Carbazole Alkaloids from Stem Bark of Murraya koenigii (L.) Spreng (original) (raw)
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 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).
C23-carbazole alkaloids from malayan Murraya koenigii (L.) spreng
Murraya koenigii (Curry leaf tree), from the Rutaceae family, is a medicinally important herb of Indian origin and now were widely distributed throughout southern Asia. The bark of Malayan Murraya koenigii was selected for phytochemical investigation. The isolation of chemical constituents from its hexane and dichloromethane extract was carried out by using different chromatographic techniques. Six carbazoles with C23-framework was isolated and identified as mahanimbine, murrayamine-J, murrayazolinol, mahanimbilol, murrayakoeninol and bicyclomahanimbine. The structural characterization of the isolated compounds was supported by spectroscopic methods, including NMR, IR, UV, MS spectra data.
Carbazole Alkaloids from Roots of Murraya Koenigii (Rutaceae)
2001
The study on petroleum ether extract of the roots of Murraya koenigii (curry leaf) which involves extraction, separations by using various chromatographic methods and structural determination by spectroscopic techniques have afforded two compounds; 3-methylcarbazole and murrayafoline A. The structure of the compounds were also confirmed by comparison with the previous works. Abstrak. Kajian terhadap ekstrak petroleum eter akar pokok Murraya koenigii (daun kari) yang melibatkan pengekstrakan, pengasingan menggunakan pelbagai kaedah kromatografi dan pengenalpastian struktur dengan teknik spektroskopi telah menghasilkan dua komponen; 3-methylcarbazole dan murrayafoline A. Struktur sebatian yang dipencilkan juga telah dibuat perbandingan dengan hasil kajian lepas.
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.
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.
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.
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.
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-...
Antidiarrhoeal activity of carbazole alkaloids from Murraya koenigii Spreng (Rutaceae) seeds
Fitoterapia, 2010
The bioassay guided fractionation of the n-hexane extract of the seeds of Murraya koenigii Spreng (Rutaceae) resulted in the isolation of three bioactive carbazole alkaloids, kurryam (I), koenimbine (II) and koenine (III). The structures of the compounds were confirmed from their 1 H-, 13 C-, and 2D-NMR spectral data. Of the three compounds (I) and (II) exhibited significant inhibitory activity against castor oil-induced diarrhoea and PGE 2-induced enteropooling in rats. The compounds also produced a significant reduction in gastrointestinal motility in the charcoal meal test in Wister rats.
Analgesic Acti-Ity of Carbazole Alkaloid from Murraya paniculata Linn. (Rutaceae)
2014
Murraya paniculata Linn. (Rutaceae) is commonly used in the treatment of pain, rheumatism diarrhea and dysentery. Leaves of this plant were standardized pharmacognostically. Preliminary phytochemical study of methanolic extract showed the presence Alkaloids, Flavonoids, Phenolic compounds, Phytosterols, Proteins and amino acids while saponins were absent Phytochemical studies led to isolation of alkaloid Isomurrayafoline B (Isb) and was tested at 10 and 20 mg/kg p.o. for in vivo analgesic activity, peripheral as well as central pain model. Isb demonstrated 80.33% and 93.87% inhibition in the number of writhes at both doses respectively. Similarly, the thermal attenuation of Isb (20 mg/kg p.o.) was found more significant (P<0.01) after 60 min of administration that remained significant upto 120 min, while Isb (10mg/kg p.o) showed significant effect (P<0.01) only after 60 minutes of administration. The isolated compound showed profound analgesic activity in both peripheral and central pain models; needs further detail studies for clinical utility. In the meantime, the study validated the uses of the plant in traditional system of treatment.
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.
Molecules, 2011
A total of three carbazole alkaloids and essential oil from the leaves of Murraya koenigii (Rutaceae) were obtained and examined for their effects on the growth of five antibiotic resistant pathogenic bacteria and three tumor cell lines (MCF-7, P 388 and Hela). The structures of these carbazoles were elucidated based on spectroscopy data and compared with literature data, hence, were identified as mahanine , mahanimbicine (2) and mahanimbine (3). The chemical constituents of the essential oil were identified using Gas Chromatography-Mass Spectroscopy (GCMS). These compounds exhibited potent inhibition against antibiotic resistant bacteria such as Staphylococcus aureus (210P JTU), Psedomonas aeruginosa (ATCC 25619), Klebsiella pneumonia (SR1-TU), Escherchia coli (NI23 JTU) and Streptococcus pneumoniae (SR16677-PRSP) with significant minimum inhibition concentration (MIC) values (25.0-175.0 mg/mL) and minimum bacteriacidal concentrations (MBC) (100.0-500.0 g/mL). The isolated compounds showed significant antitumor activity against MCF-7, Hela and P388 cell lines. Mahanimbine (3) and essential oil in particular showed potent antibacteria and cytotoxic effect with dose dependent trends (≤5.0 μg/mL). The findings from this investigation are the first report of carbazole alkaloids' potential against antibiotic resistant clinical bacteria, MCF-7 and P388 cell lines. OPEN ACCESS Molecules 2011, 16 9652
Sains Malaysiana, 2018
In this paper, antioxidant properties of Aegle marmelos (stem bark, leaves) and Murraya koenigii (stem bark, root) were evaluated by 2,2-diphenyl-1-picrylhydrazy (DPPH) free radical scavenging, 2,2'-Azino-bis(3-ethylbenzthiozoline-6-sulfonic acid) (ABTS) decolourisation, cupric reducing antioxidant capacity (CUPRAC), ferric reducing antioxidant power (FRAP) and linoleic acid/β-carotene assays. The chloroform extract of Murraya koenigii stem bark was found to possess the highest antioxidant activity in CUPRAC (1490.89 mgTE/g extract). In contrary, the hexane extract from Aegle marmelos leaves exhibited the weakest antioxidant activity in the DPPH assay (81.06 mgTE/g extract). The bioactive compound mahanimbine (7) isolated from the stem bark of Murraya koenigii was found to be the most active antioxidant agent with TEAC of 927.73 and 1649.31 mgTE/g corresponding to the ABTS and CUPRAC assays, respectively, as well as a good lipid peroxidation inhibitor with an inhibitory percentage of 70.95%. These CUPRAC and ABTS assays are the first report for Malaysian Murraya koenigii species.
