Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide

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15. Rodney A. Fernandes, Gulenur Nesha Khatun, Sanjita Moharana. Traversing the chiral pool potential of carvone in total synthesis of natural products. Tetrahedron 2024, 162 , 134104. https://doi.org/10.1016/j.tet.2024.134104
16. Asep Bayu, Siti Irma Rahmawati, Firmansyah Karim, Jonathan Ardhianto Panggabean, Dasilva Primarindu Nuswantari, Dwi Wahyu Indriani, Peni Ahmadi, Rendi Witular, Ni Luh Putu Indi Dharmayanti, Masteria Yunovilsa Putra. An In Vitro Examination of Whether Kratom Extracts Enhance the Cytotoxicity of Low-Dose Doxorubicin against A549 Human Lung Cancer Cells. Molecules 2024, 29 (6) , 1404. https://doi.org/10.3390/molecules29061404
17. James E. Barrett, Aryan Shekarabi, Saadet Inan, . Oxycodone: A Current Perspective on Its Pharmacology, Abuse, and Pharmacotherapeutic Developments. Pharmacological Reviews 2023, 75 (6) , 1062-1118. https://doi.org/10.1124/pharmrev.121.000506
18. Nokomis Ramos-Gonzalez, Barnali Paul, Susruta Majumdar. IUPHAR themed review: Opioid efficacy, bias, and selectivity. Pharmacological Research 2023, 197 , 106961. https://doi.org/10.1016/j.phrs.2023.106961
19. Rita Turnaturi, Silvia Piana, Salvatore Spoto, Giuliana Costanzo, Lorena Reina, Lorella Pasquinucci, Carmela Parenti. From Plant to Chemistry: Sources of Active Opioid Antinociceptive Principles for Medicinal Chemistry and Drug Design. Molecules 2023, 28 (20) , 7089. https://doi.org/10.3390/molecules28207089
20. Péter Angyal, Kristóf Hegedüs, Bence Balázs Mészáros, János Daru, Ádám Dudás, Anna Rita Galambos, Nariman Essmat, Mahmoud Al‐Khrasani, Szilárd Varga, Tibor Soós. Total Synthesis and Structural Plasticity of Kratom Pseudoindoxyl Metabolites**. Angewandte Chemie 2023, 135 (35) https://doi.org/10.1002/ange.202303700
21. Péter Angyal, Kristóf Hegedüs, Bence Balázs Mészáros, János Daru, Ádám Dudás, Anna Rita Galambos, Nariman Essmat, Mahmoud Al‐Khrasani, Szilárd Varga, Tibor Soós. Total Synthesis and Structural Plasticity of Kratom Pseudoindoxyl Metabolites**. Angewandte Chemie International Edition 2023, 62 (35) https://doi.org/10.1002/anie.202303700
22. Usunomena Usunobun, Augustine Okpiabhele. Telfairia occidentalis Hook f. mitigates Carbon Tetrachloride induced Nephrotoxicity in Rat. Journal of Research in Applied and Basic Medical Sciences 2023, 9 (3) , 130-137. https://doi.org/10.61186/rabms.9.3.130
23. Marjan Talebi, Mona Khoramjouy, Afsoon Feizi, Zulfıqar Ali, Ikhlas A. Khan, Neda Alsadat Ayatollahi, Seyed Abdulmajid Ayatollahi, Mehrdad Faizi. Novel multi-target therapeutic potential of the genus Inula: Advances and opportunities for neuroprotection. Pharmacological Research - Modern Chinese Medicine 2023, 7 , 100263. https://doi.org/10.1016/j.prmcm.2023.100263
24. Caroline V.L. Moreira, Ana Luiza G. Faria, Daiany P.B. Silva, Paulo César Ghedini, José Luis Rodrigues Martins, Adam W. Keasling, Jordan K. Zjawiony, Pankaj Pandey, Robert J. Doerksen, Hamilton B. Napolitano, Fábio F. da Rocha, Elson A. Costa, James O. Fajemiroye. Heteroaromatic salvinorin A analogue (P-3 l) elicits antinociceptive and anxiolytic-like effects. Fitoterapia 2023, 167 , 105488. https://doi.org/10.1016/j.fitote.2023.105488
25. Hongling Wang, Qiangqiang Zhang, Shuai Xiao, Guanjie Wang, Xuan Huang, Xingkuan Chen, Junmin Zhang. Enantioselective construction of dihydropyranone-fused indoles by [3 + 3] annulation of in situ -derived indolin-3-ones and unsaturated carboxylic esters. Organic Chemistry Frontiers 2023, 10 (11) , 2740-2745. https://doi.org/10.1039/D3QO00377A
26. Balazs R. Varga, John M. Streicher, Susruta Majumdar. Strategies towards safer opioid analgesics—A review of old and upcoming targets. British Journal of Pharmacology 2023, 180 (7) , 975-993. https://doi.org/10.1111/bph.15760
27. Kiranjot Kaur, Lovedeep Singh, Anudeep Kaur, Rajbir Bhatti. Exploring the possible mechanism involved in the anti-nociceptive effect of β-sitosterol: modulation of oxidative stress, nitric oxide and IL-6. Inflammopharmacology 2023, 31 (1) , 517-527. https://doi.org/10.1007/s10787-022-01122-8
