Isolation and structure elucidation of a steroidal moiety from Withania somnifera and in silico evaluation of antimalarial efficacy against artemisinin resistance Plasmodium falciparum kelch 13 protein

References

• Ali, S., Khan, M. N., Ali, K., Zaman, A., & Iqbal, M. (2020). Preliminary phytochemical analysis of selected plants occurring in district Nowshera, Khyber Pakhtunkhwa. Pure and Applied Biology, 9(1), 683-95. https://doi.org/10.19045/bspab.2020.90074
   Google Scholar
• Ariey, F., Witkowski, B., Amaratunga, C., Beghain, J., Langlois, A.-C., Khim, N., Kim, S., Duru, V., Bouchier, C., Ma, L., Lim, P., Leang, R., Duong, S., Sreng, S., Suon, S., Chuor, C. M., Bout, D. M., Ménard, S., Rogers, W. O., … Ménard, D. (2014). A molecular marker of artemisinin-resistant Plasmodium falciparum malaria. Nature, 505(7481), 50–55. https://doi.org/10.1038/nature12876
   PubMed Web of Science ®Google Scholar
• Azam, F. (2021). Elucidation of teicoplanin interactions with drug targets related to COVID-19. Antibiotics (Basel, Switzerland), 10(7), 856. https://doi.org/10.3390/antibiotics10070856
   PubMed Web of Science ®Google Scholar
• Azhar, M. F., Naseer, U., Aziz, A., Zafar, S., Qadir, I., Farooq, M., Ahmad, I., & Anjum, K. (2020). Antioxidant and phytochemical composition of leaves, stem and root extracts of Withania coagulans and Withania somnifera. Journal of Medicinal and Spice Plants, 24(1), 27–30.
   Google Scholar
• Bharti, V. K., Malik, J. K., & Gupta, R. C. (2016). Ashwagandha: multiple health benefits. In Nutraceuticals (pp. 717–733). Academic Press. https://doi.org/10.1016/B978-0-12-802147-7.00052-8
   Google Scholar
• Chan, X. H. S., Win, Y. N., Haeusler, I. L., Tan, J. Y., Loganathan, S., Saralamba, S., Chan, S. K. S., Ashley, E. A., Barnes, K. I., Baiden, R., Bassi, P. U., Djimde, A., Dorsey, G., Duparc, S., Hanboonkunupakarn, B., Ter Kuile, F. O., Lacerda, M. V. G., Nasa, A., Nosten, F. H., … White, N. J. (2020). Factors affecting the electrocardiographic QT interval in malaria: A systematic review and meta-analysis of individual patient data. PLoS Medicine, 17(3), e1003040. https://doi.org/10.1371/journal.pmed.1003040
   PubMed Web of Science ®Google Scholar
• Chang, H.-W., Li, R.-N., Wang, H.-R., Liu, J.-R., Tang, J.-Y., Huang, H.-W., Chan, Y.-H., & Yen, C.-Y. (2017). Withaferin a induces oxidative stress-mediated apoptosis and DNA damage in oral cancer cells. Frontiers in Physiology, 8, 634. https://doi.org/10.3389/fphys.2017.00634
   PubMed Web of Science ®Google Scholar
• Chauhan, N. B., & Mehla, J. (2015). Ameliorative Effects of Nutraceuticals in Neurological Disorders. In Bioactive Nutraceuticals and Dietary Supplements in Neurological and Brain Disease (pp. 245–260). Elsevier. https://doi.org/10.1016/B978-0-12-411462-3.00027-8
   Google Scholar
• Chaurasiya, N. D., Sangwan, N. S., Sabir, F., Misra, L., & Sangwan, R. S. (2012). Withanolide biosynthesis recruits both mevalonate and DOXP pathways of isoprenogenesis in Ashwagandha Withania somnifera L. (Dunal). Plant Cell Reports, 31(10), 1889–1897. https://doi.org/10.1007/s00299-012-1302-4
   PubMed Web of Science ®Google Scholar
• Choudhary, M. I., Yousuf., & S., Atta-ur-Rahman. (2013). Withanolides: Chemistry and Antitumor Activity. In K. G. Ramawat & J.-M. Mérillon (Eds.), Natural Products (pp. 3465–3495). Springer. https://doi.org/10.1007/978-3-642-22144-6_150
   Google Scholar
• Dar, N. J., Satti, N. K., Dutt, P., Hamid, A., & Ahmad, M. (2018). Attenuation of glutamate-induced excitotoxicity by withanolide-A in neuron-like cells: Role for PI3K/Akt/MAPK signaling pathway. Molecular Neurobiology, 55(4), 2725–2739. https://doi.org/10.1007/s12035-017-0515-5
