C23-carbazole alkaloids from malayan Murraya koenigii (L.) spreng (original) (raw)
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C23-Carbazole Alkaloids from the Bark of Murraya koenigii (L.) Spreng
Murraya koenigii (Rutaceae), locally known as curry leaf tree, is a medicinally important herb of Indian origin and now were widely distributed throughout southern Asia. The bark of Murraya koenigii was selected for phytochemical investigation. The isolation of chemical constituents from its hexane extract was carried out by using different chromatographic techniques. Four C23-carbazole alkaloids was isolated and identified as mahanimbine 1, murrayamine-J 2, murrayazolinol 3 and bicyclomahanimbine 4. Spectroscopic methods, including NMR, IR, UV, MS spectra data, were used for the structural characterization.
Carbazole Alkaloids from Stem Bark of Murraya koenigii (L.) Spreng
Journal of Basic & Applied Sciences, 2015
Murraya koenigii (L.) Spreng(curry patta) has different therapeutic uses and rich source of carbazole alkaloids. Phytochemical studies on the stem bark of M. koenigii yielded one new carbazole alkaloid, afifine, along with two known carbazole alkaloids, mahinimbine and girinimbine. These compounds were isolated using chromatographic methods and identified using spectroscopic techniques.
American Journal of Plant Sciences, 2014
Murraya koenigii were selected for phytochemical investigation. Eight carbazole alkaloids was isolated and identified using spectroscopic methods including NMR, IR, UV, MS spectra data. Crude extract and isolated compounds from the roots of this plant were screened for cytotoxic activity and antitumor promoting activity. All crude extracts of the roots including the isolated compounds, mahanimbine, mahanine and murrayafoline-A exhibited significant cytotoxic activity against CEM-SS cell line with IC50 3 µg/mL. Girinimbine inhibited EBV-activation in the antitumor promoting assay.
Two carbazole alkaloids from Murraya koenigii
Phytochemistry, 1994
The non-cyclized possible biogenetic precursors of girinimbine and mahanimbine, 2-hydroxyl-3-methyl-l-(3-methyl-2-butenyl)arbazole (girinimbilol) and 2-hydroxyl-3-methyl-1-(3,7-dimethyl-2,6-octadienyl)carbazole (mahanimbilol) have been isolated from the stem bark of Murraya koenigii. The structures were established by cyclization to dihydrogirinimbine and a new bicyclocarbazole, bicyclomahanimbiline, respectively.
CARBAZOLE ALKALOID: MURRAYA KOENIGII A VALUABLE MEDICINAL PLANT
2019
Herbal remedies have been used to cure human aliments in every possible condition. About 80% of world's population relies upon natural products. The use of medicinal plants in therapeutics utmost probably exist in the earliest documented history. Murraya koenigii (Curry leaves) is one of most significant medicinal plant used as Herb, spice and condiments. It is rich source of carbazole alkaloids. Almost whole part of plant contains varied phytoconstituents and is used to cure various types of disorder. Extensive research work has been reported in last few decades on this valuable plant. Recent studies, have thrown light on anti-diabetic and anthelmintic activities of aqueous and chloroform extract of Murraya koenigii plant. The present review, discusses Ethanobotanical properties, Pharmacognostic, Phytochemical and Pharmacological activity on Murraya koenigii (M. koenigii).
Quantitative Analysis of Bioactive Carbazole Alkaloids in Murraya koenigii
Carbazole alkaloids induce apoptosis in HL-60 cells through activation of the caspase-9/caspase-3 pathway and they are targeted as potential anticancer agents. Thus, the naturally occurring carbazole alkaloids become important as precursors for lead optimization in drug development. A method based on ultra performance liquid chromatography coupled with photodiode-array detection was developed using reverse phase isocratic elution with 85:15 acetonitrile and ammonium acetate buffer (5 mM). Seven samples of Murrya koenigii (L.) Spreng. from northcentral India (Uttar Pradesh) were analyzed. All three targeted analytes, koenimbidine (mk1), koenimbine (mk2) and mahanimbine (mk3), were well separated within 4.0 min with linearity of the calibration curves (r 2 > 0.999). The limits of detection and quantification of mk1, mk2 and mk3 were 0.7, 0.4, 0.04 µg/mL and 2.14, 1.21, 0.12 µg/mL, respectively. The natural abundance of mk1, mk2 and mk3 was 0.06 -0.20, 0.04 -0.69 and 0.13 -0.42%, w/w, respectively, in the dried powdered leaves, whereas, the tissue specific distribution of carbazole alkaloids was observed in the order of predominance, mk1 leaf>root>fruit>stem, mk2 fruit>leaf >stem>root, and mk3 fruit>leaf>root>stem. The developed method was validated for limits of detection and quantification, repeatability, accuracy, precision and stability. This is the first report on the natural abundance of the major carbazole alkaloids in M. koenigii and the method developed can be used in HPLC/UPLC systems.
