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Licensed Unlicensed Requires Authentication Published by De Gruyter May 18, 2021

Flavonolignan 2, 3-dehydroderivatives from Oenanthe javanica and their anti inflammatory activities

Rong-Rui Wei ORCID logo and Qin-Ge Ma ORCID logo


Flavonolignans, for example, silymarin and silybin, have interesting biological activities. For the first time, three new flavonolignans named oenanthenoid A-C (13) and nine known flavonolignan derivatives (412) were isolated from Oenanthe javanica. Comprehensive spectroscopic data analysis and references were used to identify all of the compounds. The anti inflammatory activities of these isolates (112) on RAW264.7 macrophage cells were investigated. Three new compounds (13) demonstrated anti inflammatory activity with IC50 values ranging from 6.5 ± 0.6 to 14.7 ± 1.6 µM. Furthermore, two compounds (11 and 12) demonstrated moderate anti inflammatory activity, with IC50 values ranging from 24.1 ± 1.2 to 62.5 ± 1.9 µM.

Corresponding author: Qin-Ge Ma, Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine & Key Laboratory of Modern Preparation of Traditional Chinese Medicine of Ministry of Education, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, P. R. China, E-mail:

Funding source: Science and Technology Project of Jiangxi Administration of Traditional Chinese Medicine

Award Identifier / Grant number: 2019A002

Funding source: Jiangxi Provincial Natural Science Foundation

Award Identifier / Grant number: 20202BAB216036

  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 Jiangxi Provincial Natural Science Foundation (20202BAB216036) and Science and Technology Project of Jiangxi Administration of Traditional Chinese Medicine (2019A002).

  3. Conflict of interest statement: The authors declare that they have no conflict of interest.


1. He, SD, Tang, MM, Zhang, ZY, Liu, HY, Luo, MF, Sun, HJ. Hypoglycemic effects of phenolic compound-rich aqueous extract from water dropwort (Oenanthe javanica DC.) on streptozotocin-induced diabetic mice. New J Chem 2020;44:5190–200. in Google Scholar

2. Lee, DH, Lee, JS, Lee, IH, Hong, JT. Therapeutic potency of fermented field waterdropwort (Oenanthe javanica (Blume) DC) in ethanol-induced liver injury. RSC Adv 2020;10:1544–51. in Google Scholar PubMed PubMed Central

3. Ma, QG, Wei, RR, Sang, ZP. Biphenyl derivatives from the aerial parts of Oenanthe javanica and their COX-2 inhibition activities. Chem Biodivers 2019;16:e1800480. in Google Scholar PubMed

4. Tang, QY, Zhou, YF, Ren, TT, Jiang, M. Research on the separation and purification of flavonoids in Oenanthe javanica by macroporous absorbents. Lishizhen Med Mater Medica Res 2009;20:2480–2.Search in Google Scholar

5. Kim, JK, Shin, EC, Park, GG, Kim, YJ, Shin, DH. Root extract of water dropwort, Oenanthe javanica (Blume) DC, induces protein and gene expression of phase I carcinogen metabolizing enzymes in HepG2 cells. SpringerPlus 2016;5:413–8. in Google Scholar PubMed PubMed Central

6. Ai, G, Huang, ZM, Liu, QC, Han, YQ, Chen, X. The protective effect of total phenolics from Oenanthe javanica on acute liver failure induced by D-galactosamine. J Ethnopharmacol 2016;186:53–60. in Google Scholar PubMed

7. Zhou, YF, Tang, QY, Peng, H, Wu, LZ. Extraction and composition analysis of crude polysaccharide from young stems of Oenanthe javanica. Food Sci 2012;33:138–42.Search in Google Scholar

8. Yang, SA, Jung, YS, Lee, SJ, Park, SC, Kim, MJ, Lee, EJ, et al.. Hepatoprotective effects of fermented field water-dropwort (Oenanthe javanica) extract and its major constituents. Food Chem Toxicol 2014;67:154–60. in Google Scholar PubMed

9. Her, Y, Shin, BN, Lee, YL, Park, JH, Kim, DW, Kim, KS, et al.. Oenanthe javanica extract protects mouse skin from UVB radiation via attenuating collagen disruption and inflammation. Int J Mol Sci 2019;20:1435. in Google Scholar PubMed PubMed Central

10. Kongkachuichai, R, Charoensiri, R, Yakoh, K, Kringkasemsee, A, Insung, P. Nutrients value and antioxidant content of indigenous vegetables from Southern Thailand. Food Chem 2015;173:836–46. in Google Scholar PubMed

11. Tang, MM, Sun, HJ, Zhang, ZY, Zhao, JL, Cao, JJ, Thakur, K, et al.. Evaluation of hot water and microwave blanching on qualities and sensory characteristics of water dropwort (Oenanthe javanica DC). J Food Process Preserv 2019;43:e14104. in Google Scholar

12. Han, YQ, Huang, ZM, Yang, XB, Liu, HZ, Wu, GX. In vivo and in vitro anti-hepatitis B virus activity of total phenolics from Oenanthe javanica. J Ethnopharmacol 2008;118:148–53. in Google Scholar PubMed

13. Liu, ZH, Zhang, L. Effects of total favone extract from shuiqin (Oenanthe javanica) on immune function of immunosuppression mice. Chin J Tradit Med Sci Technol 2016;23:423–5.Search in Google Scholar

14. Kim, JY, Kim, KH, Lee, YJ, Lee, SH, Park, JC, Nam, DH. Oenanthe javanica extract accelerates ethanol metabolism in ethanol-treated animals. BMB Rep 2009;42:482–5. in Google Scholar PubMed

