Skip to main content
SpringerLink
Log in

Stilbenoids isolated from the roots of Rheum lhasaense under the guidance of the acetylcholinesterase inhibition activity

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

Four unknown stilbenoids, including one dimer, namely 4′-methoxy-scirpusin A (5) and three monomeric stilbene glycosides, namely piceatannol-3′-O-[2′′-(3,5-dihydroxy-4-methoxybenzoyl)]-β-d-glucopyranoside (13), piceatannol-3′-O-(2′′-galloyl)-β-d-glucopyranoside (14) and piceatannol-3′-O-(6″-p-coumaroyl)-β-d-glucopyranoside (16) together with 15 described compounds, were isolated from the ethyl acetate fraction of the ethanol extract of roots of Rheum lhasaense based on the guidance of the inhibitory effect on acetylcholinesterase. The structures of the unknown compounds were established by combined spectroscopic analysis and comparing their spectral data with compounds with similar structures. Some selected components were also investigated for their inhibitory abilities on acetylcholinesterase (AChE), indicating that compound 13 may be responsible for higher inhibitory activity of the ethyl acetate fraction on AChE.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Bao B, Alisa EG-B (2003) RHEUM Linnaeus. In: Li A, Bao B, Alisa EG, Suk-pyo H, John M, Sergei LM, Hideaki O, Chong-wook P (eds) Flora of China. Science Press, Beijing, pp 277–350

    Google Scholar 

  2. Xiao P, He L, Wang L (1984) Ethnopharmacologic study of Chinese Rhubarb. J Ethnopharmacol 10:275–293. https://doi.org/10.1016/0378-8741(84)90016-3

    Article  Google Scholar 

  3. Wu CY (1983) Flora of Xizang. Science Press, Beijing

    Google Scholar 

  4. He J, Wang L, Guo H et al (2019) The review of chemistry, pharmacology and processing method of Rhubarb (Rheum species). J Food Bioact. https://doi.org/10.31665/JFB.2019.8205

    Article  Google Scholar 

  5. Gong YL, Chen J, Fang F et al (2015) Study of the chemical composition of Rheum lhasaense. Lishizhen Med Mater Med Res 26:601–602

    CAS  Google Scholar 

  6. Liu W-B, Hu L, Hu Q et al (2013) New resveratrol oligomer derivatives from the roots of Rheum lhasaense. Molecules 18:7093–7102. https://doi.org/10.3390/molecules18067093

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Xiao P, Chen B, Wamg L et al (1980) A preliminary study of the correlation between phylogeny, chemical constituents and therapeutic effects of Rheum species. Acta Pharm Sin 15:33–39

    CAS  Google Scholar 

  8. Sawda C, Moussa C, Turner RS (2017) Resveratrol for Alzheimer’s disease: Alzheimer’s disease. Ann N Y Acad Sci 1403:142–149. https://doi.org/10.1111/nyas.13431

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Yan Y, Yang H, Xie Y et al (2020) Research progress on Alzheimer’s disease and resveratrol. Neurochem Res 45:989–1006. https://doi.org/10.1007/s11064-020-03007-0

    Article  CAS  PubMed  Google Scholar 

  10. Liu S, Li Y, Yi F et al (2020) Resveratrol oligomers from Paeonia suffruticosa protect mice against cognitive dysfunction by regulating cholinergic, antioxidant and anti-inflammatory pathways. J Ethnopharmacol 260:112983. https://doi.org/10.1016/j.jep.2020.112983

    Article  CAS  PubMed  Google Scholar 

  11. Ngoc TM, Minh PTH, Hung TM et al (2008) Lipoxygenase inhibitory constituents from rhubarb. Arch Pharm Res 31:598–605. https://doi.org/10.1007/s12272-001-1199-0

    Article  CAS  PubMed  Google Scholar 

  12. Lins AP, Ribeiro MNDS, Gottlieb OR, Gottlieb HE (1982) Gnetins: resveratrol oligomers from gnetum species. J Nat Prod 45:754–761. https://doi.org/10.1021/np50024a022

    Article  CAS  Google Scholar 

  13. Shikishima Y, Takaishi Y, Honda G et al (2001) Phenylbutanoids and stilbene derivatives of Rheum maximowiczii. Phytochemistry 56:377–381. https://doi.org/10.1016/S0031-9422(00)00370-8

    Article  CAS  PubMed  Google Scholar 

  14. Kashiwada Y, Nonaka G, Nishioka I (1984) Studies on rhubarb (Rhei rhizoma). VI. Isolation and characterization of stilbenes. Chem Pharm Bull 32:3501–3517. https://doi.org/10.1248/cpb.32.3501

    Article  CAS  Google Scholar 

  15. Afsar T, Razak S, Shabbir M, Khan MR (2018) Antioxidant activity of polyphenolic compounds isolated from ethyl-acetate fraction of Acacia hydaspica R. Parker. Chem Cent J 12:5. https://doi.org/10.1186/s13065-018-0373-x

