Skip to main content
Log in

Triterpenoids from the Fruits of Wild Species of Crataegus scabrifolia and Their Lipid-Lowering Activities

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

To investigate the chemical constituents of fruits of wild species of Crataegus scabrifolia and their lipid-lowering activities. The compounds were isolated and purified by various column chromatography, and their structures were identified based on the comprehensive analyses of the physicochemical properties and spectroscopic data. The lipid-lowering activities of isolated compounds were evaluated by a cellular model of HepG2 in vitro. Ten triterpenoids were obtained from the 95% ethanol extract of the fruits of wild species of C. scabrifolia and identified as α-amyrin (I), ursolic acid (II), pomolic acid (III), tormentic acid (IV), euscaphic acid (V), 2α,19α-dihydroxy-3-oxo-urs-12-en-28-oic acid (VI), fupenzic acid (VII), oleanolic acid (VIII), β-amyrin (IX), and 3-epifriedelinol (X). Compounds (I), (IX), and (X) were isolated from the genus Crataegus for the first time, and compounds (IIIVIII) were isolated from the C. scabrifolia for the first time. Compounds (VVII) showed significant lipid-lowering activities in vitro with lipid-lowering rates of 8.9 ± 4.3%, 12.0 ± 4.6%, and 6.5 ± 5.5% at a concentration of 200 μmol/L. Molecular docking results suggested that the ACC may be a target of lipid-lowering activity for Crataegus triterpenoids.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. Chinese Pharmacopeia Commission, Chinese Pharmacopoeia, vol. 1, Beijing: China Medical Science Press, 2020.

    Google Scholar 

  2. Dong, J., Chen, J., Gong, S., Xu, J., Xu, X., and Zhang, T., Chin. Tradit. Herb. Drugs, 2021, vol. 52, pp. 2801–2818.

    Google Scholar 

  3. Wu, J., Peng, W., Qin, R., and Zhou, H., Molecules, 2014, vol. 19, pp. 1685–1712. https://doi.org/10.3390/molecules19021685

    Article  CAS  Google Scholar 

  4. Kumar, D., Arya, V., Bhat, Z.A., Khan, N.A., and Prasad, D.N., Rev. Bras. Farmacogn., 2012, vol. 22, pp. 1187–1200. https://doi.org/10.1590/S0102-695X2012005000094

    Article  CAS  Google Scholar 

  5. Vera-Sánchez, K.S., Parra-Quijano, M., Nieto-Ángel, R., and Barrientos-Priego, A.F., Plants, 2021, vol. 10, p. 2561. https://doi.org/10.3390/plants10122561

    Article  Google Scholar 

  6. Kunming Institute of Botany and Chinese Academy of Sciences, Flora Yunnanica, vol. 12, Beijing: Science Press, 2006.

    Google Scholar 

  7. Zhu, Q.-J., Lang, L.-J., Jiang, B., Shen, Y., Wang, Y., and Xiao, C.-J., J. Dali Univ., 2021, vol. 6, pp. 7–9.

    Google Scholar 

  8. Si, J.-Y., Chen, D.-H., and Gau, G.-Y., China J. Chin. Mater. Med., 1998, vol. 23, pp. 422–423.

    CAS  Google Scholar 

  9. Si, J.-Y., Gau, G.-Y., and Chen, D.-H., Nat. Prod. Res. Dev., 1994, vol. 6, pp. 49–51.

    CAS  Google Scholar 

  10. Kardar, M.N., Zhang, T., Coxon, G.D., Watson, D.G., Fearnley, J., and Seidel, V., Phytochemistry, 2014, vol. 106, pp. 156–163. https://doi.org/10.1016/j.phytochem.2014.07.016

    Article  CAS  Google Scholar 

  11. Lee, Y.-G., Kang, K.W., Hong, W., Kim, Y.H., Oh, J.T., Park, D.W., Ko, M., Bai, Y.-F., Seo, Y.-J., Lee, S.-M., Kim, H., and Kang, S.C., Bioorg. Med. Chem., 2021, vol. 45, p. 116329. https://doi.org/10.1016/j.bmc.2021.116329

    Article  CAS  Google Scholar 

  12. Isobe, T., Noda, Y., Ohsaki, A., Sakanaka, S., Kim, M., and Taniguchi, M., Yakugaku Zasshi, 1989, vol. 109, pp. 175–178. https://doi.org/10.1248/yakushi1947.109.3_175

