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Chemical Variation of Spilanthes Species (Asteraceae) a Medicinal Herb in Peninsular India - Revealed by Gcms-Ms

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Chemical Variation of Spilanthes Species (Asteraceae) a Medicinal Herb in Peninsular India - Revealed by Gcms-Ms International Journal of Pharmacy and Biological Sciences ISSN: 2321-3272 (Print), ISSN: 2230-7605 (Online) IJPBS | Volume 6 | Issue 3| JUL-SEP | 2016 | 86-97 Original Research Article – Biological Sciences CHEMICAL VARIATION OF SPILANTHES SPECIES (ASTERACEAE) A MEDICINAL HERB IN PENINSULAR INDIA - REVEALED BY GCMS-MS 1 & 2 Lavanya Devi K., 2M.B. Shivanna and 1S. Ganeshan 1Division of Plant Genetic Resources, Indian Institute of Horticultural Research, Bangalore, Karnataka, India-560089 2Department of Applied Botany, Kuvempu University, Shankaraghatta, Shimoga, Karnataka, India-577451 *Corresponding Author Email: [email protected] ABSTRACT Spilanthes (Family: Asteraceae, tribe: Heliantheae), commonly known as 'tooth-ache' plant, is used in traditional medicine for curing several diseases across the world and species are reported to be distributed in peninsular India. The study on the comparison of the chemical constituents among Spilanthes species is lacking. A systematic study of chemical compounds could contribute to the knowledge of bioactive compounds but systematics of the genus as well. In this context, species of Spilanthes in peninsular India were selected for carrying out a detailed study of their chemical composition and their significance in chemotaxonomy. The chemical compounds of Spilanthes species in peninsular India were investigated by GCMS-MS. A total of 81 compounds were identified from leaf, inflorescence and root of S. calva, S. ciliata, S. oleracea, S. paniculata, S. radicans and S. uliginosa. The hydrocarbons (28%) formed the major constituent, followed by terpenoids (15%), esters (9%), sterols (8%), aldehydes & ketones (7%), alcohols (3%) and the main bioactive principle alkamide (5%), and rest of compounds forming 25% of total constituent. The chemotaxonomic significance of these compounds in each species was discussed. The phylogeny was constructed and principal coordinate analysis was carried out to study the relationship among species. The present study documented the chemical variation among the six Spilanthes species and some were species specific. The quantification of compounds in leaf, inflorescence and root of six species could contribute to the systematics and application in modern medicines. The phylogeny revealed the distance among the plant parts and the species under study where S. ciliata and S. paniculata were closely related, to this cluster S. oleracea was grouped, then S. uliginosa followed by S. radicans. To this main cluster S. calva was grouped indicating the far distance of this native species with other species including another native species S. paniculata. KEY WORDS Spilanthes, GCMS-MS, alkamides, terpenoids, sterols, esters, phylogeny, principal coordinate analysis. INTRODUCTION like radical scavenging, diuretic (Rajesh et al. 2011), Spilanthes, of Asteraceae, is distributed in the warmer immunomodulatory (Savadi et al. 2010), antipyretic regions of both hemispheres and are used in (Trease and Evans 1972; Rajnarayana et al. 2001), traditional medicine by different civilizations in the antimicrobial (Nakatani, 1992; Krishnaswamy et al. world for tooth-ache, gastritis, gastric ulcers, mucous 1975), larvicidal (Pandey and Agarwal, 2009), membrane inflammation, burns and wounds and as molluscicidal (Timothy et al. 1982) and insecticidal local anaesthetic (Christophe, 2006; Prachayasittikul activities (Jondiko et al. 1986). Although et al. 2009; Chakraborty et al. 2011). The bioactive morphological parameters find importance in the compounds like alkamides, terpenoids, esters and identification of species of Spilanthes, there existed other compounds exhibit various biological activities certain difficulties in the distinct separation of species International Journal of Pharmacy and Biological Sciences Lavanya Devi K* et al 86 www.ijpbs.com or www.ijpbsonline.com ISSN: 2230-7605 (Online); ISSN: 2321-3272 (Print) Int J Pharm Biol Sci. with rayed and discoid florets (S. paniculata rayed in analytical techniques such as chromatography find India; discoid in other countries (Saldanha and application in distinguishing species based on Nicolson, 1976; Jansen, 1981) and its misidentification chemical compounds. as Acmella species (Jansen, 1981; Chung, 2007). Under Asteraceae, a phylogenetically young family, is known these circumstances, chemotaxonomic for secondary metabolites and distinct primary characterization could be used for differentiation of metabolites (Herout, 1971). The variation in chemical these plant taxa. Evidences in respect of chemical compounds could yield confirmative results based on finger prints have been quite useful in species which species could be