New monoterpene compounds and preparation method thereof

A technology of compound and monoterpene, which is applied in the field of new monoterpene compound and its preparation, to achieve good analgesic effect, less environmental pollution, and a single conversion product

Inactive Publication Date: 2009-10-14
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore it is difficult to obtain compounds I and II which are theoretically easier to obtain by chemical methods

Method used

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  • New monoterpene compounds and preparation method thereof
  • New monoterpene compounds and preparation method thereof
  • New monoterpene compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0042] 1. Analgesic effect of compounds I and II--rat writhing experiment

[0043] Experimental method: 50 male rats were taken and randomly divided into blank control group, positive control group, paeony glucoside injection group (100mg / kg), compound I group (100mg / kg) and compound II group (100mg / kg ), 10 animals in each group. Respectively tail vein injection of physiological saline, positive drug (Kanglaite injection), paeony glucoside injection, compound I salt solution and compound II salt solution, after 30 minutes of administration, intraperitoneal injection of 1% acetic acid (0.5ml / only), observe and record the number of writhing times in the two time periods of 0-15 minutes and 15-30 minutes after injection of acetic acid. As shown in Table 1, compounds I and II can significantly reduce the number of writhing reactions in rats, and have slightly stronger analgesic effects than paeony glucoside injection. There was also a significant difference between the positiv...

Embodiment 2

[0057] Dried herba peony slices 1Kg, boiled with water to extract twice, each time for 2 hours, the extract was filtered and passed through a reverse adsorption resin column, and then eluted with alcohol-water solution (50%), and the eluent was concentrated and then layered with alumina column Analysis was carried out to obtain 12.5 g of extract rich in pinane monoterpene glycosides (the content of paeonifloride glycosides detected by liquid phase was 42.2%). 5 g of the pinane-like monoterpene glycoside extract was dissolved and added to the fermentation broth of the bacteria [Penicillium melini 3.4474 (xxl)] that had been cultured for 48 hours, and the shake flask was removed after continuing to cultivate for 72 hours. The fermentation broth was suction filtered to remove the mycelium, the filtrate was concentrated under reduced pressure to a small volume, extracted three times with an equal amount of ethyl acetate, the extracts were combined, concentrated under reduced pressu...

Embodiment 3

[0059] 500 mg of compound I was dissolved and added to the fermentation broth of the thallus [Cocephala racemosa 3.264 (xxl)] that had been cultured for 48 hours, and the shake flask was removed after continuing to cultivate for 72 hours. The fermentation broth was suction filtered to remove the mycelium, the filtrate was concentrated under reduced pressure to a small volume, extracted three times with an equal amount of ethyl acetate, the extracts were combined, concentrated under reduced pressure, and dried in vacuo to obtain 600 mg of coarse powder. Dissolve the coarse powder with methanol, stir in 1.8g of 100-140 mesh silica gel, evaporate the solvent until dry, and wait for sample loading. Take 24g of 200-300 mesh silica gel, wet-pack the column, and then add the mixed sample silica gel for column chromatography. Using dichloromethane:methanol (30:1) as the eluent, collected in sections, detected by TLC, and combined single spots to obtain 200 mg of white powder (yield 70...

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Abstract

The invention pertains to the technical field of medicine, which discloses new monoterpene compounds and a preparation method thereof. A compound I is prepared by the following steps of conducting microbial transformation of carboxylesterase on an extract which is rich in pinane monoterpene and separating the transformation product by utilizing a silica gel column chromatography method. A compoundII is prepared by the following steps of conducting microbial transformation of glucosaccharase on the compound I and separating the transformation products by utilizing a silica gel column chromatography method. The chemical names of the compound I and the compound II are respectively (1R, 3R, 4R, 6S, 9S)-6-methyl-4-hydroxyl-1- (Bata-D-glucopyranoside oxyl)-9-(hydroxymethyl-7-oxotrane (4.3.0.0<3, 9>) nonane-8-ketone and (1R, 3R, 4R, 6S, 9S)-6-methyl-1, 4-dihydroxyl-9-(hydroxymethyl-7-oxotrane (4.3.0.0<3, 9>) nonane-8-ketone. Pharmacological tests show that the two monoterpene compounds disclosed by the invention have good antinociceptive effect. The preparation method is simple and has low cost and less pollution to environment.

Description

Technical field: [0001] The invention relates to the technical field of bioorganic chemistry, and relates to a new class of monoterpene compounds and a preparation method thereof. Background technique: [0002] In recent years, it is a research hotspot in the field of bioorganic chemistry to systematically modify and modify the structure of active monomers in natural products to prepare compounds with better activity and lower toxicity. application prospects. The inventor has been engaged in chemical and biological research of natural products for many years, especially has in-depth research on terpenoids. Oxygenated compounds of monoterpenoids have strong biological activity and are important raw materials for medicine, cosmetics and food industry. [0003] Monoterpene and monoterpene glycosides in Paeoniae officinalis are the main material basis of its activity. The representative components in Paeoniae officinalis: paeoniflorin and paeoniflorin are monoterpene glycoside...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/00C07H17/04C12P17/04C12P19/60A61K31/365A61K31/7048A61P29/00
Inventor 游松徐秀玲刘伟孙燕赵静郑亚明
Owner SHENYANG PHARMA UNIVERSITY
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