    Article  CAS  Google Scholar 

  13. Gai, C., Kong, D., and Wang, S., Chin. J. Pharm., 2010, vol. 41, pp. 580–582.

    Google Scholar 

  14. Xu, H.-X., Zeng, F.-Q., Wan, M., and Sim, K.-Y., J. Nat. Prod., 1996, vol. 59, pp. 643–645. https://doi.org/10.1021/np960165e

    Article  CAS  Google Scholar 

  15. Hattori, M., Kuo, K.-P., Shu, Y.-Z., Tezuka, Y., Kikuchi, T., and Namba, T., Phytochemistry, 1988, vol. 27, pp. 3975–3976. https://doi.org/10.1016/0031-9422(88)83061-9

    Article  CAS  Google Scholar 

  16. Acebey-Castellon, I.L., Voutquenne-Nazabadioko, L., Doan Thi Mai, H., Roseau, N., Bouthagane, N., Muhammad, D., Le Magrex Debar, E., Gangloff, S.C., Litaudon, M., Sevenet, T., Hung, N.V., and Lavaud, C., J. Nat. Prod., 2011, vol. 74, pp. 163–168. https://doi.org/10.1021/np100502y

    Article  CAS  Google Scholar 

  17. Yu, B.-L., Liu, S.-B., Huang, N.-L., Yang, L., Yang, M.-C., Fan, H.-F., and Dai, H.-F., Chin. J. Exp. Tradit. Med. Form., 2017, vol. 23, pp. 96–100.

    Google Scholar 

  18. Shen, Y., Chen, H., Lang, L.-J., Dong, X., Xiao, C.-J., and Jiang, B., Phytochem. Lett., 2021, vol. 46, pp. 172–175. https://doi.org/10.1016/j.phytol.2021.10.017

    Article  CAS  Google Scholar 

  19. Pu, S., Liu, Y., Liang, S., Liu, P., Qian, H., Wu, Q., and Wang, Y., Molecules, 2020, vol. 25, pp. 1392. https://doi.org/10.3390/molecules25061392

    Article  CAS  Google Scholar 

  20. Luo, H.-Q., Shen, J., Chen, C.-P., Ma, X., Lin, C., Ouyang, Q., Xuan, C.-X., Liu, J., Sun, H.-B., and Liu, J., Chin. J. Nat. Med., 2018, vol. 16, pp 339–346. https://doi.org/10.1016/S1875-5364(18)30065-7

    Article  CAS  Google Scholar 

  21. Nogueira, A.O., Oliveira, Y.I.S., Adjafre, B.L., De Moraes, M.E.A., and Aragão, G.F., Fund. Clin. Pharmacol., 2019, vol. 33, pp. 4–12. https://doi.org/10.1111/fcp.12402

    Article  CAS  Google Scholar 

  22. Lang, L.-J., Wang, M., Lei, C., Shen, Y., Zhu, Q.-J., Diao, H.-M., Chen, H., Shen, L., Dong, X., Jiang, B., and Xiao, C.-J., Planta Med., 2022. https://doi.org/10.1055/a-1716-0958

Download references

Funding

The work was financially supported by the Special Basic Cooperative Research Programs of Yunnan Provincial Undergraduate Universities’ Association (grant no. 2019FH001-050), the Yunnan Key Laboratory of Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan (grant no. 202105AG070003), the Yunnan Fundamental Research Projects (grant no. 202201AT070005), and the Scientific Research Initiation Fund of Dali University for Doctor (grant no. KYBS201734).

Author information

Authors and Affiliations

Authors

Contributions

Chao-Jiang Xiao and Bei Jiang conceptualized the work. Material preparation, extraction and isolation were performed by Qi-Jie Zhu, Ying Wang, and De-Quan Zhang. Biological activity assay was performed by Li-Juan Lang. Molecular docking and the draft of the manuscript were done by Chao-Jiang Xiao.

Corresponding authors

Correspondence to Bei Jiang or Chao-Jiang Xiao.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain any studies involving animals or human participants performed by any of the authors.

Conflict of Interests

The authors declare that they have no conflicts of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Qi-Jie Zhu, Lang, LJ., Wang, Y. et al. Triterpenoids from the Fruits of Wild Species of Crataegus scabrifolia and Their Lipid-Lowering Activities. Russ J Bioorg Chem 48, 1291–1298 (2022). https://doi.org/10.1134/S1068162022060292

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162022060292

Keywords:

Navigation