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Novel phenanthrene compound separated from Pholidota chinensis Lindl, preparation method and application thereof

A compound and phenanthrene-like technology, applied in the field of new phenanthrene-like compounds and their preparation, can solve problems such as unclear mechanism of action and uncertain active ingredients, and achieve the effect of huge market potential and broad application fields

Active Publication Date: 2021-01-08
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] It has been reported in the literature that Shixiantao extract has anti-tumor, anti-bacterial, anti-inflammatory, and anti-oxidant effects, but its mechanism of action is not clear due to uncertain active ingredients

Method used

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  • Novel phenanthrene compound separated from Pholidota chinensis Lindl, preparation method and application thereof
  • Novel phenanthrene compound separated from Pholidota chinensis Lindl, preparation method and application thereof
  • Novel phenanthrene compound separated from Pholidota chinensis Lindl, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Extract the whole herb part of Shixiantao with ethanol to obtain the ethanol extract;

[0039] The specific operation is as follows: take the dried whole herb part of Shixiancao, crush it, add 85% industrial ethanol according to the mass volume ratio of 1:3-5 (15kg:45L), extract three times, combine the three supernatants, concentrate in vacuum, and refrigerate at -80°C spare;

[0040] (2) The ethanol extract is put on a normal phase silica gel column, followed by petroleum ether / acetone solution (10:1, 7:1, 5:1, 3:1, 1:1, 0:1 (here refers to all acetone) , volume ratio) to carry out gradient elution, collect the eluent respectively, and concentrate the 0:1 petroleum ether / acetone solution, that is, the acetone eluent until the acetone is completely recovered;

[0041] (3) The acetone elution site is further loaded on a normal-phase silica gel column, followed by gradient elution with chloroform / methanol (30:1, 10:1, 5:1, 1:1, volume ratio), and the collected chlor...

Embodiment 2

[0047] The structure identification process of the new phenanthrene class composition in embodiment 1 is:

[0048] 1. Spectral data

[0049] 2-methoxy-3,7-dihydroxy-5H-phenanthro[4,5-bcd]pyran, brown powder, UV spectrum (methanol) λmax (logε) nm: 238 (1.58); infrared spectrum νmax cm-1: νmax 3450 ,3018,2976,2944,2904,2837,1627,1602,1529,1439,1388,1292,1152,1042,853; 1 H and 13 C NMR data, Table 1; High resolution mass spectrum: HRESIMS (m / z 267.0663 [M-H] + (calcd for C 16 h 11 o 4 ,267.0736), low resolution mass spectrum m / z:267[M-H] + .

[0050]2. Determination of the structural formula

[0051] Compound from HRESIMS (m / z 267.0663[M-H] + (calcd for C 16 h 11 o 4 ,267.0736)) deduced its molecular formula as C 16 h 12 o 4 .

[0052] to it 1 H and 13 Analysis of the C NMR data (Table 1) revealed a total of 16 carbon atom signals, 1 CH 3 Signal (δ C 56.0), 1 CH 2 Signal (δ C 64.3), 5 CH signals (δ C 106.6, 102.1, 103.9, 123.9, 126.7), nine quaternary car...

Embodiment 3

[0069] This embodiment carries out the effect of new phenanthrene compounds on Staphylococcus aureus:

[0070] 1. Experimental materials and methods:

[0071] Staphylococcus aureus subsp.aureus ATCC29213 was purchased from China General Microbiological Culture Collection Center (CGMCC). Add the sample to be tested into a 96-well culture plate, and dilute the sample in multiples, so that the final concentrations are 200 μM, 100 μM and 50 μM respectively; add bacterial liquid to each well, and the final concentration is 5×10 5 CFU / mL; Incubate at 37°C for 24 hours, measure the OD value at 625nm with a microplate reader. At the same time, the experiment set up medium blank control, bacterial control and penicillin G sodium positive drug control.

[0072] 2. Experimental results:

[0073] As shown in Table 2, the results show that the new compound (prepared in Example 1) treatment group has a good inhibitory effect on Staphylococcus aureus, and it is concentration-dependent, th...

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Abstract

The invention discloses a novel phenanthrene compound separated from Pholidota chinensis Lindl, wherein the molecular formula of the phenanthrene compound is C16H12O4, and the structural formula of the phenanthrene compound is shown in the specification. The invention further discloses a preparation method of the novel phenanthrene compound and application of the novel phenanthrene compound in preparation of drugs with an anti-staphylococcus aureus effect. According to the preparation method of the novel phenanthrene compound separated from Pholidota chinensis Lindl, the prepared 2-methoxy-3,7-dihydroxy-5H-phenanthro[4,5-bcd]pyran active substance is a novel phenanthrene compound, has an anti-staphylococcus aureus effect, is wide in application field and huge in market potential, and has important significance in discovering a novel antibacterial lead compound and promoting the development of antibacterial drugs.

Description

technical field [0001] The invention belongs to the technical field of shixiantao, and in particular relates to a novel phenanthrene compound isolated from shixiantao, its preparation method and application. Background technique [0002] Shixiantao is the whole plant of Pholidota chinensis Lindl., a plant of the genus Pholidota chinensis Lindl. in the family Orchidaceae, commonly known as Shishanglian, Shishanglian, Shichuanpan, etc. It is sweet in nature and cool in taste, and has the effects of nourishing yin, clearing away heat, promoting dampness and eliminating blood stasis. It is commonly used by folks to treat hypertension, dizziness and headaches caused by various reasons. [0003] The phytochemical constituents of the genus Stemophila mainly include phenanthrene, bibenzyl, stilbene, triterpenes, lignans, steroids and phenolic acids, among which phenanthrene compounds are the main components. Phenanthrene compounds have good pharmacological activities, such as anti-...

Claims

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Application Information

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IPC IPC(8): C07D311/78A61P31/04
CPCA61P31/04C07D311/78
Inventor 遆慧慧赵昕余茜庄子熙
Owner GUANGDONG PHARMA UNIV
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