Isomerization of glycyrrhizic acid. Antiulcer activity
Isomerization of glycyrrhizic acid. Antiulcer activity
复制标题
甘草酸的异构化。
DOI：
10.1007/bf02333885
复制
发表时间：
1996
影响因子：
0.9
通讯作者：
G. Tolstikov
中科院分区：
文献类型：
--
作者：
L. Baltina;N. Serdyuk;O. B. Flekhter;L. V. Krasnova;V. A. Davydova;A. Ismagilova;F. Zarudii;G. Tolstikov
光果甘草（Rhizoma glabra L.）和甘草（Acanthrhiza uralensis F.）[3]，以及其18 ct-GA对应物表现出广谱的药理活性，产生抗炎、抗过敏、抗病毒、祛痰、抗肿瘤和抗溃疡作用[4-10]。这两种GA异构体具有接近的物理化学组成，但反式-GA与顺式异构体的不同之处在于在水中的溶解度更高，i有机化学研究所，乌拉尔科学中心，俄罗斯科学院，乌法，巴什科托尔斯坦，俄罗斯的稳定性更高。水溶液，并且在这些溶液中缺乏凝胶形成[9]。因此，反式-GA作为用于生产化妆品[9]和稳定的水溶性药物形式[11]的表面活性剂和增溶剂是令人感兴趣的。为了得到反式异构体GA，我们已经进行了碱异构化的顺式GA含有约95%的主要成分。通过反相HPLC使用在254 nm波长下操作的UV检测器监测异构化程度。用p. -1法确定了顺式和反式GA异构体分离的最佳参数。Bondapak CN柱和移动的流动相系统0.005 M磷酸盐缓冲液-二氧六环-乙腈（210：10：10，pH 6.8，图1）和0.1 M磷酸四丁基铵-二氧六环-乙腈（210：15：10，pH 7.5，图2）。为此，根据确定的时间表采集样品，并使用所选的其中一种移动的相进行HPLC分析（图1）。从这些数据中，我们确定了在整个实验期间（11-16小时）的反应产物的平衡异构体组成。图3显示了反应物料中立体异构体分布的曲线。如所见，
(Glycyrrhiza glabra L. and Glycyrrhiza uralensis F.)[3], as well as its 18ct-GA counterpart exhibit a broad spectrum of pharmacological activity, producing antiinflammatory, antiallergic, antiviral, expectorant, antitumor, and antiulcer effects [4-10]. The two GA isomers possess close physicochemical compositions, but trans-GA differs from the cis isomer by higher solubility in water, higher stability of the i Institute of Organic Chemistry, Ural Scientific Center, Russian Academy of Sciences, Ufa, Bashkotorstan, Russia. aqueous solutions, and lack of gel formation in these solutions [9]. Therefore, trans-GA is of interest as a surfactant and solubilizing agent for the production of cosmetics [9] and stabilized water-soluble medication forms [11]. In order to obtain the trans isomer of GA, we have performed the alkaline isomerization of cis-GA containing about 95% of the major component. The degree of isomerization was monitored by reverse-phase HPLC using a UV detector operated at a wavelength of 254 nm. The optimum parameters of separation of the cis-and trans-GA isomers were obtained with a p.-Bondapak CN column and the mobile phase systems 0.005 M phosphate buffer-dioxane-acetonitrile (210: 10: 10, pH 6.8, Fig. 1) and 0.1 M tetrabutylammonium phosphate-dioxane-acetonitrile (210: 15: 10, pH 7.5, Fig. 2).The optimum process duration was established for the cis-GA isomerization in a 2 N aqueous KOI2I solution. To this end, samples were taken according to a definite time schedule and analyzed by HPLC using one of the mobile phases selected (Fig. l). From these data, we determined the equilibrium isomer composition of the reaction products during the entire experiment (11-16 h). Figure 3 shows the curves of stereoisomer distribution in the reaction mass. As is seen, the