classified with the support of characterization in plants (Joelma et al. 2011). The distinct morphological characteristics. Since Spilanthes basic categories used by folk taxonomists for is medicinally important, previous studies classification include edibility, taste, colour, smell and documented the presence of chemical compounds medicinal values that are fundamentally based on (Table 1) and their relation to disease therapy. chemical properties (Jones and Luchsinger, 1986). The Table 1: Chemical constituents documented in species of Spilanthes in previous studies S.N. Chemical compounds Species Reference Sesquiterpenes, β bisalobenes, β caryophyllene, 1. S. americana Baruah and Pathak 1999 α- caryophyllene and cadinene 2. Sesquiterpenes, bisalobenes, caryophyllene, cadinene S. americana Anon. 2013 Caryophyllene, limonene, myrcene, sabinene, cis- 3. ocimene, S. calva Begum et al. 2008 β- pinene 4. Caryophyllene S. ciliata Anon. 2013 Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- 5. S. filicaulis Wahab et al 2013 dodecatetraenamide) Ramsewak et al. 1999; Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- 6. S. acmella Bae et al. 2010; Boonen et al. dodecatetraenamide) 2008; Stacy et al. 2010 Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- 7. S. alba Standley and Calderon 1944 dodecatetraenamide) Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- 8. S. mauritiana Jondiko et al.1986 dodecatetraenamide) Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- Nakatani and Nagasimha 9. S. oleracea dodecatetraenamide) 1992 Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- 10. S. radicans Ramirez et al. 2011 dodecatetraenamide) Spilanthol (N- isobutyl 2E,4Z, 8Z, 10E- 11. S. calva Baruah and Pathak 1999 dodecatetraenamide) Nakatani and Nagasimha, 12. N (methylbutyl ) undeca (2E, 4Z) diene 8,10 diyamide- S. acmella 1992 13. N isobutyl 2E, 6Z 8E decatrienamide S. filicaulis Wahab et al. 2013 14. N isobutyl 2E, 6Z 8E decatrienamide S. americana Anon. 2013 15. N-Isobutyl-(6Z,8E)-decadienamide S. calva Baruah and Pathak, 1999 16. N-(2-Phenylethyl)(2Z,4E)-octadienamide S. radicans Ramirez et al.2011 17. (2E)-N-(3-Ethynylphenyl)-3-phenyl-2-propenamide S. radicans Charvez et al. 2003 18. Sitosterol-O-D-glucoside S. acmella Ramsewak et al. 1999 International Journal of Pharmacy and Biological Sciences Lavanya Devi K* et al 87 www.ijpbs.com or www.ijpbsonline.com ISSN: 2230-7605 (Online); ISSN: 2321-3272 (Print) Int J Pharm Biol Sci. 19. Lupenyl acetate S. ocymifolia Castillo et al. 1984 20. Stigma sterol and sitosterol S. acmella Pandey et al. 2007 21. Stigma sterol and its glycoside S. acmella Supaluk et al. 2009 22. Docosanoic acid S. oleracea Phrutivorapongkul, 2008 Lauric acid, myristic acid, palmitic acid, linoleic acid, 23. S. acmella Krishnaswamy et al. 1975 linolenic acids as their methyl esters 24. n- Hexadecanoic acid and Myristic acid S. acmella Leng et al. 2011 25. n- Hexadecanoic acid and Tetradecanoic acid S. acmella Vibha et al. 2011 Against this background, in the present study, six species of Spilanthes - S. calva, S. ciliata, S. oleracea, S. paniculata, S. radicans and S. uliginosa occurring in peninsular India were studied for their chemical compounds, which could be used as a taxonomic criteria for their characterization. The GCMS-MS, a powerful analytical method, was employed to detect compounds in complex matrices and at trace levels in Spilanthes species. MATERIALS AND METHODS three times in a separating funnel. The bottom layer Selection of plant material: In the present study, six of hexane extract was collected and concentrated to Spilanthes species viz., S. calva, S. ciliata, S. oleracea, dryness at 40° C in a rotary evaporator coupled to a S. paniculata, S. radicans and S. uliginosa growing in water pump. The dried extract was eluted with 1 ml of different regions of peninsular India were identified n-hexane: diethyl ether (1:1) and used for GCMS based on morphological characteristics with the help analysis. of descriptors detailed in flora (Manilal and Sivarajan, Gas chromatography tandem mass spectrometry 1982; Saldanha and Nicolson, 1976; Pullaiah, 1997). GCMS-MS analysis The specimens of the above plant species were The GCMS-MS analysis was carried out using Varian collected and grown in the shade net house and field 4000 Ion trap GCMS-MS (Varian, USA) with Fused gene bank of the Division of Plant Genetic Resources, silica column (column-30 m × 0.25 mm ID with 0.25 m Indian Institute of Horticultural Research, Bengaluru. film thickness). The instrument was set to an initial The herbaria and seeds of the voucher specimens temperature of 110º C, and maintained at the same were deposited in the Division of Plant Genetic temperature for 2 min. At the end of this period, the Resources, Indian Institute of Horticultural Research, oven temperature was up to 280º C (at the rate of an -1 Bengaluru. increase of 5º C min and maintained for 9 min). Preparation
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