ABSTRACT
In the present study, two new limonoids, 1α, 7α-dihydroxyl-3α-acetoxyl-12α-ethoxylnimbolinin (1) and 1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12β-ethoxylnimbolinin (2), together with other four known limonoids (3-6), were isolated from the fruits of Melia toosendan. Their structures were elucidated by means of extensive spectroscopic analyses (NMR and ESI-MS) and comparisons with the data reported in the literature. The isolated compounds were evaluated for their antibacterial activities. Compound 4 exhibited significant antibacterial activity against an oral pathogen, Porphyromonas gingivalis ATCC 33277, with an MIC value of 15.2 μg·mL(-1). Compound 2 was also active against P. gingivalis ATCC 33277, with an MIC value of 31.25 μg·mL(-1). In conlcusion, our resutls indicate that these compounds may provide a basis for future development of novel antibiotics.
Subject(s)
Anti-Bacterial Agents , Chemistry , Pharmacology , Drugs, Chinese Herbal , Chemistry , Fruit , Chemistry , Limonins , Chemistry , Magnetic Resonance Spectroscopy , Melia , Chemistry , Molecular Structure , Porphyromonas gingivalis , Spectrometry, Mass, Electrospray IonizationABSTRACT
AIM@#To study the chemical constituents of the rhizomes of Alpinia officinarum Hance.@*METHOD@#Compounds were isolated by repeated column chromatography, and their structures were elucidated on the basis of spectral analysis. The cytotoxic activities of these compounds were evaluated with the T98G and B16F10 cell lines by the MTT assay.@*RESULTS@#A dimeric diarylheptanoid, named alpinin B (1), along with three known diarylheptanoids were obtained, and their structures were identified as alpinin B (1), 1, 7-diphenyl-3,5-heptanedione (2), (4E)-1, 7-diphenylhept-4-en-3-one (3) and (4E)-7- (4-hydroxyphenyl)-1-phenylhept-4-en-3-one (4).@*CONCLUSION@#Compound 1 is a new dimeric diarylheptanoid. The biosynthetic pathway of 1 was speculated to originate from a Michael reaction between compounds 2 and 3. Compound 3 showed cytotoxicity against the human glioblastoma T98G cell line with IC50 of 27 μmol·L(-1).
Subject(s)
Humans , Alpinia , Chemistry , Antineoplastic Agents, Phytogenic , Pharmacology , Therapeutic Uses , Cell Line, Tumor , Diarylheptanoids , Chemistry , Pharmacology , Therapeutic Uses , Glioblastoma , Drug Therapy , Molecular Structure , Phytotherapy , Plant Extracts , Chemistry , Pharmacology , Therapeutic Uses , Rhizome , ChemistryABSTRACT
AIM@#To investigate the quinoline alkaloids from the roots of Dictamnus angustifolius G.Don ex Sweet (Rutaceae).@*METHOD@#The quinoline alkaloids were isolated by various column chromatographic methods and their structures were elucidated on the basis of spectral analysis.@*RESULTS@#A new quinoline alkaloid, 5-methoxylrobustine (1), along with five known quinoline alkaloids were obtained, and their structures were identified as dictamnine (2), robustine (3), isopteleine (4), γ-fagarine (5), and skimmianine (6). Cytotoxicity testing of these alkaloids showed that all of them had weak cytotoxic activities against human breast cancer cells (MCF7).@*CONCLUSION@#Compound 1 is a new quinoline alkaloid. Alkaloid 3 showed stronger anti-proliferation effect than the other alkaloids.
Subject(s)
Humans , Antineoplastic Agents, Phytogenic , Pharmacology , Therapeutic Uses , Breast Neoplasms , Drug Therapy , Cell Line, Tumor , Dictamnus , Chemistry , Hydroxyquinolines , Chemistry , Pharmacology , Therapeutic Uses , Molecular Structure , Phytotherapy , Plant Extracts , Chemistry , Pharmacology , Therapeutic Uses , Plant Roots , Chemistry , Quinolines , Chemistry , Pharmacology , Therapeutic UsesABSTRACT
AIM@#To study the chemical constituents from the aerial parts of Trachelospermum jasminoides.@*METHODS@#Compounds were isolated by various chromatographic methods and their structures were elucidated on the basis of spectral techniques. In addition, the inhibitory activity against HepG2 and HL-60 of compound 1 was evaluated.@*RESULTS@#Five compounds were isolated and identified as 3', 7-dimethoxyisoflavanone-4', 5-di-O-β-D-glucopyranoside (1), tracheloside (2), nortrachelogenin 5'-C-β-glucopyranoside (3), luteolin-4'-O-β-D-rutinoside (4), and luteolin-7-O-β-D-glucopyranoside (5).@*CONCLUSION@#Compound 1 is a new isoflavonoid glycoside. It showed weak inhibitory activity against HepG2 and HL-60 cancer cells with IC50 values of 131.5 and 58.2 μmol·L(-1), respectively.
