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Oxidized labdane diterpenoid compound as well as separation method and application thereof

A separation method and compound technology, applied in the separation/purification of carboxylic acid compounds, organic chemical methods, active ingredients of anhydride/acid/halide, etc., can solve problems such as poor effect and achieve good anti-inflammatory effect

Pending Publication Date: 2021-12-07
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Diterpenoids reported by Wang Z.H. et al. (Wang Z.H., Xu H.J., Zhai Y.Y., et al. Three new labdane-type diterpenoids from Callicarpa macrophylla Vahl., Natural Produvt Research, doi.org / 10.1080 / 14786419.2018.1509336)", part Helicanoid-type diterpenoids are anti-inflammatory, but less effective

Method used

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  • Oxidized labdane diterpenoid compound as well as separation method and application thereof
  • Oxidized labdane diterpenoid compound as well as separation method and application thereof
  • Oxidized labdane diterpenoid compound as well as separation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Preparation of highly modified helianthin-type diterpenoids

[0049] Include the following steps:

[0050](1) Pulverize the dried Auranthus nudiflora leaves, heat to boiling with 2L of water per kilogram of Aurantia nudiflora, keep boiling and extract 2 times, extract 1.5h each time, combine the extracts, concentrate under reduced pressure to obtain a crude extract ( about 300g);

[0051] (2) Take every 100 grams of crude extract and add 300 mL of distilled water to dilute to make a suspension, then use dichloromethane and ethyl acetate to extract 3 times successively, combine the organic phases, and concentrate under reduced pressure to obtain a medicinal extract; each extracted organic The volume consumption of solvent is 1.2 times of water volume.

[0052] (3) Take the medicinal extract (about 10 g) obtained by extraction with ethyl acetate in step (2), first pass through silica gel column chromatography, and use chloroform-acetone mixed solvent to carry ...

Embodiment 2

[0054] Example 2 Preparation of highly modified helianthene-type diterpenoids

[0055] Include the following steps:

[0056] (1) Grind the dried Zizhu tablets, heat to boiling with 2.5L of water per kilogram of Zizhu powder, keep boiling and extract 3 times, extract for 1 hour each time, combine the extracts, concentrate under reduced pressure to obtain the crude extract (about 320g);

[0057] (2) After diluting every 100 grams of crude extract with 400 mL of water to make a suspension, extract it 4 times with dichloromethane and ethyl acetate successively, combine the organic phases, and concentrate under reduced pressure to obtain a medicinal extract; the organic solvent extracted each time The volume dosage is 1.3 times of the water volume.

[0058] (3) Take the medicinal extract (about 12 g) obtained by extraction with ethyl acetate in step (2), first pass through silica gel column chromatography, and use chloroform-acetone mixed solvent to carry out gradient elution, an...

Embodiment 3

[0060] Example 3 Structural identification of highly modified helianthene diterpenoids

[0061] Using Spectrum ( 1 H NMR, 13 Modern structure identification techniques such as C NMR, HSQC, HMBC, NOESY) and MS determine the chemical structures of compounds I and II obtained in Example 1 and Example 2.

[0062] The structural identification data are as follows:

[0063] Compound I: It is a colorless oil, easily soluble in methanol. After high resolution mass spectrometry HRESI(-)MS(m / z 357.2032[M+Na] + , theoretical value 357.2036) determine that its molecular formula is C 20 h 30 o 4 ;according to 1 H, 13 C and two-dimensional nuclear magnetic resonance data to determine its structure, the skeleton type is helianthene diterpene. After methanol volatilized slowly, the single crystal of the compound was obtained, as shown in the figure below, the absolute configuration was determined to be 5R, 7S, 9R, 10R, that is, the compound is

[0064] 3-oxo-7-hydroxy-8(17), 13-ent-...

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PUM

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Abstract

The invention belongs to the technical field of phytochemistry, and discloses an oxidized labdane diterpenoid compound as well as a separation method and application thereof, and the C-3 site of the A ring of the compound is oxidized. The compound I and the compound II are obtained through multi-stage separation steps of water extraction, polar solvent extraction, organic solvent gradient elution, liquid chromatography separation and the like. A pharmaceutical activity experiment shows that the compound has obvious anti-inflammatory activity, and shows that the compound has a good application prospect in the aspect of preparing the medicine for preventing or treating inflammation.

Description

technical field [0001] The invention relates to a natural plant extract, in particular to an oxidized helianthin-type diterpenoid compound, a separation method and application thereof. Background technique [0002] Callicarpa nudiflora (Callicarpa nudiflora Hook.et Arn.), also known as Chaifengbai and Jiejiehong, is a plant of the genus Callicarpa in the family Verbenacase. herbs. The above-ground parts of Nadihua Zizhu can be used as medicine, which has anti-inflammatory and detoxifying effects, disperses blood stasis and swelling, antibacterial and hemostasis, etc. It is clinically used for various postoperative hemorrhagic diseases such as dermatology, gynecology, facial features, and surgery. It has been included in the new Chinese medicine varieties in the 2015 edition of "Chinese Pharmacopoeia". [0003] The research reports on the chemical constituents of Auranthus nudica are mainly flavonoids (glycosides), phenylpropanoids (glycosides), diterpenes, triterpenes, ir...

Claims

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Application Information

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IPC IPC(8): C07C59/90C07C51/42C07C51/47C07C51/48A61K31/19A61P29/00A61P1/00A61P11/00A61P1/04A61P11/08
CPCC07C59/90C07C51/42C07C51/47C07C51/48A61P29/00A61P1/00A61P11/00A61P1/04A61P11/08C07B2200/07C07C2602/28Y02A50/30
Inventor 余章昕陈光英李小宝韦银约赵禹恒曹彦翔
Owner HAINAN NORMAL UNIV
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