In this study, the chemical composition of the essential oil of Premna coriacea leaves was investigated. Extraction by hydrodistillation followed by gas chromatography and mass spectrometry (GC-MS) yielded 27 compounds representing 99.89% of the oil. The major volatile components of the oil were aromadendrene (23.51), caryophyllene (19.27), tetracontane (11.90), 17-pentatriacontene (6.61), 3',8,8'-trimethoxy-3-piperidyl-2,2'- binaphthalene-1,1',4,4'-tetrone (4.68), cis-α-bisabolene (4.65), octadecane, 3-ethyl-5-(2-ethylbutyl)- (4.21), 2-mercaptobenzothiazole (3.17) and tetratetracontane (2.38).Keywords: Premna coriacea, essential oil, aromadendrene, caryophylleneAfrican Journal of Biotechnology Vol. 12(20), pp. 2914-291

Balachandran, Indira

Naidoo, Y

Sadashiva, CT

Sharanappa, P

English

AJOL - African Journals Online

     Vol. 12(20), pp. 2914-2916, 15 May, 2013  DOI: 10.5897/AJB10.658 ISSN 1684-5315 ©2013 Academic Journals  http://www.academicjournals.org/AJB African Journal of Biotechnology      Short Communication  Chemical composition of essential oil from the leaves of Premna coriacea Clarke  C. T. Sadashiva1*, P. Sharanappa2, Y. Naidoo1 and Indira Balachandran3  1School of Life Sciences, University of KwaZulu-Natal, Durban, 4000, South Africa. 2Department of Bioscience, University of Mysore, P. G. Centre, Hassan, Karnataka, 573201, India. 3Centre for Medicinal Plant Research, Arya Vaidya Sala, Malappuram, Kottakkal, Kerala, 676503, India.  Accepted 3 May, 2013  In this study, the chemical composition of the essential oil of Premna coriacea leaves was investigated. Extraction by hydrodistillation followed by gas chromatography and mass spectrometry (GC-MS) yielded 27 compounds representing 99.89% of the oil. The major volatile components of the oil were aromadendrene (23.51), caryophyllene (19.27), tetracontane  (11.90), 17-pentatriacontene (6.61), 3',8,8'-trimethoxy-3-piperidyl-2,2'- binaphthalene-1,1',4,4'-tetrone (4.68), cis-α-bisabolene (4.65), octadecane, 3-ethyl-5-(2-ethylbutyl)- (4.21), 2-mercaptobenzothiazole (3.17) and tetratetracontane (2.38).  Key words: Premna coriacea, essential oil, aromadendrene, caryophyllene.   INTRODUCTION  The genus Premna L., belonging to the family Verbenaceae consists of 200 species distributed in the tropical and subtropical regions of Asia, Africa, Australia and the Pacific islands (Kadereit, 2004). In India, 31 species and six varieties have been recognized in Premna (Rajendran and Daniel, 2002). Premna coriacea Clarke is a large, woody climbing shrub with lenticellate branches and is endemic to Western Peninsular India (Ramaswamy et al., 2001).  All Premna species are used as ayurvedic drug Agnimantha (Keshava Murthy and Yoganarasimhan, 1990). Plants that belong to Premna genus are known to have medicinal uses like carminative, diuretic, spasmolytic, hypoglycemic, stomach disorders, oedema, constipation, piles, cardiac diseases, expectorant, depaurative (Keshava Murthy and Yoganarasimhan, 1990; Khare, 2007; Prajapati et al., 2003). Plant parts of P. coriacea are also used as substitute for ayurvedic drug ‘Agnimantha’ (Yoganarasimhan, 1996). P. coriacea is used medicinally for its laxative, stomachic, cardiac and tonic activities (Yoganarasimhan, 1996). Literature survey has revealed that extensive phytochemical work  has been  reported  in many Premna species. The heartwood of Premna tomentosa has showed the presence of apiginin derivatives and leaves containing d and dl limonene, b-caryophyllene, a sequiterpene hydrocarbon, a diterpene hydrocarbon and sesquiterpene tertiary alcohol (Khare, 2007). The stem bark of Premna latifolia gave iridoid glycosides and geniposic acid (Rao et al., 1981), diterpenes (Rao et al., 1979). Isoprenoids have been isolated from stem bark of Premna intigrifolia and P. latifolia (Rao et al., 1985), sesquiterpenes (Rao et al., 1982), premnalatin furnaoid (Rao et al., 1980), glycoside-A, glycoside-B (Rao and Subba Raju, 1981) and primarenes (Rao et al., 1982).   