%-3 Bangladesh Journal of Pharmacology Research Article Chemical composition of the leaf essential oils of Murraya koenigii (L.) Spreng and Murraya paniculata (L.) Jack $-RXUQDORIWKH%DQJODGHVK3KDUPDFRORJLFDO6RFLHW\ %'36 %DQJODGHVK-3KDUPDFRO- -RXUQDOKRPHSDJHZZZEDQJODMROLQIR $EVWUDFWHGLQGH[HG LQ $FDGHPLF 6HDUFK &RPSOHWH $VLD -RXUQDOV 2QOLQH %DQJODGHVK -RXUQDOV 2QOLQH %LRORJLFDO $EVWUDFWV %,26,6 3UHYLHZV &$% $EVWUDFWV &XUUHQW $EVWUDFWV 'LUHFWRU\ RI 2SHQ $FFHVV -RXUQDOV (0%$6(([FHUSWD 0HGLFD *RRJOH 6FKRODU +,1$5, :+2  ,QWHUQDWLRQDO 3KDUPDFHXWLFDO$EVWUDFWV2SHQ--JDWH 6FLHQFH&LWDWLRQ,QGH[([SDQGHG6&2386DQG6RFLDO6FLHQFHV&LWDWLRQ,QGH[ ,661- Chemical composition of the leaf essential oils of Murraya koenigii (L.) Spreng and Murraya paniculata (L.) Jack -DVLP8GGLQ&KRZGKXU\0G1D]UXO,VODP%KXL\DQDQG0RKDPPHG<XVXI %&6,5/DERUDWRULHV&KLWWDJRQJ&DQWRQPHQW&KLWWDJRQJ%DQJODGHVK $UWLFOH,QIR $EVWUDFW Received: Accepted: Available Online: 16 May 2008 19 May 2008 19 May 2008 DOI: 10.3329/bjp.v3i2.841 Cite this article: Chowdhury JU, Bhuiyan MNI, Yusuf M. Chemical composition of the leaf essential oils of Murraya koenigii (L.) Spreng and Murraya paniculata (L.) Jack. Bangladesh J Pharmacol. 2008; 3: 59-63. The chemical composition of the leaf oils of Murraya koenigii (L.) Spreng and M. paniculata (L.) Jack from Bangladesh was studied by gas chromatography mass spectroscopy (GC-MS). M. koenigii oil contained 39 compounds of which the major is 3-carene (54.2%) followed by caryophyllene (9.5%). Oil of M. paniculata contained 58 compounds of which the major are caryophyllene oxide (16.6%), β-caryophyllene (11.8%), spathulenol (10.2%), β-elemene (8.9%), germacrene D (6.9%) and cyclooctene, 4-methylene-6-(1-propenylidene) (6.4%). The compositions of both oils varied qualitatively and quantitatively. Introduction A systematic study on the medicinal and aromatic plants is being carried out in Bangladesh. Among these plants one finds Murraya koenigi (L.) Spreng and M. paniculata (L.) Jack of the Rutaceae family. Murraya koenigii (L.) Spreng is a small strong smelling perennial shrub or small tree commonly found in forests as undergrowth, cultivated in India for its aromatic leaves and for ornament. Leaves are used as a condiment in the preparation of curry powder, pickle, chutney, sausages and seasonings (Anonymous, 1962; Hiremath et al., 1998). The flavor and fragrance of leaves retain even after drying (Omankutty Amma et al., 1984). Leaves relieve nausea, indigestion, vomiting; eaten as a cure for diarrhea and dysentery (Anonymous, 1962; Ghani, 2003). Essential oil composition of leaves has been studied by various workers. The major constituents responsible for the aroma and flavor have been reported as pinene, sabinene, caryophyllene, cadinol and cadinene (Anonymous, 1962; Nigam and Purohit, 1961; Prakash and Natarajan, 1974; Macleod and Pieries, 1982; Hiremath et al., 1998). Raina et al. (2002) reported four genetically divers chemotypes (1) βpinene (70%), β-caryophyllene (6.5%) and α-pinene (5.4%), (2) α-pinene (65.7%), β-pinene (13.4%) and βphellandrene (7.4%), (3) β-caryophyllene (53.9%), aromadendrene (10.7%) and α-selinene (6.3%), (4) βphellandrene (30.2%), β-caryophyllene (24.2%), αpinene (15%), (E)-β-ocimene (5%) and aromadendrene (4.5%) as major constituents from various parts of India. Walde et al. (2005) reported α-pinene (52%) and cis-βocimene (34%) as major constituents in Hyderabad plants. M. paniculata (L) Jack. syn. Chalcas paniculata L. Chalcas exotica (L.) Millsp. is a very variable evergreen shrubby plant with small white flowers, small oblong fruits and hard wood, planted in gardens as an ornamental in many areas of the country. Leaves are stimulant and astringent and are used in the treatment of diarrhea, dysentery and diseases of teeth and gum; useful against rheumatism, coughs and hysteria (Anonymous, 1962; Chopra et al., 1956; Ghani, 2003). The essential oils showed significant anti-inflammatory and analgesic activities (Dash et al., 2004). Sawangjaroen et al. (2006) This work is licensed under a Creative Commons Attribution 4.0 License. You are free to copy, distribute and perform the work. You must attribute the work in the manner specified by the author or licensor. 60 Bangladesh J Pharmacol 2008; 3: 59-63 reported, it showed anti-amoebic activities. The leaves and other tissues have both stimulant and astringent properties and are used to treat diarrhea, dysentery, cuts, joint pain, body aches (Parrotta, 2001), venereal disease (Kinoshita and Firman, 1996), and as an abortive (Xiao and Wang, 1991). In addition to essential oils, tissues of orange jasmine contain the indole alkaloid yuehchukene (Xiao and Wang, 1991) and at least eight highly oxygenated flavones (Kinoshita and Firman, 1996), leaves yield oil, which contains sesquiterpenes (l-cadinene), α-sesquiterpene alcohol and methyl anthranilate (Anonymous, 1962; Chopra et al., 1956). Nureni et al. (2004) reported, the principal constituents of the leaf oil were β-cyclocitral (22.9%), methylsalicylate (22.4%), trans-nerolidol (11.7%), αcubebene (7.9%), (-)-cubenol (6.8%), β-cubebene (5.8%) and isogermacrene (5.7%). The most prominent compounds were β-caryophyllene (24.1%), with lesser amounts of germacrene D (11.9%) and bicyclogermacrene (11.8%). Some reports of the chemical composition of the leaf oil of M. paniculata of Asian or Australian origin have appeared (Garg and Nigam, 1970; Qiang et al., 1988; Brophy et al., 1994). In our study the abundance of 3-carene was the highest. It has various medicinal uses (Jeong et al., 2007; Lastbom et al., 1998). On the other hand, M. paniculata contained abundance of caryophyllene oxide which has antifungal activities (Yang et al., 1999). So, the present study deals with the investigation of the chemical components in oils obtained from leaf of M. koenigii and M. paniculata grown in Bangladesh. Materials and Methods Plant material Fresh leaves of M. koenigii and M. paniculata were collected from the plants grown in the campus of BCSIR Laboratory, Chittagong during June 2007. Two-voucher specimen (Y-325) was deposited in the herbarium of BCSIR Laboratory, Chittagong. Extraction of essential oil Leaves were harvested and air-dried for about one week. The oils were obtained by hydrodistillation for 4 hours in a Clevenger-type apparatus. The