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OBJECTIVE: To study the chemical constituents and analgesic activity of the aerial parts of Skimmia multinervia. METHODS: The chemical constituents were isolated by column chromatography packed with MCI and silica gel, respectively, and the structures of the purified compounds were elucidated by NMR and MS analysis. The analgesic activities of the extract, fractions and selected compounds from the aerial parts of S. multinervia were evaluated by using acetic acid-induced writhing test in mice model. RESULTS: The structures of compounds 1-13 are identified as skimmin (1), imperatorin (2), auraptene (3), umbelliferon (4), scopoletin (5), limonin (6), limonexic acid (7), nomilin (8), citrusin (9), taraxerol (10), kanalpin (11), skimmianine (12), and methyl vanillate (13). The extract, ethyl acetate fraction, and alkaloid fraction could reduce the times of mice writhing induced by acetic acid, and the analgesic effect of compound 3, with inhibition rate of 88.18%, was much better than that of the positive control, aspirin. CONCLUSION: Compounds 1-13 are isolated from the plant for the first time, while 7, 9, 11, and 13 are firstly isolated from Skimmia genus. The analgesic activities of S. multinervia and compound 3 are reported for the first time.
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Screening active natural products, rapid identification, and accurate isolation are of great important for modern natural lead compounds discovery. We hereby reported the isolation of seven new neotecleanin-type limonoids (-), seven new limonoids with 5-oxatricyclo[5.4.0.11., 4.]hendecane ring system (-), and two new precursors (-) together with four known limonoids (-) from the root barks of . Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR, ECD spectrum calculations and single-crystal X-ray diffraction techniques. Compounds , , , , , , showed significant anti-inflammatory activities in LPS-induced RAW 264.7 cell line, BV2 microglial cells, and -stimulated THP-1 human monocytic cells. Walrobsin M () exhibited anti-inflammatory activity with IC value of 7.96±0.36 μmol/L, and down-regulated phosphorylation levels of ERK and p38 in a dose-dependent manner.
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Two new furan fragment isomerized limonoids, meliazedalides A and B (compounds 1 and 2), were isolated from the fruits of Melia azedarach Linn.. Their chemical structures were elucidated on the basis of HR-ESI-MS and 1D and 2D NMR data, which belonged to nimbolinin- and trichilin-class, respectively. Compound 2 exhibited weak inhibitory effect on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages with IC being 37.41 μmol·L.
Subject(s)
Animals , Mice , Anti-Inflammatory Agents , Chemistry , Pharmacology , Drugs, Chinese Herbal , Chemistry , Fruit , Chemistry , Limonins , Chemistry , Pharmacology , Macrophages , Metabolism , Melia azedarach , Chemistry , Molecular Structure , Nitric Oxide , MetabolismABSTRACT
Two new limonoids, 12-ethoxynimbolinins G and H (compounds 1 and 2), and one known compound, toosendanin (Chuanliansu) (compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin (3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.
Subject(s)
Humans , Cell Line, Tumor , Cell Proliferation , Limonins , Melia , Chemistry , Molecular Structure , Plant Bark , Chemistry , Plant Extracts , Chemistry , Pharmacology , X-Ray DiffractionABSTRACT
Two new limonoids, 12-ethoxynimbolinins G and H (compounds 1 and 2), and one known compound, toosendanin (Chuanliansu) (compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin (3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.
Subject(s)
Humans , Cell Line, Tumor , Cell Proliferation , Limonins , Melia , Chemistry , Molecular Structure , Plant Bark , Chemistry , Plant Extracts , Chemistry , Pharmacology , X-Ray DiffractionABSTRACT
Four new limonoid-type nortriterpenoids, 1-detigloyl-1--methacryloylsalannin (), 28-deoxo-2,3-dihydronimbolide (), 12-acetoxy-3--acetyl-7--tigloylvilasinin () and 12-acetoxy-3--acetyl-7--methacryloylvilasinin (), along with five known ones, were isolated from seeds of A. Juss. Their structures were elucidated by various spectroscopic methods, including UV, IR, MS, NMR, X-ray crystallography, quantum chemical calculation, as well as by comparison of their spectroscopic data with those reported. In the cytotoxic assay, showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC value of 7.68±1.74 μmol/L, and inhibited growth of human cervical cancer Hela cell line, melanoma A375 cell line and promyelocytic leukemia HL-60 cell line, with IC 12.00±2.08, 17.44±2.11, and 13.95±5.74 μmol/L, respectively.
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Objective To study the chemical constituents of the fruits of Xylocarpus granatum. Methods The isolation and purification were carried out by silica gel column chromatography, Sephadex, preparative TLC, and preparative HPLC. The structures of the isolated compounds were identified with the help of HR-ESI-MS, 1H-NMR, 13C-NMR, H-H COSY, HMQC and HMBC techniques. Results Seventeen compounds were isolated and elucidated from the fruits of X. granatum, their structures were identified as: grantumin C (1), cipadesin A (2), xylocarpin G (3), febrifugin (4), tigloylseneganolide A (5), khaysin T (6), cipadesin (7), granatumin B (8), xyloccensin S (9), granaxylocarpin C (10), xylogranatin E2 (11), xyloccensin Q (12), xyloccensin P (13), cedrodorin (14), xylorumphiins D (15), hydroxydammarenone-II (16), and bis (2-ethylhexyl) phthalate (17). Conclusion Compounds 2, 7, 14, 16 and 17 are isolated from the plants of Xylocarpus Koenig for the first time. Compound 15 is obtained from X. granatum for the first time.
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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
ABSTRACTThe use of cell and plant tissue culture techniques to produce economically important active metabolites has been growing. Among these substances are total limonoid aglycones, which are produced by "pera" orange (Citrus sinensis (L.) Osbeck, Rutaceae) and have received considerable attention because of their anticancer actions. The main objective of the present study was to analyze and compare the levels of limonoid aglycones in seeds, callus cultures (originating from seeds), callus cultures (originating from hypocotyls), cell suspensions from hypocotyls cells, and cell suspensions from cotyledons. The cell cultures or C. sinensis were obtained by inoculating two strains of callus in MS medium supplemented with 2.0 µM 2,4-dichlorophenoxyacetic acid, 7.0 µM benzyl aminopurine, and 3% (w/v) sucrose in the dark. The highest concentrations of limonoid aglycone that were obtained were observed in cotyledon cell lines (240 mg/100 g dry weight) that were produced on day 21 of culture and hypocotyl cell lines on day 7 (210 mg/100 g dry weight). Explants of different origins under the same culture conditions had different limonoid aglycone content. The present results may suggest strategies for enhancing the productivity of biologically important limonoid aglycones and investigating the complex pathways of these secondary metabolites in plant tissue cultures.
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Objective: To cloning limonoid-UDP-glucosyl transferase (LGT) gene in Citrus reticulata, analyze the bioinformations of LGT, and compare the expression to provide the foundation for the composite and regulation mechanism of the active ingredient in Citri Reticulatae Semen. Methods: LGT gene was cloned the protein characteristics were analyzed using bioinformatics and constructing phylogenetic tree. The expression of LGT in the different parts was analyzed using real time-PCR. Results: A 1 530 bp LGT sequence in in C. reticulata, was obtained, which had a 1509 bp ORF and could encode 502 amino acids. And protein analysis and forecast of its secondary and tertiary structures were carried out. Gene expression analysis revealed the expression of citrus LGT was the lowest in semen, and was followed by skin, and the highest expression of fresh. Conclusion: LGT gene of C. reticulata, and is successfully cloned, analyzed, and expressed a basis for the study of matter in the synthesis and regulation of limonoids is provided.