MATERIALS AND METHODS  Plant materials  Leaves of P. coriacea were collected from Sakaleshpur, Hassan district, Karnataka, India, during the flowering period in March 2008. The plants were identified  and  authenticated  by  comparison  with *Corresponding author.  E-mail: sada1hassan@gmail.com. Tel: +27-31260 7360.  Sadashiva et al.         2915    Table 1. Chemical composition of essential oil of P. coriacea.  S/N Name of the compound Composition (%) Retention index RI 1 Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (ñ)-  1.80 7.76 943 2 1-octen-3-ol    0.57 9.11 969 3 1,6-Octadien-3-ol, 3,7-dimethyl-, 2-aminobenzoate  0.49 13.17 2157 4 Copaene 0.68 22.62 1221 5 Caryophyllene 19.27 23.69 1494 6 Aromadendrene 23.51 24.13 1386 7 α-caryophyllene  3.95 24.81 1579 8 Cis-α-bisabolene 4.65 25.14 1518 9 1,6-cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-, [s- (E,E)]- 0.60 25.71 1515 10 α-cubebene 0.71 25.96 1339 11 ç-Elemene 0.81 26.21 1465 12 α-farnesene 0.96 26.52 1458 13 Caryophyllene oxide 1.32 28.93 1507 14 Ledene oxide-(ii) 1.06 29.06 1293 15 Cyclopentadecanol      0.53 32.51 1987 16 2,5-octadecadiynoic acid, methyl ester               0.84 33.32 2112 17 Z,Z,Z-4,6,9-nonadecatriene 0.34 37.20 1934 18 2-mercaptobenzothiazole 3.17 39.13 1501 19 Heptadecane, 9-hexyl-  0.61 39.71 2243 20 Hepatodecane 9-hexyl 1.12 42.04  21 Phytol  1.42 42.43  22 2-octadecodyethanol 1.70 44.27 2328 23 Tetratetracontane         2.38 46.42 4395 24 Octadecane, 3-ethyl-5-(2-ethylbutyl)- 4.21 48.49 2413 25 17-pentatriacontene 6.61 50.49 3508 26 3',8,8'-trimethoxy-3-piperidyl-2,2'-   binaphthalene-1,1',4,4'-tetrone 4.68 51.59 4187 27 Tetracontane 11.90 58.96 4395    with Herbarium specimens. Voucher specimen (PS 25/20-3-2008) has been deposited in the Department of Bioscience, P. G. Centre, Hassan Karnataka, India.   Isolation of the essential oil  Freshly harvested samples of leaves were hydrodistilled for 6 h using a Clevenger type apparatus to obtain the essential oils. The oils were stored at 0°C in air-tight containers after drying over anhydrous sodium sulphate for GC-MS analysis.   Gas chromatography–mass spectrometry (GC-MS)  Gas chromatography-mass spectrometry (GC-MS) analysis was carried out in an Agilent gas chromatography N6890 fitted with a HP-5MS fused silica column (5% phenyl methyl polysiloxane 30 m x 0.25 mm, film thickness 0.25 μm), interfaced with an Agilent 5975C VLMSD with triple axis mass detector. Oven temperature program was 60 to 230°C at 5°C min-1. Injector temperature was kept at 280°C. Helium was used as a carrier gas and was adjusted to column velocity flow of 1.0 ml/min-1. Split ratio was 1:10, whereas split flow of 10 ml/min-1 mass range was 50 to 500.  1 μl of sample (dissolved in hexane 100% v/v) was injected into the system. Identification of oil components was achieved based on their retention   indices,   and   by  comparison   of   their   mass  spectral fragmentation patterns with those reported in the literature and stored on the MS library [NIST database (G1036A, revision D.01.00) /Chem station data system (D.02.00.275, version 2.0d)].   