oil yields (calculated per weight of dried material) were 0.5% for M. paniculata and 1.0% for M. koenigii. The oil samples were stored at 0°C in air-tight containers after drying them over anhydrous sodium sulfate for gas chromatography mass spectroscopy (GC-MS) analyses. GC-MS analysis The essential oil from leaves of M. koenigii and M. paniculata were analyzed by GC-MS electron impact ionization (EI) method on GC-17A gas chromatograph (Shimadzu) coupled to a GC-MS QP 5050A mass spectrometer (Shimadzu); fused silica capillary column (30 m x 2.5 mm; 0.3 mm film thickness), coated with DB -1 (J&W); column temperature 100°C (2 min) to 250°C at the rate of 3°C/min; carrier gas, helium at constant pressure of 90Kpa. Acquisition parameters full scan; scan range 40-350 amu. Identification of the compounds Compound identification was done by comparing the NIST library data of the peaks with those reported in literature, mass spectra of the peaks with literature data. Percentage composition was computed from GC peak areas on BP-I column without applying correction factors. Results and Discussion The essential oils from the leaves of M. koenigii and M. paniculata were analyzed by GC-MS presented in Table I. M. koenigii oil contains 39 compounds of which the major is 3-carene (54.2%) followed by caryophyllene (9.5%). Other notable compounds in the M. koenigii oil are α-thujene (1.5% ), allyl(methoxy)dimethylsilane (2.6%), β-myrcene (3.2%), α-terpinene (2.4%), g-terpinene (2.7%), cis-sabinenehydrate (1.5%), 4-terpineol (2.8%), β-elemene (1.9%), α-caryophyllene (2.8%), gelemene (2.96%), caryophyllene oxide (1.02%) and 3phenylbutyrophenone (1.15% ). Oil of M. paniculata contains 58 compounds of which the major are caryophyllene oxide (16.63% ), β-caryophyllene (11.81% ), spathulenol (10.21%), β-elemene (8.94%), germacrene D (6.95%) and cyclooctene, 4-methylene-6-(1-pro-penylidene) (6.37% ). Other major compounds in the M. paniculata oil are cyclohexene, 5,6-dietheyl-3-methyl (3.30%), d-elemene (3.57%), α-cubebene (2.96%), retinal (1%), α-caryophyllene (3.13%), copaene (2.33%), cubenol (2.36%), nerolidyl acetate (1.20%), 12-oxabi-cyclo (9.1.0)dodeca-3,7-diene,1,5,5,8–tetramethyl (2.1%), eremophilene (1.54%), ledol (2.2%) and aromadendrene oxide (1.5%). The presence of 3-carene as major compound in M. koenigii is not reported from elsewhere, completely differs from those reported by Raina et al. (2002) and Walde et al. (2005), where pinene, caryophyllenes and phellandrenes were the predominant compounds. This oil may be treated as a natural source of 3-carene, which may be studied for any bioactive properties for therapeutic uses. Also may serve as a useful compound of flavors and fragrances. The oil of M. paniculata also found different from the reports (Anonymous, 1962; Chopra et al., 1956). The study reveals that composition of two oils differs from the earlier reports and may, therefore be treated as different chemotypes. On the basis of above fact it may be concluded that M. koenigii and M. paniculata, growing widely in Bangladesh, may be utilized as a source for Bangladesh J Pharmacol 2008; 3: 59-63 61 Table I