Dihydroiso-coumarin glucoside compounds and preparation method and application thereof

Abstract

The invention discloses new dihydroiso-coumarin glucoside compounds shown in a formula I, which are extracted and separated from Periplaneta americanna medicinal materials. Through mouse auricle swelling tests, rat granulation tissue hyperblastosis tests and the like, results show that the compounds have effects of resisting inflammation, promoting wounds to heal and the like; and the compounds can be used for preparing medicines for treating inflammation, ulcers, wounds, incised wounds, fistula, burn, scalding and the like, particularly medicines for preventing and treating diseases related to inflammation resistance, promotion of granulation tissue hyperblastosis, wound healing and the like, and have high clinical application value. The invention provides a preparation method for the compounds shown in the formula I.

Description

technical field

[0001] The invention relates to medicinal chemistry, in particular to a new dihydroisocoumarin glucoside compound extracted and separated from Periplaneta americana medicinal materials, a preparation method and application thereof. Background technique

[0002] The American cockroach Periplaneta americana is an insect of the genus Periplaneta in the class of Insecta Pterosae, Blatella order, Blattedae, commonly known as "cockroach". Salty, cold; treatment: blood stasis with hard cold and heat, broken accumulation, closed throat, internal cold without children". "Cockroach" is its common name first seen in "Compendium of Materia Medica Supplements". It is also known as Shi Jiang and Hua Chong. Different places have different names, such as Stealing Oil Woman and Zao Anzi. As a huge insect family, Blattidae has existed on the earth for 320 million years, and it is a creature that appeared in the same era as dinosaurs. It is one of the most vigorous, oldest, a...

Examples

Embodiment 1

[0056] 20 kg of dried adult cockroaches (Periplaneta americana) were soaked and extracted three times with 95% ethanol at 60° C., each dosage was 160 kg, 120 kg, and 120 kg respectively, and the extraction time was 12 hours each time. Concentrate the extract under reduced pressure (60°C, -0.08MPa) to recover the solvent until there is no alcohol smell, and obtain 10kg of concentrated solution, add 20kg-40kg of deionized water to stir and dissolve, let stand to separate the layers, take the water layer, and concentrate under reduced pressure (60°C ,-0.08MPa) to a thick paste (relative density 1.20-1.30), to obtain 1.35kg of Periplaneta americana extract (containing new compound I).

Embodiment 2

[0058] 10 kg of dried adult cockroaches (Periplaneta americana) were heated and refluxed with 50% ethanol for extraction three times, each dosage was 100 kg, 80 kg, and 60 kg respectively, and the extraction time was 3 hours each time. Concentrate the extract under reduced pressure (60°C, -0.08MPa) to recover the solvent until there is no alcohol smell, and obtain 5kg of concentrated solution, add 20kg of deionized water to stir and dissolve, let stand to separate the layers, take the water layer, and concentrate under reduced pressure (60°C, -0.08MPa) 0.08MPa) to thick paste (relative density 1.20-1.30), to obtain 740g of Periplaneta americana extract (containing new compound I).

Embodiment 3

[0060] Get the Periplaneta americana extract 300g that embodiment 1 (or embodiment 2) extracts, add water 900ml to dissolve, go up D101 macroporous adsorption resin (consumption 1kg, also can use other models such as MN200, HPD100, HPD400, HPD450, AB-8 , D4020, S-8, HZ806, HP-20 and other resins), after loading the sample, the adsorbate was first washed with 5 times the column volume of water, then washed with 2 times the column volume of 10% ethanol aqueous solution to remove impurities, and then washed with 5 times the column volume The column volume was eluted with 30% ethanol aqueous solution, and the fractions eluted with 30% ethanol were collected, and the solvent was recovered to obtain the fraction containing KFX-4. Then through silica gel column chromatography, diameter-to-height ratio 1:50, silica gel (300-400 mesh) dosage 100g, eluent: n-butanol: ethyl acetate: water=3; 12:1; collect 1 fraction per 20ml , TLC method detects each fraction (developing agent: n-butanol...

technical field

[0001] The invention relates to medicinal chemistry, in particular to a new dihydroisocoumarin glucoside compound extracted and separated from Periplaneta americana medicinal materials, a preparation method and application thereof. Background technique

[0002] The American cockroach Periplaneta americana is an insect of the genus Periplaneta in the class of Insecta Pterosae, Blatella order, Blattedae, commonly known as "cockroach". Salty, cold; treatment: blood stasis with hard cold and heat, broken accumulation, closed throat, internal cold without children". "Cockroach" is its common name first seen in "Compendium of Materia Medica Supplements". It is also known as Shi Jiang and Hua Chong. Different places have different names, such as Stealing Oil Woman and Zao Anzi. As a huge insect family, Blattidae has existed on the earth for 320 million years, and it is a creature that appeared in the same era as dinosaurs. It is one of the most vigorous, oldest, a...

Examples

Embodiment 1

[0056] 20 kg of dried adult cockroaches (Periplaneta americana) were soaked and extracted three times with 95% ethanol at 60° C., each dosage was 160 kg, 120 kg, and 120 kg respectively, and the extraction time was 12 hours each time. Concentrate the extract under reduced pressure (60°C, -0.08MPa) to recover the solvent until there is no alcohol smell, and obtain 10kg of concentrated solution, add 20kg-40kg of deionized water to stir and dissolve, let stand to separate the layers, take the water layer, and concentrate under reduced pressure (60°C ,-0.08MPa) to a thick paste (relative density 1.20-1.30), to obtain 1.35kg of Periplaneta americana extract (containing new compound I).

Embodiment 2

[0058] 10 kg of dried adult cockroaches (Periplaneta americana) were heated and refluxed with 50% ethanol for extraction three times, each dosage was 100 kg, 80 kg, and 60 kg respectively, and the extraction time was 3 hours each time. Concentrate the extract under reduced pressure (60°C, -0.08MPa) to recover the solvent until there is no alcohol smell, and obtain 5kg of concentrated solution, add 20kg of deionized water to stir and dissolve, let stand to separate the layers, take the water layer, and concentrate under reduced pressure (60°C, -0.08MPa) 0.08MPa) to thick paste (relative density 1.20-1.30), to obtain 740g of Periplaneta americana extract (containing new compound I).

Embodiment 3

[0060] Get the Periplaneta americana extract 300g that embodiment 1 (or embodiment 2) extracts, add water 900ml to dissolve, go up D101 macroporous adsorption resin (consumption 1kg, also can use other models such as MN200, HPD100, HPD400, HPD450, AB-8 , D4020, S-8, HZ806, HP-20 and other resins), after loading the sample, the adsorbate was first washed with 5 times the column volume of water, then washed with 2 times the column volume of 10% ethanol aqueous solution to remove impurities, and then washed with 5 times the column volume The column volume was eluted with 30% ethanol aqueous solution, and the fractions eluted with 30% ethanol were collected, and the solvent was recovered to obtain the fraction containing KFX-4. Then through silica gel column chromatography, diameter-to-height ratio 1:50, silica gel (300-400 mesh) dosage 100g, eluent: n-butanol: ethyl acetate: water=3; 12:1; collect 1 fraction per 20ml , TLC method detects each fraction (developing agent: n-butanol...

Images