Startseite Lebenswissenschaften Two new natural products from Portulaca oleracea L. and their bioactivities
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Two new natural products from Portulaca oleracea L. and their bioactivities

  • Mingyang Song , Zheming Ying , Xixiang Ying EMAIL logo , Lianqun Jia und Guanlin Yang EMAIL logo
Veröffentlicht/Copyright: 13. Februar 2023

Abstract

Two new natural products, belonging to alkaloids, identified as ((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl acetate (1) and (5-hydroxypyridin-2-yl)methyl acetate (2), were isolated from Portulaca oleracea L. The structures were identified by spectroscopic methods, including 1D, 2D NMR, and UHPLC-ESI-QTOF/MS methods. Meanwhile, the anti-inflammatory and anticholinesterase bioactivities were found in these two compounds.


Corresponding authors: Xixiang Ying, School of Pharmacy, Liaoning University of Traditional Chinese Medicine, No. 77, Shengming 1 Road, DD Port, Dalian 116600, PR China, E-mail: ; and Guanlin Yang, School of The First Clinic and Key Laboratory of Ministry of Education for TCM Viscera-State Theory and Applications, Liaoning University of Traditional Chinese Medicine, No. 79, Chongshan Eastern Road, Shenyang, Liaoning 110847, PR China, E-mail:
Mingyang Song and Zheming Ying contributed equally to this work.

Award Identifier / Grant number: 82073990

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the National Natural Science Foundation of China (Grant 82073990).

  3. Conflict of interest statement: No potential conflict of interest was reported by the authors.

References

1. Zheng, GY, Mo, FF, Ling, C, Peng, H, Gu, W, Li, M, et al.. Portulaca oleracea L. alleviates liver injury in streptozotocin-induced diabetic mice. Drug Des Dev Ther 2017;12:47–55. https://doi.org/10.2147/dddt.s121084.Suche in Google Scholar PubMed PubMed Central

2. Rahimi, VB, Ajam, F, Rakhshandeh, H, Askari, VR. A pharmacological review on Portulaca oleracea L.: focusing on anti-inflammatory, anti-oxidant, immuno-modulatory and antitumor activities. J Pharmacopuncture 2019;22:7–15. https://doi.org/10.3831/kpi.2019.22.001.Suche in Google Scholar

3. Liu, PS, Wang, LL, Li, HF, Tan, LS, Ying, XX, Ju, BZ. Two new organic acids from Portulaca oleracea L. and their anti-inflammatory and anticholinesterase activities. Nat Prod Res 2021;8:1–9.Suche in Google Scholar

4. Song, MY, Ying, ZM, Ying, XX, Jia, LQ, Yang, GL. Three novel alkaloids from Portulaca oleracea L. and their anti-inflammatory bioactivities. Fitoterapia 2022;156:105087. https://doi.org/10.1016/j.fitote.2021.105087.Suche in Google Scholar PubMed

5. Duan, Y, Ying, ZM, He, F, Ying, XX, Jia, LQ, Yang, GL. A new skeleton flavonoid and a new lignan from Portulaca oleracea L. and their activities. Fitoterapia 2021;153:104993. https://doi.org/10.1016/j.fitote.2021.104993.Suche in Google Scholar PubMed

6. Yang, X, Ying, ZM, Liu, HR, Ying, XX, Yang, GL. A new homoisoflavone from Portulaca oleracea L. and its antioxidant activity. Nat Prod Res 2019;33:3500–6. https://doi.org/10.1080/14786419.2018.1484465.Suche in Google Scholar PubMed

7. Lei, X, Li, JM, Liu, B, Zhang, N, Liu, HY. Separation and identification of four new compounds with antibacterial activity from Portulaca oleracea L. Molecules 2015;20:16375–87. https://doi.org/10.3390/molecules200916375.Suche in Google Scholar PubMed PubMed Central

8. Bai, Y, Zang, XL, Ma, JS, Xu, GY. Anti-Diabetic effect of Portulaca oleracea L. Polysaccharideandits mechanism in diabetic rats. Int J Mol Sci 2016;17:1201. https://doi.org/10.3390/ijms17081201.Suche in Google Scholar PubMed PubMed Central

9. Shen, H, Tang, G, Zeng, G, Yang, YJ, Cai, XW, Li, DL, et al.. Purification and characterization of an antitumor polysaccharide from Portulaca oleracea L. Carbohydr Polym 2013;93:395–400. https://doi.org/10.1016/j.carbpol.2012.11.107.Suche in Google Scholar PubMed

10. Khazdair, MR, Anaeigoudari, A, Kianmehr, M. Anti-asthmatic effects of Portulaca oleracea and its constituents, a review. J Pharmacopuncture 2019;22:122–30. https://doi.org/10.3831/kpi.2019.22.016.Suche in Google Scholar

