ISOLATION AND CHARACTERIZATION OF BIOACTIVE WITHANOLIDE GLUCOSIDES, COAGULANS Y AND Z, FROM WITHANIA COAGULANS AND EVALUATION OF THEIR BIOLOGICAL ACTIVITIES
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Keywords
Solanaceae, Withania coagulans, Withanolide glucosides, Coagulin Y, Coagulans Z.
Abstract
Traditional medicine, particularly herbal treatments from the genus Withania, plays a crucial role in health management worldwide. Withania coagulans (Stock) Dunal, known for its diverse medicinal uses, is underexplored concerning its biochemical profile and therapeutic potential as functional food. This study aimed to investigate the antioxidant potential and enzyme inhibitory effects of various extracts of W. coagulans, focusing on key enzymes linked to neurodegenerative diseases, diabetes, inflammation, and skin hyperpigmentation. The plant material was collected, extracted using different solvents, and subjected to bioactive compound quantification, antioxidant testing, and enzyme inhibition assays. The methanol extract demonstrated substantial inhibitory activity, particularly against lipoxygenase (144.76 mg QE/g extract), AChE (4.10 mg GALAE/g extract), and BChE (3.71 mg GALAE/g extract). Notably, the ethyl acetate (EA) extract exhibited the highest glucosidase inhibition at 3.51 mmol ACAE/g extract. Phytochemical screening highlighted the presence of withanolides (Coagulins Y and Z and withanolides glucosides) as the major bioactive components, supporting their broad pharmacological activities. Colagulins Y (1) and Z (2), new withanolide glucosides, have been isolated from the n-butanol fraction of the methanolic extract of whole plant of Withania coagulans Dunal. Their structures were elucidated through spectroscopic analysis including FAB-MS, 2D NMR and acid hydrolysis. The study confirms the potential of Withania coagulans extracts as natural inhibitors with significant therapeutic implications, deserving further development and clinical exploration.
References
2. Ali et al.Sensitive quantification of six steroidal lactones in Withania coagulans extract by UHPLC electrospray tandem mass spectrometry Steroids (2015).
3. Atta-ur-Rehman, Yousaf, M.; Gul, W.; Qureshi, S.; Choudhary, M.I.; Voelter, W.; Hoff, A.; Jens, F.; Naz, A. (1998). Five new withanolides form Withania coagulans, Heterocycles, 48, 1801-1811.
4. Barad, R.; Soni, P.; Upadhyay, S.; Upadhyay, U. Withania coagulans and Psidium guajava: An Overview. Int. Res. J. Pharm. Appl. Sci. 2013, 3, 42–47.
5. Bhandari, M.M. Flora of Indian Desert; MPS Reports: Jodhpur, India, 1990.
6. Chen L-X, He H, and Qiu F. 2011. Natural withanolides: An overview. Nat. Prod. Rep. 28: 705-740.
7. Chen, Z.L.; Wang, B.D.; Chen, M.Q. (1987. Steroidal bitter principles from Tacca plantaginea. Structures of taccalonolide A and B, Tetrahedron Letters, 28, 1673-1678.
8. Chen, Z.L.; Wang, B.D.; Shen, J.H. (1988. Taccalonolide C and D, two pentacyclic steroids of Tacca plantaginea, Phytochemistry, 27, 2999-3001.
9. F. Fazio et al. Withania coagulans fruit extract a possible useful additive in ameliorating growth and immunity of Labeo rohita (Hamilton, 1822). Nat. Prod. Res. (2023)
10. Franklinos L. H. V., Jones K. E., Redding D. W., Abubakar I. The effect of global change on mosquito-borne disease. The Lancet Infectious Diseases . 2019;19(9):e302–312. doi: 10.1016/s1473-3099(19)30161-6. [DOI] [PubMed] [Google Scholar]
11. Gilani, S.A.; Kikuchi, A.; Watanabe, K.N. Genetic Variation within and among Fragmented Populations of Endangered Medicinal Plant, Withania coagulans (Solanaceae) from Pakistan and Its Implications for Conservation. Afr. J. Biotechnol. 2009, 8, 2948–2958.
12. Glotter, E., 1991. Withanolides and related ergostane-type steroids Nat. Prod. Rep. 8: 415-440.
13. Glotter, E.; Kirson, I.; Lavie, D.; Abraham, A. (1978. Bio-organic Chemistry (Ed. E. E. van Tamelen, Academic Press, New York, II, p. 57.
14. Gupta, R.; Sonawane, T.; Pai, S. An Overview on Pharmaceutical Properties and Biotechnological Advancement of Withania coagulans. Adv. Tradit. Med. 2021, 22, 673–683. (CrossRef)
15. Hara, S.; Okabe, H.; Mihashi, K. (1987. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl-thiazolidine-4(R-carboxylate, Chemical and Pharmaceutical Bulletin, 35, 501-506.
16. K. Ahmad et al. Ethnoveterinary medicinal plant knowledge and practice among the tribal communities of Thakht-e-Sulaiman hills, West Pakistan J. Ethnopharmacol. (2015)
17. Khan, M.I.; Maqsood, M.; Saeed, R.A.; Alam, A.; Sahar, A.; Kieliszek, M.; Miecznikowski, A.; Muzammil, H.S.; Aadil, R.M. Phytochemistry, Food Application, and Therapeutic Potential of the Medicinal Plant (Withania coagulans): A Review. Molecules, 2021, 26, 6881. [CrossRef]
18. Ksebati, M.B.; Schmitz, F. J. (1988. Minabeolides: A group of withanolides from a soft coral, Minabea sp., Journal of Organic Chemistry, 53, 3926-3929.