28. Barnali Paul, Sashrik Sribhashyam, Susruta Majumdar. Opioid signaling and design of analgesics. 2023, 153-176. https://doi.org/10.1016/bs.pmbts.2022.06.017
29. Akhilesh, Anurag T. K Baidya, Ankit Uniyal, Bhanuranjan Das, Rajnish Kumar, Vinod Tiwari. Structure-based virtual screening and molecular dynamics simulation for the identification of sphingosine kinase-2 inhibitors as potential analgesics. Journal of Biomolecular Structure and Dynamics 2022, 40 (23) , 12472-12490. https://doi.org/10.1080/07391102.2021.1971559
30. . Alkaloids I. 2022, 264-315. https://doi.org/10.1039/BK9781839165641-00264
31. Hafiza Yusra Nazeer, Muhammad Omer Iqbal, Asma Mumtaz, Muhammad Masood Ahmed, Romana Riaz, Muhammad Fawad Rasool. In vivo antioxidants, chemical characterization and biochemical and medicinal potential of Murraya koenigii in cisplatin-induced nephrotoxicity. Drug Development and Industrial Pharmacy 2022, 48 (10) , 566-574. https://doi.org/10.1080/03639045.2022.2140352
32. Marc Halang, Martin E. Maier. Formal Total Synthesis of Salvinorin A. ChemistryOpen 2022, 11 (10) https://doi.org/10.1002/open.202200015
33. Jun-Sheng Zhang, De-Feng Xu, Yin-Yin Wang, Ren-Fen Ma, Hua Zhang. Clerodane furanoditerpenoids from the stems of Tinospora sinensis. Archives of Pharmacal Research 2022, 45 (5) , 328-339. https://doi.org/10.1007/s12272-022-01383-5
34. Kai Yue, Jonathan L. Katz, Xiji Shu. Physiological dependence to mitragynine indicated by a rapid cross-dependence procedure with heroin-dependent mice. Psychopharmacology 2022, 239 (3) , 897-908. https://doi.org/10.1007/s00213-022-06080-1
35. Thiruventhan Karunakaran, Kok Zhuo Ngew, Ahmad Alif Danial Zailan, Vivien Yi Mian Jong, Mohamad Hafizi Abu Bakar. The Chemical and Pharmacological Properties of Mitragynine and Its Diastereomers: An Insight Review. Frontiers in Pharmacology 2022, 13 https://doi.org/10.3389/fphar.2022.805986
36. Muhammad Omer Iqbal, Muhammad Masood Ahmed, Shafia Arshad, Usman Javaid, Imran Ahmad Khan, Majid Manzoor, Shumaila Andleeb, Romana Riaz, Shaukat Hussain Munawar, Zahid Manzoor, Asma Mumtaz. Nephroprotective Effects of Alhagi camelorum against Cisplatin-Induced Nephrotoxicity in Albino Wistar Rats. Molecules 2022, 27 (3) , 941. https://doi.org/10.3390/molecules27030941
37. Srijita Bhowmik, Juraj Galeta, Václav Havel, Melissa Nelson, Abdelfattah Faouzi, Benjamin Bechand, Mike Ansonoff, Tomas Fiala, Amanda Hunkele, Andrew C. Kruegel, John. E. Pintar, Susruta Majumdar, Jonathan A. Javitch, Dalibor Sames. Site selective C–H functionalization of Mitragyna alkaloids reveals a molecular switch for tuning opioid receptor signaling efficacy. Nature Communications 2021, 12 (1) https://doi.org/10.1038/s41467-021-23736-2
38. Anna M. Gutridge, Soumen Chakraborty, Balazs R. Varga, Elizabeth S. Rhoda, Alexander R. French, Arryn T. Blaine, Quinten H. Royer, Haoyue Cui, Jinling Yuan, Robert J. Cassell, Márk Szabó, Susruta Majumdar, Richard M. van Rijn. Evaluation of Kratom Opioid Derivatives as Potential Treatment Option for Alcohol Use Disorder. Frontiers in Pharmacology 2021, 12 https://doi.org/10.3389/fphar.2021.764885
39. Lisa L. Wilson, Soumen Chakraborty, Shainnel O. Eans, Thomas J. Cirino, Heather M. Stacy, Chloe A. Simons, Rajendra Uprety, Susruta Majumdar, Jay P. McLaughlin. Kratom Alkaloids, Natural and Semi-Synthetic, Show Less Physical Dependence and Ameliorate Opioid Withdrawal. Cellular and Molecular Neurobiology 2021, 41 (5) , 1131-1143. https://doi.org/10.1007/s10571-020-01034-7
40. Rajendra Uprety, Tao Che, Saheem A Zaidi, Steven G Grinnell, Balázs R Varga, Abdelfattah Faouzi, Samuel T Slocum, Abdullah Allaoa, András Varadi, Melissa Nelson, Sarah M Bernhard, Elizaveta Kulko, Valerie Le Rouzic, Shainnel O Eans, Chloe A Simons, Amanda Hunkele, Joan Subrath, Ying Xian Pan, Jonathan A Javitch, Jay P McLaughlin, Bryan L Roth, Gavril W Pasternak, Vsevolod Katritch, Susruta Majumdar. Controlling opioid receptor functional selectivity by targeting distinct subpockets of the orthosteric site. eLife 2021, 10 https://doi.org/10.7554/eLife.56519