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小叶爬崖香中苷类化合物的研究

涂鹏煌, 姚志仁, 金美玲, 宁冠宇, 黄亚萍, 潘珂, 殷志琦

涂鹏煌,姚志仁,金美玲,等. 小叶爬崖香中苷类化合物的研究[J]. 中国药科大学学报,2024,55(2):202 − 208. DOI: 10.11665/j.issn.1000-5048.2023122704
引用本文: 涂鹏煌,姚志仁,金美玲,等. 小叶爬崖香中苷类化合物的研究[J]. 中国药科大学学报,2024,55(2):202 − 208. DOI: 10.11665/j.issn.1000-5048.2023122704
TU Penghuang, YAO Zhiren, JIN Meiling, et al. Study of glycosides from Piper sintenense Hatusima[J]. J China Pharm Univ, 2024, 55(2): 202 − 208. DOI: 10.11665/j.issn.1000-5048.2023122704
Citation: TU Penghuang, YAO Zhiren, JIN Meiling, et al. Study of glycosides from Piper sintenense Hatusima[J]. J China Pharm Univ, 2024, 55(2): 202 − 208. DOI: 10.11665/j.issn.1000-5048.2023122704

小叶爬崖香中苷类化合物的研究

详细信息
    通讯作者:

    殷志琦: Tel:13813879136  E-mail:chyzq2005@126.com

  • 中图分类号: R284.1

Study of glycosides from Piper sintenense Hatusima

  • 摘要:

    为探究胡椒属植物小叶爬崖香(Piper sintenense Hatusima)中苷类化学成分,采用硅胶、ODS、MCI GEL CHP20P、Sephadex LH-20柱色谱和半制备高效液相等色谱技术,从小叶爬崖香95%乙醇提取物的正丁醇部位分离获得9个苷类化合物。根据理化性质及核磁共振数据,以上化合物被鉴定为(2S)-2-羟基-1-(4-羟基-3-甲氧基苯基)-1-丙酮-2-O-β-D-葡萄糖苷(1)、苯乙醇-β-D-葡萄糖苷(2)、苄醇-β-巢菜糖苷(3)、苄醇-β-樱草糖苷(4)、苯乙醇-β-D-呋喃芹菜糖基-(1''→2')-β-D-葡萄糖苷(5)、红景天苷(6)、苯乙醇-β-樱草糖苷(7)、(顺)-3-己烯醇-β-巢菜糖苷(8)、(顺)-3-己烯醇-β-樱草糖苷(9)。其中化合物1为新化合物,化合物3~9为首次从胡椒属中分离得到。

    Abstract:

    In order to investigate the chemical constituents of glycosides in Piper sintenense Hatusima, column chromatographic techniques such as silica gel, ODS, MCI GEL CHP20P, Sephadex LH-20, and semi-preparative high performance liquid chromatography were used to afford nine glycosides from the n-butanol part of the 95% ethanol extract of Piper sintenense Hatusima. Based on the physicochemical properties and NMR data, the above compounds were identified as (2S)-2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone-2-O-β-D-glucopyranoside (1), 2-phenylethyl β-D-glucopyranoside (2), benzyl α-L-arabinopyranosyl-(1''→6')-β-D-glucopyranoside (3), benzyl β-D-xylopyanosyl-(1''→6')-β-D-glucopyranoside (4), phenethyl β-D-apiofuranosyl-(1''→ 2')-β-D-glucopyranoside(5), salidroside (6), phenethanol β-D-xylopyanosyl-(1''→6')-β-D-glucopyranoside (7), (Z)-hexenyl-O-α-L-arabinopyranosyl-(1''→6')-O-β-D-glucopyranoside (8), (Z)-hexenyl-O-β-D-xylopyanosyl-(1''→6')-O-β-D-glucopyranoside (9). Compound 1 was identified as a new compound, and compounds 3-9 were isolated from the genus Piper for the first time.

  • Figure  1.   Chemical structures of compounds 19

    Arap: Arabinopyranosyl; Xylp: Xylopyranosyl; Apif: Apiofuranosyl

    Figure  2.   Key 1H-1H COSY and HMBC (H→C) correlations of compound 1

    Figure  3.   Experimental and calculated ECD spectra of compound 1

    Table  1   NMR data of compound 1 (CD3OD, J in Hz)

    PositionδH a)δC b)1H-1H COSYHMBC (H→C)
    Agly1128.0
    27.63 (d, 2.0)112.5C-1, 3, 4, 6, 7
    3149.4
    4154.4
    56.92 (d, 8.5)116.1H-6C-1, 3, 4
    67.69 (dd, 8.5, 2.0)125.5H-5C-2, 4, 7
    7201.1
    85.56 (q, 7.0)76.2H-9C-9, 1'
    91.52 (d, 7.0)20.5H-8C-7, 8
    3-OMe3.96 (s)56.5C-3
    Glc1'4.31 (d, 7.5)103.4H-2'C-8, 5'
    2'3.33 c)75.4H-1', 3'C-4'
    3'3.30 c)78.2H-2', 4'C-5'
    4'3.32 c)71.6H-3', 5'C-3'
    5'3.36 c)77.9H-4', 6'C-4'
    6'3.93 (dd, 12.0, 2.0) 3.70 (dd, 12.0, 5.5)62.9H-5'C-5'
    a) Measured at 500 MHz; b) Measured at 125 MHz; c) Overlapped signals
    下载: 导出CSV
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出版历程
  • 收稿日期:  2023-12-26
  • 刊出日期:  2024-04-24

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