Phytochemical profiling of the bioactive principles of Alysicarpus glumaceus (Vahl) DC. aerial parts

Abstract

Background and Aims: Alysicarpus glumaceus is a plant used in Africa, Asia and some parts of the Arabian Peninsula with folkloric claims of having anti-tussive, anti-asthmatic, anti-diarrheal, abortifacient, anti-psychotic, anti-inflammatory, diuretic and stimulatory activities. The aim of this study was to determine the phytoconstituents present in the methanol extract (ME) of Alysicarpus glumaceus and its fractions. Methods: Standard qualitative phytochemical screening methods such as thin layer chromatography (TLC), gas chromatography mass spectrometry (GC-MS) and fourier-transform infrared (FT-IR) spectroscopy were employed for the profiling of the plant and identification of the phytoconstituents. Results: The phytochemical screening revealed the presence of alkaloids, cardiac glycosides, flavonoids, saponins, steroids, tannins and terpenes. GC-MS chromatogram showed a total of 57 peaks with 38 different compounds identified, out of which 15 of the compounds were fatty acids mainly 3-Quinolinecarboxylic acid, 6,8-difluoro-4-hydroxy-, ethyl ester; cis-Vaccenic acid; 9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)- Octasiloxane, 1,1,3,3,5,5,7,7,9,9,11,11,13,13,15,15- hexadecamethyl-; 1-methyl-4-phenyl-5-thioxo-1,2,4-triazolidin-3-one; 2-Pentanone, 4-hydroxy-4-methyl-; Hexadecanoic acid; Palmitoleic acid; 9,12-Octadecadienoic acid and 9,17-Octadecadienal. While FT-IR spectras indicated the presence of carbonyl, alcohol, carboxylic acid, and aliphatic functional groups. Additionally, ethyl acetate fraction showed the peak characteristics of the aromatic (=C-H)/olefinic (=C-H) functional group. Conclusion: The study showed that fatty acids were the major constituents of Alysicarpus glumaceus.

Keywords

• Alysicarpus glumaceus
• phytoconstituents
• gas chromatography-mass spectrometry (GC-MS)

References

1. • Abbasi-Maleki, S. & Mousavi, Z. (2017). Hydroethanolic extract of Carthamus tinctorius induces antidepressant-like effects: modulation by dopaminergic and serotonergic systems in tail suspension test in mice. Iranian Journal of Basic Medical Science, 20, 1063-1073.
2. • Abdoun, S., Hassan, T.I., Gaber, D.A. & El- Sharekh, A. (2019). Antidepressant activity of A. hierochuntica L. effervescent granules using forced swimming test. Journal of Innovations in Pharmaceutical and Biological Sciences (JIPBS), 6(2), 38-44.
3. • Abraham, R., Riemersma, R.A., Wood, D., Elton, R. & Oliver, M.F. (1989). Adipose fatty acid composition and the risk of serious ventricular arrhythmias in acute myocardial infarction. American Journal of Cardiology, 63:269–72.
4. • Akpuaka, A, Ekwenchi, M.M., Dashak, D.A., & Dildar, A. (2013). Biological activities of characterized isolates of n-Hexane extract of Azadirachta indica A. Juss (Neem) Leaves. Nature and Science.; 11(5):142-145
5. • Allen, O.N. & Allen, C.K. (1981). The leguminosae: A source book of characteristics, uses and modulation. Macmillan Publishers Ltd., London, United Kingdom. 5-29.
6. • Aly, A. A., A. Hassan, A., Makhlouf, M. M., & Bräse, S. (2020). Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs. Molecules, 25(13), 3036. http://dx.doi. org/10.3390/molecules25133036
7. • Aminu, M.D. (2017). Emerging Perspectives on Drugs of Abuse: A Focus on Gadagi Consumption in Kano, Nigeria. Advances in Psychology and Neuroscience. Special Issue: Substance Abuse: Perspectives, Trends, Issues and the Way Forward. 2(2-1), 7-14. doi: 10.11648/j.apn.s.2017020201.12
8. • Aneesh, T.P., Thomas, E., Thomas, D.G., & Anandan R. (2013). GC-MS analysis of phytochemical compounds present in the rhizomes of Nervillia aragoana GAUD. Asian Journal of Pharmaceutical and Clinical Research, 6(3), 68-74.

