Volatile Secondary Metabolites with Potent Antidiabetic Activity from the Roots of Prangos pabularia Lindl.—Computational and Experimental Investigations
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Abstract
(1) Background: Almost 500 million people worldwide are suffering from diabetes. Since ancient times, humans have used medicinal plants for the treatment of diabetes. Medicinal plants continue to serve as natural sources for the discovery of antidiabetic compounds. Prangos pabularia Lindl. is a widely distributed herb with large reserves in Tajikistan. Its roots and fruits have been used in Tajik traditional medicine. To our best knowledge, there are no previously published reports concerning the antidiabetic activity and the chemical composition of the essential oil obtained from roots of P. pabularia. (2) Methods: The volatile secondary metabolites were obtained by hydrodistillation from the underground parts of P. pabularia growing wild in Tajikistan and were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Protein tyrosine phosphatase 1B (PTP-1B) inhibition assay and molecular docking analysis were carried out to evaluate the potential antidiabetic activity of the P. pabularia essential oil. (3) Results: The main constituents of the volatile oil of P. pabularia were 5-pentylcyclohexa-1,3-diene (44.6%), menthone (12.6%), 1-tridecyne (10.9%), and osthole (6.0%). PTP-1B inhibition assay of the essential oil and osthole resulted in significant inhibitory activity with an IC50 value of 0.06 ± 0.01 and 0.93 ± 0.1 μg/mL. Molecular docking analysis suggests volatile compounds such as osthole inhibit PTP-1B, and the results are also in agreement with experimental investigations. (4) Conclusions: Volatile secondary metabolites and the pure isolated compound (osthole) from the roots of P. pabularia exhibited potent antidiabetic activity, twenty-five and nearly two times more than the positive control (3-(3,5-dibromo-4-hydroxybenzoyl)-2-ethylbenzofuran-6-sulfonic acid-(4-(thiazol-2-ylsulfamyl)-phenyl)-amide)) with an IC50 value of 1.46 ± 0.4 μg/mL, respectively.
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Research context
OpenAlex topics: Protein Tyrosine Phosphatases · Natural product bioactivities and synthesis · Plant chemical constituents analysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China
Research Institution “Chinese-Tajik Innovation Center for Natural Products”, Ayni St. 299/2, Dushanbe 734063, Tajikistan
Center for Research in Innovative Technologies, Academy of Sciences of the Republic of Tajikistan, Ayni St. 299/3, Dushanbe 734063, Tajikistan
Department of Pharmaceutical Technology, Avicenna Tajik State Medical University, Rudaki 139, Dushanbe 734003, Tajikistan
Department of Chemistry, National University of Tajikistan, Rudaki 17/2, Dushanbe 734003, Tajikistan
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA
Funding
Chinese Academy of Sciences President’s International Fellowship Initiative · Central Asian Drug Discovery & Development Center of Chinese Academy of Sciences · Foreign young scholar · CAS “Light of West China” Program
References (62)
Show source-provided references
1. WHO (2014). About Diabetes, World Health Organization.
2. International Diabetes Federation (2017). IDF Diabetes Atlas, International Diabetes Federation.
3. Aromatic medicinal plants from Tajikistan (Central Asia)10.3390/medicines2010028 ↗
4. Egamberdieva, D., and Öztürk, M. (2018). Medicinal plants of Tajikistan. Vegetation of Central Asia and Environs, Springer.10.1007/978-3-319-99728-5 ↗
5. Sharopov, F. (2015). Phytochemistry and Bioactivities of Selected Plant Species with Volatile Secondary Metabolites. [Ph.D. Thesis, University of Heidelberg].
