Novel panax stipuleanatus saponin analogue as well as synthesis method and application thereof

A technology of notoginseng saponins and analogues, applied in the field of synthesis of novel notoginseng saponins analogues, can solve problems such as resource difficulties, achieve high yields, solve drug resistance problems, and achieve short routes

Active Publication Date: 2022-04-22
YUNNAN UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, Pingbian notoginseng is a national key second-class protected wild plant, and its artificial domestication is still in the research

Method used

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  • Novel panax stipuleanatus saponin analogue as well as synthesis method and application thereof
  • Novel panax stipuleanatus saponin analogue as well as synthesis method and application thereof
  • Novel panax stipuleanatus saponin analogue as well as synthesis method and application thereof

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Experimental program
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Effect test

preparation example Construction

[0030] Synthesis method of novel screenside pentaseng saponin analogues, including (1) synthesis of disaccharide saponin 8 and (2) synthesis of new screenside pentaseng saponin analogue A, the specific steps are:

[0031] (1) Synthesis of disaccharide saponin 8: taking D- glucose as the starting material, after full acetylation, synthesizing thioside 1 with p-toluenethiophen under the action of boron trifluoride diethyl ether of Lewis acid; thioside 1 is hydrolyzed under alkaline conditions of sodium methanol, and the synthetic compound 2 is protected by benzyl fork, and the 2-hydroxy of acetyl selective protective compound 2 is obtained to the glycosylthioside receptor 3; after D-glucose perbenzoylation, the glucose trifluoroacetimide ester donor is synthesized with N-phenyl trifluoroacetimide chloride 4 Glycosacylate receptor 3 and glucose trifluoroacetimide donor 5 were given disaccharide 6 under the action of trimethylsilyl trifluoromethanesulfonate; oleanolic acid reacted wit...

Embodiment 1

[0037] Synthesis method of novel screenside pentaseng saponin analogue A

[0038] Synthesis of thioside (1).

[0039]

[0040] Add NaOAc (12.2 mmol, 1.0 g) with Ac in a dry round-bottom bottle 2 O(99.4 mmol, 9.4 mL), heated to reflux, D-glucose (10 mmol, 1.8 g) was added in 3 times within 15 min, reflux stirring reaction for 4 h, thin layer chromatography detection reaction was complete. The reaction liquid was cooled to room temperature, crushed ice was added, and the white solid was quickly precipitated by sonication. Filtered, washed the filter cake with water until no acidity, dissolved in hot ethanol (5 mL), added petroleum ether (100 mL), cooled at low temperature overnight to precipitate the white solid, filtered, petroleum ether washed filter cake, to give a white solid 1,2,3,4,6-five- O -Acetyl-β-D-glucose. Weigh 1, 2, 3, 4, 6-Five- O -Acetyl-β-D-glucose (2.6 mmol, 1.0 g), 4Å molecular sieve, TolSH (5.2 mmol, 0.6 g), soluble in dried DCM (10 mL). Cool to 0 °C, N 2 Slowl...

Embodiment 2

[0089] Take a little new screen edge panax notoginseng saponin analogue A, screen edge panax notoginseng total saponin and mixture of the two, add methanol to dissolve, respectively, on the same thin layer of chromatography plate, with dichloromethane - methanol - water as the unfolding agent to unfold, dry, spray with orcinol color developer, baked and dried on a 105 °C electric heater, inspected in daylight, thin layer chromatography as seen Figure 7 For the novel screen edge of the pentaseng saponin analogue A. Among them, 68 is a new type of screenside trisax pentaseng saponin analog, totally screenside triax notoginseng total saponin, mixed with a new type of screenside pentaseng saponin analogue A and screenside panax notoginseng total saponin mixture. As can be seen from the figure, the screen edge of the total saponin does not contain the new screen edge of the panax notoginseng saponin analogue A.

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Abstract

The invention discloses a novel panax stipuleanatus saponin analogue as well as a synthesis method and application thereof. Oleanolic acid, D-glucose and L-arabinose are used as initial raw materials to synthesize an oleanolic acid benzyl ester receptor, a glycosyl thioglycoside receptor and a glycosyl trifluoroacetimidate donor. The novel panax stipuleanatus saponin analogue, namely oleanolic acid 3-O-beta-D-glucopyranosyl-(1-> 3)-[alpha-L-furan arabinosyl-(1-> 4)]-beta-D-glucopyranosyl A, is obtained by performing glycosylation reaction on a receptor and a glycosyl donor to remove benzylidene, performing catalytic hydrogenation by 10% Pd/C and finally performing saponification in an alkaline solution. The method is short in route and high in yield. The novel panax stipuleanatus saponin analogue provided by the invention is combined with fluconazole to generate a synergistic effect of resisting drug-resistant candida albicans, and the problem of drug resistance of deep fungal infection is expected to be further solved.

Description

Technical field [0001] The present invention belongs to the field of medicinal chemistry technology, specifically relates to a new screenside pentaseng saponin analogue, synthetic method and application thereof. Background [0002] In recent years, with the popularization of broad-spectrum antibiotics, immunosuppressants, antitumor drugs, the occurrence of immunodeficient diseases, and transplant surgery, the incidence of invasive fungal infections (IFIs) has increased year by year, seriously threatening human health and life, and more than 1.5 million people die of IFIs every year. Among them, Candida albicans ( Candida albicans ) is the main pathogenic bacteria that cause IFIs. Candida albicans is a symbiotic bacterium present in the mucous membranes of the human body and is generally harmless to health. When the body's immunity declines, Candida albicans can cause superficial infections, and even IFIs, are the most common nosocomial infection fungus and have become the 4th m...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07H15/256C07H1/00A61K31/704A61K31/4196A61P31/10
CPCC07J63/008C07H15/256C07H1/00A61K31/704A61K31/4196A61P31/10A61K2300/00Y02P20/55
Inventor 倪广惠殷珊王睿睿廖一川张文平吴艳丹赵胤刘瑞娜
Owner YUNNAN UNIV OF TRADITIONAL CHINESE MEDICINE
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