Skip to main content
SpringerLink
Log in

Chemical constituents from Viburnum fordiae Hance and their anti-inflammatory and antioxidant activities

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Three new neolignans, fordianoles A-C (1–3), characterized as (7S,8R)-4-hydroxy-3,3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneolignan-7,7′,9-triol, (7R,8R)-4-hydroxy-3,3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneolignan-7,7′,9-triol, and (7R,8R)-4-hydroxy-3,3′,5′-trimethoxy-8,4′-oxyneolignan-7,9,9′-triol-7′-one, together with an unusual γ-lactone, 3-(3,4-dihydroxyphenyl)-4-pentanolide (4), and twenty-five known compounds (5–29) were isolated from the aerial parts of Viburnum fordiae Hance. Their structures including absolute configurations were determined by spectroscopic and chemical methods. Among them, compounds 6, 7, 11–15, 17–28 were isolated from the Viburnum genus for the first time. The anti-inflammatory and antioxidant activities of all compounds were evaluated in vitro. Compounds 15, 19, 20 and 29 showed significant inhibitory activity on NO production in RAW264.7 cells stimulated by LPS with IC50 values ranging from 8.60 to 13.92 μM. Meanwhile, compounds 1–4, 15, 19, 20, 22, 23, 25, 26 and 29 exhibited varying antioxidant activities through DPPH, ABTS free radical scavenging and FRAP assays.

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

  • Aasen AJ, Kimland B, Enzell CR (1973) Tobacco chemistry. 18. absolute configuration of (9R)-9-hydroxy-4,7E-megastigmadien-3-one (3-oxo-α-ionol). Acta Chem Scand 27:2107–2114

    Article  CAS  Google Scholar 

  • Arnoldi A, Merlini L (1985) Asymmetric synthesis of 3-methyl-2-phenyl-1,4-benzodioxanes. Absolute configuration of the neolignans eusiderin and eusiderin C and D. J Chem Soc, Perkin Trans 1:2555–2557

    Article  Google Scholar 

  • Benyahia S, Benayache S, Benayache F, León F, Quintana J, López M, Hernández JC, Estévez F, Bermejo J (2005) Cladocalol, a pentacyclic 28-nor-triterpene from Eucalyptus cladocalyx with cytotoxic activity. Phytochemistry 66:627–632

    Article  PubMed  CAS  Google Scholar 

  • Besombes S, Robert D, Utille JP, Taravel FR, Mazeau K (2003) Molecular modeling of syringyl and p-hydroxyphenyl β-O-4 dimers. Comparative study of the computed and experimental conformational properties of lignin β-O-4 model compounds. J Agric Food Chem 51:34–42

    Article  PubMed  CAS  Google Scholar 

  • Biswas SK (2016) Does the interdependence between oxidative stress and inflammation explain the antioxidant paradox? Oxid med cell longev 2016:5698931

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Bjelakovic G, Nikolova D, Gluud LL, Simonetti RG, Gluud C (2007) Mortality in randomized trials of antioxidant supplements for primary and secondary prevention: systematic review and meta-analysis. JAMA 297:842–857

    Article  PubMed  CAS  Google Scholar 

  • Carman RM, Robinson WT, Wallis CJ (2005) The 3-hydroxycineoles. Aust J Chem 58:785–791

    Article  CAS  Google Scholar 

  • Chen XQ, Shao LD, Pal M, Shen Y, Cheng X, Xu G, Peng LY, Wang K, Pan ZH, Li MM, Leng Y, He J, Zhao QS (2015) Hupehenols A-E, selective 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors from Viburnum hupehense. J Nat Prod 78:330–334

    Article  PubMed  CAS  Google Scholar 

  • Deng XH, Zheng CJ, Wu Y, Qin LP (2013a) Chemical constituents of whole plant of Veronicastrum axillare (Sieb. et Zucc.) Yamazaki. Chin Pharm J 48:777–781

    CAS  Google Scholar 

  • Deng Y, He JB, Guan KY, Zhu HJ (2013b) Studies on the chemical constituents of Cynanchum auriculatum. Nat Prod Res Dev 25:729–732

    CAS  Google Scholar 

  • Gan ML, Zhang YL, Lin S, Liu MT, Song WX, Zi JC, Yang YC, Fan XN, Shi JG, Hu JF, Sun JD, Chen NH (2008) Glycosides from the root of Iodes cirrhosa. J Nat Prod 71:647–654

    Article  PubMed  CAS  Google Scholar 

  • Gao L, Tian H, Lv PJ, Wang JP, Wang YF (2015) Chemical constituents of Sapium sebiferum leaves. Zhongguo Zhongyao Zazhi 40:1518–1522

