Three new flavonol glycosides from Fissistigma pallens

Nguyen Xuan Nhiem, Ngo Sy Thinh, Nguyen Thi Bich Thu, Luu The Anh, Tran Minh Ngoc, Bui Huu Tai, Pham Hai Yen, Phan van Kiem, Chau van Minh, Seonju Park, Seung Hyun Kim

Research output: Contribution to journalArticle

Abstract

Three new flavonol glycosides, fissflavosides A-C (1–3), together with six known flavonol glycosides, kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (4), kaempferol 3-O-α-L-rham-nopyranosyl-(1→6)-β-D-galactopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (6), rhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (7), rutin (8), and isorhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (9) were isolated from the methanol extract of the Fissistigma pallens leaves. Their chemical structures were determined by 1D-, 2D-NMR, and MS data as well as in comparison with reported data in the literature. Compounds 1–9 showed weak cytotoxic activity on three human cancer cell lines, HT-29, A-2058, A-549 with IC50 ranging from 134.6 to 162.6 µM. In addition, the antioxidant capacities of compounds were also tested by ORAC assay. All compounds showed significant antioxidant with trolox equivalents ranging from 4.4 to 8.6 µM at the concentration of 1.0 µM. The results indicated 7 and 8 having meaningful reducing capacity of copper (I) ions of 2.7 to 6.9 µM at the concentrations of 1 and 2 µM.

Original languageEnglish
Pages (from-to)2177-2182
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume83
Issue number12
DOIs
Publication statusPublished - 2019 Jan 1

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Annonaceae
Glycosides
Galactose
Antioxidants
Rutin
Inhibitory Concentration 50
Methanol
Copper
Assays
Cells
Nuclear magnetic resonance
Ions
Cell Line
3-hydroxyflavone
kaempferol
Neoplasms

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Cite this

Nhiem, N. X., Thinh, N. S., Thu, N. T. B., Anh, L. T., Ngoc, T. M., Tai, B. H., ... Kim, S. H. (2019). Three new flavonol glycosides from Fissistigma pallens. Bioscience, Biotechnology and Biochemistry, 83(12), 2177-2182. https://doi.org/10.1080/09168451.2019.1654848
Nhiem, Nguyen Xuan ; Thinh, Ngo Sy ; Thu, Nguyen Thi Bich ; Anh, Luu The ; Ngoc, Tran Minh ; Tai, Bui Huu ; Yen, Pham Hai ; van Kiem, Phan ; van Minh, Chau ; Park, Seonju ; Kim, Seung Hyun. / Three new flavonol glycosides from Fissistigma pallens. In: Bioscience, Biotechnology and Biochemistry. 2019 ; Vol. 83, No. 12. pp. 2177-2182.
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abstract = "Three new flavonol glycosides, fissflavosides A-C (1–3), together with six known flavonol glycosides, kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (4), kaempferol 3-O-α-L-rham-nopyranosyl-(1→6)-β-D-galactopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (6), rhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (7), rutin (8), and isorhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (9) were isolated from the methanol extract of the Fissistigma pallens leaves. Their chemical structures were determined by 1D-, 2D-NMR, and MS data as well as in comparison with reported data in the literature. Compounds 1–9 showed weak cytotoxic activity on three human cancer cell lines, HT-29, A-2058, A-549 with IC50 ranging from 134.6 to 162.6 µM. In addition, the antioxidant capacities of compounds were also tested by ORAC assay. All compounds showed significant antioxidant with trolox equivalents ranging from 4.4 to 8.6 µM at the concentration of 1.0 µM. The results indicated 7 and 8 having meaningful reducing capacity of copper (I) ions of 2.7 to 6.9 µM at the concentrations of 1 and 2 µM.",
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Nhiem, NX, Thinh, NS, Thu, NTB, Anh, LT, Ngoc, TM, Tai, BH, Yen, PH, van Kiem, P, van Minh, C, Park, S & Kim, SH 2019, 'Three new flavonol glycosides from Fissistigma pallens', Bioscience, Biotechnology and Biochemistry, vol. 83, no. 12, pp. 2177-2182. https://doi.org/10.1080/09168451.2019.1654848

Three new flavonol glycosides from Fissistigma pallens. / Nhiem, Nguyen Xuan; Thinh, Ngo Sy; Thu, Nguyen Thi Bich; Anh, Luu The; Ngoc, Tran Minh; Tai, Bui Huu; Yen, Pham Hai; van Kiem, Phan; van Minh, Chau; Park, Seonju; Kim, Seung Hyun.

In: Bioscience, Biotechnology and Biochemistry, Vol. 83, No. 12, 01.01.2019, p. 2177-2182.

Research output: Contribution to journalArticle

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AU - Nhiem, Nguyen Xuan

AU - Thinh, Ngo Sy

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AU - Ngoc, Tran Minh

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AU - Kim, Seung Hyun

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