Neolignans and flavonol glycosides from the leaves of Viburnum lutescens Blume

Le Duc Thien, Duong Thi Dung, Nguyen Phuong Minh, Nguyen Hai Dang
Author affiliations

Authors

  • Le Duc Thien Graduate University of Science and Technology, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam
  • Duong Thi Dung Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam
  • Nguyen Phuong Minh Military Institute of Chemistry and Environment, Phu Vinh, Hoai Duc, Ha Noi, Viet Nam
  • Nguyen Hai Dang University of Science and Technology of Hanoi, VAST, 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam

DOI:

https://doi.org/10.15625/2525-2518/16060

Keywords:

Viburnum lutescens, Caprifoliaceae, neolignan, flavonol glycoside

Abstract

Four neolignans, (7S,8S)-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside (1), (7S,8S)-dihydrodehydrodiconiferyl alcohol 9′-O-β-D-glucopyranoside (2), (7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (3), and (7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 9′-O-β-D-glucopyranoside (4)  and five flavonol glycosides, kaempferol-3-O-β-D-glucopyranoside (5), kaempferol 3-O-rutinoside (6), kaempferol 3-O-α-L-rhamnopyranosyl (1→6)-β-D-galactopyranoside (7), kaempferol 3-O-β-D-galactopyranoside (8), and quercetin 3-O-β-D-glucopyranoside (9) were isolated from the methanol extract of Viburnum lutescens Blume leaves. Their chemical structures were elucidated by 1D- and 2D-NMR spectra and comparison with those reported in the literature. Compounds 1, 2, and 4 were reported from Viburnum genus for the first time.

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References

REFERENCES

Wang X. Y., Shi H. M., Li X. B. - Chemical constituents of plants from the genus Viburnum, Chemistry & Biodiversity 7 (2010) 567-593. DOI: https://doi.org/10.1002/cbdv.200800254

Chi V. V. - Vietnamese dictionary of medical plants, Medical Publisher, Ha Noi, Vol. 1, 2012.

Lee S., Song I. H., Lee J. H., Yang W. Y., Oh K. B., Shin J. - Sortase A inhibitory metabolites from the roots of Pulsatilla koreana, Bioorganic & Medicinal Chemistry Letters 24 (2014) 44-48. DOI: https://doi.org/10.1016/j.bmcl.2013.12.006

Kuang H. X., Xia Y. G., Yang B. Y., Wang Q. H., Lü S. W. - Lignan constituents from Chloranthus japonicus Sieb, Archives of Pharmacal Research 32 (2009) 329-334. DOI: https://doi.org/10.1007/s12272-009-1303-1

Shu J., Liang F., Zhu G., Liu X., Yu J., Huang H. - Lignan glycosides from the rhizomes of Smilax trinervula and their biological activities, Phytochemistry Letters 20 (2017) 1-8. DOI: https://doi.org/10.1016/j.phytol.2017.03.002

Kazuma K., Noda N., Suzuki M. - Malonylated flavonol glycosides from the petals of Clitoria ternatea, Phytochemistry 62 (2003) 229-237. DOI: https://doi.org/10.1016/S0031-9422(02)00486-7

Lee K. H., Tagahara K., Suzuki H., Wu R. Y., Haruna M., Hall I. H., Huang H. C., Ito K., Iida T., Lai J. S. - Antitumor agents. 49. Tricin, kaempferol-3-O-β-D-glucopyranoside and (+)-nortrachelogenin, antileukemic principles from Wikstroemia indica, Journal of Natural Products 44 (1981) 530-535. DOI: https://doi.org/10.1021/np50017a003

Machida K., Sagawa H., Onoguchi R., Kikuchi M. - Three new glycosides from Viburnum plicatum THUNB. var. tomentosum MIQ, Helvetica Chimica Acta 93 (2010) 290-297. DOI: https://doi.org/10.1002/hlca.200900232

Calderón-Montaño J. M., Burgos-Morón E., Pérez-Guerrero C., López-Lázaro M. - A review on the dietary flavonoid kaempferol, Mini Reviews in Medicinal Chemistry 11 (2011) 298-344. DOI: https://doi.org/10.2174/138955711795305335

Hasan A., Ahmed I., Jay M., Voirin B. - Flavonoid glycosides and an anthraquinone from Rumex chalepensis, Phytochemistry 39 (1995) 1211-1213. DOI: https://doi.org/10.1016/0031-9422(95)00071-E

Scharbert S., Holzmann N., Hofmann T. - Identification of the astringent taste compounds in black tea infusions by combining instrumental analysis and human bioresponse, Journal of Agricultural and Food Chemistry 52 (2004) 3498-3508. DOI: https://doi.org/10.1021/jf049802u

Park S. Y., Kim J., Lee S. Y., Bae K. H., Kang S. S. - Chemical constituents of Lathyrus davidii, Natural Product Sciences 14 (2008) 281-288.

Matsuda N., Sato H., Yaoita Y., Kikuchi M. - Isolation and absolute structures of the neolignan glycosides with the enantimetric aglycones from the leaves of Viburnum awabuki K. KOCH, Chemical & Pharmaceutical Bulletin 44 (1996) 1122-1123. DOI: https://doi.org/10.1248/cpb.44.1122

Katagiri S., Watanabe Y., Yaoita Y., Kikuchi M., Machida K. - Two new phenolic glycosides from Viburnum plicatum var. plicatum f. plicatum, Natural Product Communications 6 (2011) 1901-1904. DOI: https://doi.org/10.1177/1934578X1100601227

Gao Y., Yang W. Q., Yang K., Jiang X. J., Li X. M., Wang F. - New iridoid glycosides from Viburnum punctatum, Phytochemistry Letters 28 (2018) 145-148. DOI: https://doi.org/10.1016/j.phytol.2018.10.010

Mohamed M. A., Marzouk M. S., Moharram F. A., El-Sayed M. M., Baiuomy A. R. - Phytochemical constituents and hepatoprotective activity of Viburnum tinus, Phytochemistry 66 (2005) 2780-2786. DOI: https://doi.org/10.1016/j.phytochem.2005.07.019

Lu D., Yao S. - Phenolic Glycoside from the Roots of Viburnum dilatatum, Natural Product Communications 4 (2009) 945-946. DOI: https://doi.org/10.1177/1934578X0900400714

Wu B., Wu S., Qu H., Cheng Y. - Secondary metabolites from Viburnum erosum, Biochemical Systematics and Ecology 36 (2008) 817-819. DOI: https://doi.org/10.1016/j.bse.2008.08.004

Thinh N. S., Thu N. T. B., Khoi N. M., Ngoc T. M., Khoi N. M., Tai B. H., Kiem P. V., Nhiem N. X. - Flavonol glycosides from the leaves of Fissitigma pallens ( Fin. & Gagn.) Merr, Vietnam Journal of Science and Technology 58 (2020) 526-532. DOI: https://doi.org/10.15625/2525-2518/0/0/14811

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Published

21-04-2022

How to Cite

[1]
L. Duc Thien, D. Thi Dung, N. Phuong Minh, and N. Hai Dang, “Neolignans and flavonol glycosides from the leaves of Viburnum lutescens Blume”, Vietnam J. Sci. Technol., vol. 60, no. 2, pp. 175–182, Apr. 2022.

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Natural Products

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