9. • Ansorena, D., Gimeno, O., Astiasarán, I., & Bello, J. (2001). Analysis of volatile compounds by GC–MS of a dry fermented sausage: chorizo de Pamplona. Food Research International, 34(1), 67– 75. doi:10.1016/s0963-9969(00)00133-2
10. • Banwo, O.A. (2013). Phytochemical and some pharmacological studies of the aerial part of Alysicarpus ovalifolius schumach & thonn family: fabaceae. (masters’ thesis). http://library.abu.edu,ng
11. • Bashir, M., Uzair, M. & Bashir A. (2018). Ethnobotanical, Phytochemical and pharmacological aspects of genus Alysicarpus. International Journal of Pharmacy, 8(4), 1-25.
12. • Bawa B. (2012). Phytochemical study and central nervous system activity of the plant Alysicarpus glumaceus (Vahl) DC. family: Legumunaceae. (masters’ thesis). http://library.abu.edu,ng
13. Bekalo, T.H., Woodmatas, S.D. & Woldemariam Z.A. (2009). An ethnobotanical study of medicinal plants used by local people in the lowlands of konta special woreda, southern nations, nationalities and peoples regional state, Ethiopia. Journal of Ethnobiology and Ethnomedicine, 5, 26. doi: 10.1186/1746-4269-5-26.
14. • Benedec, D., Vlase L., Oniga I., Mot, A.C., Damian, G., Hanguna, D… Silaghi-Dumitrescu, R. (2013). Polyphenolic composition, antioxidant and antibacterial activities for two Romanian subspecies of Achillea distans Waldst. et Kit ex willd. Molecules, 18(8), 8725-8739. doi:10.3390/molecules18088725.
15. • Biradar, R.S. & Rachetti, D.B. (2013). Extraction of some secondary metabolites & thin layer chromatography from different parts of Centella asiatica L. American Journal of Life Sciences, 1(6), 243-247.
16. • Burkill, H.M. (1985). The Useful Plants of West Tropical Africa, vol. 4. 2nd Edition. Published by Royal Botanic Gardens, Kew, Richmond, Surrey TW8 3AE; 17.
17. • CIRAD, 2010-Centre de Cooperation international en recherché agronomique pour le development databases (French Agricultural Research Centre for International Development). (http:// www.feedipedia.org) Accessed on 19/07/2018.
18. • Crews, P., Rodriquez, J., Jaspars M. & Crews, R.J. (1998). Organic Structure Analysis. Oxford University Press- Oxford, New York.
19. • Dingman, S.L (2002). Water in soils: infiltration and redistribution. Physical hydrology, second edition, upper saddle river, New Jersey: Prentice-Hall, Inc. 646.
20. • Dracheva, L.V., Dorozhko, E.V., Avramchuk, O.A., Korotkova, E.I., Ryzhkova, E.P., Li, H. & Danilova, I.V. (2009). Voltammetric study of the antioxidant activity of propionic acid bacteria in liquid cultures. Moscow University Biological Sciences Bulletin, 64, pp.157-160 •
21. Du, B., Tang, X., Liu, F., Zang, C., Zhao, G., Ren, F. & Leng, X. (2014). Antidepressant-like effects of the hydroalcoholic extract of Hemerocallis citrina and its potential active components. BMC Complementary and Alternative Medicine, 14, 326.
22. • Dutta, J., (2013). Phytochemical analysis and TLC fingerprinting of methanolic extract of three medicinal plants. International Research Journal of Pharmacy, 4(6), 123-126.
23. • Easwaran, L. & Ramani, V.L. (2014). Phytochemical examination and GC-MS studies of the medicinal plant Naravelia zeylanica. International Journal of Research and Development in Pharmacy and Life Sciences, 3(5), 1180-1188.
24. • Facchini, P.J., (2001). Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation and metabolic engineering. Annu Rev Plant Physiology Plant Molecular Biology, 52(1), 29-66. doi: 10.1146/ annurev. arplant. 52.1.29.
