Flavonoid glycoside and isoquinoline alkaloid complex for inhibiting multi-drug-resistant staphylococcus aureus and preparation of carrier-free nano-drug of flavonoid glycoside and isoquinoline alkaloid complex
A technology of isoquinoline alkaloids and flavonoid glycoside complexes, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., and can solve problems such as no therapeutic effect, toxicity and inflammation, and low drug loading capacity
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Embodiment 1
[0050] This example prepares the complex by the method comprising the following steps.
[0051] The selected raw materials are natural flavonoid glycosides represented by baicalin, scutellarin, and wogonin and their derivative products, as well as berberine, palmatine, coptisine, jatrorrhizine, epiberberine, and cork Alkali is a representative natural isoquinoline alkaloid and its derivatives.
[0052] Taking the baicalin-berberine complex as an example, weigh baicalin and berberine with a molar ratio of 10:1 to 1:10 and dissolve them in water respectively, heat, and adjust the flavonoid glycosides to pH=6-10 to obtain clarification Clear solution. Mix and stir, centrifuge to obtain a precipitate, wash three times with water, and freeze-dry to obtain a brownish-yellow powder, which is the complex. The preparation method of other 23 kinds of complexes is the same.
[0053] The complex prepared in Example 1 was further analyzed by mass spectrometry (static spray-HRMS, Waters,...
Embodiment 2
[0060] In the present embodiment, part of the complex prepared in Example 1 is characterized by NMR (Avance IIIHD400MHz spectrometer, Bruker, America), and the results are as follows:
[0061] NMR attribute of baicalin-berberine complex: 1 H NMR (400MHz, DMSO-d 6 ): δ (ppm) 6.93 (overlap, 2H, H-3, 8, BA), 8.03 (d, J=7.2Hz, 1H, H-2', 6', BA), 7.55-7.62 (m, 3H , H-3', 4', 5', BA), 4.97 (d, J=5.1Hz, 1H, H-1", BA), 3.23-3.36 (m, 3H, H-2", 3", 4″, BA), 3.60 (d, J=9.6Hz, 1H, H-5″, BA), 7.74 (s, 1H, H-1, BBR), 7.02 (s, 1H, H-4, BBR) , 3.19 (m, 2H, 5-CH 2 -, BBR), 4.93 (m, 2H, 6-CH 2 -, BBR), 9.94 (s, 1H, H-8, BBR), 8.08 (d, J=9.0Hz, 1H, H-11, BBR), 7.93 (d, J=9.0Hz, 1H, H-12 , BBR), 8.90 (s, 1H, H-13, BBR), 6.14 (s, 2H, 15-CH 2 -, BBR), 4.07 (s, 3H, 9-OCH 3 , BBR), 3.97(s, 3H, 10-OCH 3 , BBR).
[0062] NMR assignment of scutellarin-berberine complex: SCU-BBR NPs 1 HNMR (400MHz, DMSO-d 6 ): 6.81 (s, 1H, H-8, SCU), 6.99 (s, 1H, H-4, BBR), 7.75 (d, J=7.4Hz, 2H, H-2′, 6′, SCU)...
Embodiment 3
[0065] In the present embodiment, the antibacterial activity of the complex prepared in Example 1 is measured, and the method is as follows:
[0066] The inhibitory effect of the complex on pathogenic bacteria Staphylococcus aureus, opportunistic pathogenic bacteria Escherichia coli, probiotics Bacillus subtilis and Enterococcus faecium, and clinically isolated multidrug-resistant Staphylococcus aureus were observed by turbidimetric method. Staphylococcus aureus, Escherichia coli, probiotics Bacillus subtilis and Enterococcus faecium were all obtained from the College of Life Sciences, Beijing University of Traditional Chinese Medicine. Multidrug-resistant Staphylococcus aureus was obtained from the Laboratory Department of Dongzhimen Hospital, Beijing University of Traditional Chinese Medicine (sample number: 19PXTH0119). The complex powder prepared in Example 1 was sealed and stored at 4°C. Dissolve in LB medium to 1×10 4 The μg / mL stock solution is ready for use (DMSO con...
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