   PubMed Web of Science ®Google Scholar
• Dhanani, T., Shah, S., Gajbhiye, N. A., & Kumar, S. (2017). Effect of extraction methods on yield, phytochemical constituents and antioxidant activity of Withania somnifera. Arabian Journal of Chemistry, 10, S1193–S1199. https://doi.org/10.1016/j.arabjc.2013.02.015
   Web of Science ®Google Scholar
• Dhar, N., Razdan, S., Rana, S., Bhat, W. W., Vishwakarma, R., & Lattoo, S. K. (2015). A decade of molecular understanding of withanolide biosynthesis and in vitro studies in Withania somnifera (L.) Dunal: Prospects and perspectives for pathway engineering. Frontiers in Plant Science, 6, 1031. https://doi.org/10.3389/fpls.2015.01031
   PubMed Web of Science ®Google Scholar
• Dinesh, P., & Rasool, M. (2019). Herbal formulations and their bioactive components as dietary supplements for treating rheumatoid arthritis. In Bioactive Food as Dietary Interventions for Arthritis and Related Inflammatory Diseases (pp. 385–399). Elsevier. https://doi.org/10.1016/B978-0-12-813820-5.00022-2
   Google Scholar
• Dongre, S., Langade, D., & Bhattacharyya, S. (2015). Efficacy and safety of Ashwagandha Withania somnifera root extract in improving sexual function in women: A pilot study. BioMed Research International, 2015, 1–9. https://doi.org/10.1155/2015/284154
   Web of Science ®Google Scholar
• Du, Y., Giannangelo, C., He, W., Shami, G. J., Zhou, W., Yang, T., Creek, D. J., Dogovski, C., Li, X., & Tilley, L. (2022). Dimeric artesunate glycerophosphocholine conjugate nano-assemblies as slow-release antimalarials to overcome kelch 13 mutant artemisinin resistance. Antimicrobial Agents and Chemotherapy, 13, e02065–21. https://doi.org/10.1128/aac.02065-21
   Google Scholar
• Gul, R., Jan, S. U., Faridullah, S., Sherani, S., & Jahan, N. (2017). Preliminary phytochemical screening, quantitative analysis of alkaloids, and antioxidant activity of crude plant extracts from Ephedra intermedia indigenous to Balochistan. The Scientific World Journal, 2017, 5873648. https://doi.org/10.1155/2017/5873648
   Google Scholar
• Hage-Melim, L. I., da, S., Federico, L. B., de Oliveira, N. K. S., Francisco, V. C. C., Correia, L. C., de Lima, H. B., Gomes, S. Q., Barcelos, M. P., Francischini, I. A. G., & da Silva, C. H. T. d P. (2020). Virtual screening, ADME/Tox predictions and the drug repurposing concept for future use of old drugs against the COVID-19. Life Sciences, 256, 117963. https://doi.org/10.1016/j.lfs.2020.117963
   PubMed Web of Science ®Google Scholar
• Hii, J., Hustedt, J., & Bangs, M. J. (2021). Residual malaria transmission in select countries of Asia-Pacific region: Old wine in a new barrel. The Journal of Infectious Diseases, 223(Suppl 2), S111–S142. https://doi.org/10.1093/infdis/jiab004
   PubMedGoogle Scholar
• Jain, M., Nevin, R. L., & Ahmed, I. (2016). Mefloquine-associated dizziness, diplopia, and central serous chorioretinopathy: A case report. Journal of Medical Case Reports, 10(1), 305. https://doi.org/10.1186/s13256-016-1091-4
   PubMedGoogle Scholar
• Jofily, P., Pascutti, P. G., & Torres, P. H. M. (2021). Improving blind docking in DOCK6 through an automated preliminary fragment probing strategy. Molecules (Basel, Switzerland), 26(5), 1224. https://doi.org/10.3390/molecules26051224
   PubMed Web of Science ®Google Scholar
• Kamaraj, B., & Purohit, R. (2014). Computational screening of disease-associated mutations in OCA2 gene. Cell Biochemistry and Biophysics, 68(1), 97–109. https://doi.org/10.1007/s12013-013-9697-2
   PubMed Web of Science ®Google Scholar
