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Volatile Chemical Constituents of Nepeta Raphanorhiza Benth Growing in Kashmir Valley. Tauheeda Hassan1,*, Shakeel-U-Rehman2*, Bilal A

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Volatile Chemical Constituents of Nepeta Raphanorhiza Benth Growing in Kashmir Valley. Tauheeda Hassan1,*, Shakeel-U-Rehman2*, Bilal A Tauheeda Hassan and Shakeel-u-Rehma et al. / Journal of Pharmacy Research 2011,4(9),3128-3129 Research Article Available online through ISSN: 0974-6943 www.jpronline.info Volatile Chemical Constituents of Nepeta raphanorhiza Benth growing in Kashmir valley. Tauheeda Hassan1,*, Shakeel-u-Rehman2*, Bilal A. Bhat3, Manzoor A.Rather2,Khursheed A. Bhat2, Abdul S. Shawl 2, Ghulam H. Dar1 1 Department of Botany, University of Kashmir, Srinagar-190006, India. 2 Natural Product Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Srinagar-190005, India. 3Department of Zoology, University of Kashmir, Srinagar - 190006, India. Received on: 28-06-2011; Revised on: 15-07-2011; Accepted on:11-08-2011 ABSTRACT The essential oil composition of the aerial parts of N. raphanorhiza is reported for the first time. Capillary GC & GC-MS analysis of the essential oil led to the identification of 16 components accounting for 97.5% of the total oil composition .Sesquiterpene hydrocarbons dominated the oil composition accounting for 65.3 % followed by monoterpenes hydrocarbons constituting 1 9.5 % of the total o il composition. The major components were (Z) -ß- farnesene (49.2%), d- 3-carene (12.3%), a-bisabolene (9.4%) and germacrene-d-4-ol (5.8%). Keywords: Nepeta raphanorhiza, Lamiaceae, GC, GC-MS, (Z)-ß- farnesene, d-3-carene, a-bisabolene. 1. INTRODUCTION Nepeta is a multiregional genus of the family Lamiaceae comprising about 250 and head space analyzer using a fused silica capillary Column (30m x 0.32 mm, species distributed mainly in Southwest & central Asia, Europe, North Africa film thickness 0.25ìm) Coated with dimethyl polysiloxane (RTX-5). Oven & North America. About 30 species occur in India, mostly distributed in temperature was programmed from 60 to 280 0 C at 3 0 C/min, with temperate Himalayas & a few on foothills & plains [1, 2]. Several species of Injector temperature 230 0C and detector temperature 250 0C. Injection vol- the genus Nepeta are rich in interesting biological activities and are used in traditional system of medicine as laxative to treat dysentery, kidney and liver ume 1µl, nitrogen was used as a carrier gas (1.0 ml/min). diseases and teeth troubles [3];they are also used as diuretic, diaphoretic, 2.4 Gas Chromatography-Mass Spectrometry vulnerary, antispasmodic, antiasthmatic, tonic, febrifuge and sedative agents [3,4,5,6]. Several Nepeta species are also reported to reduce serum lipids and GC-MS analysis was carried on a Varian Gas Chromatograph series 3800 fitted with a VF-5 ms fused silica capillary colu mn (60m x 0.25mm, film thickness anti-inflammatory effects [7, 8]. Most Nepeta species are rich in essential oils 0.25µm) co upled with a 4000 s eries mass detector under the following and various biologically active iridoids/monoterpene nepetalactones have been reported in several Nepeta species possessing diverse biological activities, viz., conditions: injection volume 0.5 µl with split ratio 1:60, helium as carrier gas at 1.0 ml/min constant flow mode, injector temperature 230 OC, oven feline attractant, canine attractant, insect repellant and arthropod defense [9, temperature 60 0 C to 280 0C at 3 0C/min. Mass spectra: electron impact 10]. (EI+) mode,70 ev and ion source temperature 250 0C. Mass spectra were recorded over 50-500 a.m.u range. Identification of the essential oil constitu- Nepeta raphanorhiza locally known as “Kanz-gogal” is a low growing peren- ents was done on the basis of Retention Index (RI, determined with respect to nial herb with tubers growing up to 20 mm in diameters, stem prostrate ranging homologous series of n-alkanes (C -C , Polyscience Corp., Niles IL) under the 10-25 cm. Leaves are green, broad triangular,ovate. It is mainly found in 9 24 same experimental conditions), co-injection with standards (Sigma Aldrich Afghanistan, Pakistan & Northwest India. Its rhizome is edible and is eaten by and standard isolates), MS Library search (NIST 98 and WILEY), by compar- the locals. As part of our Institute’s programme to screen the rich aromatic flora of the region for new essential oils and aroma chemicals, we report here ing with the MS literature data [12,13].The relative percentages of the indi- vidual components were calculated based on GC peak area (FID response) for the first time the essential oil composition of Nepeta raphanorhiza grow- without using correction factors. ing in Jammu and Kashmir (India) using a combination of capillary GC and GC- MS analytical techniques. 