25. • Falowo, A.B., Muchenje, V., Hugo, A., Aiyegoro, O.A. & Fayemi, P.O. (2017). Antioxidant activities of Moringa oleifera L. and Bidens pilosa L. leaf extracts and their effects on oxidative stability of ground raw beef during refrigeration storage, CyTA - Journal of Food, 15(2), 249-256. Doi: 10.1080/19476337.2016.1243587
26. • Fernandes, M.F., Mutch, D.M. & Leri, F. (2017). The Relationship between fatty acids and different depression-related brain regions, and their potential role as biomarkers of response to antidepressants. Nutrients, 9, 298.
27. • Haerdi, F. (1964). Afrikanische Heilpflanzen. Die Eingeborenen- Heilpflanzen des Ulanga- Distriktes Tanganjikas (Ostafrika). Acta tropica, Suppl. 8, 1-278: Verlag für Recht und Gesellschaft (Basel)
28. • Hamazakic K, Suzuki N, Kitamura KI, Hattori A, Nagasawa T, Itomura M, Hamazaki T. (2016). Is vaccenic acid (18:1t n-7) associated with an increased incidence of hip fracture? An explanation for the calcium paradox. Prostaglandins Leukotrienes and Essential Fatty Acids,109, 8–12.
29. • Harborne, J.B. (1973). Phytochemical Methods. Chapman and Hall, Ltd London, 49.
30. • Hoffman, L.D., Friedmann, A., Saltman, P. & Polich, J. (1999). Neuroelectric assessment of nutrient intake. International Journal of Psychophysiology, 32, 93-106.
31. • Horrigan L.A., Kelly J.P., & Connor T.J. (2006). Immunomodulatory effects of caffeine: friend or foe? Pharmacology and Therapeutics, 111: 877–892.
32. • Ingole, S.N., (2016). Phytochemical analysis of leaf extract of Ocimum americanum L. (Lamiaceae) by GC-MS method. World Scientific News, 37: 76-87.
33. • Jäger, K. & Saaby, L. (2011). Flavonoids and the CNS. Molecules, 16, 1471- 1485.
34. • Jonathan, G. & Tom, J.M. (2008). Secondary metabolites and the higher classification of Angiosperms. Nordic Journal of Botany, 3(1), 5-34.
35. • Jost, R. (2002). Milk and Dairy Products, Ullmanns Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA; doi/10.1002/14356007.
36. • Kauri R, & Arora S. (2015). Alkaloids-important therapeutic secondary metabolites of plant origin. Journal of Critical Review, 2: 1-8.
37. • Krishnaiah, D., Devi, T., Bono, A. & Sarbatly, R. (2009). Studies on phytochemical constituents of six malaysian medicinal plants. Journal of Medicinal Plants Research, 3(2), 067-072.
38. • Kumaradevan, G., Damodaran, R., Mani, P., Dineshkumar, G., & Jayaseelan, T., (2015). Phytochemical Screening and GC-MS Analysis of Bioactive Components of Ethanol Leaves Extract of Clerodendrum Phlomidis (L.), American Journal of Biological and Pharmaceutical Research, 2(3), 142-148.
39. • Kure, C., Timmer, J., & Stough, C. (2017). The Immunomodulatory Effects of Plant Extracts and Plant Secondary Metabolites on Chronic Neuroinflammation and Cognitive Aging: A Mechanistic and Empirical Review. Frontiers in pharmacology, 8, 117. https:// doi.org/10.3389/fphar.2017.00117
40. • Lantz R.C, Chen G.J, Sarihan M., Sólyom A.M., Jolad S.D. & Timmermann B.N. (2007). The effect of extracts from ginger rhizome on inflammatory mediator production. Phytomedicine, 14: 123–128.
41. • Lim, C.S., Wong, W.F., Rosli, R, Ng, K.P., Seow, H.F., Chong, P.P. (2009). 2-dodecanol (decyl methyl carbinol) inhibits hyphal formation and SIR2 expression in C. albicans. Journal of Basic Microbiology, 49(6), 579-83. Doi: 10.1002/jobm.200900035. PMID: 19810039.
