Chemical composition of essential oil of four flavouring plants used by the tribal people of Bandarban hill district in Bangladesh

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1 , ISSN Vol. 2, No. 1, pp , March 2012 RESEARCH ARTICLE Chemical composition of essential oil of four flavouring plants used by the tribal people of Bandarban hill district in Bangladesh Mohammed MOHIUDDIN* 1, Mohammed Jasimuddin CHOWDHURY 2, M. Khairul ALAM 1, Mohammad Kamal HOSSAIN 32 1 Bangladesh Forest Research Institute, P.O. Box No. 273, Chittagong, Bangladesh 2 Bangladesh Council of Scientific and Industrial Research Laboratories, Dhaka, Bangladesh 3 Institute of Forestry and Environmental Sciences, Chittagong University, Chittagong, Bangladesh *Corresponding Author, Tel: (O), Fax: Article History: Received 13 th November 2011, Revised 30 th January 2012, Accepted 30 th January Abstract: Choto oinchin ( Elsholtzia incisa Benth), boro oinchin ( Plectranthus incanus Link), jhum bahor pata ( Sesali daucifolium W & A) and jhongaju (Ocimum basilicum var. purpurascens) are flavouring plant species widely grown in jhum by the tribal people of the Bandarban Hill District. Essential oil composition of these four species was analyzed by GC-MS analysis methods. Results showed that Sesali daucifolium contains 73 compounds of which dihydrocoumarin, 5,7, 8-trimethyl was the highest (27.51%), followed by d-camphene (19.83%), terpinolene (13.70%), and β-mycrene (6.52%). Plectranthus incanus contains 67 chemicals and copane is the major component (21.47%), followed by pipertone oxide (21.18 %), fenchone (12.19%), 2-carane (6.30%). Essential oil of aerial parts of Elsholtzia incisa contains 47 compounds and the main component was phenol 2,3,5,6-teramethyl/ druenol (33.44%), followed by terpinolene (19.57%), O-cymene (9.74%), Z -ocimene (7.32%), Z -carene (5.10%), 4-Terpineol (2.89%), β-myreene (2.52%), L - phellandrene (2.50%), cis Sabinenehydrate (2.09%) and caryophyllene (1.87%). Essential oil of aerial parts of Ocimum basilicum var. purpurascens contains 58 components and main component was methyl cinnamate % followed by linalool (16.40%), tau-cadinol (4.37%), α-bergamotene (3.03 %), γ-muurolene (2.06%), sulfone- methyl styryl (1.68 %), and methyl chavicol (1.55%). Essential oil of Ocimum basilicum var. purpurascens contains highest percentage of methyl cinnamate, 59.62% in leaves and 64.34% in inflorescence. Keywords: Chemical composition; Essential oil; Flavoring plants; tribal; Bandarban. Introduction The hilly region of Bandarban hill district is rich in wild resources, which are used as food, vegetables, oils, spices and other purposes. The tribal people of these areas have rich heritage of using different food plants both cultivated and wild from their surrounding forest areas. Among them a good number of species like choto oinchin ( Elsholtzia incisa Benth), boro oinchin ( Plectranthus incanus Link), jhum bahor pata (Sesali daucifolium W & A) and jhongaju (Ocimum basilicum var. purpurascens) are the important flavoring plant species cultivated in the jhum (shifting cultivation). The first three species are used as culinary herb and also sold in the market. Jhongaju having sweet smell is used as plants in hair and ear deodorant by the Murong tribal people. It is observed that the tribal peoples use the pungent smell plants to drive away the insects when they work in the field. Use of aromatic herbs and species by the antiquity is well documented in ancient writings, Old Testament, early Greek and Roman documents, in medieval manuscripts and in present literatures (Heath 1973). Species mainly depend upon the chemical constituents of essential oil for their aroma and flavoring characteristics. Spices and herbs provide pleasant beneficial flavoring agents for medicine frequently in the form of essential oils that excite a reflux flow of saliva and many diseases, psychosomatic and psychological disorders are accompanied by loss of appetite and combination *Corresponding author: ( ) uddinm59<a.t.>gmail.com 2012 Open Access Science Research Publisher

