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Sulfur-containing compound with nerve protection effect and application thereof

A neuroprotection and nerve cell protection technology, applied in the field of medicine, can solve problems such as weak inhibitory activity

Inactive Publication Date: 2014-09-17
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, only six sulfur-containing substances have been found, three of which were isolated by us for the first time. We found that these six sulfur-containing substances (including the three that have been discovered) have tyrosinase inhibitory effect, but the inhibitory activity Neither strong

Method used

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  • Sulfur-containing compound with nerve protection effect and application thereof
  • Sulfur-containing compound with nerve protection effect and application thereof
  • Sulfur-containing compound with nerve protection effect and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 N-L-γ-glutamyl-S-coniferyl-L-cysteine ​​and N-[N-L-γ-glutamyl-S-[3-(4-hydroxy-3-methoxyphenyl)-2-propenyl]-L-cysteinyl Preparation of ]-glycine

[0023] (1) Take 15kg of pineapple fruit, cut it into small pieces, mince it with a juice extractor, then extract it with 10L of 95% ethanol for 3 times, filter the part of the ethanol extraction with gauze, then centrifuge at 2000r / min, and recover under reduced pressure at 45°C Solvent until dry, weighed; then add an appropriate amount of deionized water, mix the sample with Amberlite XAD-16 at a ratio of 2:1 (dry ratio), and then apply Amberlite XAD-16 macroporous resin column chromatography, with different concentrations of ethanol Elution (H 2 O / EtOH, v / v, 1 / 0, 9 / 1, 4 / 1, 7 / 3, 3 / 2, 1 / 1, 2 / 3, 3 / 7 and 0 / 1), each eluted 6 column volume, respectively to obtain 9 (Fr.1-9) components. Among them, the component Fr.4 (H 2 O / EtOH, 7 / 3) by MCI column chromatography, with different concentrations of methanol / water (v / v, ...

Embodiment 2

[0033] Embodiment 2 Preparation of N-L-γ-glutamyl-S-sinapyl-L-cysteine ​​and S-sinapylglutathione

[0034] (1) Pineapple extraction, macroporous resin segmentation, MCI and Sephadex LH-20 separation are the same as in Example 1. The difference is that the component Fr.2'' is further separated by preparative HPLC.

[0035] (2) Preparative liquid chromatography separation conditions

[0036] Instrument: Waters600 preparative liquid chromatograph equipped with 2487 dual-wavelength detector.

[0037] Chromatographic column: Phenomenex Luna C18 (2) column (250×21.2 mm, 5 μm).

[0038] Mobile phase: CH 3 CN-H 2 O (v / v, 17 / 83); detection wavelength: 254nm. The chromatographic peaks at 23.7 and 28.3 minutes were collected respectively, and the solvent was recovered to obtain N-L-γ-glutamyl-S-sinapyl-L-cysteine ​​and S-sinapylglutathione.

[0039] (3) NMR data and mass spectrometry data of N-L-γ-glutamyl-S-sinapyl-L-cysteine ​​are as follows:

[0040] 1 H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0043] The preparation of embodiment 3S-sinapyl-L-cysteine

[0044] (1) Pineapple extraction, macroporous resin segmentation, MCI and Sephadex LH-20 separation are the same as in Example 1. The difference is that the component Fr.3'' is further separated by preparative HPLC.

[0045] (2) Preparative liquid chromatography separation conditions

[0046] Instrument: Waters600 preparative liquid chromatograph equipped with 2487 dual-wavelength detector.

[0047] Chromatographic column: Phenomenex Luna C18 (2) column (250×21.2 mm, 5 μm).

[0048] Mobile phase: CH 3 CN-H 2 O (v / v, 15 / 85); detection wavelength: 254nm. The chromatographic peak at 21.3 min was collected, and the solvent was recovered to obtain S-sinapyl-L-cysteine.

[0049] (3) The nuclear magnetic resonance data and mass spectrometry data of S-sinapyl-L-cysteine ​​are as follows:

[0050] 1 H NMR (500MHz, DMSO-d 6 ): δ6.80 (2H, s, H-2, 6), 6.40 (1H, d, J=15.6Hz, H-7), 6.10 (1H, d t, J=15.6, 7.3Hz, H-8) , 3.3...

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Abstract

The invention provides a sulfocompound with a nerve protection effect from pineapple fruit and preparation and application thereof, belonging to the field of medicine. A sulfur-containing compound with a nerve protection effect is separated from the pineapple fruit through various separation means. The compound has a structural formula (I). Cell experiments indicate that the compound has a better protection effect on nerve cells, and can prevent or treat Parkinson, Alzheimer, Huntington, drug abuse, depression and stroke diseases caused by degeneration or injury of nerve cells resulting from various factors.

Description

technical field [0001] The invention relates to a method for isolating and preparing a class of neuroprotective compounds from pineapple fruit, and the use of the compounds and their derivatives in the preparation of drugs for preventing and treating neuronal decline or damage caused by various reasons The application belongs to the field of medicine. Background technique [0002] Pineapple, also known as pineapple, is the fruit of the bromeliad plant pineapple Ananas comosus (L.) Merr. Pineapples are distributed in many tropical and subtropical regions, and are planted in many southerly regions of my country such as Fujian, Guangdong, Hainan, and Guangxi. Pineapple juice is popular because of its pleasant aroma, delicious taste and rich in vitamin C and B1; the fruit or juice of pineapple is widely used in food, such as pizza, cake, ice cream, etc., due to the above benefits. In mainland China, Hong Kong and Chinese gathering areas around the world, pineapple is also ofte...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/023C07C323/58A61K38/06A61K31/198A61P25/28A61P25/14A61P25/16A61P25/30A61P25/24A61P9/10A23L1/305
Inventor 郑宗平王明福巢剑非
Owner JIANGNAN UNIV
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