Bacteriostatic heterocycles from Euodia lunu-ankenda

Manandhar, Mangala D.; Hussaini, F. A.; Kapil, R. S.; Shoeb, A.

doi:10.1016/s0031-9422(00)80844-4

Cited by 32 publications

(16 citation statements)

References 11 publications

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“…The classical synthetic protocols for the above quinoline intermediates and natural products suffer from some disadvantages such as low yield, 15 lack of easy availability/ preparation of the reagent, [16][17][18] prolonged reaction time, multiple steps, requirement of excess of reagents/catalysts, need for special apparatus and harsh reaction conditions. 16,17 In this connection and by knowing the advantages of microwave reactions, [19][20][21] we felt that the synthesis of the above intermediates and quinoline alkaloids using microwave irradiation in an unaltered domestic microwave oven would make the task much easier than the thermal synthesis.…”

Section: Methodsmentioning

confidence: 99%

“…16,17 In this connection and by knowing the advantages of microwave reactions, [19][20][21] we felt that the synthesis of the above intermediates and quinoline alkaloids using microwave irradiation in an unaltered domestic microwave oven would make the task much easier than the thermal synthesis. Hence we wish to report a convenient and efficient synthesis of 4-hydroxy-2-quinolinone and 4-methoxy-1-methyl-2-quinolinone derivatives under microwave irradiation.…”

Section: Methodsmentioning

confidence: 99%

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Microwave-assisted synthesis of quinoline alkaloids: 4-Methoxy-1-methyl-2-quinolinone and its analogs

Nadaraj¹,

Selvi²,

Sasi³

2006

Arkivoc

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The microwave-induced synthesis of some quinoline alkaloids of the type 4-methoxy-1-methyl-2-quinolinone including folimine is reported. The precursors 4-hydroxy-2-quinolinone derivatives were effectively prepared in a single step from aniline and diethylmalonate using ptoluenesulfonic acid as a catalyst and these intermediates were converted to the titled quinoline alkaloids by treatment with dimethyl sulfate, N,N-dimethylformamide and potassium carbonate. The presented synthentic procedure is a convenient, simple and fast alternative for synthesizing 4-methoxy-1-methyl-2-quinolinone and its derivatives.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Microwave-assisted synthesis of quinoline alkaloids: 4-Methoxy-1-methyl-2-quinolinone and its analogs

Nadaraj¹,

Selvi²,

Sasi³

2006

Arkivoc

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“…A decoction of the roots is used to treat fever and rheumatism (Perry & Metzger, 1980). The leaf of the plant has been reported to show fungicidal (Kumar, Karunaratne, Sanath, Meegalle, & Macleod, 1990), antioxidant and nitric oxide inhibitory activities (Abas, Lajis, Israf, Khozirah, & Umi Kalsom, 2006), while its aerial parts shown antibacterial (Manandhar, Hussaini, Kapil, & Shoeb, 1985;Rasadah & Zakaria, 1988). Phytochemical studies on the leaves of the species collected from Sri Lanka revealed the presence of furoquinone alkaloids and acetophenones (Kumar et al, 1990), while the leaves collected in Vietnam were shown to contain benzopyrans as major constituents (Kamperdick, Van, Sung, & Adam, 1997;Nguyen, Kamperdick, Tran, & Adam, 1998).…”

Section: Introductionmentioning

confidence: 99%

Discrimination of young and mature leaves of Melicope ptelefolia using 1H NMR and multivariate data analysis

et al. 2011

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a b s t r a c tThe 'Ulam', a traditional Malay dish, are plants that can be eaten raw, as a form of local salad. The shoots and young leaves of Melicope ptelefolia are among the popular species, believed to be high in nutritional and medicinal values. The metabolomic fingerprinting analysis of the ethanolic extracts of leaves of M. ptelefolia was carried out using 1 H Nuclear Magnetic Resonance (NMR) spectroscopy and multivariate data analysis in order to differentiate young and mature leaves and to evaluate the variation of their chemical composition. Principle component analysis (PCA) of the 1 H NMR spectra showed a clear discrimination between the young and mature leaves extracts by PC3 and PC4. The compounds responsible for the differentiation were identified by comparison of 1 H NMR chemical shifts and qualitative HPLC. The young leaves were found to be richer in fatty acids and the levels of the three marker compounds, p-Ogeranylcoumaric acid, 2,4,6-trihydroxy-3-geranylacetophenone and 2,4,6-trihydroxy-3-prenylacetophenone, were clearly higher. The mature leaves contain higher levels of sugars and glycosidic components.