3. RESULTS AND DISCUSSION The essential oil components identified in N. raphanorhiza are shown in Table 2. MATERIALS AND METHODS 1.The average oil yield was 0.1% calculated on fresh weight basis. GC and GC- MS analysis led to the identification of 16 components representing 97.5% of 2.1. Plant Material the total oil composition. The GC-MS total ion chromatogram (TIC) is shown The plant material of Nepeta raphanorhiza was collected from Pulwama in figure 1 . The essential oil is dominated by the presence of sesquiterpene region of Kashmir valley during April 2010 and identified in the Centre for hydrocarbons constituting 65.3% followed by monoterpene hydrocarbons which Biodiversity and Taxonomy (CBT), Department of Botany, University of constitute 19.5% of the total oil composition. The principal components of Kashmir, Srinagar (India). A voucher specimen has been deposited in the the sesquitrepene hydrocarbons were (Z)-ß- farnesene (49.2%), a-bisabolene Herbarium of CBT (voucher No. KASH-2705).The fresh plant material was (9.4%), ß-caryophyllene (3.2%) and a-humulene (2.0%), d-3-carene was the finely chopped and then subjected to hydro-distillation using Clevenger-type main constituent of monoterpene hydrocarbons (12.3%). Some other chemi- apparatus for 3 hours. The oil yield was found to be 0.1% as calculated on fresh cal constituents with lesser quantity in the oil were sabinene (2.5%), germacrene- weight basis. The oil was dried over anhydrous Na2SO 4 and stored in a sealed D-4-ol (5.8%), and caryophyllene oxide (3.4%). The characteristic feature of vial at - 40C until analysis. the essential oil composition was the low quantity of 4aa, 7ß, 7a a-nepetalactone isomer. 2.3 Gas Chromatography Gas chromatography was carried out on Perkin Elmer auto system XL Gas The essential oils of several species of the genus Nepeta such as N. sintenisii [14], Chromatograph 8500 series equipped with flame ionization detector (FID) N. atlantica, N. tuberosa, N. granatensis , N. cataria [15], N. cephalotes [16], N. nuda [17] and N.coerulea [18] have been examined and are characterized *Corresponding author. by the presence of one or more of the nepetalactone isomers viz, 1.Tauheeda Hassan 4aa,7a,7ab- nepetalactone, 4aa,7b,7ab-nepetalactone and 4aa,7a, Department of Botany, 7aa-nepetalactone. These isomers have been labeled as the biochemical mark- University of Kashmir, ers of the Nepeta essential oils and are very useful in chemotaxonomic studies. Srinagar-190006, India. However, several of the Himalayan Nepeta species which are found in Jammu Tel.: + 91-9906911106 and Kashmir like N.floccosa, N.discolor, N.royleana, N.leucophylla, N. E-mail:[email protected] govaniana, N. clarkii, N. elliptica, N.erecta [18,19] contain either low con- tent of these nepetalactones or are absent. Comparing our results with other 2.Shakeel-u-Rehman Himalayan Nepeta species, it implies that various marker constituents other Natural Product Chemistry Division, than the nepetalactone isomers have been identified in these essential oils. Indian Institute of Integrative Medicine (CSIR), Srinagar-190005, India. Tel.: + 91-9906911106 E-mail:[email protected] Journal of Pharmacy Research Vol.4.Issue 9. September 2011 3128-3129 Tauheeda Hassan and Shakeel-u-Rehma et al. / Journal of Pharmacy Research 2011,4(9),3128-3129 Figure 1: The HS-SPME GC-MS total ion chromatogram of the leaf volatiles of Nepeta raphanorhiza growing in Kashmir valley. REFERENCES 1. J.D.Hooker (1975). Flora of British India.vol.iv.P.Repd.M/S Bishen singh Table 1. Chemical composition of the essential oil of Nepeta raphanorhiza. Mahendra Pal Singh, New Cannaught place Dehradun and M/S periodical xperts,Del in (1973). RI Compound % composition 2. The Wealth of India (1966). Raw materials Vol.viii.p.12-13. Publication and 937 a-Pinene 1.6 information Directorate, CSIR, New Delhi. 947 Camphene 0.4 3. K.H.C Baser, N. Kirimer, M. Kurkcuoglu and B. Demirci (2000). Essential oils 972 Sabinene 2.5 of Nepeta species growing in Turkey, Chem. Nat. Compd. 36, 356 359. 976 b-Pinene 1.2 4. M. Dabiri and F Sefidkon (2003). Composition of essential oil of 1011 d-3- Carene 12.3 Nepeta crassifolia Boiss Buhse, Flav. Fragr. J. 18, 225-227. 1016 a-Terpinene 1.5 1290 Bornyl acetate 1.8 5. A.Rapisarda, E.M.Galati, O. Tzakou, M. Flores, and N. Miceli (2001). Nepeta 1394 Nepeta lactone- (4aá,7â,7aá) 0.5 sibthorpii Bentham (Lamiaceae): Micromorphological analysis of leaves and 1419 ß-Caryophllene 3.2 flowers, Farmaco 56, 413-415. 1443 (Z)-ß-Farnesene 49.2 6. A. Zargari (1990). Medical Plants, 4, Tehran University Publications, Tehran, 1454 a-Humulene 2.0 pp. 106-111. 1486 Germacrene D 0.8 7. O.P. Agarwal, D.S. Khanna and R.B.Arora (1978). Studies of anti- atheroscle- 1509 a-Bisabolene 9.4 rotic action of ‘ Nepeta hindostana in pigs, Arterry 4, 487-496. 1525 d-Cadinene 0.7 1578 Germacrene-D-4-ol 5.8 8. S.A. Prokopenko and A.V. Spiridonov (1985). Betulin from 1587 Caryophyllene oxide 3.4 Transcaucasian clover (Nepeta), Farm. Zhurnal. 6, 70. 1656 a-Cadinol 1.0 9. A.O. Tucker and S. S. Tucker (2009).
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