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Flavonoid compound as well as preparation method and application thereof

A technology of flavonoids and compounds, applied in organic chemistry methods, drug combinations, organic chemistry, etc., can solve problems such as carcinogenicity, achieve high safety and effectiveness, simple and easy separation path, and expand application value

Active Publication Date: 2020-09-18
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In recent years, the development of effective, low-toxicity, and fast external contraceptives has been a hot spot in the field of reproductive medicine. The current contraceptives are many and mature, and they are widely used. However, female oral contraceptives also have problems such as early pregnancy, bleeding, and carcinogenicity. Therefore, it is very necessary to develop safe and effective in vitro contraceptives

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  • Flavonoid compound as well as preparation method and application thereof
  • Flavonoid compound as well as preparation method and application thereof
  • Flavonoid compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Separation and purification of flavonoid compound Rhynchone A

[0035] The Luhuo of this embodiment is collected from Zaoyang County, Xiangyang City, Hubei Province, and is identified as the dried root of Rhynchosia volubilis Lour., a plant of the genus Luhuo of the legume family. Grinding with a pulverizer until passing through a 24-mesh sieve, soaking and extracting with 70% acetone water for 5 times, adding 6L of solvent for the first time, completely submerging the traditional Chinese medicine Luhuo, standing at room temperature for 24 hours, filtering out the extract, and then adding 70% Acetone water 4.5L, stand at room temperature for 24h, filter out the extract again, repeat the same method until cold soaking 5 times, finally combine the extracts, concentrate under reduced pressure to obtain the first crude extract with a volume of 1L.

[0036] Fully suspend the first crude extract with distilled water to a volume of 1.5L, extract with 1.5 times the vo...

Embodiment 2

[0044] The identification of embodiment 2 flavonoid compound Rhynchone A

[0045] The compound obtained by extracting the examples is subjected to high-resolution mass spectrometry, NMR spectrum detection and structural analysis, and the compound is analyzed using a nuclear magnetic resonance instrument (Bruker Avance III 500MHz NMR spectrometer). 1 H-NMR (500MHz, CDCl 3 ), 13 C-NMR (CDCl 3 ,ppm,125MHz), HSQC, HMBC and 1 H- 1 H COZY detection, HRMS chart of the compound, 1 H-NMR (500MHz, CDCl 3 ), 13 C-NMR (CDCl 3 ,ppm,125MHz), HSQC, 1 H- 1 H COZY and HMBC are respectively as Figure 1-6 As shown, the spectral data obtained by it are shown in Table 1 below:

[0046]

[0047]

[0048] The obtained light yellow oily solid compound, HR-ESI-MS shows quasi-molecular ion peak [M-H] - It is m / z435.1794, (calculated value: [M-H] - 435.1808). The carbon spectrum shows a total of 26 carbon signals, which are consistent with the number of carbon atoms in the molecular...

Embodiment 3

[0057] Embodiment 3 compound Rhynchone A performance

[0058] 1. Effect of compound Rhynchone A on intracellular calcium content of human sperm in vitro

[0059] 1) Sperm sample processing

[0060] Human semen was passed upstream method (add 4mL sEBBS medium to a 50mL centrifuge tube, then add 1mL semen sample at the bottom, 37°C; 5% CO 2 Incubate for 1 hour, draw 3-4mL supernatant) After purification, adjust the sperm concentration to 1×10 7 individual / mL.

[0061] 2) Sperm staining

[0062] After mixing 494 μL upstream purified sperm suspension with 1 μL 2.5 mM Fluo-4 AM (Molecular Probes, Eugen, OR, USA, prepared with DMSO) and 5 μL 5% Pluronic F-127 (Molecular Probes, prepared with sEBBS medium), 37°C; 5% CO 2 Stain in the incubator for 30 minutes (staining at room temperature is also possible, but keep away from light, it is recommended to stain in a 37-degree incubator). Wash twice with sEBBS medium (without dye), and resuspend the pellet with 500 μL sEBBS medium. ...

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Abstract

The invention relates to the technical field of preparation of chemical components of traditional Chinese medicines, in particular to a flavonoid compound as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification, the invention also provides a preparation method of the flavonoid compound, and the flavonoid compound is prepared bytaking dry roots of Rhynchosia volubilius Lour. as a raw material and sequentially adopting acetone extraction, petroleum ether extraction, silica gel column chromatography, gel column chromatographyseparation and high performance liquid chromatography (HPLC) purification. The flavonoid compound can competitively inhibit progesterone through a calcium ion channel acting on human sperms so as to influence sperm activity and show an anti-fertility effect, can be applied to preparation of sperm function related drugs and contraceptive drugs, is derived from anti-fertility traditional Chinese medicines, and is high in safety and effectiveness.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical components of traditional Chinese medicines, in particular to a flavonoid compound and its preparation method and application. Background technique [0002] Luhuo is the dry root of Rhynchosia volubilis Lour., a plant of the genus Luhuo in the leguminous family. It is entwined with herbaceous vines and grows in weeds or climbing trees on hillsides at an altitude of 200-1200m. It is distributed in all provinces in the Yangtze River Basin. Luhuo has the effects of expelling wind and dampness, promoting blood circulation, detoxification, reducing swelling and relieving pain. The main drug in the Northwest folk contraceptive prescription is used for female birth control. The water decoction and alcohol extract of Luhuo root have anti-fertility and anti-pathogenic microorganism effects, but the active ingredient is unknown. [0003] In recent years, the development of effective, low-to...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/352A61P15/00A61P15/16
CPCA61P15/00A61P15/16C07B2200/07C07D493/04
Inventor 方进波罗韬李红钢向槿
Owner HUAZHONG UNIV OF SCI & TECH
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