6. In vitro anti-diabetic effect and chemical component analysis of 29 essential oils products10.1016/j.jfda.2014.02.004 ↗
7. Polymorphisms within the protein tyrosine phosphatase 1B (PTPN1) gene promoter: Functional characterization and association with type 2 diabetes and related metabolic traits10.1373/clinchem.2007.088146 ↗
8. Numonov, S., Edirs, S., Bobakulov, K., Qureshi, M.N., Bozorov, K., Sharopov, F., Setzer, W.N., Zhao, H., Habasi, M., and Sharofova, M. (2017). Evaluation of the antidiabetic activity and chemical composition of Geranium collinum root extracts—Computational and experimental investigations. Molecules, 22.10.3390/molecules22060983 ↗
9. Combinatorial control of the specificity of protein tyrosine phosphatases10.1016/S0955-0674(00)00196-4 ↗
10. Protein-tyrosine phosphatase 1B substrates and metabolic regulation10.1016/j.semcdb.2014.09.020 ↗
11. A review on protein tyrosine phosphatases—an important target for various diseases10.22159/ajpcr.2018.v11i7.25615 ↗
12. Association testing of the protein tyrosine phosphatase 1B gene (PTPN1) with type 2 diabetes in 7,883 people10.2337/diabetes.54.6.1884 ↗
13. Protein tyrosine phosphatase 1B inhibitors as antidiabetic agents—A brief review10.1016/j.bioorg.2016.12.004 ↗
14. Physiological and biochemical characteristics leaf different layers of vegetative and generative shoots Prangos pabularia (Prangos pabularia Lindl.)
15. Medicinal plant of Tajikistan
16. Chemical composition and some allelopathic aspects of essential oils of (Prangos ferulacea L.) Lindl at different stages of growth
17. Comparative evaluation of cytotoxic and apoptogenic effects of several coumarins on human cancer cell lines: Osthole induces apoptosis in p53-deficient H1299 cells
18. An in vitro ethnopharmacological study on Prangos ferulacea: A wound healing agent10.15171/bi.2017.10 ↗
19. A new bisabolene derivative from the essential oil of Prangos uechtritzii fruits10.1055/s-2000-8627 ↗
20. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils10.1515/chem-2018-0051 ↗
21. Tabanca, N., Wedge, D.E., Li, X.C., Gao, Z., Ozek, T., Bernier, U.R., Epsky, N.D., Baser, K.H., and Ozek, G. (2018). Biological evaluation, overpressured layer chromatography separation, and isolation of a new acetylenic derivative compound from Prangos platychlaena ssp. platychlaena fruit essential oils. J. Planar Chromatogr.—Mod. TLC, 31.
22. New coumarin from the roots of Prangos pabularia10.1080/14786419.2017.1413558 ↗
23. Comparison of hydrodistillation and microdistillation methods for the analysis of fruit volatiles of Prangos pabularia Lindl., and evaluation of its antimicrobial activity10.1016/j.sajb.2007.05.002 ↗