Subject(s)
Humans , Apocynaceae , Chemistry , Cell Line, Tumor , Cell Proliferation , Flavonoids , Chemistry , Pharmacology , Glycosides , Chemistry , Pharmacology , Molecular Structure , Plant Components, Aerial , Chemistry , Plant Extracts , Chemistry , PharmacologyABSTRACT
AIM@#To study the chemical constituents from the seeds of Griffonia simplicifolia Baill.@*METHODS@#The chemical constituents were isolated and purified by a combination of chromatographic materials including silica gel, Sephadex LH-20, and preparative TLC. Their structures were elucidated on the basis of MS and NMR data analysis. The cytotoxic activities were evaluated against HepG2 cancer cell line using the MTT colorimetric method.@*RESULTS@#A new β-carboline alkaloid, griffonine (1), together with seven known alkaloids, hyrtioerectine B (2), 3-carboxy-6-hydroxy-β-carboline (3), hyrtiosulawesine (4), 5-hydroxyindole-3-carbaldehyde (5), 5-hydroxy-3-(2-hydroxyethyl) indole (6), trigonelline (7), and 5-hydroxytryptamine (8) were isolated and identified. Alkaloids 1, 2 and 4 showed growth inhibitory effects on the HepG2 cell line with IC50 values of 23.5, 9.6 and 19.3 μmol·L(-1), respectively.@*CONCLUSION@#Alkaloid 1 is new and was named griffonine. Alkaloids 2-7 were isolated from this plant for the first time. Alkaloids 1, 2 and 4 were potentially cytotoxic.
Subject(s)
Humans , Alkaloids , Chemistry , Pharmacology , Carbolines , Chemistry , Pharmacology , Cell Proliferation , Griffonia , Chemistry , Hep G2 Cells , Plant Extracts , Chemistry , Pharmacology , Seeds , ChemistryABSTRACT
AIM@#To study the chemical constituents of Siegesbeckia pubescens.@*METHODS@#The chemical constituents were isolated by extraction, crystallization and various chromatographic methods, and the chemical structures were elucidated on the basis of spectral analysis. In addition, the cytotoxic activity of compound 1 was evaluated using human lung cancer cell A 549.@*RESULTS@#Four compounds were obtained, and their structures were identified as (E)-3-(3-oxobut-1-enyl)phenyl dimethylcarbamate (1), ent-2-oxo-15, 16, 19-trihydroxypimar-8(14)-ene (2), 16-acetylkirenol (3), 3, 7-dimethylquercetin (4).@*CONCLUSION@#Compound 1 is a new carbamate, and the IC(50) in MTT method of compound 1 was 58 μg·mL(-1).
Subject(s)
Humans , Antineoplastic Agents, Phytogenic , Pharmacology , Therapeutic Uses , Asteraceae , Chemistry , Carbamates , Pharmacology , Therapeutic Uses , Cell Line, Tumor , Inhibitory Concentration 50 , Lung Neoplasms , Drug Therapy , Molecular Structure , Phytotherapy , Plant Components, Aerial , Chemistry , Plant Extracts , Chemistry , Pharmacology , Therapeutic Uses , QuercetinABSTRACT
AIM@#To investigate the chemical constituents of the aerial part of Euphorbia hirta Linn.@*METHODS@#The chemical constituents were isolated and purified by various chromatographic techniques, and their structures were elucidated on the basis of spectroscopic analysis.@*RESULTS@#Nine compounds were isolated and identified as scopoletin (1), scoparone (2), isoscopoletin (3), quercetin (4), isorhamnetin (5), pinocembrin (6), kaempferol (7), luteolin (8), gallic acid (9).@*CONCLUSION@#Among them compounds 1-3, 5-8 were found from this plant for the first time.