15. Lee, DYW, Liu, YZ. Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (Milk Thistle). J Nat Prod 2003;66:1171–4. in Google Scholar PubMed

16. Ninh, PT, Ha, CTT, Thai, TH, Hanh, NP, Khang, NS, Dung, NT, et al.. Chevalierinol A and B, two new neolignan sesquiterpenoids from Magnolia chevalieri. Nat Prod Res 2020;1:1–7. in Google Scholar PubMed

17. Zhou, D, Li, Y, Chen, G, Yang, YQ, Mi, Y, Lin, B, et al.. Structural elucidation and anti-neuroinflammatory activities of lignans from the testas of Vernicia montana. Bioorg Chem 2020;97:103690. in Google Scholar PubMed

18. Xiao, CM, Jia, XH, Du, HF, Zhao, HX, Du, CL, Tang, WZ, et al.. Three new C-geranylated flavonoids from Paulownia catalpifolia T. Gong ex D.Y. Hong seeds with their inhibitory effects on xanthine oxidase. Phytochem Lett 2020;36:162–5. in Google Scholar

19. Liu, YP, Yu, XM, Zhang, W, Wang, T, Jiang, B, Tang, HX, et al.. Prenylated chromones and flavonoids from Artocarpus heterophyllus with their potential antiproliferative and anti-inflammatory activities. Bioorg Chem 2020;101:104030. in Google Scholar PubMed

20. Ma, QG, Wei, RR, Yang, M, Huang, XY, Wang, F, Sang, ZP, et al.. Molecular characterization and bioactivity of coumarin derivatives from the fruits of Cucumis bisexualis. J Agric Food Chem 2018;66:5540–8. in Google Scholar PubMed

21. Kato, E, Kushibiki, A, Satoh, H, Kawabata, J. Silychristin derivatives conjugated with coniferylalcohols from silymarin and their pancreatic α-amylase inhibitory activity. Nat Prod Res 2020;34:759–65. in Google Scholar PubMed

22. Polyak, SJ, Morishima, C, Lohmann, V, Pal, S, Lee, DYW, Liu, Y, et al.. Identifification of hepatoprotective flavonolignans from silymarin. Proc Natl Acad Sci 2010;107:5995–9. in Google Scholar PubMed PubMed Central

23. Pourová, J, Applová, L, Macáková, K, Vopršalová, M, Migkos, T, Bentanachs, R, et al.. The effect of silymarin flavonolignans and their sulfated conjugates on platelet aggregation and blood vessels ex vivo. Nutrients 2019;11:2286. in Google Scholar PubMed PubMed Central

24. Awasthi, S, Saraswathi, NT. Silybin, a flavonolignan from milk thistle seeds, restrains the early and advanced glycation end product modification of albumin. RSC Adv 2015;5:87660–6. in Google Scholar

25. Ma, QG, Wei, RR, Zhou, B, Sang, ZP, Liu, WM, Cao, ZL. Antiangiogenic phenylpropanoid glycosides from Gynura cusimbua. Nat Prod Res 2019;33:457–63. in Google Scholar PubMed

26. Wei, RR, Ma, QG, Zhong, GY, He, JW, Sang, ZP. Isolation and characterization of flavonoid derivatives with anti-prostate cancer and hepatoprotective activities from the flowers of Hosta plantaginea (Lam.) Aschers. J Ethnopharmacol 2020;253:112685. in Google Scholar PubMed

27. Ma, QG, Wei, RR, Sang, ZP. Structural characterization and hepatoprotective activity of naphthoquinone from Cucumis bisexualis. Nat Prod Commun 2020;15:1–6. in Google Scholar

28. Ma, QG, Wei, RR, Shang, DL, Sang, ZP, Liu, WM, Cao, ZL. Hepatoprotective and neuroprotective flavanes from the fruits of Ulmus pumila L. (Ulmaceae). Pak J Pharm Sci 2019;32:2059–64.Search in Google Scholar

29. Ma, QG, Wei, RR, Sang, ZP, Dong, JH. Structurally diverse coumarin-homoisoflavonoid derivatives with hepatoprotective activities from the fruits of Cucumis bisexualis. Fitoterapia 2021;149:104812. in Google Scholar PubMed

30. Ma, QG, Wei, RR, Yang, M, Huang, XY, Wang, F, Dong, JH, et al.. Isolation and characterization of neolignan derivatives with hepatoprotective and neuroprotective activities from the fruits of Citrus medica L. var. Sarcodactylis Swingle. Bioorg Chem 2021;107:104622. in Google Scholar PubMed

31. Ma, QG, Wei, RR, Zhang, XD, Sang, ZP, Dong, JH, Lu, QX, et al.. Tropolone derivatives with hepatoprotective and antiproliferative activities from the aerial parts of Chenopodium album Linn. Fitoterapia 2020;146:104733. in Google Scholar PubMed

32. Li, W, Yang, HJ. Isolation and identifification of lignans and other phenolic constituents from the stem bark of Albizia julibrissin durazz and evaluation of their nitric oxide inhibitory activity. Molecules 2020;25:206. in Google Scholar PubMed PubMed Central

33. Zhang, XR, Zhu, HT, Wang, D, Yang, Z, Yang, CR, Zhang, YJ, et al.. Five new lignans from Terminalia chebula var. tomentella (Kurz) C. B. Clarke. Fitoterapia 2020;143:104571. in Google Scholar PubMed

Received: 2021-01-01
Accepted: 2021-05-02
Published Online: 2021-05-18
Published in Print: 2021-11-25

© 2021 Walter de Gruyter GmbH, Berlin/Boston

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