CHEMICAL COMPOSITION OF THE ESSENTIAL OIL FROM THE LEAVES OF CIPADESSA BACCIFERA (ROTH.) MIQ.HTML Full Text
CHEMICAL COMPOSITION OF THE ESSENTIAL OIL FROM THE LEAVES OF CIPADESSA BACCIFERA (ROTH.) MIQ.
- R. Kavitha *1, A.K. Bopaiah 2 and Amzad Basha Kolar 3
Research & Development Centre 1, Bharathiar University, Coimbatore, Tamil Nadu, India
Department of Botany 2, PG Studies and Research Centre, St .Joseph's College, Bengaluru, Karnataka India.
Division of Biological Sciences 3, Department of Life sciences, Bangalore University, Bengaluru, Karnataka India
ABSTRACT: Cipadessa baccifera (Roth.) Miq. of Meliaceae family, is an ethnobotanically important plant and is widely used in folklore medicine for treating a range of maladies including diabetes, dysentery, malaria, rheumatism, piles, head ache, and psoriasis. The present study was aimed at investigating the essential oil composition from the leaves of C. baccifera. The essential oil was extracted through hydrodistillation and its chemical composition was analyzed by gas chromatography and mass spectrometry technique (GC-MS). The yield of essential oil based on the dry weight of the plant was 1.1% (v/w). Forty one different phytoconstituents accounting for 99.62% of essential oil were identified. The study showed the presence of Sesquiterpenes as the major group of compounds representing 78.14% of the total essential oil. Significant Sesquiterpenes identified were Caryophyllene (17.32%), Isoledene (9.12%), 1S, Cis-Calamenene (7.42%) and β-Sesquiphellandrene(7.32%). Sesquiterpenes are known to exhibit pharmacological activities and the present report could contribute for their further use as anticancer, immunosuppressive and anti-inflammatory agents
Cipadessa baccifera, hydrodistillation,
Sesquiterpenes, Caryophyllene, Isoledene, GC-MS
INTRODUCTION: Essential oils or ethereal oils are concentrated hydrophobic and aromatic volatile products of secondary metabolism secreted by oil cells, glandular hairs or secretion ducts in different parts of the plants and are concerned with the vital processes, giving a characteristic odor, protecting the plants from diseases and insect attacks 1, 2, 3. The essential oils have been in use for centuries; in ancient civilizations of Rome, Egypt, Greece and the Far East as perfume, food flavors and for medicinal purposes.
Presently, essential oils have received great attention for their broad spectrum action, uses in agronomic, perfumery, food, sanitary, cosmetic industries 4, conventional, alternative medicines 5 and having profound applications in treating coronary heart diseases 6, hypertension 7, hyperglycemia 8 and cancer 9, 10, 11.The biological activity of essential oils is generally determined by the relative concentration and major compounds present in them, which plays a key role in drug synthesis. Hence screening and characterization of plant essential oils are very important 12, 13. Cipadessa baccifera (Roth.) Miq. belonging to the family Meliaceae, is a shrub distributed in North Circars, Deccan, Western Ghats of India and Southwest of China. It is a traditional medicinal plant used by folklore of India for treating a range of maladies, including diabetes, dysentery, malaria, rheumatism, piles, head ache, and psoriasis 14, 15, 16, 17.Review of literature reveals the presence of essential oils in the leaves of Meliaceae members viz. Azadirechta indica 18, Melia dubia 19, Toona and Cedrela species 20 and Cedrela Mexicana 21 however, there are no studies on the chemical analysis of essential oils in C. baccifera. There is a correlation between the volatile phytochemical compounds of essential oils present in medicinal plants and the biological activities they exert 22. In view of this, the present study focuses on the extraction and chemical analysis of essential oils from the leaves of C. baccifera.
MATERIALS AND METHODS:
The plant samples were collected from Thavarekere, Magadi Taluk, Bangalore Rural district in the months of November to January. Identification of C.baccifera (Roth.) Miq. was authenticated by National Ayurvedic Dietetics Research Institute, Bengaluru; with vide voucher specimen number, RRCBI-8971. Voucher specimen is also maintained in the herbarium of the Research Centre, St. Joseph's College, Bengaluru.
xtraction of the Essential Oil:
Fresh, healthy and infection free samples of leaves of C.baccifera were collected, shade dried, pulverized and stored in air tight containers at room temperature. About 100g of the leaf powder was subjected to hydrodistillation for 10 hours in a Clevenger apparatus 23. The extracted oil samples were collected by solubilizing in hexane, which was then allowed to evaporate completely at room temperature. The hydrodistillation extractions were repeated several times and the oil obtained was pooled and stored in vials at 4ºC in a refrigerator for further analysis.