2 of bitters and oils can be used to stimulate appetite (Heath 1973). The essential oils are important mainly for their fragrance, flavour, and some of the important constituents have economic uses such as the source of thymol, eugenol, cineole, cinnamaladehyde, benzoic acid, benzaldehyde, citral citronellal, geraniol, etc., (Manzoor-i- Khuda et al. 1984). The essential oils are widely used as additives in many perfumes, cosmetics and soaps industries (E ncycl. Brit and 1975; Varandhan 1958). Essential oils are also used as antiseptics and some of them have analgesic, hemolytic or anti-enzymatic action and some acts as sedatives, stimulant and stomachics (Encycl. Brit and 1975; Maryzeller and Henry 1958; Alat and Kapur 1982, Chandra and Kapur 1971). Among all the species, jhongaju (Ocimum basilicum) also known as basil or sweet basil is the most important species cultivated and utilized throughout the world and its aromatic leaves are used fresh or dried as flavouring agent for foods, confectionary products and beverages (Marotti 1996). Traditionally the plant is used in folk medicine as carminative, stimulant and antispasmodic properties, and its essential oil mainly used in food industries perfumery and also possesses antimicrobial activities ( Prasad et al. 1985). The essential oil exhibits insecticidal properties which can be economically used in the production of effective insecticides to be used in food commodities without danger of toxicity to human being (Umeric et al. 1998). The chemical composition of the plants plays an important role from commercial point of view. There is no information on the chemical composition of the essential oil of the four species except that of jhongaju ( Ocimum basilicum var. purpurascens) (Chowdhury et al. 2001a, 2001b; Mondello et al. 2002) from Bangladesh. So, an attempt has been taken to determine the composition of essential oils of these four species. Methodology All the plants were collected from the Jhum (shifting cultivation) practiced by the tribal people of the Bandarban hill district during December The essential oils of the 107 leaves and inflorescence of the plants were isolated by hydro-distillation method for 4 hrs using Clevenger apparatus (Clevenger 1928). The oil obtained were dried over anhydrous sodium sulphate and analyzed by GC-MS. GC-MS analysis The essential oil from aerial parts of choto oinchin ( Elsholtzia incisa Benth), boro oinchin (Plectranthus incanus Link), jhum bahor pata (Sesali daucifolium W & A) and jhongaju (Ocimum basilicum var. purpurascens) were analyzed by GC-MS electron impact ionization (EI) method on GC-17A gas chromatograph (Sh i- madzu) coupled to a GC-MS QP 5050A Mass Spectrometer (Shimadzu); fused silica capillary column (30m x 2.5mm; 0.25 µm film thickness), coated with DB-1 (J&W); co lumn temperature 100 o C (2 min) to 250 o C at the rate of 3 o C/min; carrier gas, helium at constant pressure of 90Kpa. Acquisition parameters full scan; scan range amu. Comparing with the NIST library data the compounds were identified. Results and Discussion The detail chemical composition of the essential oils of aerial parts of jhum bahor pata (Sesali daucifolium W&A) (Figure -1) given in Table 1, shows 73 compounds of which the major compound dihydrocoumarin, 5,7,8-trimethyl was the highest (27.51%), followed by d - camphene (19.83%), terpinolene (13.70%), and β-mycrene (6.52%). The other important chemicals were limonene (4.01%), caryophyllene (2.98%), exo-2-hydrojeinoole (2.87%), β- selinen (2.10%), exo -2-hydrojeinoole (2.87%), [E] ocimene (1.89%), 4 -terpineol (1.66%), and thymol (1.47%). The powder of dry fruits yield 2.5 percent essential oil having aromatic odour and clove like taste. The monoterpene fractions consisting of 80% of the oil, contain up to 11 percent of B- cyclolavendulal (C 10 H 16 O) and the low boiling fraction of the oil is composed of d- limonene (47%) along with bergaptene, isov a- leric acid, unidentified acid and a phenolic acid traces (Anon. 1972)

Figure 1: Jhum bahor pata (Sesali daucifolium) Table 1: Composition of essential oils of aerial parts of jhum bahor pata (Seseli daucifolium) 1 α-thujene 0.32 2 α-pinene 0.57 3 Camphene 0.

43 14 Terpinolene 13.70 15 L-Fenchone 0.12 16 Linalool 0.36 17 Cyclohexanol, 1-ethyl 0.03 18 2.6-Dimethyl-11, 3,5,7-Octatetraene 0.02 19 Bicyclo[3.2.1]Oct-2-ene,-3-methyl-4-0.