11. Farkhondeh, T, Samarghandian, S. The therapeutic effects of Portulaca oleracea L. in hepatogastric disorders. Gastroenterol Hepatol 2019;42:127–32. https://doi.org/10.1016/j.gastrohep.2018.07.016.Suche in Google Scholar PubMed

12. Khazdair, MR, Anaeigoudari, A, Kianmehr, M. Anti-asthmatic effects of Portulaca oleracea and its constituents, a review. J Pharmacopuncture 2019;22:122–30. https://doi.org/10.3831/kpi.2019.22.016.Suche in Google Scholar

13. Qiao, JY, Li, HW, Liu, FG, Li, YC, Tian, S, Cao, LH, et al.. Effects of Portulaca oleracea extract on acute alcoholic liver injury of rats. Molecules 2019;24:2887. https://doi.org/10.3390/molecules24162887.Suche in Google Scholar PubMed PubMed Central

14. Zhao, HG, Li, S, Luo, FL, Tan, Q, Li, H, Zhou, WK. Portulaca oleracea L. aids calcipotriol in reversing keratinocyte differentiation and skin barrier dysfunction in psoriasis through inhibition of the nuclear factor κB signaling pathway. Exp Ther Med 2015;9:303–10. https://doi.org/10.3892/etm.2014.2116.Suche in Google Scholar PubMed PubMed Central

15. Rahimi, VB, Rakhshandeh, H, Raucci, F, Buono, B, Shirazinia, R, Samzadeh Kermani, A, et al.. Anti-inflammatory and anti-oxidant activity of Portulaca oleracea extract on LPS-induced rat lung injury. Molecules 2019;24:139. https://doi.org/10.3390/molecules24010139.Suche in Google Scholar PubMed PubMed Central

16. Iranshahy, M, Javadi, B, Iranshahi, M, Jahanbakhsh, SP, Mahyari, S, Hassani, FV, et al.. A review of traditional uses, phytochemistry and pharmacology of Portulaca oleracea L. J Ethnopharmacol 2017;205:158–72. https://doi.org/10.1016/j.jep.2017.05.004.Suche in Google Scholar PubMed

17. Xu, L, Ying, ZM, Wei, WJ, Hao, D, Wang, HB, Zhang, WJ, et al.. A novel alkaloid from Portulaca oleracea L. Nat Prod Res 2017;31:902–8. https://doi.org/10.1080/14786419.2016.1253081.Suche in Google Scholar PubMed

18. Guo, SN, Tao, XJ, Duan, Y, Cui, XY, Zhang, WJ, Ying, XX, et al.. Lat Am J Pharm 2020;39:1575–8.Suche in Google Scholar

19. Yang, X, Zhang, WJ, Ying, XX, Stien, D. New flavonoids from Portulaca oleracea L. and their activities. Fitoterapia 2018;127:257–62. https://doi.org/10.1016/j.fitote.2018.02.032.Suche in Google Scholar PubMed

20. Tian, JY, Ying, ZY, Lan, XJ, Li, YJ, Leng, AJ, Ying, XX. Two new metabolites from Portulaca oleracea and their anti-inflammatory activities. Phytochem Lett 2022;48:114–9. https://doi.org/10.1016/j.phytol.2022.02.007.Suche in Google Scholar

21. Shen, J, Cheng, JZ, Zhu, SG, Zhao, J, Ye, QY, Xu, YY, et al.. Regulating effect of baicalin on IKK/IKB/NF-kB signaling pathway and apoptosis-related proteins in rats with ulcerative colitis. Int Immunopharm 2019;73:193–200. https://doi.org/10.1016/j.intimp.2019.04.052.Suche in Google Scholar PubMed

22. Lopez-Rodriguez, AB, Hennessy, E, Murray, CL, Nazmi, A, Delaney, HJ, Healy, D, et al.. Acute systemic inflammation exacerbates neuroinflammation in Alzheimer’s disease: IL-1β drives amplified responses in primed astrocytes and neuronal network dysfunction. Alzheimers Dement 2021;17:1735–55. https://doi.org/10.1002/alz.12341.Suche in Google Scholar PubMed PubMed Central

23. Ng, A, Tam, WW, Zhang, MW, Ho, CS, Husain, SF, McIntyre, RS, et al.. IL-1β, IL-6, TNF-α and CRP in elderly patients with depression or Alzheimer’s disease: systematic review and meta-analysis. Sci Rep 2018;8:12050. https://doi.org/10.1038/s41598-018-30487-6.Suche in Google Scholar PubMed PubMed Central