19. Kuroyanagi M, Murata M, Nakane T, Shirota O, Sekita S, Fuchino H, Shinwari Z. K. 2012. Leishmanicidal active withanolides from a Pakistani medicinal plant, Withania coagulans Chem. Pharm. Bull. 60: 892-897.
20. L. Holst et al. Safety and efficacy of herbal remedies in obstetrics – review and clinical implications. Midwifery (2011).
21. Lateef, T., Qureshi, S.A. 2014. Ameliorative effect of Withania coagulans on experimentally induced hyperlipidemia in rabbits. Journal of Natural Remedies, 14, 83-88.
22. M. Alba et al. Effects of Withania coagulans fruit powder and vitamin C on growth performance and some blood components in heat stressed broiler chickensLivest. Sci. (2015)
23. M. Beg et al. A withanolide coagulin-L inhibits adipogenesis modulating Wnt/β-catenin pathway and cell cycle in mitotic clonal expansion Phytomedicine (2014).
24. M. Goyal Traditional plants used for the treatment of diabetes mellitus in Sursagar constituency, Jodhpur, Rajasthan – an ethnomedicinal survey J. Ethnopharmacol. (2015).
25. Mabberley, D.I. 1987. The Plant Book. Cambridge University Press, Cambridge, New York.
26. Mathur D, Agrawal R.C. 2011. Withania coagulans a review on the morphological and pharmacological properties of the shrub. World Journal of Science and Technology 1:30-37.
27. Mughal, U.R.; Mehmood, R.; Malik, A.; Ali, B.; Tareen, R.B. (2012. Flavonoidal Constituents from Spiraea brahuica, Helvetica Chimica Acta, 95, 100-105.
28. Nasir, Y.J. 1985. Solanaceae. In: Flora of Pakistan. (Eds.: E. Nasir and S.I. Ali. Missouri Botanical Press, Missouri, No. 168: 1-61.
29. Pandey, I.; Nama, K.S. Withania coagulans (Stocks) Dunal: A Rare Ethnomedicinal Plant of the Western Rajasthan Desert. Int. J. Pharmaceut. Biomed. Res. 2015, 2, 34–40.
30. Pavia, D.L.; Lampman, G.M.; Kriz, G.S. (1979. Introduction to spectroscopy, Saunders College Publishing Co., Philadelphia, , p. 41.
31. R. Ahmad et al. Evaluation of apoptotic activity of Withania coagulans methanolic extract against human breast cancer and Vero cell lines J. Ayurveda Integr. Med. (2017)
32. Rathore, M.S.; Khatri, K.; Kheni, J.; Shekhawat, N.S. Biotechnological Advancement in an Important Medicinal Plant, Withania coagulans: An Overview and Recent Updates. In Biotechnological Approaches for Medicinal and Aromatic Plants; Kumar, N., Ed.; Springer: Singapore, 2018; pp. 445–465.
33. Ray, A.B.; Gupta, M. (1994. Withasteroids, a Growing Group of Naturally Occurring Steroidal lactones, Progress in the Chemistry of Organic Natural Product, 63, 1-106.
34. S.A. Khan et al. Isolation, characterization and DFT studies of epoxy ring containing new withanolides from Withania coagulans Dunal Spectrochim. Acta A Mol. Biomol. Spectrosc. (2019)
35. Scott, I. (1964. Interpretation of the Ultraviolet Spectra of Natural Products, Pergamon Press, Oxford, p. 64.
36. Srivastava, C.; Siddiqui, I.R.; Singh, J.; Tiwari, H.P. (1992. An antifeedant and insecticidal steroid and a new hydroxyl ketone from Cassia siamea bark. Journal of Indian Chemical Society, 69, 111.
37. Tusting L. S., Thwing J., Sinclair D., et al. Mosquito larval source management for controlling malaria. Cochrane Database of Systematic Reviews. 2013;8 doi: 10.1002/14651858.cd008923.pub2.CD008923 [DOI] [PMC free article] [PubMed] [Google Scholar]
38. Verma P. K, Rajurkar S, Gaikwad N. J, Kamboj V. 2010. The isolation and structure elucidation of new Withanolides from Withania coagulans with antidiabetic activity. Acta Pharmaceutica Sciencia 52 :155-157.
39. Watt G.A. 1972. ‘Dictionary of the Economic Products of India’. Cosmo Publications, Delhi-6, India, 6, 309.
40. Zhou, X.L.; He, X.J.; Wang, G.H.; Yao, X.S. (2006. Steroidal saponins from Solanum nigrum. Journal of Natural Products, 69, 1158-1163.
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Hayat Bibi
Department of Chemistry, Sardar Bahadur Khan Women University, Quetta, Pakistan
Saima Maher
Department of Chemistry, Sardar Bahadur Khan Women University, Quetta, Pakistan
Shamim Khan
Department of Pharmacy, Sardar Bahadur Khan Women University, Quetta, Pakistan
Fareeda Behlil
Assistant Professor, Department of Chemistry, Faculty of Basic Science, Sardar Bahadur Khan Women University, Quetta, Pakistan
Shaista Anjum
Department of Botany, University of Balochistan, Quetta, Pakistan
Huma Tareen
Assistant Professor Department of Chemistry, Sardar Bahadur Khan Women University, Quetta, Pakistan
Farrukh Bashir
Associate Professor, Department of Chemistry, Sardar Bahadur Khan Women’s University Quetta, Pakistan