和厚朴酚原料药中相关酚类物质的含量测定及结构鉴定

doi:10.5246/jcps.2013.05.061

和厚朴酚原料药中相关酚类物质的含量测定及结构鉴定

张宝宝, 王弘, 陈世忠^*

北京大学医学部药学院天然药物学系, 北京 100191

收稿日期:2012-10-12 修回日期:2012-12-12 出版日期:2013-09-15 发布日期:2013-09-15
通讯作者: 陈世忠*

Quantification and structural identification of related phenolic compounds in the raw medicinal material honokiol

Baobao Zhang, Hong Wang, Shizhong Chen^*

Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2012-10-12 Revised:2012-12-12 Online:2013-09-15 Published:2013-09-15
Contact: Shizhong Chen*

摘要/Abstract

摘要： 建立和厚朴酚原料药中厚朴醛B (6), 厚朴醛E (4), 8',9'-二羟基和厚朴酚(7)的含量测定方法。采用Diomonsil™ C₁₈ 色谱柱 (250 mm×4.6 mm, 5 μm); 流动相为水(A)和甲醇(B); 梯度洗脱条件为0~55 min, B为40%~56.5%; 55~67 min, B为56.5%~51.5%; 67~80 min, B为51.5~70%; 80~170 min, B为70%。流速为1.0 mL/min, 检测波长为256 nm, 柱温为35 °C。厚朴醛B, 厚朴醛E, 8',9'-二羟基和厚朴酚分别在0.00864~0.07776 mg/mL, 0.01488~0.13392 mg/mL和0.01568~0.10976 mg/mL范围内与峰面积成良好的线性关系。平均加样回收率分别为100.30%, 99.63% 和 98.29%。本文建立的含量测定方法简单, 快速, 准确, 重现性好, 可用于和厚朴酚原料药的质量评价。此外, 我们应用硅胶柱, 半制备高效液相色谱从制备和厚朴酚原料药过程中产生的剩余杂质中分离得到除上述三个化合物外的另五个相关酚类物质, 赤式-7-O-甲基和厚朴三醇 (1), 苏式-7-O-甲基和厚朴三醇 (2), 7-O-乙基和厚朴三醇 (3), 厚朴醛C (5)及和厚朴酚 (8), 并利用1D 和2D NMR 对这八个化合物进行了结构鉴定。其中, 化合物1和2 为赤式、苏式异构体, 我们首次报道了它们的相对结构。化合物3和7为新化合物。

关键词: 和厚朴酚, 原料药, 相关物质, 厚朴

Abstract:

High-performance liquid chromatography (HPLC) was used to quantify magnaldehyde B (6), magnaldehyde E (4) and 8',9'-dihydroxyhonokiol (7) simultaneously in the raw Chinese medicinal material honokiol. The separation was performed on a reversed-phase C₁₈ column by using a gradient elution with mobile phases of water (A) and methanol (B). The mobile phase gradient was run from 40% B to 56.5% B in 55 min, 55-67 min from 56.5% to 51.5%, 67-80 min from 51.5% to 70%, 80-170 min at 70%. The elution was carried out at a flow rate of 1.0 mL/min at the column temperature of 35 ^оC with the UV detection wavelength at 256 nm. Magnaldehyde B, magnaldehyde E and 8',9'-dihydroxyhonokiol showed good linear relationships with peak areas in the range of 0.00864 to 0.07776 mg/mL, 0.01488 to 0.13392 mg/mL and 0.01568 to 0.10976 mg/mL, respectively. Their corresponding average recoveries were 100.30%, 99.63% and 98.29%, respectively. Our results showed that the established method is simple, rapid, and accurate with good reproducibility for evaluating the quality of raw Chinese medicinal material honokiol. Moreover, another five phenolic compounds, namely erythro-7-O-methylhonokitriol (1), threo-7-O-methylhonokitriol (2), 7-O-ethylhonokitriol (3), magnaldehyde C (5), honokiol (8), together with compounds 4, 6 and 7, were isolated and purified from the remaining substance in the process of preparing the raw material honokiol by silica gel column and semi-preparative HPLC. Their structures were characterized by 1D and 2D NMR spectroscopy. Among them, compounds 1 and 2 were reported to have common planar structures and their relative configurations were identified for the first time. Compounds 3 and 7 were not only obtained from the raw medicinal material for the first time but also novel compounds.

Key words: Honokiol, Raw medicinal material, Magnaldehyde, Magnolia officinalis

中图分类号:

R284.1

Supporting: Foundation item: Major Projects of National Science and Technology on New Drug Creation and Development (Grant No. 2009ZX09102-146).
^*Corresponding author: Tel./Fax: 86-10-82802723

张宝宝, 王弘, 陈世忠^*. 和厚朴酚原料药中相关酚类物质的含量测定及结构鉴定[J]. , DOI: 10.5246/jcps.2013.05.061.

Baobao Zhang, Hong Wang, Shizhong Chen^* . Quantification and structural identification of related phenolic compounds in the raw medicinal material honokiol[J]. , DOI: 10.5246/jcps.2013.05.061.

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