RESULTS  The yield of essential oils from fresh leaves of P. coriacea was 0.082%. The qualitative and quantitative composition of the oil, analyzed by GC-MS is presented in Table 1. In total, 27 compounds were identified, representing 99.89% in the oil. The major volatile components of the oil were aromadendrene (23.51%), caryophyllene (19.27%), tetracontane  (11.90%), 17-pentatriacontene (6.61%), 3',8,8'-trimethoxy-3-piperidyl-2,2'-   binaphthalene-1,1',4,4'-tetrone (4.68%), cis-α-bisabolene (4.65%), octadecane, 3-ethyl-5-(2-ethylbutyl)- (4.21%), α-caryophyllene(3.95%), 2-mercaptobenzothiazole (3.17) and tetratetracontane (2.38%).  The minor compounds were bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (±)- (1.80%), 2-octadecodyethanol (1.70%), phytol (1.40%), caryophyllene oxide (1.32%), Hepatodecane9-hexyl (1.12%), ledene oxide-(II) (1.03%), α-farnesene  (0.96%),  2916        Afr. J. Biotechnol.    2,5-octadecadiynoic acid, methyl ester (0.84), τ-elemene (0.81%), β-cubebene (0.71%), copaene (0.68%), 1,6-cyclodecadiene, 1-methyl-5-methylene- (0.60%), 1,9-n-heptadecane (0.61%), 1-octen-3-ol(0.57%), cyclopentadecanol (0.53%), 1,6-octadien-3-ol, 3,7-dimethyl-, 2-aminobenzoate (0.49%) and Z,Z,Z-4,6,9-nonadecatriene (0.34%). The results indicate that the chemical composition of the leaf oil of P. coriacea was different from the essential oil composition of other Premna spp., like P. tomentosa and Premna barbata (Lakshminarayen and Muthana, 1953; Chanotiya et al., 2009). The major constituents reported from other Premna species are D-, DL-limonene and 1-octen-3-ol (Lakshminarayen and Muthana, 1953; Chanotiya et al., 2009). The present work revealed that armodendrene could be a good chemical marker of P. coriacea, since it has not been reported in other species. Mulyaningsih et al. (2010) showed that Aromadendrene had antibacterial activity against growth of Staphylococcus saprophyticus. The sesquiterpene aromadendrene bears a reactive exocyclic methylene group and a cyclopropane ring which can alkylate proteins and thereby disturb the conformation of protein. Additionally, since the compound is highly lipophilic, it causes disruption of cellular biomembranes (Sikkema et al., 1994, Wink, 2007, 2008). The second major compound of caryophyllene is a natural bicyclic sesquiterpene with a strongly spicy and woody odour that is responsible for the distinctive flavour of black pepper and clove oil; the oil from the stems and flowers of Syzygium aromaticum. Beta-caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic anti-inflammatory effects in mice (Ghelardini et al., 2001). In conclusion, the study of the essential oil of leaves of P. coriacea showed the presence of aromadendrene, caryophyllene and phytol. Further research can be performed to determine methods of effectively administering extracts of P. coriacea for medicinal use.   REFERENCES  Chanotiya CS, Yadav AK, Singh AK (2009) Leaf oil composition of Premna barbata Wall. Ex. Sch. From Kumon region of Uttarkand.  JEOR 21(1):76-77. Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A (2001). Local anesthetic activity of beta-caryophyllene. 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Chemical composition of essential oil from the leaves of Premna coriacea Clarke

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Chemical composition of essential oil from the leaves of Premna coriacea Clarke

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