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Vokapalane-type diterpene derivative, preparation method and application thereof

A technology of vocapane-type and derivatives, which is applied in the field of vocapane-type diterpene derivatives and their preparation, and can solve the problems of no maintenance effect, side effects, and slow onset of immunosuppressants

Active Publication Date: 2022-07-22
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, aminosalicylic acid drugs are the main drugs for the treatment of mild and moderate UC, but they have relatively large toxic and side effects; adrenal glucocorticoids are drugs for suppressing acute active inflammation, but long-term use has no maintenance effect; immunosuppressants have slow onset of action , with severe side effects of myelosuppression

Method used

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  • Vokapalane-type diterpene derivative, preparation method and application thereof
  • Vokapalane-type diterpene derivative, preparation method and application thereof
  • Vokapalane-type diterpene derivative, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] 20.0kg of hematoxylinum seeds, peeled to obtain 9.0kg of seed kernels, extracted with 75% ethanol for 3 times, the ratio of material to liquid is 1:8, each time 2h, the solvent is recovered under reduced pressure, the extract is dispersed with distilled water, followed by It was extracted three times with equal volumes of chloroform, ethyl acetate and n-butanol to obtain 214.0 g of chloroform layer extract.

[0055] The obtained chloroform layer extract 214.0g was separated by silica gel open column chromatography, and the mobile phase was eluted with a gradient of dichloromethane: methanol (100:0-1:1), and the obtained fractions were analyzed by silica gel thin layer chromatography, and the same was combined. After fractionation, 10 fractions of eluate were obtained.

[0056] Fraction 18.8 g of dichloromethane:methanol=100:2 was separated. Using silica gel column chromatography, eluting with a gradient of petroleum ether:ethyl acetate, at 15:1, the yellow solid was se...

Embodiment 2

[0058] Screening of in vitro anti-inflammatory activities of diterpene derivatives of vokaparaane

[0059] (1) Cell culture

[0060] RAW264.7 cells in DMEM, 5% FBS, 37 °C, 5% CO 2 cultured under conditions.

[0061] (2) Activity test

[0062] To test the in vitro anti-inflammatory activity of the test drugs, the compounds at a final concentration of 10 μM were incubated with LPS-stimulated RAW264.7 cells for 6 h, and then the inflammatory cytokines IL-1β, IL-6 and TNF-α were detected by q-PCR. alpha mRNA levels.

[0063] The experimental results are shown in Table 1-3.

[0064] Table 1 The effect of vokapalane-type diterpene derivatives on LPS-induced expression of IL-1β mRNA in RAW264.7 cells

[0065]

[0066] Table 2 The effect of vokapalane-type diterpene derivatives on LPS-induced expression of pro-inflammatory factor IL-6 mRNA in RAW264.7 cells

[0067]

[0068] Table 3 The effect of vokapalane-type diterpene derivatives on LPS-induced TNF-α mRNA expression in...

Embodiment 3

[0072] The effect of compound 3 on dextra sulfate sodium (DSS)-induced ulcerative colitis in mice was tested.

[0073] (1) Model establishment

[0074] First, 6-8 weeks old C57BL / 6 mice (20±2g) were randomly divided into 5 groups, 5 mice in each group, namely: Normal group, DSS group, compound 3 group (10mg / kg) and dexamethasone group (Dex) (1 mg / kg). DSS with a concentration of 3% was prepared with distilled water, and the model group and each administration group drank freely for 7 days. Then, the model group and each administration group were changed to distilled water to drink freely for 3 days, and the Normal group was given distilled water to drink freely for 10 days. Mice were sacrificed every day. From the first day of modeling to the tenth day of sacrifice, compound 3 solution (compound 3 was first dissolved in DMSO and then suspended in PBS, wherein DMSO:PBS=1:100) was administered by intraperitoneal injection. The DSS group was intraperitoneally injected with DMS...

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Abstract

The invention belongs to the technical field of medicine, and relates to a voucapane-type diterpene derivative and a preparation method and application thereof. The structure of the derivative is as follows: wherein, the A / B ring is trans-parallel combined; the C ring is a benzene ring; R 1 , R 2 , R 3 , R 7 and R 8 is any one or more of H, OH, OAc, =O, and one or more of esters derived from -OH at the corresponding position; R 6 is H or OH; R 4 , R 5 and R 9 for‑CH 3 , ‑CH 2 Any one or more of OH, ‑COOH, ‑CHO, and ‑CH in the corresponding position 2 One or more of OH and -COOH derived esters. The wokaparaane-type diterpenes and pharmaceutically acceptable salts, isomers or pharmaceutical compositions thereof have immunomodulatory and anti-inflammatory effects, and can be used for preparing immunomodulators or anti-inflammatory drugs, especially anti-inflammatory drugs. Ulcerative colitis medication.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a voucapane-type diterpene derivative and a preparation method and application thereof. Background technique [0002] Caesalpinia Bonduc (Linn) Roxb. is a genus of leguminous cloud, also known as large stipule cloud. It is distributed in tropical and subtropical regions. In my country, it is mainly distributed in Guangdong, Guangxi and Taiwan. Its main medicinal parts are seeds, which have antimalarial, antipyretic, antispasmodic, rheumatic, expectorant, and antitussive effects, and are mostly used to treat dysentery, headache, fever, gastrointestinal discomfort, and asthma. Studies have shown that diterpenoids isolated from thorn hematoxylinum and the same genus (Yunshi genus) have good antimalarial properties (Kalauni S K, Awale S, Tezuka Y, et al. Antimalarial Activity of Cassane-and Norcassane- Type Diterpenes from Caesalpinia crista and Their Structure-Activity Relationship[...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77A61P29/00A61P37/02A61P1/04A61K31/343
CPCC07D307/77A61P29/00A61P37/02A61P1/04C07B2200/07
Inventor 高慧媛刘婷申雪英李先哲李楠袁久志
Owner SHENYANG PHARMA UNIVERSITY
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