3 Figure 1: Jhum bahor pata (Sesali daucifolium) Table 1: Composition of essential oils of aerial parts of jhum bahor pata (Seseli daucifolium) 1 α-thujene α-pinene Camphene d-camphene β-pinene B-Myrcene α-phellandrene Carene m-cymene Limonene [E] Ocimene γ-terpinene Cis-Sabinenehydrate Terpinolene L-Fenchone Linalool Cyclohexanol, 1-ethyl Dimethyl-11, 3,5,7-Octatetraene Bicyclo[3.2.1]Oct-2-ene,-3-methyl methylene 20 Isothujol Isobuhyl1,4-Cycloheptadiene trans-2-nonenal Terpineol Azulene p-cymene-8-ol Terpinyl acetate cis-piperitol Neryl acetate Phenrylpontane Citral Geraniol Eicosyne Bornyl acetate Thymol Methyl cinnamate α-cubebene Neryl propionate Copaene γ-muurolene Cyclopentyl cyclohexane Caryophyllene ,6,10-Dodecatriene,7,11-dimethyl methylene 43 α-caryophyllene Demethoxyageratochromene Acoradien β-himachalene Germacrene D β-selinene Chamigrene α-farnesene δ-cadinene exo-2-hydroxjcinoole trans-nerolidol Seychellene Ledene alcohol Germacrene D-4-ol Caryophyllene oxide Tetracyco [ (3.8) 0(3.9)] Undecanol, ,4,11,11-tetramethyl 59 Carotol Apiol β-humulene Cubenol β-cedren-9-l-ol tau-muurolol Himachala-2,4-diene α-cadinol Butylidenephthalide Methylnorbornene H-Cycloprople (e) azulene, decahydro -1, 1, trimethy l-4-methylene 70 Dictyopterene A Dihydrocoumarin, 5,7, 8-trimethyl (3H) Naphthalenone, 4,4a, 5,6-tetrahydro ,3,5,6-tetamethylterephthalaldehyde 0.18 The results of chemical analysis of the essential oil of aerial parts of bara oinchin ( Plectranthus incanus Link) (Figure -2) are given in Table 2. The essential oil contains 67 components. The major components are Copaene 21.47%, Piperitone oxide 21.18%, Fenchone 12.19%, 2-Carene 6.30%, Limonene 4.07 %.

1,6,10-Dodecatriene, 7,11-dimethyl-3- methylene 3.77%, Camphor 3.21%, Germacrene D 2.21%, α-caryophyllene 2.13 % and δ- Cadinene 1.68%. It is reported that the leaves and tops of this plant gave (0.

4 1,6,10-Dodecatriene, 7,11-dimethyl-3- methylene 3.77%, Camphor 3.21%, Germacrene D 2.21%, α-caryophyllene 2.13 % and δ- Cadinene 1.68%. It is reported that the leaves and tops of this plant gave (0.2ml/100 g) essential oil, which is potentially active against a number bacteria. The essential oil possessed also a cardiac depressant, respiratory stimulant, and vasoconstrictor actions (Anonymous 1969). Figure 2: Boro oinchin (Plectranthus incanus) Table 2: Composition of essential oils of aerial parts of bara oinchin (Plectranthus incanus) 1 3-Hexen-1-ol Tricyclene α-thujene α-pinene Camphene Sabinene B-Pinene Octen-3-ol Octanone β-myrcene Carene L-Phellandrene Carene O-Cymene Limonene E-Ocimene γ-terpinene Fenchone Camphor Linalool ,6-Dimethyl-1,3,5,7-Octatetraene Fenchyl acetate Allyl cyclohexene cis-sabinene hydrate cis-2-pinanol Caranol, (1S, 3S, 6R) Bicyclo (3.2.1) Oct-2-one, 3-methyl methylene 28 2,4-Decadien-1-ol, (E.E) Borneol Carveol ,6-Octadienal, 3,7-Dimethyl Terpineol P-Cymen-8-ol Terpinyl acetate Thujone Piperitone oxide (2E) -2-Hexenyl laurate Heptadecanol, acetate Diosphenol Verbenone Thymol Octahydroindole P-Menthane-1,2,3-triol Piperitone α-cubebene Aciphyllene Copaene Germacrene D Cinarolone Caryophyllene α-bergamotene β-sesquiphellandrene Zingiberene α-caryophyllene ,6,10-Dodecatriene, 7,11-dimethyl methylene 56 Cubenol β-bisabolene δ-cadinene α-bisabolol tarns-α-bergamotene Epi-bicyclosesquiphellandrene Cinerone δ-cadinol α-cadinol Octacosane Phytol Allyl -4-methylphenol 0.23 The essential oil of aerial parts of choto oinchin ( Elsholtzia incisa Benth) (Figure -3) contains 47 compounds (Table 3). The main component is druenol (33.44%), followed by