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Zhang Y, Yan G, Sun C et al (2018) Apoptosis Effects of Dihydrokaempferol Isolated from Bauhinia championii on Synoviocytes. Evid Based Complement Alternat Med 2018:1–10. https://doi.org/10.1155/2018/9806160

    Article  Google Scholar 

  17. Liu Z, Huang Y, Yang K, Wang Y (2017) Isolation and identification of polyphenols from the leaves of Castanopsis fordii Hance. Nat Prod Res Dev 29:67–73

    Google Scholar 

  18. Tisserant L-P, Hubert J, Lequart M et al (2016) 13 C NMR and LC-MS profiling of stilbenes from elicited grapevine hairy root cultures. J Nat Prod 79:2846–2855. https://doi.org/10.1021/acs.jnatprod.6b00608

    Article  CAS  PubMed  Google Scholar 

  19. Yakubu O, Adebayo A, Dokunmu T et al (2019) Cytotoxic Effects of Compounds Isolated from Ricinodendron heudelotii. Molecules. https://doi.org/10.3390/molecules24010145

    Article  PubMed  PubMed Central  Google Scholar 

  20. Masum MN, Choodej S, Yamauchi K, Mitsunaga T (2019) Isolation of phenylpropanoid sucrose esters from the roots of Persicaria orientalis and their potential as inhibitors of melanogenesis. Med Chem Res 28:623–632. https://doi.org/10.1007/s00044-019-02312-w

    Article  CAS  Google Scholar 

  21. Kong Q, Ren X, Jiang L et al (2010) Scirpusin A, a hydroxystilbene dimer from Xinjiang wine grape, acts as an effective singlet oxygen quencher and DNA damage protector: Scirpusin A, a hydroxystilbene dimer from Xinjiang wine grape. J Sci Food Agric 90:823–828. https://doi.org/10.1002/jsfa.3890

    Article  CAS  PubMed  Google Scholar 

  22. He C-N, Peng Y, Xu L-J et al (2010) Three new oligostilbenes from the seeds of Paeonia suffruticosa. Chem Pharm Bull 58:5

    Google Scholar 

  23. Kurihara H, Kawabata J, Ichikawa S, Mizutani J (1990) -)-ε-Viniferin and related Oligo-stilbenes from Carex pumila Thunb. (Cyperaceae). Agric Biol Chem 54:1097–1099. https://doi.org/10.1271/bbb1961.54.1097

    Article  CAS  Google Scholar 

  24. Lemière G, Gao M, De Groot A et al (1995) 3′,4-Di-O-methylcedrusin: synthesis, resolution and absolute configuration. J Chem Soc Perkin Trans 1:1775–1779. https://doi.org/10.1039/P19950001775

    Article  Google Scholar 

  25. Park S, Kim YN, Kwak HJ et al (2018) Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné. Bioorg Med Chem Lett 28:552–557. https://doi.org/10.1016/j.bmcl.2018.01.063

    Article  CAS  PubMed  Google Scholar 

  26. Ganchimeg D, Batbold B, Murata T et al (2019) Flavonoids isolated from the flowers of Pulsatilla flavescens and their anti-piroplasm activity. J Nat Med 73:633–640. https://doi.org/10.1007/s11418-019-01294-8

    Article  CAS  PubMed  Google Scholar 

  27. Tanaka T, Nakashima T, Ueda T et al (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 55:899–901. https://doi.org/10.1248/cpb.55.899

    Article  CAS  Google Scholar 

  28. Ellman GL, Courtney KD, Andres V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–95. https://doi.org/10.1016/0006-2952(61)90145-9

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This present work was financially supported in part by Major Scientific and Technological Special Project for “The Drug Innovation Major Project” (No. 2018ZX09711001-008), the CAMS Innovation Fund for Medical Sciences (CIFMS) ID: 2016-I2M-1-012.

Author information

Authors and Affiliations

  1. Institute of Medicinal Plant Development (IMPLAD), Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, 100193, China

    Qing Liu, Jie Shen, Pei Li, Yue Li, Chunnian He & Peigen Xiao

  2. Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Beijing, 100193, China

    Qing Liu, Jie Shen, Pei Li, Yue Li, Chunnian He & Peigen Xiao

Authors
  1. Qing Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jie Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yue Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Chunnian He
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Peigen Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chunnian He.

Ethics declarations

Conflict of interest

The authors declare that there is no conflict of interest in the present study.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 6497 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, Q., Shen, J., Li, P. et al. Stilbenoids isolated from the roots of Rheum lhasaense under the guidance of the acetylcholinesterase inhibition activity. J Nat Med 75, 372–380 (2021). https://doi.org/10.1007/s11418-020-01478-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-020-01478-7

Keywords

Search

Navigation