium (Lour.) Skeels.</p><p><b>METHOD</b>The compounds were isolated by various chromatographic techniques and their structures were elucidated by their physicochemical properties and the analysis of their spectroscopic data.</p><p><b>RESULT</b>Seven compounds were isolated and identified as corchoionoside C (1), 1'-O-beta-D-glucopyranosyl (2R,3S)-3-hydroxynodakenetin (2), quercetin-3-O-robinobioside (3), rutin (4), quercetin-3-O-scillabioside (5), keampferol-3-O-alpha-L-rhamnopyranosyl(1-->2) [alpha-L-rhamnopyranosyl(1-->6)]-beta-D-glucopyranoside (6), mauritianin (7).</p><p><b>CONCLUSION</b>Compounds 1-7 were isolated from the genus Clausena for the first time.</p>
Subject(s)
Chemical Phenomena , Chromatography, High Pressure Liquid , Clausena , Chemistry , Organic Chemicals , ChemistryABSTRACT
This study is to investigate the protective effect of (-) clausenamide against the neurotoxicity of okadaic acid in SH-SY5Y cell line, and injection beta-amyloid peptide25-35 (Abeta25-35) to the cerebral ventricle in ovariectomy (OVX) rats. MTT assay, LDH assay, and Hoechst 33258 staining were used to detect the effect of (-) clausenamide on the toxicity of okadaic acid in SH-SY5Y cell line. The animal model was induced by ovariectomized and injection of Abeta25-35 in the cerebroventricle of rats. The effect of (-) clausenamide on learning and memory deficiency was observed by step-through test. Electron microscope, Nissl body staining, and HE staining were used to examine the morphological changes in hippocampus and cerebral cortex neurons. Pretreatment of (-) clausenamide and LiCl decreased the rate of cell death from MTT, LDH release, and apoptosis from Hoechst 33258 staining in SH-SY5Y cell line. The step-through tests showed (-) clausenamide could improve the ability of learning and memory. The Nissl body staining and HE staining experiments also showed the neuroprotective effects of (-) clausenamide on the neurons of hippocampus and cerebral cortex. (-) Clausenamide has the protective effects against the neurotoxicity induced by okadaic acid and Abeta25-35.
Subject(s)
Animals , Female , Humans , Rats , Amyloid beta-Peptides , Toxicity , Apoptosis , Cell Line, Tumor , Cell Survival , Cerebral Cortex , Cell Biology , Clausena , Chemistry , Drugs, Chinese Herbal , Pharmacology , Hippocampus , Cell Biology , L-Lactate Dehydrogenase , Metabolism , Lactams , Pharmacology , Learning , Lignans , Pharmacology , Memory Disorders , Neuroblastoma , Metabolism , Pathology , Neurons , Neuroprotective Agents , Pharmacology , Okadaic Acid , Toxicity , Ovariectomy , Peptide Fragments , Toxicity , Plants, Medicinal , Chemistry , Rats, Sprague-DawleyABSTRACT
<p><b>AIM</b>To study the excretion of (-)-clausenamide in rats.</p><p><b>METHODS</b>The urine, feces and bile were collected at predetermined time points after (-)-clausenamide was orally administrated to 6 rats (30 mg x kg(-1)). The concentrations of (-)-clausenamide and its metabolite 6-OH-(-)-clausnamide were determined by HPLC-MS/MS method using glipzide as the internal reference, and the accumulative excretion amount of (-)-clausenamide and 6-OH-(-)-clausenamide was calculated in the urine, feces and bile, separately.</p><p><b>RESULTS</b>(-)-Clausenamide was recovered mostly (44%) from feces in 112 hours, 7.1% was found from urine in 120 hours and 0.013% was detected from bile in 24 hours. The accumulative excretions of 6-OH-(-)-clausenamide were 0.92% , 0.46% and 0.0003% of the administered dose from feces, urine and bile, respectively.</p><p><b>CONCLUSION</b>The major amount of (-)-clausenamide was recovered from feces after (-)-clausenamide was orally administrated to rats (30 mg kg(-1)).</p>
Subject(s)
Animals , Female , Male , Rats , Administration, Oral , Bile , Metabolism , Chromatography, High Pressure Liquid , Clausena , Chemistry , Feces , Chemistry , Lactams , Chemistry , Pharmacokinetics , Urine , Lignans , Chemistry , Pharmacokinetics , Urine , Mass Spectrometry , Neuroprotective Agents , Pharmacokinetics , Urine , Plant Leaves , Chemistry , Plants, Medicinal , Chemistry , Rats, Sprague-Dawley , StereoisomerismABSTRACT
Studying on Clausena lansium (Lour.) samples collected from Pu Mat, Nghe An province in March 2004 to isolate and determine structure of some sterol compounds. Bough samples were dried and pounded leached with methanol in 20 days. Methanol extract was collected via distilling process to get solvents. Extracting with ethyl acetate, n-butanol and then distilling to get solvent we collected corresponding sediments. The corresponding solid extracts were collected by extract method with ethyl acetate, n-butanol solvents and then segment distill. A1, A2 solids were isolated by chromatographic method and segment crystallization. Using EI - MS, 1H - NMR, 13C - NMR spectroscopic methods to determine structure, A1 were identified as beta - sitosterol and A2 as stigmasterol. This is the first time these compounds isolated from Clausena lansium (Lour.) in Vietnam