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Coumarin compound acidulated by glucal and application thereof

A technology of glucuronic acid and coumarin, which is applied in the field of medicine and can solve the problem of anti-cancer activity reports only targeting

Inactive Publication Date: 2009-12-30
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, although daphnetin and escin have been reported to have anti-inflammation, their anti-cancer activity is only reported against renal cancer cells [Finn GJ et al., (2002) Cancer Letters183: 61-68]

Method used

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  • Coumarin compound acidulated by glucal and application thereof
  • Coumarin compound acidulated by glucal and application thereof
  • Coumarin compound acidulated by glucal and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1 preparation compound GLU002 and GLU003

[0064] Weigh 1g daphnetin (7,8-dihydroxycoumarin) sample (measured by HPLC external standard method, content is 99%, LC-MS spectrogram see figure 1 ) was dissolved in 1ml of methanol system, added to the 100ml reaction system of potassium phosphate buffer (pH 7.4) containing rat liver microsomes (0.5mg / m1) and UDPGA (5μM) and fully reacted for 2h, HPLC detection showed daphnetin conversion completely. After centrifugation, the reaction solution was rotary evaporated to 10ml, and passed through a reverse phase (YMC, C18 column) high-performance liquid chromatography system, using a mobile phase of water: acetonitrile (50:50) to rinse at a flow rate of 1ml / min to obtain 80mg of compound GLU002 (content 98%, LC-MS spectrum see figure 2 ) and 78mg GLU003 (content 95%, LC-MS spectrum see image 3 ). The preparation of other glucuronidated coumarin compounds is similar to the reaction conditions and steps.

Embodiment 2

[0065] Embodiment 2 Glucuronidated coumarin compound anti-arthritis experiment

[0066] Twenty-one SD rats with a body weight of about 200 g were injected into the right paw with 0.1 ml of Freund's complete adjuvant, and were randomly divided into 3 groups after 7 days, that is, group A fed with 50 mg / kg of glucuronidated coumarin compounds every day, Group B fed distilled water daily. In addition, 7 SD rats without any treatment were set as the normal control group C. After 21 days, the size of the swelling on the right paw of the rats in each experimental group was measured, and blood was collected from the carotid artery to measure the serum immune indexes. The relevant results are shown in Table 1.

[0067] Table 1 Experimental results of rat arthritis model

[0068]

[0069]

[0070] Mean±S.D., n=7.

[0071] #P<0.05 vs. normal group.

[0072] *P<0.01 vs. model group.

Embodiment 3

[0073] Embodiment 3 glucuronidated coumarin compound antitumor activity experiment

[0074] In vitro anti-tumor activity test: leukemia cells (K562), non-small cell lung cancer cells (A549), colon cancer cells (HT-29), ovarian cancer cells (OVCAR-3), human osteosarcoma cells (Saos-2), Six kinds of tumor cells including breast cancer cells (MCF-7) were used to determine the in vitro antitumor activity of twenty kinds of glucuronidated coumarin compounds. Six kinds of tumor cells were inoculated in 96-well flat-bottomed culture plates respectively, added with sterile culture medium of RPMI 1640+10% NBS+gentamycin, and incubated at 37°C in CO 2 Incubate in an incubator for 24h. After the drug is dissolved with DMSO, it is diluted with a culture medium to a solution with different concentration gradients, and the final concentration of DMSO is lower than 0.1%. After being cultured for 48 h under the action of the test compound, the cell viability was determined by the SRB method...

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Abstract

The invention relates to a coumarin compound acidulated by glucal and application thereof. The compound has a structure showed in the right formular, wherein R is one of-H, -OH, -CH3, -OCH3, -NH2 or ester group; and R1, R2, R3 and R4 are one of -H, -OH, -CH3, -SH, -OCH3, -NH2 or glucal acid group. The coumarin compound acidulated by the glucal has the activities of resisting arthritic and tumor.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a series of glucuronidated coumarin compounds and applications thereof. Background technique [0002] Coumarin compounds widely exist in plants and microbial metabolites such as Umbelliferae, Fabaceae, Rutaceae, Compositae, Saxifragaceae, Daphneaceae, etc. At present, there are more than 1,300 coumarin compounds that have been discovered [Bruneton J et al., (1999) Lavoisier Publishing: Paris, 225-459.]. Preliminary studies have shown that this type of compound has a wide range of medicinal activities including: anti-inflammatory, anti-coagulation, anti-tumor and AIDS. At the same time, there is an obvious metabolic relationship between structure and activity of these compounds [Thuong PD et al., (2009) Phytother.Res.]. Such as: hyoscyamine as an antifungal agent and warwarin as an anticoagulant. [0003] Lin Guoqiang et al. (CN 1679540A) derived and synthesized a s...

Claims

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Application Information

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IPC IPC(8): C07H17/075A61K31/7048A61P19/02A61P35/00
Inventor 杨凌梁思成葛广波刘慧鑫张延延
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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