Preparation method of novel oleanane triterpenoid saponin derivative

A technology of oleanane-type and triterpene saponins, which is applied to the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of harsh reaction conditions, high cost, and many steps, and achieve mild reaction conditions, The effect of low price and high yield

Active Publication Date: 2017-10-24
亿利耐雀生物科技有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0009] Purpose of the invention: the present invention will solve the problems of harsh reaction conditions, many steps, high cost and long period in the current technology, and provide a new preparation method of oleanane-type triterpene saponin derivatives, which is relatively economical and efficient. The operation is convenient, the starting materials are cheap and easy to obtain, and can be implemented industrially

Method used

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  • Preparation method of novel oleanane triterpenoid saponin derivative
  • Preparation method of novel oleanane triterpenoid saponin derivative

Examples

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Embodiment 1

[0026] Weigh 10g of glycyrrhizic acid and place it in the reactor, then add 80g of [Emim] BF4 ionic liquid, stir to dissolve; add 3g of concentrated sulfuric acid, at a temperature of 30°C, the raw material is hydrolyzed by concentrated sulfuric acid under the ionic liquid system for 3 hours To obtain glycyrrhetinic acid monoglucuronide, adjust the pH of the reaction solution to 8 with ammonia water, after standing for stratification, separate the ionic liquid and the water phase in the reaction solution, and rotate the lower water phase to obtain a solid under reduced pressure. Dissolved in 80g of methanol, cooled and recrystallized to obtain 7.07g of pure glycyrrhetinic acid monoglucuronide, with a yield of 90%.

Embodiment 2

[0028] Weigh 10g of glycyrrhizic acid and place it in the reactor, then add 60g of [Emim] PF6 ionic liquid, stir to dissolve; add 4g of concentrated sulfuric acid, at a temperature of 40°C, the raw material is hydrolyzed by concentrated sulfuric acid under the ionic liquid system for 2 hours To obtain glycyrrhetinic acid monoglucuronide, adjust the pH of the reaction solution to 8 with ammonia water, after standing for stratification, separate the ionic liquid and the water phase in the reaction solution, and rotate the lower water phase to obtain a solid under reduced pressure. Dissolved in 80g of ethanol, cooled and recrystallized to obtain 7.30g of pure glycyrrhetinic acid monoglucuronide, with a yield of 93%.

Embodiment 3

[0030] Weigh 10g of glycyrrhizic acid and place it in the reactor, then add 100g of [Emim]ClO2 ionic liquid, stir to dissolve; add 4g of concentrated sulfuric acid, and at a temperature of 45°C, the raw material is hydrolyzed by concentrated sulfuric acid under the ionic liquid system for 2 hours To obtain glycyrrhetinic acid monoglucuronide, adjust the pH of the reaction solution to 9 with ammonia water, after standing for stratification, separate the ionic liquid and the water phase in the reaction solution, and rotate the lower water phase to obtain a solid under reduced pressure. Dissolved in 70g of glacial acetic acid, cooled and recrystallized to obtain 7.12g of pure glycyrrhetinic acid monoglucuronide, with a yield of 90.7%.

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Abstract

The invention discloses a preparation method of a novel oleanane triterpenoid saponin derivative. The preparation method comprises the following steps: (1) adding glycyrrhizic acid into an ionic liquid and fully dissolving the glycyrrhizic acid in proportion to prepare a glycyrrhizic acid dissolved liquid; (2) adding concentrated sulfuric acid in proportion into the dissolved liquid, and after reaction, adjusting the pH value and separating an aqueous liquid from the system; and (3) performing concentration and crystallization of an organic solvent to obtain the oleanane triterpenoid saponin derivative. The preparation method disclosed by the invention is mild in reaction condition and high in yield, can be recycled and is suitable for industrial production.

Description

technical field [0001] The invention relates to chemical synthesis, in particular to a preparation method of a novel oleanane-type triterpene saponin derivative. Background technique [0002] Glycyrrhetinic acid monoglucuronate is a new oleanane-type triterpene saponin derivative, and its structure is shown in the following formula: [0003] [0004] Glycyrrhetinic acid monoglucuronide [0005] Glycyrrhetinic acid monoglucuronate (GAMG) is the product of hydrolysis of glycyrrhizic acid (GL) to lose the glucuronic acid group at the outer end. GAMG has the same anti-inflammation, anti-virus, anti-tumor, anti-digestive ulcer, anti-allergic, liver-protecting, blood-lipid-lowering, antitussive, expectorant and throat-moistening effects similar to glycyrrhizic acid. Its sweetness is 5 times that of GL and more than 1000 times that of sucrose. In addition, GAMG has the characteristics of good solubility, convenient transportation in vivo and low toxicity, which makes it have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07H15/256C07H1/00
Inventor 魏元刚钟慧杨永安金显友易铭左婧
Owner 亿利耐雀生物科技有限公司
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