Gas Chromatography - Mass Spectrometry:
GC-MS analysis of leaf essential oil was performed using Shimadzu GC-MS-QP-2010S instrument. The compounds were separated using RTX-5 capillary column (30m 0.25 mm id; 0.25 µm film thickness). An aliquot of 1µL oil was injected into the column using 10:1 split injection, the injection port temperature was set at 225ºC. Initial temperature of oven was kept at 130ºC then programmed to 165 ºC at a rate of 2ºC/min, then it was ramped to 200ºC at 10ºC/min and finally increased to 300ºC, at the rate of 20ºC and held for 5 min. The helium gas was used as carrier gas with flow 1.0 mL /min. Significant quadrupole MS operating parameters included interface temperature of 300ºC and ion source temperature of 200ºC. The mass spectrometer was operated in the 70eV EI mode, with scan mass range of 40-600 m/z at 0.5s, sampling rate of 1.0 scan/s. The compounds were identified by comparing mass spectra of each peaks with NIST 5 and WILEY library 24, 25, 26.
RESULTS AND DISCUSSION: The hydrodistillation of leaf of C. baccifera yielded 1.1% (v/w) pale yellow oil. The GC-MS analysis results showed 41 chemical compounds, accounting for 99.62% oil. The compounds and their relative percentage concentration in the order of their elution are listed (Table 1).
FIG.1: CHROMATOGRAM OF ESSENTIAL OIL OF CIPADESSA BACCIFERA LEAF
TABLE1: THE COMPOSITION OF ESSENTIAL OIL OF CIPADESSA BACCIFERA LEAF
|Compound Name||Retention Time||Area (%)|
|32||Bicyclo[5.2.0] nonane, 2-methylene-4,8,8-trimethyl-4-vinyl-||21.627||7.64|
|39||6.β.Bicyclo[4.3.0] nonane, 5β-iodomethyl-1 β-isopropenyl-4 α,5 α-dimethyl-||23.992||1.61|
|40||Farnesol Isomer A||24.366||2.05|
|41||9,19-Cycloergost-24(28)-en-3-ol, 4,14-dimethyl-acetate(3 β.,4 α.,5.α,)-||25.05||3.01|
Chemically essential oils are very complex natural mixtures which contain about 20-60 components of different concentrations. They are characterized by 2-3 major components present in fairly higher concentration compared to others present in trace amounts. Terpenes (monoterpenes, ditepenes sesquiterpenes) form the major constituent of the essential oil, while minor constituents include low molecular weight aliphatic and aromatic compounds.
The major compounds identified were Caryophyllene (17.32%), Isoledene (9.12%), Bicyclo [5.2.0]nonane, 2-methylene-4,8,8-trimethyl-4-vinyl (7.64%), 1S,Cis-Calamenene (7.42%) and β-Sesquiphellandrene(7.32%). The chromatogram patterns of the essential oil from leaf of C.baccifera revealed the presence of sesquiterpenes as major components (Fig 1). Caryophyllene was the major sesquiterpene found in the oil besides traces of their derivatives. The other notable compounds (with concentrations less than 5%) were β-Farnesene, α Humulene, Zingiberene, Farnesol, Longipinane, Aromadendrene, δ Cadinene, Caryophellene oxide, β Himachalene, Alloaromadendrene, 2-Octylfuran, Isospathulenol, trans Farnesol, Farnesol isomer A and 9, 19-Cycloergost-24(28)-en-3-ol,4,14 -dimethyl-acetate, (3 beta.,4 alpha,5,alpha).
Sesquiterpenes have been reported as the major component of leaf essential oil of Meliaceae members with 69% present in A. Indica 27, 73.99% in M. Azaderach 28 and 58.27% in the different parts of Trichilea connaroides 29. It is noteworthy that in the present investigation 25 out of the 41 compounds identified representing 78.14% of the total leaf essential oil were sesquiterpenes and their derivatives. As major phytoconstituents they determine the biological properties of the essential oil and are used as anti cancer, immunosuppressive and anti inflammatory agents 30.Reports indicate that Caryophyllene, a bicyclic sesquiterpene is a major constituent in the essential oil obtained from leaves of Meliaceae members; A.indica (12.73%) 18, Cedrela mexicana (19%) 21 and M.dubia (6.07%) 19 . The present study showed significant concentration of Caryophyllene in the essential oil obtained from the leaves of C.baccifera (17.84%) (Table 1). Caryophyllene and Caryophyllene oxide are attributed with antibacterial, anti-inflammatory 31, analgesic 32, antiproliferative, neuroprotective, and anticancer properties 33, 34. They are also used in the manufacture of medicaments, in the treatment of chronic degenerative diseases like rheumatoid arthritis, osteoarthritis, ulcerative colitis, psoriasis, atopic eczema, atherosclerosis and non-degenerative diseases like depression, cellulites and allergies 35.