• Kamaraj, B., & Purohit, R. (2016). Mutational analysis on Membrane Associated Transporter Protein (MATP) and their structural consequences in Oculocutaeous Albinism Type 4 (OCA4)-A molecular dynamics approach: MATP Protein - A molecular dynamics approach. Journal of Cellular Biochemistry, 117(11), 2608–2619. https://doi.org/10.1002/jcb.25555
   PubMed Web of Science ®Google Scholar
• Kamaraj, B., Rajendran, V., Sethumadhavan, R., Kumar, C. V., & Purohit, R. (2015). Mutational analysis of FUS gene and its structural and functional role in amyotrophic lateral sclerosis 6. Journal of Biomolecular Structure & Dynamics, 33(4), 834–844. https://doi.org/10.1080/07391102.2014.915762
   PubMed Web of Science ®Google Scholar
• Kaul, S. C., Ishida, Y., Tamura, K., Wada, T., Iitsuka, T., Garg, S., Kim, M., Gao, R., Nakai, S., Okamoto, Y., Terao, K., & Wadhwa, R. (2016). Novel methods to generate active ingredients-enriched Ashwagandha leaves and extracts. PloS One, 11(12), e0166945. https://doi.org/10.1371/journal.pone.0166945
   PubMed Web of Science ®Google Scholar
• Kaushik, N. (2020). HPLC analysis of Withania somnifera (Linn.) Dunal reveals two chemotypes in Indian germplasm and seasonal and genetic variability in Withaferin A – Content [Preprint]. Plant Biology. https://doi.org/10.1101/2020.07.31.231316
   Google Scholar
• Kumar, A., & Purohit, R. (2014). Use of long term molecular dynamics simulation in predicting cancer associated SNPs. PLoS Computational Biology, 10(4), e1003318. https://doi.org/10.1371/journal.pcbi.1003318
   PubMed Web of Science ®Google Scholar
• Kumar, A., Rajendran, V., Sethumadhavan, R., & Purohit, R. (2013a). Roadmap to determine the point mutations involved in cardiomyopathy disorder: A Bayesian approach. Gene, 519(1), 34–40. https://doi.org/10.1016/j.gene.2013.01.056
   PubMed Web of Science ®Google Scholar
• Kumar, A., Rajendran, V., Sethumadhavan, R., & Purohit, R. (2013b). Evidence of colorectal cancer-associated mutation in MCAK: A computational report. Cell Biochemistry and Biophysics, 67(3), 837–851. https://doi.org/10.1007/s12013-013-9572-1
   PubMed Web of Science ®Google Scholar
• Kumar, A., Rajendran, V., Sethumadhavan, R., Shukla, P., Tiwari, S., & Purohit, R. (2014). Computational SNP analysis: Current approaches and future prospects. Cell Biochemistry and Biophysics, 68(2), 233–239. https://doi.org/10.1007/s12013-013-9705-6
   PubMed Web of Science ®Google Scholar
• Kumar, B., Faheem, n., Sekhar, K. V. G. C., Ojha, R., Prajapati, V. K., Pai, A., & Murugesan, S. (2022). Pharmacophore based virtual screening, molecular docking, molecular dynamics and MM-GBSA approach for identification of prospective SARS-CoV-2 inhibitor from natural product databases. Journal of Biomolecular Structure & Dynamics, 40(3), 1363–1386. https://doi.org/10.1080/07391102.2020.1824814
   PubMed Web of Science ®Google Scholar
• Kumar, R., Gupta, K., Saharia, K., Pradhan, D., & Subramaniam, J. R. (2013). Withania somnifera root extract extends lifespan of Caenorhabditis elegans. Annals of Neurosciences, 20(1), 13–16. https://doi.org/10.5214/ans.0972.7531.200106
   PubMedGoogle Scholar
• Lee, S. R., Lee, B. S., Yu, J. S., Kang, H., Yoo, M. J., Yi, S. A., Han, J.-W., Kim, S., Kim, J. K., Kim, J.-C., & Kim, K. H. (2022). Identification of anti-adipogenic withanolides from the roots of Indian ginseng (Withania somnifera). Journal of Ginseng Research, 46(3), 357–366. https://doi.org/10.1016/j.jgr.2021.09.004
   PubMed Web of Science ®Google Scholar
• Liu, X., Chen, L., Liang, T., Tian, X.-D., Liu, Y., & Zhang, T. (2017). Withaferin A induces mitochondrial-dependent apoptosis in non-small cell lung cancer cells via generation of reactive oxygen species. Journal of B.U.ON.: Official Journal of the Balkan Union of Oncology, 22(1), 244–250.