BioMed Research International
Murraya koenigii is a well-known Indian medicinal herb, and a carbazole alkaloid (mahanine) from this plant causes apoptosis in cancer cells. Here, we investigated how seasonal and geographical variations influence carbazole alkaloids composition and medicinal property of this plant against cancer cells in vitro and in vivo. Leaflets were collected from various places in different seasons for three years. A mahanine-enriched fraction (MEF) was prepared in two steps using ethanol and water. The best plant was selected based on the highest percent of mahanine. MEF prepared from leaflets of nine different locations showed a different concentration of identified markers (mahanine, mahanimbine, and koenimbine) which exhibited differential reduced metabolic activity against ovarian cancer, mahanine being the best. Our systematic study revealed that mahanine content was highest during September–December. Interestingly, MEF from southern part (tropical zone) exhibited 43 ± 2.5% mahanine com...
Antioxidants, 2020
The discovery of several revitalizing molecules that can stop or reduce the pathology of a wide range of diseases will be considered a major breakthrough of the present time. Available synthetic compounds may provoke side effects and health issues, which heightens the need for molecules from plants and other natural resources under discovery as potential methods of replacing synthetic compounds. In traditional medicinal therapies, several plant extracts and phytochemicals have been reported to impart remedial effects as better alternatives. Murraya koenigii (M. koenigii) belongs to the Rutaceae family, which is commonly used as a medicinally important herb of Indian origin in the Ayurvedic system of medicine. Previous reports have demonstrated that the leaves, roots, and bark of this plant are rich sources of carbazole alkaloids, which produce potent biological activities and pharmacological effects. These include antioxidant, antidiabetic, anti-inflammatory, antitumor, and neuroprotective activities. The present review provides insight into the major components of M. koenigii and their pharmacological activities against different pathological conditions. The review also emphasizes the need for more research on the molecular basis of such activity in various cellular and animal models to validate the efficacy of M. koenigii and its derivatives as potent therapeutic agents.
Alkaloids, Coumarin and Cinnamic Acid Derivative from Murraya koenigii (Linn.) Spreng
Dhaka University Journal of Pharmaceutical Sciences, 2015
A total of seven compounds were isolated from the methanol extract of leaves of Murraya koenigii (Linn.) Spreng. The isolated compounds were characterized as arborinine , ferulic acid , umbelliferone , mahanimbine (4), koenimbine (5), koenidine and O-demethyl murrayanine by extensive spectroscopic studies, including high field NMR analysis as well as co-TLC with authentic samples, whenever possible. This is the first report of occurrence of arborinine (1) and ferulic acid (2) from Murraya species.
Molecules, 2012
Girinimbine, a carbazole alkaloid isolated from the stem bark of Murraya koenigii was tested for the in vitro anti-tumour promoting and antioxidant activities. Anti-tumour promoting activity was determined by assaying the capability of this compound to inhibit the expression of early antigen of Epstein-Barr virus (EA-EBV) in Raji cells that was induced by the tumour promoter, phorbol 12-myristate 13-acetate. The concentration of this compound that gave an inhibition rate at fifty percent was 6.0 µg/mL and was not cytotoxic to the cells. Immunoblotting analysis of the expression of EA-EBV showed that girinimbine was able to suppress restricted early antigen (EA-R). However, diffused early antigen (EA-D) was partially suppressed when used at 32.0 µg/mL. Girinimbine exhibited a very strong antioxidant activity as compared to -tocopherol and OPEN ACCESS was able to inhibit superoxide generation in the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced differentiated premyelocytic HL-60 cells more than 95%, when treated with the compound at 5.3 and 26.3 µg/mL, respectively. However girinimbine failed to scavenge the stable diphenyl picryl hydrazyl (DPPH)-free radical.
Asian Journal of Chemistry, 2013
Phytochemical studies on different parts of Murraya koenigii (L.) have resulted in the isolation of six carbazole alkaloids which have been identified as mahanimbine (1), girinimbine (2), murrayacine (3), murrayanine (4), murrayafoline-A (5) and 3-methylcarbazole (6) together with β-sitosterol. The structures of these compounds were established using spectroscopic techniques. The crude extracts and chemical constituents obtained from the isolation work were tested on its larvicidal activity against dengue fever mosquito, Aedes aegypti. Hexane extract from stem bark, roots and leaves of Murraya koenigii showed strong activity against Aedes aegypti followed by chloroform extract of the roots and leaves. Methanol extract of the leaves also showed strong activity while methanol extract of the roots showed moderate activity. Besides, chloroform and methanol extracts from stem bark showed strong activity. Similarly, pure compounds isolated from the plant, mahanimbine (1), girinimbine (2), murrayacine (3), murrayanine (4) and murrayafoline A (5) exhibited strong activity against Aedes aegypti with LC50 values of less than 3 µg/mL.