terpinolene (19.57%), O -cymene (9.74%), Z - ocimene (7.32%), Z -carene (5.10%), 4- Terpineol (2.89%), β- myreene (2.52%), L - phellandrene (2.50%), cis Sabinenehydrate (2.09%) and caryophyllene (1.

5 terpinolene (19.57%), O -cymene (9.74%), Z - ocimene (7.32%), Z -carene (5.10%), 4- Terpineol (2.89%), β- myreene (2.52%), L - phellandrene (2.50%), cis Sabinenehydrate (2.09%) and caryophyllene (1.87%). There is very limited information on the essential oils of this species. Anon (1952) reported that dried herb yields 2 % golden yellow essential oils having specific gravity 0.97(α), and it also contains elsholtzia ketone (C 10 H 14 O 2 ) but no aldehyde or phenol. The oil is esteemed in Japan as an antipyretic and diuretic (Anon.1952) Z-Ocimene Terpinolene Acetophenone cis - Sabinenehydrate α,p-dimethylstyrene Linalool Tidecyne Myrtenyl acetate trans- chrysanthene Spathulenol Borneol Terpineol P-Cymen-8-ol Terpinyl acetate Thymol methyl other cis -Piperitol trans-3-caren-2-ol Neryl acetate Thymol Druenol Caryophyllene tert-Bulylated dydroxyanisole Methyl cinnamate Octahydroindole γ- Muurolene α-caryophyllene Curcumene Germacrene D Zingiberene γ-elemene γ-muurolene β-sesquiphellandrene trans-nerolidol α-bergamatene Caryophyllene oxide 1.19 Figure 3: Choto oinchin (Elsholtzia incisa) Table 3: Composition of essential oils aerial parts of Choto oinchin (Elsholtzia incisa) 1 α-pinene Butylbenzene Camphene Sabinene β-pinene β-myrcene α-phellandrene Carene O-Cymene ,6-Dimethyl-1,3,5,7-Octatetraene D-Limonene β-phellandrene 0.34 The essential oil of aerial parts of jhongaju (Ocimum basilicum var. purpurascens) (Figure- 4) contains 58 components (Table 4). The main component was methyl cinnamate %, followed by linalool (16.40 %), tau -cadinol (4.37%), α-bergamotene (3.03 %), γ-muurolene (2.06%), sulfone- methyl styryl (1.68 %), and methyl chavicol (1.55%). The essential oil of inflorescence of Ocimum brasilicum var prurpurascens contains 30 components (Table 5). The main component was methyl cinnamate ( ) %), followed by linalool (19.24 %), tau-cadinol (5.01%), germacrene D (2.05%), B-elemene (1.63%), methyl chavicol (1.60), α-bergamotene (1.59) and germacrene D-4-ol (1.09). Fifteen compounds of between the essential oil of aerial parts and inflorescence of jhongaju ( O. basilicum var. purpurascens). These compounds are Benzaldehyde, 1-Octen- 3-ol, β-myrcene, Limonene, Methyl benzoate,

Benzeneacetlaldehyde, γ-terpinene, Fenchone, Linalool, Methyl chavicol, Methyl cinnamate, Copaene, α-caryophyllene, Germacrene D and tau-cadinol.

