NMR Characterization of Two Flavonyl Glycosides Isolated from Daphniphyllum angustifolium Hutch.

Abstract

Abstract:

Two bioactive compounds were isolated from Daphniphyllum angustifolium Hutch. and purified by column chromatography with D101 macroporous resin adsorption, Sephadex LH-20 and Pre-HPLC. The compounds were characterized by UV, ESI-MS, ¹H NMR, ¹³C NMR and 2D NMR (HSQC, HMBC and NOESY) techniques. The ¹H NMR and ¹³C NMR signals of the compounds were assigned. Their structures were elucidated as 5,4′-dihydroxyflavanone-7-O-α-L-rhamnopyranosyl (1→2) -β-D-glucopyranoside and 7,4′-dihydroxy-isofavone-8-C-β-D-glucopyranoside, respectively.

Key words: NMR, 5,4′-dihydroxy-flavanone-7-O-α-L-rhamnopyranosyl（1→2）-β-D-glucopyranoside, 7,4′-dihydroxy-isofavone-8-C-β-D-glucopyranoside, 2D NMR, Daphniph yllum angustifolium Hutch.

CLC Number:

O482.53
O641

HU Ming-Feng, CHEN Lian-Qing, WANG Kui-Wu. NMR Characterization of Two Flavonyl Glycosides Isolated from Daphniphyllum angustifolium Hutch.[J]. Chinese Journal of Magnetic Resonance, 2010, 27(2): 259-265.

References

[1] Li Zheng-yu(李震宇), Guo Yue-wei(郭跃伟). Progress in the study of daphniphyllum alkaloids(虎皮楠生物碱研究进展)[J]. Chinese J Org Chem(有机化学), 2007, 27(5): 565-575.

[2] Zhen Mian(郑勉), Min Tian-lu(闵天禄). Chinese Flora(中国植物志), Vol.45(1) [M]. Beijing(北京): Science Press(科学出版社), 1980.

[3] Zhan Z J, Zhang C R, Yue J M. Caldaphnidines A-F, six new daphniphyllum alkaloids from daphniphyllum calycinum[J]. Tetrahedron, 2005, 61(46): 11 038-11 045.

[4] Zhen Wang-jun(郑万钧). Zhongguo Shumu Zhi(中国树木志), Vol.2[M], Beijing(北京): China Forestry Publishing House(中国林业出版社), 1985.

[5] Li Wan-hua(李万华), Li Qin(李琴), Wang Xiao-gang(王小刚)，et al. Isolation and structural elucidation of the flavonoids from the stings of gleditsia sinensis L (皂角刺中黄酮类化学成分的分离鉴定) [J]. Journal of Northwest University(西北大学学报), 2005, 35(6): 763-770.

[6] Bao Shi-an(鲍时安), Luo Ren-sheng(罗仁生), Mao Xi-an(毛希安). NMR evidences for 1-2 connection in quercetin-3-(6-hydroxy-trans-cinnamoyl-gucosyl)rhamnosyol(槲皮素-3-鼠李糖-(6-对羟基反式桂皮酰)葡萄糖甙1-2连接的NMR谱证据) [J]. Chinese J Magn Reson (波谱学杂志),1999, 16(2): 139-142.

[7] Negi P S, Jayaprakasha G K. Antibacterial activity of grapefruit(Citrus paradisi) peel extract[J]. Eur Food Res Technol, 2001, 213: 484-487.

[8] Wang Zhao-xia（王朝霞）, Ren Zhi-hua(任志华), Yan Jing(闫静)，et al. Total synthesis of glycosylflavone parkinsonin B(黄酮糖苷Parkinsonin B的全合成)[J]. Chinese J Org Chem (有机化学), 2006, 26(9): 1 254-1 258.

[9] Hu Yin-yu(胡银玉), Xiao Yan(肖燕), Zhao Na(赵娜), et al. Calculation of ¹³C chemical shifts of dihydroflavone using a model based on atomic electronegativity interaction vector(二氢黄酮类化合物的核磁共振碳谱模拟研究)[J]. Chinese J Magn Reson(波谱学杂志), 2005, 22(4): 383-388.

[10] Cheng G, Bai Y J, Zhao Y Y, et al. Flavonoids from ziziphus jujuba mill var. spinosa[J].Tetrahedron, 2000, 56(45): 8 915-8 920.

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NMR Characterization of Two Flavonyl Glycosides Isolated from Daphniphyllum angustifolium Hutch.

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