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3,4-open-ring helianthemum diterpenoid type compounds, preparing method thereof and applications of the compounds

A compound and diterpenoid technology, applied in the field of 3,4-split-helicanane-type diterpenoids, can solve problems such as unclear active ingredients, achieve anti-inflammatory activity, high clinical application value and development prospects , less toxic and side effects

Active Publication Date: 2015-01-07
HAINAN MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the active ingredient has not been identified

Method used

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  • 3,4-open-ring helianthemum diterpenoid type compounds, preparing method thereof and applications of the compounds
  • 3,4-open-ring helianthemum diterpenoid type compounds, preparing method thereof and applications of the compounds
  • 3,4-open-ring helianthemum diterpenoid type compounds, preparing method thereof and applications of the compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Extraction and identification of compounds I and II of the present invention (method 1)

[0036] After pulverizing the leaves (12.5kg) of Auranthus nudiflora, extracting them under reflux with water for 3-10 times, the ratio of the amount of solvent added to the mass of Auranthus nudiflora leaves is (8-15)L:1kg; The time is 3 hours, the solvent is recovered under reduced pressure, the extract is concentrated, the extracts are combined, filtered, evaporated to dryness under reduced pressure, and the extract is obtained. The extract was suspended in 8000ml of distilled water and extracted with chloroform (3 times). The obtained extracts were combined and concentrated to obtain about (50 g) of chloroform extract. a. Take the chloroform extract and load it onto a silica gel chromatographic column. Different gradients of petroleum ether-acetone mixed solvents (petroleum ether:acetone—200:1-0:100, v / v) were used for elution, and fractions were collected according ...

Embodiment 2

[0038] Example 2 Extraction and identification of compounds I and II of the present invention (method 2)

[0039] After pulverizing the leaves (12.5kg) of Auranthus nudiflora, extracting them under reflux with water for 3-10 times, the ratio of the amount of solvent added to the mass of Auranthus nudiflora leaves is (8-15)L:1kg; The time is 3 hours, the solvent is recovered under reduced pressure, the extract is combined and concentrated to 8000ml, separated by HPD100 macroporous resin adsorption chromatographic column, and then washed with H 2 O, volume fraction 30%, volume fraction 60%, volume fraction 90% ethanol solution elution; Ether: acetone—200:1-0:100, v / v) for elution, and fractions were collected according to the different gradients of the eluent used. b. The (petroleum ether: acetone—100:12, v / v) fractions were separated by column chromatography packed with thin-layer chromatography silica gel. Different gradients of petroleum ether-dichloromethane mixed solvents...

Embodiment 3

[0041] Embodiment 3 Characterization of compounds I and II of the present invention

[0042] After testing the physical and chemical properties and spectral data of compounds I and II, their structures were determined (see figure 1 and figure 2 ). The NMR data of compounds Ⅰ and Ⅱ are shown in Table 1 (see Figure 3-Figure 6 ), the high-resolution mass spectrometry data are shown in Table 2.

[0043] Table 1 NMR data of compounds Ⅰ and Ⅱ a

[0044]

[0045] a. 1 The test condition of H-NMR is 600MHz, and the spectroscopic reagent of compound Ⅰ is CD 3 OD, the patterning reagent of compound Ⅱ is Pyr-d; 13 The test condition of C-NMR is 150MHz, and the spectral reagent of compound Ⅰ is CD 3 OD, the patterning reagent of compound II is Pyr-d.

[0046] Table 2 High resolution mass spectrometry data of compounds Ⅰ and Ⅱ

[0047] sample name

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Abstract

3,4-open-ring helianthemum diterpenoid type compounds, a preparing method thereof and applications of the compounds are disclosed. The structure formulas of the compounds are shown as formulas I and II. The compounds are used for preparation of medicines or healthcare products for inhibiting inflammation, and for preventing and / or treating gynecologic inflammation and acute infectious hepatitis.

Description

technical field [0001] The invention belongs to the field of biochemistry and medicine, and relates to a class of 3,4-split-helicanane type diterpenoids, a preparation method and application thereof. Background technique [0002] Inflammation is a complex defense response of the body with vascular system to damaging factors. Exogenous and endogenous damage factors can cause various damage changes in the cells and tissues of the body, and at the same time, a series of complex reactions also occur locally and throughout the body to limit and eliminate the damage factors, clear and absorb them. The body's comprehensive defense response to necrosis of tissue and cells and repair the damage is called inflammation. [0003] Nitric oxide (NO) is a biologically active gas molecule, an important regulator of intercellular information transmission, and has the function of mediating cellular immunity and inflammatory toxicity. The excessive production of NO is closely related to infl...

Claims

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Application Information

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IPC IPC(8): C07D309/32C07C59/11C07C51/42
CPCC07C51/42C07C59/46C07C2601/14C07D307/54
Inventor 董琳刘明生张小坡
Owner HAINAN MEDICAL COLLEGE
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