Lignan glycosides from the stems of Viburnum melanocarpum and their α-glucosidase inhibitory activity
Abstract
Two new lignan glycosides (1, 2) and four known lignan glycosides (3–6) 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.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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).
Employment or leadership: None declared.
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).
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Artikel in diesem Heft
- 10.1515/hf-2020-frontmatter1
- Original Articles
- Genotypic variation in the basic density, dynamic modulus of elasticity and tracheid traits of Pinus elliottii in three progeny trials in southern China
- Moisture-dependent orthotropic viscoelastic properties of Chinese fir wood during quenching in the temperature range of 20 to −120°C
- Comparison of whole-tree wood property maps based on near-infrared spectroscopic calibrations utilizing data at different spatial resolutions
- Variation and serial correlation of modulus of elasticity between and within European oak boards (Quercus robur and Q. petraea)
- Natural durability of subfossil oak: wood chemical composition changes through the ages
- Thermo-vacuum treatment of poplar (Populus spp.) plywood
- Dynamic moisture sorption and dimensional stability of furfurylated wood with low lignin content
- From hollow lignin microsphere preparation to simultaneous preparation of urea encapsulation for controlled release using industrial kraft lignin via slow and exhaustive acetone-water evaporation
- Short Note
- Lignan glycosides from the stems of Viburnum melanocarpum and their α-glucosidase inhibitory activity