   PubMed Web of Science ®Google Scholar
• Madhu, S., Komala, M., & Pandian, P. (2021). formulation development and characterization of withaferin-A loaded polymeric nanoparticles for Alzheimer’s disease. BioNanoScience, 11(2), 559–566. https://doi.org/10.1007/s12668-020-00819-w
   Web of Science ®Google Scholar
• Meena, A. K., Rekha, P., Perumal, A., Gokul, M., Swathi, K. N., & Ilavarasan, R. (2021). Estimation of withaferin-A by HPLC and standardization of the Ashwagandhadi lehyam formulation. Heliyon, 7(2), e06116. https://doi.org/10.1016/j.heliyon.2021.e06116
   PubMed Web of Science ®Google Scholar
• Mehta, V., Chander, H., & Munshi, A. (2021). Mechanisms of anti-tumor activity of Withania somnifera (Ashwagandha). Nutrition and Cancer, 73(6), 914–926. https://doi.org/10.1080/01635581.2020.1778746
   PubMed Web of Science ®Google Scholar
• Moujir, L. M., Llanos, G. G., Araujo, L., Amesty, A., Bazzocchi, I. L., & Jiménez, I. A. (2020). Withanolide-type steroids from Withania aristata as potential anti-leukemic agents. Molecules (Basel, Switzerland), 25(23), 5744. https://doi.org/10.3390/molecules25235744
   PubMed Web of Science ®Google Scholar
• Pattar, S. V., Adhoni, S. A., Kamanavalli, C. M., & Kumbar, S. S. (2020). In silico molecular docking studies and MM/GBSA analysis of coumarin-carbonodithioate hybrid derivatives divulge the anticancer potential against breast cancer. Beni-Suef University Journal of Basic and Applied Sciences, 9(1), 36. https://doi.org/10.1186/s43088-020-00059-7
   Google Scholar
• Rajasekar, S., Elango, R., & Paranthaman, S. R. (2018). Analysis of Ashwagandha (Withania somnifera) alkaloid by HPLC methods. International Journal of Creative Research Thoughts, 6(1), 1143–1150.
   Google Scholar
• Rana, S., Bhat, W. W., Dhar, N., Pandith, S. A., Razdan, S., Vishwakarma, R., & Lattoo, S. K. (2014). Molecular characterization of two A-type P450s, WsCYP98A and WsCYP76A from Withania somnifera (L.) Dunal: Expression analysis and withanolide accumulation in response to exogenous elicitations. BMC Biotechnology, 14(1), 89. https://doi.org/10.1186/s12896-014-0089-5
   PubMedGoogle Scholar
• Rosenthal, P. J. (2021). Has artemisinin resistance emerged in Africa? The Lancet. Infectious Diseases, 21(8), 1056–1057. https://doi.org/10.1016/S1473-3099(21)00168-7
   PubMed Web of Science ®Google Scholar
• Saleem, S., Muhammad, G., Hussain, M. A., Altaf, M., & Bukhari, S. N. A. (2020). Withania somnifera L.: Insights into the phytochemical profile, therapeutic potential, clinical trials, and future prospective. Iranian Journal of Basic Medical Sciences, 23(12), 1501–1526.