    PubMed  Google Scholar 

  • He L, Yang SL, Wu DS, Cui T, Wei D, Ding ZT (2012) Coumarins from Skimmia arborescens and its anti-inflammatory effect. Zhongguo Zhongyao Zazhi 37:811–813

    PubMed  CAS  Google Scholar 

  • Huang Y, Shao HK, Li K, Liu SQ, Xie ST (2014) Chemical analysis and activity evaluation of anti-inflammatory constituents of Ficus microcarpa L. f. Chin Tradit Patent Med 36:1227–1233

    CAS  Google Scholar 

  • Huang XX, Bai M, Zhou L, Lou LL, Liu QB, Zhang Y, Li LZ, Song SJ (2015) Food byproducts as a new and cheap source of bioactive compounds: lignans with antioxidant and anti-inflammatory properties from Crataegus pinnatifida seeds. J Agric Food Chem 63:7252–7260

    Article  PubMed  CAS  Google Scholar 

  • In SJ, Seo KH, Song NY, Lee DS, Kim YC, Baek NI (2015) Lignans and neolignans from the stems of Vibrunum erosum and their neuroprotective and anti-inflammatory activity. Arch Pharm Res 38:26–34

    Article  PubMed  CAS  Google Scholar 

  • Ishikawa T, Fujimatu E, Kitajima J (2002) Water-soluble constituents of anise: new glucosides of anethole glycol and its related compounds. Chem Pharm Bull 50:1460–1466

    Article  PubMed  CAS  Google Scholar 

  • Iwagawa T, Yaguchi S, Hase T, Okubo T, Kim M (1992) Gomojosides, labdane diterpenoids from Viburnum suspensum. Phytochemistry 31:1311–1315

    Article  CAS  Google Scholar 

  • Iwai K, Kim MY, Onodera A, Matsue H (2006) α-Glucosidase inhibitory and antihyperglycemic effects of polyphenols in the fruit of Viburnum dilatatum Thunb. J Agric Food Chem 54:4588–4592

    Article  PubMed  CAS  Google Scholar 

  • Jang DS, Han AR, Park G, Jhon GJ, Seo EK (2004) Flavonoids and aromatic compounds from the rhizomes of Zingiber zerumbet. Arch Pharm Res 27:386–389

    Article  PubMed  CAS  Google Scholar 

  • Jing WG, Wang ZM, Zhao Y, Fu J, Zhao XL, Liu A (2014) Chemical constituents from seeds of Brassica campestris. Zhongguo Zhongyao Zazhi 39:2521–2525

    PubMed  CAS  Google Scholar 

  • Kikuzaki H, Hara S, Kawai Y, Nakatani N (1999) Antioxidative phenylpropanoids fromberries of Pimenta dioica. Phytochemistry 52:1307–1312

    Article  CAS  Google Scholar 

  • Li BZ, Wang BG, Jia ZJ (1998) Pentacyclic triterpenoids from Rubus xanthocarpus. Phytochemistry 49:2477–2481

    Article  CAS  Google Scholar 

  • Li H, Luo YG, Ma Y, Zeng J, Zhang X, Wang D, Hu CL (2013) Cytotoxic lignans from Viburnum foetidum. Arch Pharm Res 36:1211–1214

    Article  PubMed  CAS  Google Scholar 

  • Li W, Tian XY, Xiao CJ, Jiang B (2014) Chemical constituents from the underground parts of Isodon phyllostachys (II). Chin Pharm J 49:1382–1385

    CAS  Google Scholar 

  • Liu B, Liu MT, Gan ML, Zhao F, Wu XL, Yu Y, Yue ZG, Lin S, Wang SJ, Zhu CG, Shi JG (2012) Chemical constituents from roots of Machilus yaoshansis. Zhongguo Zhongyao Zazhi 37:1227–1231

    PubMed  CAS  Google Scholar 

  • Niu CS, Wang YD, Qu J, Yu SS, Li Y, Liu YB, Ma SG, Lv HN, Chen X, Xu S (2014) Chemical constituents from roots of Illicium majus. Zhongguo Zhongyao Zazhi 39:2689–2692

    PubMed  CAS  Google Scholar 

  • Ren J, Qin JJ, Cheng XR, Yan SK, Jin HZ, Zhang WD (2013) Five new sesquiterpene lactones from Inula hupehensis. Arch Pharm Res 36:1319–1325

    Article  PubMed  CAS  Google Scholar 

  • Sadhu SK, Khatun A, Ohtsuki T, Ishibashi M (2008) Constituents from Hoya parasitica and their cell growth inhibitory activity. Planta Med 74:760–763