Constituents of leaf essential oil from M. koenigii and M. paniculata Compounds from M. koenigii % Compounds from M. paniculata % Sabinene 0.1 3-Hexen-1-ol, formate 0.1 1 α-Thujene 1.5 2 3-Carene 54.2 3 Camphene 0.1 Limonene 0.3 4 Allyl(methoxy)dimethylsilane 2.6 Linalool 0.1 5 β-Myrcene 3.2 Cyclohexene,3,4-diethenyl-3-mehyl 0.6 6 α-Phellandrene 0.1 Cyclohexene,5,6-diethenyl-3-methyl 3.3 7 α-Terpinene 2.4 Azulene 0.1 8 m-Cymene 0.3 Ocimene 0.1 9 Limonene 0.8 cis-3-Hexenyl valerate 0.2 10 β-Phellandrene 0.5 2-Cyceohexen-1-one, 2-methyl-5-(1-methylethenyl) 0.1 11 Eucalyptol 0.1 1H-Imidazole 0.1 12 (E)-Ocimene 0.2 d-Elemene 3.6 13 g-Terpinene 2.7 α-Cubebene 3.0 14 cis-Sabinenehydrate 1.5 Germacrene D 6.9 15 Linalool 0.2 3,9-Dodecadiene 0.1 16 4-Terpineol 2.8 b-Caryophyllene 11.8 17 Naphthalene 0.1 Caryophyllene oxide 16.6 18 Terpinyl acetate 0.1 Cyclooctene, 4-methylene-6-(1-propenylidene) 6.4 19 cis-Piperitol 0.1 Retinal 1.0 20 Isobornyl acetate 0.1 α-Caryophyllene 3.1 21 d-Elemene 0.04 β-Humulene 0.2 22 Neryl propionate 0.04 Copaene 2.3 23 1-Chloroheptacosane 0.1 g-Elemene 0.3 24 β-Elemene 1.9 Cubenol 2.4 25 Caryophyllene 9.5 α-Bulnesene 0.1 26 α-Caryophyllene 2.8 Calamenene 0.3 27 Eudesma-4(14),11-diene 0.2 3-Tetradecynoic acid 0.2 28 g-Elemene 2.0 Lanceol, cis 0.3 29 d-Cadinene 0.1 β-Vatirenine 0.1 30 Nerolidyl acetate 0.2 β-Elemene 8.9 31 Caryophyllene oxide 1.0 Nerolidyl acetate 1.2 32 0.1 Alloaromadendrene oxide 0.3 33 12-Oxabicyclo[9.1.0]dodeca-3,7-diene, 1,5,5,8-tetramethyl1,4-Methanoazulen-9-ol, decahydro1,5,5,8a-tetramethyl Compounds from M. koenigii 0.1 Spathulenol 34 Cubenol 0.1 D-Verbenone 0.6 35 0.1 Pyrimdine-2(1H) thione, 3,4-dihydro -6-methyl, 4-phenyl 0.5 36 2(1H)-Naphthalenone, 4a,5,6,7,8,8ahexahydro-4a,8a-dimethylα-Cadinol 0.1 3-Carene 0.9 37 Juniper camphor 0.5 2.1 38 3-Phenylbutyrophenone 1.2 12-Oxabicyclo(9,1,0) dodeca-3,7-diene,1,5,5,8 - tetramethyl Globulol 39 Phytol 0.9 Eremophilene 1.5 -4-methanol,5-methyl 10.2 Compounds from M. paniculata 0.2 Bangladesh J Pharmacol 2008; 3: 59-63 62 Table I Constituents of leaf essential oil from M. koenigii and M. paniculata (Cont.) Compounds from M. koenigii % Compounds from M. paniculata % 40 2(1H) Naphthalenone, 4a,5,6,7,8,8a-hexahydro, 4a,8adimethyl 0.3 41 Tau-Muurolol 0.9 42 Ledol 2.2 43 Aromadendrene oxide 1.5 44 α-Calaconene 0.3 45 Longifolenealdehyde 0.6 46 11-Hexadecyn-1-ol 0.2 47 Cycloisolongifolene, 8-hydroxyendo 0.3 48 Longipinocarveol, trans 0.2 49 Carveol 0.1 50 1-Cyclohexene-1-ethanol, 2,6,6-trimethyl 0.1 51 1-Methyl verbenol 0.2 52 Cyclopropane, 1-bromo-2,2,3,3-tetramethyl-1prop-1-ynyl 0.2 53 Corymbolone 0.1 54 0.1 55 2(4a,8-Dimethyl-1, 3,3,4,4a,5,6,7-octahydro-naphthalene2-yl) -prop-2-en-1-ol Ledene alcohol 56 Aristolene oxide 0.3 57 6-Isopropenyl-4,8a-dimethyl 1,2,3,5,6,7,8,8a, octahydro naphthalen-2-ol Longifolene-[12]-epoxide 1.0 58 0.7 0.1 the isolation of natural 3-carene and caryophyllene oxide respectively. Jeong JG, Kim YS, Min TY, Kim SH. Low concentration of 3carene stimulates the differentiation of mouse osteoblastic MC3T3-E1 subclone 4-cells. Phytotherapy Res. 2007; 22: 1822. 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