CONCLUSION: Bioactive components of the essential oils play a key role in the drug synthesis, have medicinal and (ethno-) pharmacological properties and provide an alternate approach to combat ailments. The present investigation is the first report of GC-MS analysis of the essential oil obtained from leaves of C. baccifera. The results reveal the presence of sesquiterpenes (78.14%) as the major significant constituent which could be potential targets of pharmaceutical interest attributed with anticancer, anti-inflammatory, anti-diabetic, immune-suppressive and antimicrobial activities. The results of the present study provide a reference point for further research in the development of new therapeutic agents.
ACKNOWLEDGEMENT: The authors wish to thank the P.G and Research Department of Botany, St. Josheph's College, Bengaluru and Head of the Department of Post Graduate Studies and Research in Biotechnology, Government Science College, Bengaluru for providing facilities for conducting this research work.
- Guenther E: The essential oil. D. Van Nostrand, New York, 1948.
- Sara Burt: Essential oils their antibacterial properties and potential applications in foods- A review. International journal of Food Microbiology. 2004; 94: 223-253.
- Evans WC: Trease and Evans Pharmacognosy. Elsevier. Noida India 2008.
- Bakkali F, Averbeck S, Averbeck D and Idaomar M: Biological effects of Essential oils: A Review. Food and Chemical Toxicology.2008; 46(2), 446-475.
- Tylor VE: Herbs of choice Pharmaceutical Products. Press Binghamtom 1994.
- Bordia A: Effect of garlic on blood lipids in patients with coronary heart disease. American Journal of Clinical Nutrition.1981; 34(10):2100-103.
- Lahlou S, Interaminense Lde F, Leal-Cardoso JH, Morais SM and Duarte GP: Cardiovascular effects of the essential oil of Ocimum gratissimum leaves in rats: role of the autonomic nervous system. Clinical and Experimental Pharacol and Physiology. 2004; 31(4):219-225.
- Abdollahi M, Salehnia A, Mortazavi S, Ebrahimi M, Shafiee A, Fouladian F, et al: Antioxidant, antidiabetic, antihyperlipidermic, reproduction stimulatory properties and safety of essential oil of Satureja khuzestanica in rat in vivo. Medical Science Monitor. 2003; 9(9):331-335.
- DeAngelis L: Brain tumours. New England Journal of Medicine: Research and Review. 2001; 344(2): 114-123.
- Motakii H, Hibasami H, Yamada Y, Katsuzaki H, Imai K and Komiya T: Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not in human stomach cancer cell line. Oncology Reports.2002; 9(4):757-760.
- de'Sousa AC, Alviano DS, Blank Af, Alves PB, Alviano CS and Gattass CR. Melissa officianlis L. Essential oil: antitumour and antioxidant activities. Journal of Pharmacy and Pharmacology.2004; 56(5):677-681.
- Hammer KA, Carson CF and Riley TV: Antimicrobial activity of essential oils and other plant extracts. Journal of Applied Microbiology. 1999; 86: 985-990.
- Hernandez T, Canales M, Teran B, Avila O, Duran A, Garcia AM, Hernandez H, Angeles-Lopez O, Fernandez-Araiza G and Avila G: Antimicrobial activity of essential oil and extracts of Cordia currasaavica ( Boraginaceae ). Journal of Ethnopharmacology. 2007; 111:137-141.
- Malarvannan S, Giridharan R, Sekar S, Prabavathy VR and Sudha Nair: Ovicidal activity of crude extracts of few traditional plants against Helicoverpa armigera (Hubner) (noctuidae: Lepidoptera). Journal of Biopesticides.2009; 2(1):64-71.
- Amit R and Shailendra S: Limonoids: Overview of significant bioactive triterpenes distributed in plant kingdom. Biological and Pharmaceutical Bulletin. 2006; 29(2):191-201.
- Liang L, Zhong CC and Xiao ZY: Chemical Components from leaves of greyhair Cipadessa (Cipadessa cinerascence). Zhongcaoyao.1991; 22:6-8.
- Liang L, Zhong CC, Xiao ZY: Chemical Components from leaves of greyhair Cipadessa (Cipadessa cinerascence) (III). Zhongcaoyao.1994; 25:236-237.
- Indra Prasad Pandey, Sayed Farooq Ahmed, Suman Chhimwal and Shalini Pandey: Chemical Composition and Wound healing activity of Volatile oil of Leaves of Azadirachta indica Juss. Advances in Pure and Applied Chemistry (APAC). 2012; 62 (1): 3.
