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Lucid ganoderma meroterpenoid compound and medical composite thereof and application thereof

A compound and medicinal salt technology, applied in the field of heteroterpenoids, can solve problems such as drug withdrawal

Active Publication Date: 2017-09-15
峨眉山国芝堂生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since 1970, research on aldose reductase inhibitors has become a hot spot in drug research for the treatment of diabetes. Some types have entered clinical trials or been marketed, but many drugs have been withdrawn due to problems in clinical trials.
There are still few aldose reductase inhibitors available for clinical use. In our long-term study, a compound with aldose reductase inhibitory activity was isolated from the ethyl acetate crude extract of the fruiting bodies of Chizhi, Mount Emei.

Method used

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  • Lucid ganoderma meroterpenoid compound and medical composite thereof and application thereof
  • Lucid ganoderma meroterpenoid compound and medical composite thereof and application thereof
  • Lucid ganoderma meroterpenoid compound and medical composite thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1 prepares the extract of Ganoderma lucidum

[0017] Ganoderma lucidum fruiting bodies were cut into pieces and weighed 2500 grams. Reflux extraction with 10L aqueous solution of 95% ethanol by volume for 3 times, 1 hour each time. The extracts were combined, concentrated and dried under reduced pressure to obtain 170 g of extract.

[0018] The extract was further dissolved with 600 ml of distilled water, extracted three times with an equal volume of n-hexane, and the organic phase was discarded. The aqueous phase was extracted three times with an equal volume of ethyl acetate, the aqueous phase was discarded, and the ethyl acetate extracts were combined. Evaporate ethyl acetate to dryness with a rotary evaporator to obtain 49 g of extract, which is denoted as GS.

Embodiment 2

[0019] The preparation of embodiment 2 compound

[0020] Ganoderma lucidum crude extract ethyl acetate layer GS is separated by silica gel column chromatography, with n-hexane: ethyl acetate system (n-hexane: the volume ratio of ethyl acetate is 1:0, 50:1, 30:1, 20:1, 15:1, 10:1, 4:1, 2:1), dichloromethane: methanol system (the volume ratio of dichloromethane: methanol is 1:0, 100:1, 50:1, 30:1, 10:1 , 5:1) gradient elution was performed sequentially, each gradient was washed with 4 retention volumes, and each retention volume was one fraction. According to the behavioral analysis of thin-layer chromatography, merging of similar fractions obtains fraction GS-1 in normal hexane: ethyl acetate (volume ratio is 1:0) system; in normal hexane: ethyl acetate (volume ratio is 100:1 ~30:1) to obtain fraction GS-2~5; Obtain fraction GS-6, GS-7 in n-hexane: ethyl acetate (volume ratio is 20:1); Obtain fraction GS-6 in n-hexane: ethyl acetate (volume ratio 10:1) to obtain fraction GS-8...

Embodiment 3

[0023] Confirmation of Example 3 Compound 1-3

[0024] NMR, IR, and mass spectrometry were performed on the three prepared compounds to determine the structure of each compound.

[0025] The nuclear magnetic resonance instruments used are Varian Mercury-500 and -600 MHz, the infrared chromatograph is Nicolet IS5FT-IR, and the mass spectrometers are Bruker APEX III 7.0T and APEX II FT-ICR.

[0026] It was confirmed that compound 1 is a new natural product, which is a farnesyl substituted heteroterpenoid compound containing skeleton I of p-hydroxyphenol.

[0027]

[0028] Compound 1 (Ganomycin J)

[0029] The structural formula of compound 1 is as follows:

[0030]

[0031] (R,2Z,5E)-2-(2-(2,5-Dihydroxyphenyl)ethylidene)-9,10-dihydroxy-6,10-dimethylundec-5-enoic acid

[0032] (R,2Z,5E)-2-(2-(2,5-dihydroxyphenyl)ethylene)-9,10-dihydroxy-6,10-dimethylundec-5-enoic acid

[0033] The carbon spectrum and hydrogen spectrum confirmation data of the NMR of compound 1 are shown...

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PUM

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Abstract

The invention discloses a meroterpenoid compound, a medical composite thereof and the application thereof. The compound has the structure shown as chemical formula (I). The compound has the activity on inhibiting aldose reductase and has a good application prospect.

Description

technical field [0001] The present invention relates to heteroterpenoids, in particular to the heteroterpenoids extracted from fungi and their use as aldose reductase inhibitors. Background technique [0002] Ganoderma lucidum (Leyss.ex Fr.) Karst. belongs to Eumycota, Basidiomycotina, Hymenomycetes, Aphyllophorales, Gamodermataceae , Ganoderma (Ganoderma). It is recorded in "Chinese Materia Medica" that "it is sweet in nature; flat in taste; non-toxic; it belongs to the lung, heart, spleen, and kidney meridians. It benefits qi and blood; calms the mind; strengthens the spleen and stomach. It is mainly used to treat fatigue, palpitations, insomnia, dizziness, and fatigue. , chronic cough, asthma, coronary heart disease, silicosis, and tumors." "Chinese Pharmacopoeia" lists Ganoderma lucidum as a traditional Chinese medicinal material, in which Ganoderma lucidum polysaccharides, triterpenes, nucleosides, alkaloids, amino acid polypeptides, trace elements and other ingredient...

Claims

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Application Information

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IPC IPC(8): C07D307/58C07C59/52A61P3/10A23L33/10A23L31/00
CPCA23L31/00A23L33/10A23V2002/00C07B2200/09C07C59/52C07D307/58A23V2200/328A23V2250/208
Inventor 刘宏伟马兵杨波宝丽陈保送
Owner 峨眉山国芝堂生物科技有限公司
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