Startseite Lignan glycosides from the stems of Viburnum melanocarpum and their α-glucosidase inhibitory activity
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Lignan glycosides from the stems of Viburnum melanocarpum and their α-glucosidase inhibitory activity

  • Chunchao Zhao ORCID logo EMAIL logo , Jia Chen , Jianhua Shao ORCID logo EMAIL logo , Jie Shen , Wenyan Gu , Xiaohui Zhang und Yusi Sha
Veröffentlicht/Copyright: 21. August 2019
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Abstract

Two new lignan glycosides (1, 2) and four known lignan glycosides (36) have been isolated from the ethanolic extract of the stems of Viburnum melanocarpum through repeated column chromatography. Their structures including absolute configurations were confirmed by spectroscopic data [one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectra (HRESIMS), optical rotatory dispersion (ORD) and circular dichroism (CD)] and chemical methods. Additionally, the α-glucosidase inhibitory activity of these compounds was tested in vitro. Compound 1 exhibited the strongest inhibitory activity against α-glucosidase with a half-maximal inhibitory concentration (IC50) value of 10.3 μM.

Acknowledgments

We are grateful to the Analytical Detective Center, Yangzhou University, for recording the UV, IR, CD, MS and NMR spectra.

  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 (no. 31201563, Funder Id: http://dx.doi.org/10.13039/501100001809).

  3. Employment or leadership: None declared.

  4. Honorarium: None declared.

References

Chen, J., Shao, J.H., Zhao, C.C., Dong, Z.L., Shen, J., Liu, W.Y., Zhao, M., Fan, J.D. (2018) A novel norneolignan glycoside and four new phenolic glycosides from the stems of Viburnum fordiae Hance. Holzforschung 72:259–266.10.1515/hf-2017-0151Suche in Google Scholar

Gowri, P.M., Tiwari, A.K., Ali, A.Z., Rao, J.M. (2007) Inhibition of α-glucosidase and amylase by bartogenic acid isolated from Barringtonia racemosa Roxb. seeds. Phytother. Res. 21:796–799.10.1002/ptr.2176Suche in Google Scholar PubMed

Herrera Braga, A.C., Zacchino, S., Badano, H., Sierra, M.G., Ruveda, E.A. (1984) 13C NMR spectral and conformational analysis of 8-O-4′ neolignans. Phytochemistry 23:2025–2028.10.1016/S0031-9422(00)84963-8Suche in Google Scholar

Kim, K.H., Moon, E., Kim, S.Y., Lee, K.R. (2010) Lignans from the tuber-barks of Colocasia antiquorum var. esculenta and their antimelanogenic activity. J. Agric. Food Chem. 58:4779–4785.10.1021/jf100323qSuche in Google Scholar PubMed

Liao, S.G., Wu, Y., Yue, J.M. (2006) Lignans from Wikstroemia hainanensis. Helv. Chim. Acta 89:73–80.10.1002/hlca.200690014Suche in Google Scholar

Liimatainen, J., Karonen, M., Sinkkonen, J., Helander, M., Salminen, J.P. (2012) Characterization of phenolic compounds from inner bark of Betula pendula. Holzforschung 66:171–181.10.1515/HF.2011.146Suche in Google Scholar

Long, L.P., Wang, L.S., Qi, S.Z., Yang, Y.R., Gao, H.Y. (2019) New sesquiterpenoid glycoside from the rhizomes of Atractylodes lancea. Nat. Prod. Res. Available at: https://doi.org/10.1080/14786419.2018.1553170. Accessed 08 January 2019.10.1080/14786419.2018.1553170Suche in Google Scholar PubMed

Rangel-Huerta, O.D., Pastor-Villaescusa, B., Aguilera, C.M., Gil, A. (2015) A systematic review of the efficacy of bioactive compounds in cardiovascular disease: phenolic compounds. Nutrients 7:5177–5216.10.3390/nu7075177Suche in Google Scholar PubMed PubMed Central

Shi, J.G. Lignan Chemistry. Chemical Industry Press, Beijing, China, 2010. pp. 27–29.Suche in Google Scholar

Shi, S.Y., Peng, M.J., Zhang, Y.P., Peng, S. (2013) Combination of preparative HPLC and HSCCC methods to separate phosphodiesterase inhibitors from Eucommia ulmoides bark guided by ultrafiltration-based ligand screening. Anal. Bioanal. Chem. 405:4213–4223.10.1007/s00216-013-6806-4Suche in Google Scholar PubMed

Smeds, A.I., Češková, I., Eklund, P.C., Willför, S.M. (2012) Identification of new lignans in Norway spruce knotwood extracts. Holzforschung 66:553–567.10.1515/hf-2011-0218Suche in Google Scholar

Song, J.Z., Cheung, L.M., Liu, X., Qiao, C.F., Zhou, Y., Li, S.L., Chen, S.L., Xu, H.X. (2010) Development and validation of an ultra-high-performance liquid chromatographic method for the determination of a diastereomeric impurity in (+)-pinoresinol diglucoside chemical reference substance. J. Sep. Sci. 33:1909–1915.10.1002/jssc.201000053Suche in Google Scholar PubMed

Takahashi, K., Nakagawa, T. (1966) Studies on constituents of medicinal plants. VIII. The stereochemistry of paulownin and isopaulownin. Chem. Pharm. Bull. 14:641–647.10.1248/cpb.14.641Suche in Google Scholar PubMed

Wang, D.M., Pu, W.J., Wang, Y.H., Zhang, Y.J., Wang, S.S. (2012) A new isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum. Molecules 17:4595–4603.10.3390/molecules17044595Suche in Google Scholar PubMed PubMed Central

Yue, Z.G., Qin, H., Li, Y.H., Sun, Y., Wang, Z.P., Yang, T.H., Liu, L., Wang, M.C., Feng, F., Mei, Q.B. (2013) Chemical constituents of the root of Jasminum giraldii. Molecules 18:4766–4775.10.3390/molecules18044766Suche in Google Scholar PubMed PubMed Central

Zhang, H.Y., Zhang, Z.Y. Compendium of Chinese Medicinal Material Resources. Science Press, Beijing, China, 1994. p. 1211.Suche in Google Scholar

Zhao, C.C., Chen, J., Shao, J.H., Shen, J., Xu, X.Q., Li, K.H., Gu, W.Y., Zhao, M., Fan, J.D. (2018a) Isolation of neolignan and phenolic glycosides from the branches of Viburnum macrocephalum f. keteleeri and their α-glucosidase inhibitory activity. Holzforschung 72:1017–1024.10.1515/hf-2018-0081Suche in Google Scholar

Zhao, C.C., Chen, J., Shao, J.H., Shen, J., Li, K.H., Gu, W.Y., Li, S.H., Fan, J.D. (2018b) Neolignan constituents with potential beneficial effects in prevention of type 2 diabetes from Viburnum fordiae Hance Fruits. J. Agric. Food Chem. 66: 10421–10430.10.1021/acs.jafc.8b03772Suche in Google Scholar PubMed

Zhuang, L.G., Seligmann, O., Jurcic, K., Wagner, H. (1982) Inhaltsstoffe von Daphne tangutica. Planta Med. 45:172–176.10.1055/s-2007-971368Suche in Google Scholar


Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/hf-2019-0159).


Received: 2019-05-30
Accepted: 2019-07-17
Published Online: 2019-08-21
Published in Print: 2019-12-18

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