Subject(s)
Euphorbia , Chemistry , Flavonoids , Chemistry , Molecular Structure , Phenols , Chemistry , Plant Components, Aerial , Chemistry , Plant Extracts , ChemistryABSTRACT
To study the chemical constituents of the fruits of Melia toosendan, three limonoids were isolated and purified by repeated silica gel column chromatography and preparative HPLC from the EtOAc extract of M. toosendan. Their structures were determined by their physico-chemical properties and spectroscopic data (1D-NMR, 2D-NMR) as: 24, 25, 26, 27-tetranorapotirucalla-(apoeupha)-1alpha-tigloyloxy-3alpha, 7alpha-dihydroxyl-12alpha-acetoxyl-14, 20, 22-trien-21, 23-epoxy-6, 28-epoxy (1), nimbolinin B (2), and trichilinin D (3), separately. Compound 1 is a new compound, and compound 2 is obtained from this plant for the first time.
Subject(s)
Fruit , Chemistry , Limonins , Chemistry , Melia , Chemistry , Molecular Structure , Plants, Medicinal , ChemistryABSTRACT
From the chloroform-soluble fraction of the ethanol extracts of the whole plant of Taxus chinensis var. mairei (Lemee et Lev1), four compounds were isolated by using repeated column chromatography on silica gel and Sephadex LH-20. Based on spectroscopic data (UV, IR, ESI-MS, 1H NMR and 13C NMR), the compounds were identified as taxamairin K (1), 2alpha, 4alpha-dideacetoxy-7beta-benzoyloxy-5beta,20-epoxy-9alpha, 10beta, 13alpha, 15-tetrahydroxy-11(15-->1) abeotaxa-11-ene (2), 7beta-xylosyl-taxol (3), 10-deacetoxy-7-xylosyl-taxol (4). Among them, taxamairin K is a new compound.
Subject(s)
Diterpenes , Chemistry , Molecular Structure , Plants, Medicinal , Chemistry , Taxus , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of the rhizomes of Smilax china.</p><p><b>METHOD</b>The constituents of the rhizomes of S. china were isolated and purified by repeated silica gel and Sephadex LH-20 chromatography, and their structures were elucidated on the basis of spectral analysis.</p><p><b>RESULT</b>Thirteen compounds were obtained and identified as kaemperol-7-O-beta-D-glucopyranoside (1), engeletin (2), isoengeletin (3), kaempferol (4), dihydrokaempferol (5), dihydrokaempferol-5-O-P-D-glucopyranoside (6), rutin (7), kaempferol- 5-O-beta-D-glucopyranoside (8), 3, 5, 4'-trihydroxystibene (9), vanillic acid (10), 3, 5-dimethoxy4-O-beta-D-glu-copyranosylcinnamic acid (11), beta-sitosterol (12), and beta-daucosterol (13) , respectively.</p><p><b>CONCLUSION</b>Compounds 1, 3, 7, 8, and 11 were isolated from this plant for the first time, and compounds 8 and 11 were isolated from the genus Smilax for the first time.</p>
Subject(s)
Chromatography , Flavonoids , Chemistry , Flavonols , Chemistry , Glycosides , Chemistry , Kaempferols , Chemistry , Magnetic Resonance Spectroscopy , Plants, Medicinal , Chemistry , Rhizome , Chemistry , Sitosterols , Chemistry , Smilax , Chemistry , Vanillic Acid , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical constituents of Evodia rutaecarpa (Juss.) Benth.</p><p><b>METHODS</b>The crude total alkaloids were enriched by acid-base treatment and solvent extraction. Isolation and purification were carried out by silica gel column chromatography and recrystallization etc. Structural determination of the pure compounds were based on physico-chemical properties and various spectral data analysis (1HNMR, 13CNMR, UV, IR, 1H-1H COSY, HMQC, HMBC, ESIMS, HREIMS, NOESY).</p><p><b>RESULTS</b>Fourteen compounds were obtained from Evodia rutaecarpa, ten of them were identified as evodianinine (1), rutaecarpine (2), evodiamine (3), wuchuyuamide I (4), hydroxyevodiamine (5), limonin (6), daucosterol (7), triacontanoic acid (8), nonacosane (9) and beta-sitosterol (10).</p><p><b>CONCLUSION</b>Compound 1 is a new alkaloid named evodianinine.</p>