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Cycloneolignan-type lignan enantiomers and their preparation and application

A technology of enantiomers and lignans, applied in medical preparations containing active ingredients, separation/purification of carboxylic acid esters, drug combinations, etc., can solve problems that have not yet been patented or reported in literature, and achieve The effect of novel structure

Active Publication Date: 2022-02-15
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The enantiomers and activities of the cycloneolignan-type lignans involved in the present invention have not been patented or reported in the literature so far.

Method used

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  • Cycloneolignan-type lignan enantiomers and their preparation and application
  • Cycloneolignan-type lignan enantiomers and their preparation and application
  • Cycloneolignan-type lignan enantiomers and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the preparation of formula 1a compound and formula 1b compound:

[0048] Take the dried Isatis indigo medicinal material, soak overnight with 2 times the volume of ethanol water, then extract 2-3 times with 5-8 times the volume of ethanol water, the volume concentration of ethanol is 70-80%, and the extraction adopts heating and reflux extraction or ultrasonic extraction. Combine all the extracts, concentrate under reduced pressure, recover the solvent, and dry to obtain the extract after completing the concentration under reduced pressure. The extract is separated by polyamide column chromatography, and the mixed solvent of ethanol-water with a volume ratio of 30-90% is used for gradient elution. Among them, 30% of the eluted part is separated by HP-20 macroporous resin column chromatography, and gradient elution is carried out with a mixed solvent of ethanol-water with a volume ratio of 0-90%. The 60% eluted part was separated by ODS column chromatogra...

Embodiment 2

[0049] Embodiment 2: MTT method detects the impact of formula 1a compound and formula 1b compound on human neuroblastoma SH-SY5Y cell viability:

[0050] 1. Cell culture

[0051] Neuroblastoma SH-SY5Y cell line (purchased from American Type Culture Collection ATCC, Manassas, USA) and DMEM medium containing 10% FBS (purchased from Logan Hyclone, Logan, USA), at 37°C, 5% CO 2 After 24 hours, the cells adhered to the wall, and the old culture medium was discarded.

[0052] 2. Cell grouping

[0053] Blank group: cultured only with DMEM complete medium without any drugs.

[0054] Model group: After the cells were cultured in DMEM complete medium for 4 hours, 1mM MPP was added + , continue to cultivate for 36 hours.

[0055] Group 1a: After the cells were cultured in complete DMEM medium for 4 hours, different concentrations (12.5 μM, 25 μM, 50 μM) of the compound of formula 1a were added for 1 hour, and then 1 mM MPP was added + , continue to cultivate for 36 hours.

[0056]...

Embodiment 3

[0064] Embodiment 3: Annexin V-FITC / PI double staining method detects formula 1a compound and formula 1b compound to MPP + Effects of induced apoptosis in human neuroblastoma SH-SY5Y cells.

[0065] 1. Cell culture steps are the same as in Example 1

[0066] 2. Cell grouping

[0067] The specific steps are the same as in Example 2, wherein the concentrations of the compound of formula 1a and the compound of formula 1b are both 12.5 μM.

[0068] 3. Annexin V-FITC / PI double staining

[0069] The apoptosis rate was detected by Annexin V-FITC and PI apoptosis detection kit. First stained with AnnexinV-FITC and then stained with PI for 15 minutes at room temperature. The apoptosis rate was quantified by flow cytometry (Becton Dickinson, Franklin Lakes, USA).

[0070] 4. Statistical processing is the same as in Example 2

[0071] 5. Experimental results

[0072] Experimental results such as Figure 14 As shown, compared with the control group, 1mM MPP alone + When treated, ...

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Abstract

The invention belongs to the technical field of medicine, and relates to cycloneoliginoid lignan enantiomers and their preparation and application. It specifically relates to a pair of cycloneolignan-type lignan enantiomers isolated from the leaves of the medicinal plant Isatis indigo and a preparation method thereof. The medicinal parts of the leaves of the woad are extracted with ethanol and concentrated under reduced pressure. After the crude extract was obtained, it was suspended in water, eluted with different types of open chromatographic columns and an alcohol-water system, and then enantiomers were obtained by preparative HPLC and chiral resolution. The enantiomer provided by the invention has anti-PD activity, which can enrich the new medical application of Isatis indigo leaves for anti-PD. The compound obtained by the invention has novel structure, reasonable method design, simple process, low cost, low energy consumption and low pollution in the production process.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to cycloneoliginoid lignan enantiomers and their preparation and application. Specifically, it relates to a pair of new cycloneoliginoid lignan enantiomers isolated from the leaves of the medicinal plant Isatis indigo and its new anti-PD medical application. Background technique [0002] Parkinson's disease (PD) is a neurodegenerative disease that occurs frequently in the elderly. The main clinical features are movement disorders, including progressive slowness of movement, muscle rigidity, resting tremor, and abnormal posture and gait. A large number of non-motor symptoms (NMS), such as hyposmia, constipation, depression, sleep disturbance, etc. Patients in the late stage of the disease are often unable to take care of themselves due to balance disorders, falls, freezing of gait, dysphagia and language barriers, and even lie in bed for a long time, seriously reducing the quality of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/48C07C69/757A61K31/216A61P25/16A61P25/00
CPCC07C67/48C07C69/757A61P25/16A61P25/00C07C2601/04C07B2200/07
Inventor 宋少江黄肖霄娄丽丽洪伟奚宇菲宋晓宇刘思帆
Owner SHENYANG PHARMA UNIVERSITY
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