Abstract
A two-step chemical process for controlled degradation of escin, affording a mixture of olean-12-ene sapogenins, was elaborated and scaled up. The main component of the mixture—protoescigenin—was isolated and purified, in the form of its corresponding monohydrate, without resource to chromatographic methods. This material was further converted into the high purity 3,24;16,22-di-O,O-isopropylidene derivative in a validated large scale laboratory process.
Highlights
Escin, a saponin complex from horse chestnut seeds (Aesculus hippocastanum L.), constitutes a traditional herbal drug which enjoys a good clinical reputation as a treatment for chronic venous insufficiency and capillary blood vessel leakage [1,2,3,4]
A great many modern medicines stem from natural products, their early development is frequently hampered by lack of active substance because the initial isolation procedure is inefficient, while technical process elaboration securing API supply of appropriate quality and in quantities suitable for pre-clinical and clinical studies, usually lags behind
In our studies, which are inspired by escin saponin complex as a useful drug inherited from ethnopharmacological tradition, but not compatible with modern medicine requirements, we decided to address the problem of substance availability and specified quality from the very beginning
Summary
Escin (aescin), a saponin complex from horse chestnut seeds (Aesculus hippocastanum L.), constitutes a traditional herbal drug which enjoys a good clinical reputation as a treatment for chronic venous insufficiency and capillary blood vessel leakage [1,2,3,4]. In many cases biologically active natural products are transformed through semi-synthesis on their way to modern drugs [8,9] and saponins bearing triterpenoid aglycons are no exception [10,11]. This avenue may prove unmanageable when the native complex is considered, we propose a more radical approach to exploitation of the complex anew, in which the saponin mixture is perceived as a source of a hitherto unavailable raw material—protoescigenin (1, Scheme 1). Reagents and Conditions: (i) (a) H2SO4, MeOH, reflux, (b) KOH, H2O
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