银杏叶聚戊烯醇的分离纯化及其亲水衍生物的合成

doi:10.3969/j.issn.0253-2417.2019.01.006

林产化学与工业 ›› 2019, Vol. 39 ›› Issue (1): 41-45.doi: 10.3969/j.issn.0253-2417.2019.01.006

银杏叶聚戊烯醇的分离纯化及其亲水衍生物的合成

张昌伟¹,马余璐¹,陶冉¹,叶建中¹,王成章^1,^2,*()

1. 中国林业科学研究院林产化学工业研究所；生物质化学利用国家工程实验室；国家林业局林产化学工程重点开放性实验室；江苏省生物质能源和材料重点实验室，江苏南京 210042
2. 中国林业科学研究院林业新技术研究所，北京 100091

收稿日期:2018-09-05 出版日期:2019-02-25 发布日期:2019-03-14
通讯作者: 王成章 E-mail:wangczlhs@sina.com
作者简介:张昌伟(1987—)，男，河南信阳人，助理研究员，博士，主要从事天然产物的研究与开发
基金资助:
江苏省生物质能源与材料重点实验室项目(JSBEM-S-201708);江苏省青年基金(SBK2018040639)

Separation, Purification and Hydrophilic Derivative Synthesis of Ginkgo biloba Leaves Polyprenol

Changwei ZHANG¹,Yulu MA¹,Ran TAO¹,Jianzhong YE¹,Chengzhang WANG^1,^2,*()

1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key and Open Lab. of Forest Chemical Engineering, SFA; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
2. Research Institute of Forestry New Technology, CAF, Beijing 100091, China

Received:2018-09-05 Online:2019-02-25 Published:2019-03-14
Contact: Chengzhang WANG E-mail:wangczlhs@sina.com
Supported by:
江苏省生物质能源与材料重点实验室项目(JSBEM-S-201708);江苏省青年基金(SBK2018040639)

摘要/Abstract

摘要：

首先对银杏叶聚戊烯醇含量测定的方法及方法学进行了考察，结果表明：采用高效液相色谱，以C18为色谱柱，以异丙醇/甲醇(体积比32:18)为流动相，在210 nm下测定聚戊烯醇具有较高的精密度(RSD为0.89%)、较好的稳定性(RSD为3.26%)，平均加标回收率为97.4%(RSD为1.75%)。然后通过正己烷提取、皂化、乙醇和丙酮脱蜡，以及硅胶柱层析(V(乙醚):V(正己烷)=3:97)获得纯度为98.6%的聚戊烯醇。在此基础上，对高纯度聚戊烯醇末端羟基进行亲水改性，先与邻苯二甲酰亚胺进行光延反应(mitsunobu反应)，再与水合肼进行还原反应，合成了氨基聚戊烯醇，并通过红外和核磁共振氢谱对其结构进行了表征，确认了氨基聚戊烯醇的成功合成。

关键词: 聚戊烯醇, 分离, 纯化, 亲水改性

Abstract:

The analytical methodology and method performance for the determination of polyprenol in Ginkgo biloba leaves were investigated for the first time. The results showed that of the high performance liquid chromatography with C18 as chromatographic column, isopropanol methanol(volume ratio, 32:18) as mobile phase, 210 nm as detection wavelength showed high precision(RSD=0.89%) and good stability(RSD=3.26%). In addition, the average standard recovery and RSD value of polyprenol were 97.4% and 1.75%, respectively. Then, polyprenol with the purity of 98.6% was obtained by extraction with n-hexane, saponification, de-waxing with ethanol and acetone, and silica gel column chromatography(V(diethyl ether):V(n-hexane)=3:97). On this basis, the terminal hydroxyl group of high-purity polyprenol was modified to synthesize aminopolyprenol. Firstly, by mitsunobu reaction with phthalimide, followed by reduction reaction with hydrazine hydrate, to obtain aminopolyprenol. The structure of amino polyprenol was characterized by infrared and nuclear magnetic resonance spectroscopy, which confirmed the aminopolyprenol was successfully synthesized.

Key words: polyprenol, separation, purification, hydrophilic modification

中图分类号:

TQ35

张昌伟,马余璐,陶冉,叶建中,王成章. 银杏叶聚戊烯醇的分离纯化及其亲水衍生物的合成[J]. 林产化学与工业, 2019, 39(1): 41-45.

Changwei ZHANG,Yulu MA,Ran TAO,Jianzhong YE,Chengzhang WANG. Separation, Purification and Hydrophilic Derivative Synthesis of Ginkgo biloba Leaves Polyprenol[J]. Chemistry and Industry of Forest Products, 2019, 39(1): 41-45.

图/表 3

参考文献 16

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样品/mg sample	加入量/mg addition amount	理论值/mg theoretical value	测得总量/mg total amount	回收率/% recovery rate	平均回收率/% average recovery rate	RSD/%
0.366	0.200	0.566	0.585	103.4	102.7	1.79
0.366	0.200	0.566	0.576	101.8
0.366	0.300	0.666	0.672	100.9
0.366	0.300	0.666	0.671	100.8
0.366	0.400	0.766	0.799	104.3
0.366	0.400	0.766	0.804	105.0

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银杏叶聚戊烯醇的分离纯化及其亲水衍生物的合成

Separation, Purification and Hydrophilic Derivative Synthesis of Ginkgo biloba Leaves Polyprenol

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