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A kind of pyran ring-containing phenolic compound and its preparation method and application

A compound and extract technology, applied in the field of pyran ring-containing phenolic compounds and their preparation, to achieve the effects of low toxicity, strong anti-tumor activity in vitro, and good medicinal value

Inactive Publication Date: 2018-08-14
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no relevant report on the isolation of pyranyl ring-containing phenolic compounds from Selaginella

Method used

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  • A kind of pyran ring-containing phenolic compound and its preparation method and application
  • A kind of pyran ring-containing phenolic compound and its preparation method and application
  • A kind of pyran ring-containing phenolic compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1) Take 8.861 kg of dry aboveground parts of Selaginella tamariscina (P.Beauv.) Spring, crush them, and reflux extract them with 95% ethanol for 3 times, combine the extracts, and recover under reduced pressure Solvent, obtains Selaginella extract;

[0028] 2) Place the Selaginella extract in dichloromethane, ultrasonically dissolve it for 30 minutes (frequency is 50KHz), discard the precipitated insoluble matter, collect the filtrate, and obtain the purified extract;

[0029] 3) The obtained purified extract was subjected to gradient elution by silica gel column chromatography, the solvent system was dichloromethane and methanol (50:1→1:1, volume ratio), the samples were collected in sections, and combined by TLC. The bottle obtains 19 sections of fractions, and then detects with HPLC-UV analysis, and finds that the 11th section is a fraction containing the target compound; the above-mentioned fraction containing the target compound is passed through a reversed-phase c...

Embodiment 2

[0039] Repeat Example 1, except that the extraction medium in step 1) is changed from 95% ethanol to 75% ethanol.

[0040] The obtained product was analyzed by NMR and HRESIMS, etc., and determined to be the target compound 2,2,3,8-tetrahydroxyphenyl-1H-2-benzopyran-6-carboxylic acid.

Embodiment 3

[0042] Repeat Example 1, the difference is: change the extraction solvent in step 1) from volume concentration of 95% ethanol to volume concentration of 100% methanol.

[0043] The obtained product was analyzed by NMR and HRESIMS, etc., and determined to be the target compound 2,2,3,8-tetrahydroxyphenyl-1H-2-benzopyran-6-carboxylic acid.

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Abstract

The invention discloses a phenol compound containing a pyranoid ring and a preparation method and an application thereof. The preparation method of the phenol compound containing the pyranoid ring comprises the following steps: by taking selaginella tamariscina as a raw material, obtaining selaginella tamariscina extract; performing treatment on the selaginella tamariscina extract by silica gel column chromatography, performing gradient elution by taking a mixed solution composed of dichloromethane and methanol or a mixed solution composed of petroleum ether and acetone as a solvent system, and collecting a fraction containing a target compound by virtue of TLC and HPLC-UV analysis and detection; and successively separating the fraction containing the target compound with a reversed phase column, a sephadex column and a preparation liquid phase to obtain the phenol compound containing the pyranoid ring. The obtained target compound has relatively high antitumor activity in vitro on various tumor cell strains, is relatively small in toxicity to normal cells, and has relatively good potential medicinal value.

Description

technical field [0001] The invention relates to a phenolic compound, in particular to a pyranyl ring-containing phenolic compound and its preparation method and application. Background technique [0002] Selaginella tamariscina (P.Beauv.) Spring, Selaginella tamariscina (P.Beauv.) Spring, Selaginella tamariscina (P.Beauv.) Spring, is a perennial herb of the genus Selaginella, also known as Nine Dead Resurrection Grass, Rock Cypress Grass, Jaundice Selaginella; it is mainly distributed in China, Russia, Siberia, North Korea, Japan and the Philippines, etc. It is one of the authentic medicinal materials in Guangxi. It is both ornamental and medicinal, and the whole plant has the effects of hemostasis and astringency. [0003] Modern pharmacological studies have shown that Selaginella not only has traditional anti-inflammatory and detoxifying effects, but also has antibacterial, antiviral, immune-enhancing, anti-tumor, sedative and analgesic, hypoglycemic, and antispasmodic ef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/76A61P35/00
CPCC07D311/76
Inventor 王恒山梁东姚维娜黄日镇王春姑潘英明张斌代禄梅
Owner GUANGXI NORMAL UNIV
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