24. The identification of suberosin from Prangos pabularia essential oil and its mosquito activity against Aedes aegypti
25. Chemical and allelopathic analyses of essential oils of Prangos pabularia Lindl. from Iran
26. Adams, R. (2007). Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, Allured Publishing Corp. [4th ed.].
27. The bioactive and volatile constituents of Prangos acaulis (DC) Bornm extracted using hydrodistillation and nanoscale injection techniques
28. Chemical composition of the essential oil of Prangos asperula Boiss. subsp. haussknechtii (Boiss.) Herrnst. et Heyn fruits
29. Chemical composition and antimicrobial activity of essential oils isolated from aerial parts of Prangos asperula Boiss. (Apiaceae) growing wild in Lebanon
30. Isolation and identification of osthol from the fruits and essential oil composition of the leaves of Prangos asperula Boiss
31. A review on major constituents of various essential oils and its application
32. Composition of the essential oil of Prangos ferulacea (L.) Lindl10.1080/10412905.1996.9700617 ↗
33. Chemical constituents and antibacterial activity of essential oil of Prangos ferulacea (L.) Lindl. fruits
34. Isolation of phenolic derivatives and essential oil analysis of Prangos ferulacea (L.) Lindl. aerial parts
35. Insecticidal activity of essential oil of Prangos ferulacea (Umbelliferae) against Ephestia kuehniella (Lepidoptera: Pyralidae) and Trichogramma embryophagum (Hymenoptera: Trichogrammatidae)10.3906/tar-1211-15 ↗
36. The influence of plant growth satge, individuals of species, and extraction methods on the essential oil content and the chemical composition of Prangos ferulacea (L.) Lindl10.15666/aeer/1504_17651776 ↗
37. Chemical composition and antibacterial activity of essential oil of Prangos ferulacea (L.) Lindl
38. Chemical composition and antimicrobial activity of essential oil of Prangos ferulaceae (L.) Lindl from Iran10.1080/14786410802379539 ↗
39. Composition of the essential oil of Prangos heyniae H. Duman et M. F. Watson, a new endemic from Turkey10.1002/(SICI)1099-1026(200001/02)15:1<47::AID-FFJ869>3.0.CO;2-9 ↗
40. Essential oil composition of two Prangos Lindl. (Apiaceae) species from Turkey
41. Fast determination of Prangos uloptera essential oil by nanoporous silica-polypyrrole SPME fiber
42. Chemical composition of the oil of Prangos uloptera DC10.1080/10412905.2001.9699620 ↗
43. Variations of essential oils in fresh and dried aerial parts of Prangos uloptera
44. Essential oil composition of the fruit of Prangos uloptera (Apiaceae) DC. from Turkey
45. Constituents, biological activities and quality control parameters of the crude extract and essential oil from Arracacia tolucensis var. multifida10.1016/j.jep.2007.05.015 ↗
46. A strategy based on gas chromatography-mass spectrometry and virtual molecular docking for analysis and prediction of bioactive composition in natural product essential oil10.1016/j.chroma.2017.04.031 ↗
47. Chemical constituents of Blumea balsamifera of Indonesia and their protein tyrosine phosphatase 1B inhibitory activity
48. New triterpenoids with protein tyrosine phosphatase 1B inhibition from Cedrela odorata10.1080/10286020.2014.919281 ↗
49. Essential oil of Cymbopogon citratus against diabetes: Validation by in vivo experiments and computational studies
50. Osthole: A review on its bioactivities, pharmacological properties, and potential as alternative medicine10.1155/2015/919616 ↗
51. Osthole, a potential antidiabetic agent, alleviates hyperglycemia in db/db mice10.1016/j.cbi.2009.08.003 ↗
52. Osthole enhances glucose uptake through activation of AMP-activated protein kinase in skeletal muscle cells10.1021/jf2036559 ↗
53. Coumarins improved type 2 diabetes induced by high-fat diet and streptozotocin in mice via antioxidation10.1139/cjpp-2017-0612 ↗
54. MolDock: A New Technique for High-Accuracy Molecular Docking10.1021/jm051197e ↗
55. Structural basis for inhibition of protein-tyrosine phosphatase 1B by isothiazolidinone heterocyclic phosphonate mimetics10.1074/jbc.M606873200 ↗
56. Allosteric inhibition of protein tyrosine phosphatase 1B10.1038/nsmb803 ↗
57. Structure-based design of protein tyrosine phosphatase-1B inhibitors10.1016/j.bmcl.2005.03.068 ↗
58. 1,2,3,4-Tetrahydroisoquinolinyl sulfamic acids as phosphatase PTP1B inhibitors10.1016/j.bmcl.2005.12.051 ↗
59. Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: Capturing interactions with Asp4810.1016/j.bmcl.2006.06.051 ↗
60. Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor10.1016/j.bmcl.2008.04.064 ↗
61. In-silico screening for anti-Zika virus phytochemicals10.1016/j.jmgm.2016.08.011 ↗
62. Setzer, M.S., Byler, K.G., Ogungbe, I.V., and Setzer, W.N. (2017). Natural products as new treatment options for trichomoniasis: A molecular docking investigation. Sci. Pharm., 85.