24. Jang, JH, Son, Y, Kang, SS, Bae, CS, Kim, JC, Kim, SH, et al.. Neuropharmacological potential of gastrodia elata blume and its components. Evid Based Complement Alternat Med 2015;2015:309261. https://doi.org/10.1155/2015/309261.Suche in Google Scholar PubMed PubMed Central

25. Ma, YF, Li, XT, Zhang, WJ, Ying, XX, Stien, D. A trace alkaloid, oleraisoindole A from Portulaca oleracea L. and its anticholinesterase effect. Nat Prod Res 2021;35:350–3. https://doi.org/10.1080/14786419.2019.1627356.Suche in Google Scholar PubMed

26. Cui, XY, Ying, ZM, Ying, XX, Jia, LQ, Yang, GL. Three new alkaloids from Portulaca oleracea L. and their bioactivities. Fitoterapia 2021;154:105020. https://doi.org/10.1016/j.fitote.2021.105020.Suche in Google Scholar PubMed

27. Tatiya-Aphiradee, N, Chatuphonprasert, W, Jarukamjorn, K. Immune response and inflammatory pathway of ulcerative colitis. J Basic Clin Physiol Pharmacol 2018;30:1–10. https://doi.org/10.1515/jbcpp-2018-0036.Suche in Google Scholar PubMed

28. Wang, G, Xu, B, Shi, F, Du, M, Li, Y, Yu, T, et al.. Protective effect of methane-rich saline on acetic acid-induced ulcerative colitis via blocking the TLR4/NF-κB/MAPK pathway and promoting IL-10/JAK1/STAT3-mediated anti-inflammatory response. Oxid Med Cell Longev 2019;2019:7850324. https://doi.org/10.1155/2019/7850324.Suche in Google Scholar PubMed PubMed Central

29. Zhong, ZY, Liang, S, Sanchez-Lopez, E, He, F, Shalapour, S, Lin, XJ, et al.. New mitochondrial DNA synthesis enables NLRP3 inflammasome activation. Nature 2018;560:198–203. https://doi.org/10.1038/s41586-018-0372-z.Suche in Google Scholar PubMed PubMed Central

30. Liu, DM, Yu, X, Sun, HY, Zhang, W, Liu, G, Zhu, L. Flos lonicerae flavonoids attenuate experimental ulcerative colitis in rats via suppression of NF-κB signaling pathway. Naunyn-Schmiedeberg’s Arch Pharmacol 2020;393:2481–94. https://doi.org/10.1007/s00210-020-01814-4.Suche in Google Scholar PubMed

31. Uddin, MS, Al Mamun, A, Kabir, MT, Ashraf, GM, Bin-Jumah, MN, Abdel-Daim, MM. Multi-target drug candidates for multifactorial Alzheimer’s disease: AChE and NMDAR as molecular targets. Mol Neurobiol 2021;58:281–303. https://doi.org/10.1007/s12035-020-02116-9.Suche in Google Scholar PubMed

32. Rees, TM, Brimijoin, S. The role of acetylcholinesterase in the pathogenesis of Alzheimer’s disease. Drugs Today 2003;39:75–83. https://doi.org/10.1358/dot.2003.39.1.740206.Suche in Google Scholar PubMed

33. Liu, XL, Wu, HB, Tao, XJ, Ying, XX, Stien, D. Two amide glycosides from Portulaca oleracea L. and its bioactivities. Nat Prod Res 2021;35:2655–9. https://doi.org/10.1080/14786419.2019.1660333.Suche in Google Scholar PubMed

34. Xu, W, Ying, ZM, Tao, XJ, Ying, XX, Yang, GL. Two new amide alkaloids from Portulaca oleracea L. and their anticholinesterase activities. Nat Prod Res 2021;35:3794–800. https://doi.org/10.1080/14786419.2020.1739040.Suche in Google Scholar PubMed

35. Ellman, GL, Courtney, KD, Andres, VJr, Featherstone, RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95. https://doi.org/10.1016/0006-2952(61)90145-9.Suche in Google Scholar PubMed

36. Topcu, G, Kolak, U, Ozturk, M, Boga, M, Damla Hatipoglu, S, Bahadori, F, et al.. Investigation of anticholinesterase activity of a series of Salvia extracts and the constituents of Salvia staminea. NPJ 2013;3:3–9. https://doi.org/10.2174/2210315511303010003.Suche in Google Scholar


Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znc-2022-0197).


Received: 2022-10-03
Accepted: 2023-01-26
Published Online: 2023-02-13
Published in Print: 2023-05-25

© 2023 Walter de Gruyter GmbH, Berlin/Boston

Heruntergeladen am 30.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/znc-2022-0197/html
Button zum nach oben scrollen