6 Benzeneacetlaldehyde, γ-terpinene, Fenchone, Linalool, Methyl chavicol, Methyl cinnamate, Copaene, α-caryophyllene, Germacrene D and tau-cadinol. But there are differences in percentage of the compounds. Figure 4: Jhongaju ( Ocimum basilicum var. purpurascence Table 4: Chemical composition of leaf essential oil of jhongaju (O. basilicum var. purpurascens) 1 α-bergamotene β-bisabolene α-cadinol α-caryophyllene β-cedren-9-α-ol δ-guaiene γ-muurolene α-muurolene β-myrcene β-sesquiphellandrene γ-terpinene Hydrindanone Octan-3-ol R, α, Pinene Carene Cyclohexen-1-ol, 2-methyl, 5-(1- methylethenyl) Isopropyl-4-methyl -1-decen-4-ol Methyl, 1-Heptanol Acetyl-1-methyl-cyclohexene Terpineol acetate Anethole Azulene Benzaldehyde Benzene acetaldehyde Bergamotol Z-α-trans Bicyclo (4.2.0) Octane, 6,7-dimethyl Calamenene Caprylyl acetate Caryophyllene Caryophyllene oxide Cinnamyl acetate Copaene Cubenol Epi-bicyclosesquiphellandrene Epoxylinalool Fenchone Germacrene D Hexyl acetate Isopulegol Lanceol, cis Limonene Limonene oxide Linalool Methyl benzoate Methyl chavicol Methyl cinnamate Methyl hydrocinnamate Neryl acetate O-Cymene Piperitone oxide Sabinene Styrene Squalene Stilbene Sulfone, methyl styryl tau-cadinol trans -Nerolidol Vinyl amyl ketone 0.01 The results of the present study show differences in chemical composition of essential oils in the leaves and the inflorescence in Ocimum basilicum var. purpurascens. The species contains highest percentage of methyl cinnamate, 59.62%, in the leaves (Table 4) and 64.34% in the inflorescence (Table 5). The data conform to the findings of Sobti and Pushpagandan (1982) who found 60-65% methyl cinnamate. Singh and Bordoloi (1991) found 61.2% methyl cinnamate and 29.5% linalool in the leaves. On the other hand, Choudhury et al. (2001a, b) and Mondello et al. (2002) reported contrasting findings who reported that the major components of the essential oil were linolool

7 ( %), gerauiol ( %), geranyl acetate ( %) and terpine-4-ol ( %). Table 5: Composition of essential oil of inflorescence of jhongaju (O. basilicum var. purpurascens) 1 Bntanoic acid, 2-methyl-methyl ester Benzaldehyde β-phellandrene Octen-3-ol β-myrcene Cycloctanol P-Cymene Limonene Methyl-1,5-heptadien-4-ol Benzeneacetlaldehyde γ-terpinene 12 Octyl trifluoro acetate Fenchone Methyl benzoate Linalool Methyl chavicol Octyl acetate Thymol Methyl cinnamate Copaene α-bergamotene α-caryophyllene Germacrene D Valencene α-bulnesene B-Elemene δ-cadinol Germacrene D-4-ol tau-cadinol (5.01) α-bisabolol 0.26 Pushpangadan and Bradu (1995) noted that the essential oils of O. basilicum var. purpurascens contain 60% linalool and 20% methyl cinnamate. It has also been reported that characteristics and composition of oil from different region vary and four types of oil are recognized. So, it can be concluded the species variety in the present study are chemically different from the variety studied by Chowdhury et al. (2001a, b) and Mondello et al. 2002). So the species variety in the present study may be a new chemo-type of methyl cinnamate linalool. 112 The results showed that all the plants contains higher percentage of some different compounds of essential oil and these can be used in many perfumes, cosmetics, antiseptics, analgesic, hemolytic, sedatives, stimulant, stomachic and soaps industries. Ocimum basilicum leaves are used fresh or dried as flavouring agent for foods, baked goods, pickles, confectionary products and beverages (Marotti et a l.1996, Anon. 1966). Essential oil potentiality to be used for scenting dental and oral preparations, soap perfumes and also possesses antimicrobial activities (Anon. 1966, Prasad et al. 1985). Conclusion The chemical composition of all the species shows that numbers of chemicals are present in good percentage, which may be potentially important for future industrial uses like food industries, perfumery, and antimicrobial and insecticidal product development. The chemicals of the essential oil containing plants are sometimes more important for chemical characters than morphological features. This applies not only to the economic uses of the plants, but also useful for the industrial uses and also opens scope for research to make new medicines and preservatives. On the other hand, the essential oils can play an important role in determining the taxonomic problems at variety label by chemo-type classification. References Alat, C. K., Kapur, B. M Cultivation and Utilization of Aromatic Plants, RRL CSIR, Jammu-Tawi. Anon. 1952, 1966, 1969, and The Wealth of India, Raw materials. Vol. III, VII, VIII, IX CSIR, New Delhi, India, India. (PP ; 82-84; ; ). Chandra, V., Kapur, L.D Medicinal and aromatic plants used in Pharmaceutical Industry, Part-1. Indian Drugs Annual. Chowdhury, J.U., Yusuf, M., Begum J. 2001a. Studies on Morphological Characters, Herbage yield, Essential oil content and compositions seven types of Ocimum from