- Murugesan S, Senthilkumar N, Rajeshkannan C and Vijayalakshmi KB: Phytochemical characterization of Melia dubia for their biological properties. Pelagia Research Library. 2013; 4(1): 36-40.
- Beatriz HLNS Maia, Jose R de Paula, Josue Sant Ana, M.Fatima das GF da Silva, Joao B Fernandes, Paulo C Vieira, Merilene do SS Costa, Orlando S, Ohashi and Jose Natalino M Silva: Essential oils of Toona and Cedrela species (Meliaceae): Taxonomic and ecological implications. Journal of the Brazilian Chemical Society. 2000; 11(6):629-639.
- Ogunwnade, Isiaka A, Ekundayo, Olusegun, Olawore, Nureni O, Adeleke and Kasaki A: constituents of essential oil of the leaves and stem bark of Cedrela mexicana grown in Nigeria. Journal of Essential Oil Research. 2005; 17(3):289.
- Belkacem N, Djaziri R, Lahfa F, El-Haci IA, and Boucherit Z: “Phytochemical screening and in vitro antioxidant activity isolated bioactive compounds from Tridax procumbens Linn”. Pakistan Journal of Biological Sciences.2013; 16(24):1971–1977.
- Clevenger JH: Apparatus for the determination of volatile oil. Journal of American Pharmacists Association.1928; 17:346.
- National Institute of Standard and Technology. NIST/ EPA/ NIH Mass spectral database. US Department of commerce, Gaithersburg, MD. 2002.
- McLafferty FW and Stauffer DB: The Wiley/NBS registry of mass spectral data. New York. J Wiley and Sons,1989.
- Adams RP: Identification of essential oil components by Gas Chromatography/ Mass spectroscopy. Illinois, USA. Allured Publishing Corporation, 2001.
- Dara Dastan, Maryam Pezhmanmehr, Naser Askari, Samad Nejad Ebrahimi and Javad Hadian: Essential Oil Compositions of the Leaves of Azadirachta indica Juss from Iran. Journal Of Essential Oil-Bearing Plants. 2013; 13 (3): 357 - 361.
- Kharkwal GC, Pande C, Tewari G, Panwar A and Pande V: Volatile terpenoid composition and antimicrobial activity of flowers of Melia azedarach Linn from North West Himalayas, India. Journal of Indian Chemical Society.2015; 92:141-145.
- Ravindra Kumar, Gowrav Verma, Om Prakash and Panth AK: head space GC/MS analysis of volatile constituents of Trichilea connaroides Wight &Arn. Extract and there in vitro Antiplasmodium activity against Plasmodium falciparam Research Journal of Phytochemistry.2011;1-7
- Andre-Pichette, Jean-legault and Claude-Made L: Antitumor methods and compositions comprising sesquiterpene derivatives. FPL Pharma. 2010. Inc., http://www.patentdocs.com
- Tung YT, Chua MT, Wang SY and Chang ST: Anti-inflammation activities of essential oil and its constituents from indigenous Cinnamon (Cinnamomun osmophloeum) twigs. Bioresource Technology. 2008; 99:3908-3913.
- Chavan, M.J, Wakte PS and Shinde DB: Analgesic and anti-inflammatory activity of caryophyllene oxide from Annona squamosa bark. Phytomedicine. 2010; 17: 149–151.
- Silva SL, Figueiredo PMS and Yano T: Chemotherapeutic potential of the volatile oils from Zanthoxylum rhoifolium Lam leaves. European Journal of Pharmacology.2007; 576: 180-188.
- Kubo I, Chaudhuri SK, Kubo Y, Sanchez Y, Ogura T, Saito T, Ishikawa H and Haraguchi H: Cytotoxic and antioxidative sesquiterpenoids from Heterotheca inuloides. Planta Medica.1996; 62:427-430.
- Pianowski LF, Joao B and Brandao CD: Use of Caryophyllenes in the manufacture of medicaments and treatment of bodily conditions of inflammation and inflammatory pain. 2010. http:// www.patentdocs.com
How to cite this article:
Kavitha KR, Bopaiah AK and Kolar AB: Chemical Composition of the Essential Oil from the Leaves of Cipadessa Baccifera (Roth.) Miq. Int J Pharm Sci Res 2016; 7(1): 392-96.doi: 10.13040/IJPSR.0975-8232.7 (1).392-96.
All © 2013 are reserved by International Journal of Pharmaceutical Sciences and Research. This Journal licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported License.
K. R. Kavitha *, A.K. Bopaiah and Amzad Basha Kolar
Research & Development Centre, Bharathiar University, Coimbatore, Tamil Nadu, India
14 September, 2015
09 November, 2015
04 December, 2015
01 January, 2016