    Article  PubMed  CAS  Google Scholar 

  • Shao ZX, Liu AQ, Lu B, Yao JZ (1992) Exploitation and utilization on Viburnum plants in Yunnan. Chin Wild Plant 11:29–31

    Google Scholar 

  • Shen YC, Lin CL, Chien SC, Khalil AT, Ko CL, Wang CH (2004) Vibsane diterpenoids from the leaves and flowers of Viburnum odoratissimum. J Nat Prod 67:74–77

    Article  PubMed  CAS  Google Scholar 

  • Tamura H, Fujita A, Takagi Y, Kitahara T, Mori K (1994) Simple synthesis of dehydrololiolide. Biosci Biotech Biochem 58:1902–1903

    Article  CAS  Google Scholar 

  • Wang JC, Li GZ, Lv N, Gao L, Cao L, Shen LG, Si JY (2016) Chemical constituents from the fruiting bodies of Cryptoporus volvatus. Arch Pharm Res 39:747–754

    Article  PubMed  CAS  Google Scholar 

  • Wu HB, Zhao YN, Li DM, Lv XW, Wang WS (2013) Studies on the chemical constituents from Sambucus adnata Wall. Nat Prod Res Dev 25:345–348

    CAS  Google Scholar 

  • Yilmaz BS, Altun ML, Orhan IE, Ergene B, Citoglu GS (2013) Enzyme inhibitory and antioxidant activities of Viburnum tinus L. relevant to its neuroprotective potential. Food Chem 141:582–588

    Article  PubMed  CAS  Google Scholar 

  • Yin W, Song ZR, Liu JQ, Zhang GS (2015) Chemical constituents of Osmanthus fragrans. Zhongguo Zhongyao Zazhi 40:679–685

    PubMed  CAS  Google Scholar 

  • Zhang AL, Yu M, Xu HH, Si JP (2013a) Constituents of Dendrobium devonianum and their antioxidant activity. Zhongguo Zhongyao Zazhi 38:844–847

    PubMed  CAS  Google Scholar 

  • Zhang ZL, Zuo YM, Luo GM, Luo YJ, Wang YY, Yang YQ (2013b) Study on the chemical components of Gardenia jasminoides (II). Zhong Yao Cai 36:401–403

    PubMed  CAS  Google Scholar 

  • Zhao M, Chen LJ, Pei SC, Sun WJ, Li J, Zhang SJ (2014a) Chemical constituents of Ledum palustre (I). Chin Tradit Herbal Drugs 45:1532–1535

    CAS  Google Scholar 

  • Zhao M, Wu S, Li J, Tang WX, Wang JL, Zhang SJ (2014b) Chemical constituents from Euphorbia lunulata. Zhongguo Zhongyao Zazhi 39:2289–2294

    PubMed  CAS  Google Scholar 

  • Zhonghuabencao Editorial Board (1999) Zhonghuabencao. Shanghai Scientific and Technical Press, Shanghai, pp 553–554

    Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 31201563); Open foundation of green pesticides and biotechnology key laboratory of Guizhou University of Ministry of Education (2017GDGP0102/2017GDGP0103). We are also grateful to the Analytical Detective Center, Yangzhou University, for recording CD, IR, UV, MS and NMR spectra.

Author information

Authors and Affiliations

  1. Jiangsu Key Laboratory of Crop Genetics and Physiology/Co-Innovation Center for Modern Production Technology of Grain Crops, Yangzhou University, Yangzhou, 225009, People’s Republic of China

    Jia Chen, Jianhua Shao, Jie Shen, Ziling Dong & Wenyan Liu

  2. College of Bioscience and Biotechnology, Yangzhou University, Yangzhou, 225009, People’s Republic of China

    Chunchao Zhao

  3. School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, 110016, People’s Republic of China

    Min Zhao

  4. School of Pharmacy, Guizhou Medical University, Guiyang, 550004, People’s Republic of China

    Judi Fan

Authors
  1. Jia Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jianhua Shao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chunchao Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jie Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ziling Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Wenyan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Min Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Judi Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jianhua Shao or Chunchao Zhao.

Ethics declarations

Conflict of interest

The authors declare that there is no conflict of interest.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 3159 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chen, J., Shao, J., Zhao, C. et al. Chemical constituents from Viburnum fordiae Hance and their anti-inflammatory and antioxidant activities. Arch. Pharm. Res. 41, 625–632 (2018). https://doi.org/10.1007/s12272-018-1026-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-018-1026-2

Keywords

Search

Navigation