   PubMed Web of Science ®Google Scholar
• Sharma, V., Gupta, A. P., Bhandari, P., Gupta, R. C., & Singh, B. (2007). A validated and densitometric HPTLC method for the quantification of withaferin-A and withanolide-A in different plant parts of two morphotypes of Withania somnifera. Chromatographia, 66(9-10), 801–804. https://doi.org/10.1365/s10337-007-0396-2
   Web of Science ®Google Scholar
• Siddiqui, F. A., Boonhok, R., Cabrera, M., Mbenda, H. G. N., Wang, M., Min, H., Liang, X., Qin, J., Zhu, X., Miao, J., Cao, Y., & Cui, L. (2020). Role of Plasmodium falciparum kelch 13 protein mutations in P. falciparum populations from Northeastern Myanmar in mediating Artemisinin resistance. mBio, 11(1), e01134-19. https://doi.org/10.1128/mBio.01134-19
   Google Scholar
• Sukumar, B. S., T. B, T., & H.K, S. (2020). Phyto physico-chemical profile of Ashwagandha (Withania somnifera Dunal). Journal of Ayurveda and Integrated Medical Sciences (JAIMS), 5(06), 120–129. https://doi.org/10.21760/jaims.5.6.17
   Google Scholar
• Thu, A. M., Phyo, A. P., Landier, J., Parker, D. M., & Nosten, F. H. (2017). Combating multidrug-resistant Plasmodium falciparum malaria. The FEBS Journal, 284(16), 2569–2578. https://doi.org/10.1111/febs.14127
   PubMed Web of Science ®Google Scholar
• Tilley, L., Straimer, J., Gnädig, N. F., Ralph, S. A., & Fidock, D. A. (2016). Artemisinin action and resistance in Plasmodium falciparum. Trends in Parasitology, 32(9), 682–696. https://doi.org/10.1016/j.pt.2016.05.010
   PubMed Web of Science ®Google Scholar
• van der Pluijm, R. W., Tripura, R., Hoglund, R. M., Pyae Phyo, A., Lek, D., ul Islam, A., Anvikar, A. R., Satpathi, P., Satpathi, S., Behera, P. K., Tripura, A., Baidya, S., Onyamboko, M., Chau, N. H., Sovann, Y., Suon, S., Sreng, S., Mao, S., Oun, S., … Dondorp, A. M. (2020). Triple artemisinin-based combination therapies versus artemisinin-based combination therapies for uncomplicated Plasmodium falciparum malaria: A multicentre, open-label, randomised clinical trial. The Lancet, 395(10233), 1345–1360. https://doi.org/10.1016/S0140-6736(20)30552-3
   PubMed Web of Science ®Google Scholar
• Vinod, S., & Senthil, K. (2021). Withaferin A – A natural multifaceted therapeutic compound. Current Botany, 8(12), 36–52. https://doi.org/10.25081/cb.2021.v12.6867
   Google Scholar
• Wang, F., Zhao, J., Bai, J., Gao, K., Cui, D., Chen, Y., Song, Y., Jia, Y., & Wen, A. (2019). Liquid chromatography-tandem mass spectrometry to assess the pharmacokinetics and tissue distribution of withaferin A in rats. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 1122–1123, 90–95. https://doi.org/10.1016/j.jchromb.2019.05.016
   PubMed Web of Science ®Google Scholar
• Wei, C., Zhao, C.-X., Liu, S., Zhao, J.-H., Ye, Z., Wang, H., Yu, S.-S., & Zhang, C.-J. (2019). Activity-based protein profiling reveals that secondary-carbon-centered radicals of synthetic 1,2,4-trioxolanes are predominately responsible for modification of protein targets in malaria parasites. Chemical Communications (Cambridge, England), 55(64), 9535–9538. https://doi.org/10.1039/c9cc03719e
   PubMed Web of Science ®Google Scholar
• Widodo, N., Priyandoko, D., Shah, N., Wadhwa, R., & Kaul, S. C. (2010). Selective killing of cancer cells by Ashwagandha leaf extract and its component Withanone involves ROS signaling. PloS One, 5(10), e13536. https://doi.org/10.1371/journal.pone.0013536
   PubMed Web of Science ®Google Scholar