42. • Lim, J. N., Oh, J. J., Wang, T., Lee, J. S., Kim, S. H., Kim, Y. J., & Lee, H. G. (2014). trans-11 18:1 vaccenic acid (TVA) has a direct anticarcinogenic effect on MCF-7 human mammary adenocarcinoma cells. Nutrients, 6(2), 627–636. https://doi.org/10.3390/ nu6020627Moscow University Biological Sciences Bulletin., 64, pp.157-160
43. • Middleton, E, Kandaswami, C., & Theoharides, T.C. (2000). The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacology Review, 52, 673–751.
44. • Morgan, N.G. & Dhayal, S. (2010). Unsaturated fatty acid as cytoprotective agents in the pancreatic B-cells. Journal of Prostaglandins, Leukotrienes and Essential Fatty Acids, 82(4-6), 231-6. Doi: 10.1016/j.plefa.2010.02.018.
45. • Morris, H.V., Dawson, G.R., Reynolds, D.S., Atack, J.R. & Stephens, D.N. (2006). Both alpha 2 and alpha 3 GABA-A receptor subtypes mediate the anxiolytic properties of benzodiazepine site ligands in the conditioned emotional response paradigm. European Journal of Neuroscience, 23, 2495-2504.
46. • Mozaffarian, D., Cao, H., King, I.B., Lemaitre, R.N., Song, X., Siscovick, D.S., & Hotamisligil, G.S. (2010); Circulating palmitoleic acid and risk of metabolic abnormalities and new-onset diabetes. The American Journal of Clinical Nutrition, 92(6), 1350–1358. doi:10.3945/ajcn.110.003970
47. • Ncube, N.S., Afolayan, A.J. & Okoh, A. (2008). Assessment techniques of antimicrobial properties of natural compounds of plant origin: current methods and future trends. African Journal of Biotechnology, 7(12), 1797-1806.
48. • Parekh, A., Smeeth, D., Milner, Y., & Thure, S. (2017). The Role of Lipid Biomarkers in Major Depression. Healthcare (Basel, Switzerland), 5(1), 5. https://doi.org/10.3390/healthcare5010005
49. • Parmar, S.K., Sharma, T.P., Airao, V.B., Bhatt, R., Aghara, R, Chavda, S, Rabadiya. S.O. & Gangwal, A.P. (2013). Neuropharmacological effects of triterpenoids. Phytopharmacology, 4(2), 354-372.
50. • Pandya, P.R. (2009). A study of the weed flora of some cultivated fields of Bharuch district. (Unpublished doctorate thesis). Saurashtra University, Porbandar-India.
51. • Pavia, D.L., Lampman G.M., Kriz G.S, & Engel R.G. (2011); Introduction to Organic Laboratory Techniques: A Small Scale Approach. Third Edition; Cengage Learning- Canada.
52. • Pemminati, S., Gopalakrishna, H., Shenoy, A., Sahu, S., Mishra, S., Meti, V. & Vinod, N. (2010). Antidepressant activity of aqueous extract of fruits of Emblica officinalis in mice. International Journal of Applied Biology and Pharmaceutical Technology, 1, 449-454.
53. • Phani, G.K., Anilakumar, K.R. & Naveen, S. (2015). phytochemicals having neuroprotective properties from dietary sources and medicinal herbs. Pharmacognosy Journal, 7(1), 1-17.
54. • Rahman, M.M., Ahmad, S.H., Mohamed, M.T.M., & Ab Rahman, M.Z. (2014). Antimicrobial compounds from leaf extracts of Jatropha curcas, Psidium guajava, and Andrographis paniculata. The Scientific World Journal 2014, 635240-635240. Doi:10.1155/2014/635240
55. • Rajeev K, Prabodh C.S & Mohammed S.Y. (2011). Pharmacological significance of triazole scaffold, Journal of Enzyme Inhibition and Medicinal Chemistry, 26(1), 1-21. Doi: 10.3109/14756360903524304
56. • Ragavendran, P., Sophia, D., Raj, C.A. & Gopalakrishnan, V.K. (2011). Functional group analysis of various extracts of aerva lanata (l.,) by FTIR spectrum. Pharmacologyonline, 1: 358-364.