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“…elleryana, a plant traditionally used in Manus, Papua New Guinea, for cough and fever has demonstrable in vitro activity against H37Ra strain of M.tuberculosis. It is reasonable to hypothesize that this activity may be related to antimicrobial activities reported for alkaloid quinoline metabolites of other Evodia species [9][10][11].…”

Section: Resultsmentioning

confidence: 99%

Anti-TB activity of Evodia elleryana bark extract

et al. 2007

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An ethyl acetate extract of bark from Evodia elleryana produced significant growth inhibition of Mycobacterium tuberculosis at concentrations only minimally inhibitory to human T cells. The crude extract yielded 95% inhibition of TB at 50 μg/ml. The crude extract yielded 29 % growth inhibition of human T-cells in culture at that concentration. KeywordsEvodia elleryana; TB; Mycobacterium tuberculosis PlantEvodia elleryana (Melicope elleryana) (Rutaceae), locally called sehit, harvested in 2004 from the Kurti region of Manus Island, Papua New Guinea was identified by Dr. Osia Gideon and Mr. Pius Piskaut of the University of Papua New Guinea Herbarium. Use in traditional medicinePeople of the Kurti region of Manus commonly use Evodia elleryana for cough and fever, especially whooping cough. Women occasionally use the plant to control fertility. A water extract of bark is taken internally for treatment of fever and cough. Previous work has reported a broad spectrum of antimicrobial activity for various plant parts and extracts [1]. Previously isolated constituentsQuinoline alkaloid and flavanoids [2][3][4]. Tested materialSoxhlet extracts (hexane, ethyl acetate and methanol in sequence) of bark, stem and leaves were tested. *Corresponding author. Tel.: +801 581 4547; fax + 801 585 5111. lbarrows@pharm.utah.edu. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. NIH Public Access Studied activityInhibition of M. tuberculosis growth was quantified using a colorimetric MTT assay [5,6]. Rifampicin and isoniazid (Sigma) were used as positive controls in the TB inhibition assay. Drugs and plant extracts were dissolved in DMSO to produce stock solutions of 10 mg/ml. DMSO was used as the negative control. Other chemical and culture supplies were purchased from commercial sources (Sigma and Becton Dickenson, respectively). M. tuberculosis cultures were dispensed into a 96 well culture plate at 50.000 to 100.000 cells per well, in 200 μl of 7H9 medium with 10% ADC (albumin-dextrose-catalase) enrichment. 1 μl of DMSO or DMSO containing drug or extract was added in duplicate wells. After 4 d incubation at 37°C, MTT (5 mg/ml) was added in 10 μl DMSO and incubated overnight. Viable tuberculosis metabolizes the MTT to a purple formazan metabolite which is solubilized by the addition of 50 μl 50%DMF, 5% SDS. After 2 h the 570 nm absorbance was quantified in a microtiter plate reader. The percent inhibition of TB growth was calculated by averaging inhibition of duplicate test wells and comparing the signal to that for the control growth (DMSO only) wells.Inhibition of Human T cell leuke...

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Bacteriostatic heterocycles from Euodia lunu-ankenda

Cited by 32 publications

References 11 publications

Microwave-assisted synthesis of quinoline alkaloids: 4-Methoxy-1-methyl-2-quinolinone and its analogs

Microwave-assisted synthesis of quinoline alkaloids: 4-Methoxy-1-methyl-2-quinolinone and its analogs

Discrimination of young and mature leaves of Melicope ptelefolia using 1H NMR and multivariate data analysis

Anti-TB activity of Evodia elleryana bark extract

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