Organic & biomolecular chemistry, 2016
In our present study, four new, designated as murrayakonine A-D (), along with 18 known carbazole alkaloids were isolated from CHCl3 : MeOH (1 : 1) crude extracts of the stems and leaves of Murraya koenigii (Linn.) Spreng. The structures of the all isolated compounds were characterized by analysis of HR-ESI-MS and NMR (1D and 2D spectroscopy) results, and comparison of their data with the literature data. For the first time, all the isolates were evaluated for their anti-inflammatory activities, using both in vitro and in vivo experiments, against the key inflammatory mediators TNF-α and IL-6. The new compound murrayakonine A (), O-methylmurrayamine A () and mukolidine () were proven to be the most active, efficiently inhibiting TNF-α and IL-6 release in a dose-dependent manner and showing decreased LPS induced TNF-α and IL-6 production in human PBMCs. Furthermore, all the isolates were screened for their antimicrobial potential, and the compounds girinimbine () (IC50 3.4 μM) and 1-...
Antioxidative Activity of Carbazoles from Murraya koenigii Leaves
Journal of Agricultural and Food Chemistry, 2001
The antioxidative properties of the leaves extracts of Murraya koenigii using different solvents were evaluated based on the oil stability index (OSI) together with their radical scavenging ability against 1-1-diphenyl-2-picrylhydrazyl (DPPH). The methylene chloride (CH 2 Cl 2 ) extract and the ethyl acetate (EtOAc) soluble fraction of the 70% acetone extract significantly prolonged the OSI values comparable to those of R-tocopherol and BHT. Five carbazole alkaloids were isolated from the CH 2 Cl 2 extract and their structures were identified to be euchrestine B (1), bismurrayafoline E (2), mahanine (3), mahanimbicine (4), and mahanimbine (5) based on 1 H and 13 C NMR and mass (MS) spectral data. The OSI value of carbazoles at 110°C decreased in the order 1 and 3 > R-tocopherol > BHT > 2 > 4, 5 and control. It is assumed that compounds 1 and 3 contributed to the high OSI value of the CH 2 Cl 2 extract of M. koenigii. The DPPH radical scavenging activity for these carbazoles was in the order ascorbic acid > 2 > 1, 3 and R-tocopherol > BHT > 4 and 5.
QuantitativeAnalysis of BioactiveCarbazole Alkaloids in Murraya koenigii(L.) Spreng
Natural Product Communications, 2014
Carbazole alkaloids induce apoptosis in HL-60 cells through activation of the caspase-9/caspase-3 pathway and they are targeted as potential anticancer agents. Thus, the naturally occurring carbazole alkaloids become important as precursors for lead optimization in drug development. A method based on ultra performance liquid chromatography coupled with photodiode-array detection was developed using reverse phase isocratic elution with 85:15 acetonitrile and ammonium acetate buffer (5 mM). Seven samples of Murrya koenigii (L.) Spreng. from north-central India (Uttar Pradesh) were analyzed. All three targeted analytes, koenimbidine (mk1), koenimbine (mk2) and mahanimbine (mk3), were well separated within 4.0 min with linearity of the calibration curves (r 2 > 0.999). The limits of detection and quantification of mk1, mk2 and mk3 were 0.7, 0.4, 0.04 µg/mL and 2.14, 1.21, 0.12 µg/mL, respectively. The natural abundance of mk1, mk2 and mk3 was 0.06 -0.20, 0.04 -0.69 and 0.13 -0.42%, w/w, respectively, in the dried powdered leaves, whereas, the tissue specific distribution of carbazole alkaloids was observed in the order of predominance, mk1 leaf>root>fruit>stem, mk2 fruit>leaf >stem>root, and mk3 fruit>leaf>root>stem. The developed method was validated for limits of detection and quantification, repeatability, accuracy, precision and stability. This is the first report on the natural abundance of the major carbazole alkaloids in M. koenigii and the method developed can be used in HPLC/UPLC systems.