57. • Sagdinc, S.G., Azkeskin, C., & Eşme, A. (2018). Theoretical and spectroscopic studies of a tricyclic antidepressant, imipramine hydrochloride. Journal of Molecular Structure, 1161: 169–184. doi:10.1016/j.molstruc.2018.02.056.
58. • Sajid, I., Bijan, K., Zamiul, R., Mominul, I. & Ekramul, H. (2013). CNS depressant and antinociceptive activities of the aerial parts of Mimosa pudica. European Journal of Applied Sciences, 5, 127-133.
59. • Saradha, M. & Paulsamy, S. (2013). GC-MS analysis for bioactive compounds from methanolic leaf and stem bark extracts of Hildegardia populifolia (Roxb.) Schott & Endl. International Journal of Pharmaceutical Sciences Review and Research, 23(2), 52, 328-332.
60. • Saric-Kundalic, B., Dobe, S.C., Klatte-Asselmeyer V. & Saukel J. (2010). Ethnobotanical study on medicine use of wild and cultivated plants in middle, south and west Bosnia and Herzegovina. Journal of Ethnopharmacology, 131:33À5520.
61. • Scott, D.A., Wright, C.E. & Angus, J.A. (2004). Evidence that CB-1 and CB-2 cannabinoid receptors mediate antinociception in neuropathic pain in the rat. Pain, 109, 124-131 • Senthil, J., Rameashkannan, M.V. & Mani, P. (2016). Phytochemical profiling of ethanolic leaves extract of Ipomoea sepiaria (Koenig Ex. Roxb). International Journal of Innovative Research in Science, Engineering and Technology, 5(3), 3140-3147.
62. • Sofowora, A. (1993). Phytochemical Screening of Medicinal Plants and Traditional Medicine in Africa, Spectrum Books Ltd, Ibadan, Nigeria.
63. • Smedman, A.E., Gustafsson, I.B., Berglund, L.G. & Vessby, B.O. (1999). Pentadecanoic acid in serum as a marker for intake of milk fat: relations between intake of milk fat and metabolic risk factors. American Journal of Clinical Nutrition, 69(1), 22-9.
64. • Talukdar, A.D., Choudhury, M.D., Chakraborty, M. & Dutta, B.K. (2010). Phytochemical screening and TLC profiling of plant extracts of Cyathea gigantea (Wall. Ex. Hook.) Haltt. and Cyathea brunoniana. Wall. ex. Hook. (Cl. & Bak.); Assam University Journal of Science & Technology: Biological and Environmental Sciences, 5(1), 70-74.
65. • Trease, G.E. & Evans, W.C (2004). Phytochemistry, In Textbook pf Pharmacognosy 13th Edition, Balliere, Tindall and Cansell Ltd. London.
66. • Umberto Q. (2016). CRC world dictionary of medicinal and poisonous plants: common names, scientific names, eponyms, synonyms, and etymology, ISBN 1482250640, 9781482250640; CRC Press, 221-223.
67. • Venkatesh, R., Vidya, R. & Kalaivani, K. (2014). Gas chromatography and mass spectrometry analysis of Solanum villosum (Mill) (Solanaceae). International Journal of Pharmaceutical Sciences and Research, 5(12), 5283-5287 .
68. • Wintola, O.A. & Afolayan A.J. (2011). Phytochemical constituents and antioxidant activities of the whole leaf extract of Aloe ferox Mill. Pharmacognosy Magazine, 7(28), 325-334.
69. • Yu, F.R., Lian, X.Z., Guo, H.Y., McGuire, P.M., Li, R.D., Wang, R. & Yu, F.R. (2005). Isolation and characterization of methyl esters and derivatives from Euphorbia kansui (Euphorbiaceae) and their inhibitory effects on the human SGC-7901 cells. Journal of Pharmaceutical Science, 8, 528–535.
70. • Zamaria, N. (2004). Alteration of polyunsaturated fatty acid status and metabolism in health and disease. Reproduction, Nutrition, Development, 44(3), 273-282.