Sulfur-containing diene compound and preparation method and application thereof

A technology of diene compounds and compounds, which is applied in the field of pharmaceutical active ingredients, can solve the problems of less separation and identification of the pharmacological activity of monomer components, and no connection of anti-tumor pharmacological activity of monomer components, so as to achieve a wide range of pharmacological activities and high product purity , the effect of easy operation

Active Publication Date: 2021-07-16
丽水市中医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Rubus hirsutus Thunb. (Rubus hirsutus Thunb.) is a plant of the genus Rubus (Rubus L.) in the Rosaceae (Rosaceae), also known as Yeduli and Sanyuepao. , a large amount of resources; fenugreek is widely used in the folk, and the whole plant can be used as medicine. The fruit part contains chemical components such as phenols, flavonoids and anthocyanins, which have the functions of expelling wind and dampness, clearing heat and stopping bleeding. It is generally used for rheumatic joints Pain, acute jaundice and other diseases; at present, there are relatively few studies on Pompomia at home and abroad, especially the separation and identification of its monomer components and the pharmacological activities of monomer components, and no monomer components have been identified. It is associated with its anti-tumor pharmacological activity, therefore, its usable range as a drug needs to be further expanded

Method used

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  • Sulfur-containing diene compound and preparation method and application thereof
  • Sulfur-containing diene compound and preparation method and application thereof
  • Sulfur-containing diene compound and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0032] Take 10kg of pomegranates, crush them, extract them with 10L of methanol for 2 weeks, suspend the methanol extract with 1L of distilled water after concentration, extract the water suspension with 1L of ethyl acetate for 3 times, and concentrate the ethyl acetate extract to obtain leaching Paste 260g; Mix sample with silica gel (100 mesh, 100g), carry out normal phase silica gel column chromatography (200-300 mesh, 1kg; Silica gel column size L 500mm, ), followed by gradient elution with a mixture of petroleum ether and ethyl acetate at a volume ratio of 9:1, 7:1, 4:1, 3:1, 1:1, 1:3, 1:9, each gradient Elution of 5 L; fractions detected by TLC, the fractions with an elution ratio of 7:1 (petroleum ether: ethyl acetate) were collected, combined and concentrated to obtain 300 mg of crude product with a purity of 60% and a yield of 3%, and then recrystallized with acetone (room temperature) , 100 mg of the target compound was obtained with a purity of 99% and a yield of...

Embodiment 2

[0034] Take 10kg of pomegranates, pulverize, extract with 5L of ethanol under reflux, suspend the ethanol extract with 1L of distilled water after concentration, extract the water suspension with 1L of chloroform for 3 times, and obtain 234g of extract after the chloroform extract is concentrated; (100 mesh, 100g) mixed sample, carry out normal phase silica gel column chromatography (200-300 mesh, 1kg; Silica gel column size L 500mm, ), followed by gradient elution with a mixture of petroleum ether and ethyl acetate at a volume ratio of 9:1, 7:1, 4:1, 3:1, 1:1, 1:3, 1:9, each gradient Elution of 5 L; fractions detected by TLC, the fractions with an elution ratio of 7:1 (petroleum ether: ethyl acetate) were collected, combined and concentrated to obtain 260 mg of crude product with a purity of 65% and a yield of 2.6%, and then recrystallized with acetone (room temperature) , 120 mg of the target compound was obtained with a purity of 99% and a yield of 1.2%.

Embodiment 3

[0036] Take 10kg of pulverized pomegranates, pulverize, extract with 5L methanol and ethanol mixture, concentrate the methanol / ethanol extract to obtain 366g extract, mix the sample with 100g diatomaceous earth, soak 3 times in 5L chloroform, and carry out normal phase silica gel Column chromatography (200-300 mesh, 1kg; silica gel column size L 500mm, ), followed by gradient elution with a mixture of petroleum ether and ethyl acetate at a volume ratio of 9:1, 7:1, 4:1, 3:1, 1:1, 1:3, 1:9, each gradient Elution 5L; TLC detects fraction, collects the fraction of elution ratio 10:1 (chloroform:methanol) and merges, concentrates, and obtains crude product 350mg, purity 60%, yield 3.5%, then with acetone / n-hexane (volume ratio 2: 3) Recrystallization (at room temperature) to obtain 210 mg of the target compound with a purity of 99% and a yield of 2.1%.

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Abstract

The invention discloses a sulfur-containing diene compound and a preparation method and application thereof. The molecular formula of the sulfur-containing diene compound is C17H16O5S; the extraction method of the compound comprises the following steps: leaching rubus hirsutus in an organic solvent to obtain a leaching solution, concentrating the leaching solution, and adding water to prepare a water suspension; extracting the water suspension, and concentrating an extracting solution to obtain an extract; and separating and purifying the extract to obtain the sulfur-containing diene compound. The sulfur-containing diene compound with a novel structure is separated and identified from rubus hirsutus, and the compound has anti-tumor pharmacological activity and can be used for preparing anti-tumor drugs or functional food.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical active ingredients, in particular to a sulfur-containing diene compound and its preparation method and application. Background technique [0002] Rubus hirsutus Thunb. (Rubus hirsutus Thunb.) is a plant of the genus Rubus (Rubus L.) in the Rosaceae (Rosaceae), also known as Yeduli and Sanyuepao. , a large amount of resources; fenugreek is widely used in the folk, and the whole plant can be used as medicine. The fruit part contains chemical components such as phenols, flavonoids and anthocyanins, which have the functions of expelling wind and dampness, clearing heat and stopping bleeding. It is generally used for rheumatic joints Pain, acute jaundice and other diseases; at present, there are relatively few studies on Pompomia at home and abroad, especially the separation and identification of its monomer components and the pharmacological activities of monomer components, and no monomer comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61P35/00A23L33/105
CPCC07D495/04A61P35/00A23L33/105A23V2002/00A23V2200/30A23V2250/21
Inventor 林娜张晓芹陈礼平邱伟文雷后兴叶垚敏毛佳乐
Owner 丽水市中医院
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