8 Bangladesh. Bangladesh J. For. Sci. 30(1):1-6. Chowdhury, J. U., Begum J., Yusuf, M. 2001b. Ocimum basilicum var. purpurascens and its essential oil from Bangladesh. Bangladesh J. Sci.& Tech,. 3(2): Clevenger, J. F Apparatus for the determination of Volatile oils. Journal of American Pharmaceutical Association, 17:346. Encycl. Brit Encyclopedia Britannica, Vol South Michigan Avenue, Chicago, Illinois , U.S.A. P-715. Encycl. Brit Encyclopedia Britannica, Vol South Michigan Avenue, Chicago, Illinois , U.S.A. P-428. Gayer, G. J., Kite, C. G., Goldstone, J. F. Bryan, S.E., Paton, A., Putievskt, E Infraspecific Taxonomy and essential oil Chemotypes in Sweet Basil Ocimum basilicum. Photochemistry, 43(5): Heath, H. B Herbs and spices for food manufacture. In Proceedings of the Conference on species, held at the London School of Pharmacy, Brunswick Square, London WC 1N 1AX, 10th to 14 th April 1972, Tropical Products Institute 56/62 Gray s Inn Road, London Wc1X8LU. pp Manzoor-i- Khuda, M., Faruq, M.O., Rahman, M., Yusuf, M., Wahab, M. A., Chowdhury, J Studies on the essential oil bearing plants of Bangladesh. Bangladesh J. Sci. Ind. Res. XIX (1-4), pp Marotti, M., Picccalia, R., Giovanelli, E Difference in essential oil characteristics. J. Agric. Food Chem. 44: Mondello, L., Zappia, G., Cotroneo, A., Bonaccorsi, I., Chowdhury, JU., Yusuf, M., Giovanni, D Studies on the essential oil bearing plants of Bangaldesh. Part VIII.+ Composition of some Ocimum Oils O. basilicum L. var. purpurascens; O. Sanctum L. green; O. sanctum L. purplu; O. americanum L., citral type; O. americanum L. camphor type. Flavour Fragr. J. 17: Prasad, G., Kuman, A., Singh, A.K., Bhattacharya, A.K., Singh, K., Sharma, V. D Antimicrobial activity of essential oils of some Ocomum Species and Clove Oil. Filoteerapia, 57 (6): Pushpangadan, P. and Bradu, B.L In Advances in Horticulture, Vol. II, Medicinal and Aromatic Plants, In: Chadha, K. L., Gupta, R. (Eds.), Mathotra Publishing House, New Delhi, India. pp Singh, R. S. and Bordoloi, D.N Changes in the linalool and methyl cinnamate amounts in methyl cinnamate rich clone of Ocimum basilicum at different growth stages. J. Essen. Oil Research, 3: Sobti, S.N. and Pushpagandan, P Cultivation and Utilization of Aromatic plants, In Ata, C.K., Kapur, B.M., (Eds.), RRL, CSIR, Jammu-Tawi, India. pp Umeric, S. C., Anaso, H.U.; and Anyasoro, L. J.C Insecticidal Potentials of Ocimum basilicum Leaf Extract (Short Co m- munication). Bio-resource Technology, 64: Varandhan, C Essential Oils and Aromatic Chemicals, CSIR, New Delhi, India.

GC/MS BATCH NUMBER: G40106

GC/MS BATCH NUMBER: G40106 ESSENTIAL OIL: GINGER ROOT C02 BOTANICAL NAME: ZINGIBER OFFICINALE ORIGIN: INDONESIA KEY CONSTITUENTS PRESENT IN THIS BATCH OF GINGER ROOT C02 OIL % ar-curcumene 13.7 [6]-GINGEROL