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Hellebore petunidin space isomer compound and preparation and application thereof
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A technology of spatial isomers and compounds, which is applied in the field of dienolactone compounds, can solve the problem of few reports of spatial isomers
Inactive Publication Date: 2013-02-27
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology
[0004] There are more than 250 kinds of such compounds reported so far, but there are very few reports of spatial isomers
Method used
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Embodiment 1
[0023] Embodiment 1: Preparation of bufadienolactone extract
[0024] Get 5Kg of toad skin and extract 3 times with 95% ethanol, the amount of alcohol used is 10 times, and the extraction time is 120 minutes each time. %-50% ethanol for elution, and then 70%-100% ethanol for elution, collect the latter, recover the solvent under reduced pressure, and dry to obtain 62 g of bufadienolactone extract.
Embodiment 2
[0025] Embodiment 2: Preparation of bufadienolactone fraction
[0026] The bufadienolactone extract obtained in Example 1 was separated by preparative HPLC (XterraC18, A: 0.1% (v / v) formic acid in water; B: 0.1% (v / v) formic acid in acetonitrile, gradient conditions: 5% B to 95% B, 60 min;), during the separation process, an ultraviolet detector is used for detection, and the detection wavelength is 300 nm. Each fraction was collected according to the retention time of different sample peaks during the detection process; a total of 20 fractions (Fraction1-20) were collected.
Embodiment 3
[0027] Embodiment 3: the preparation of compound I
[0028] Fraction 5 reclaims the solvent, separates through HPLC (cyclodextrin chromatographic column, A: n-hexane; B: isopropanol, gradient condition: 5% B ~ 30% B, 55min), collects wherein main chromatographic peak, recovers solvent respectively , determined by NMR experiments, obtained a fraction 3mg containing compound I (peak 3), and the HPLC detection content was 99%, and the rationale was determined. The data are as follows: white powder, HR-MS, [M+H]+(m / z) : 417.2275, UV: 298nm, 1 HNMR (CD 3 OD, 400MHz) δ: 10.12 (1H, s), 8.01 (1H, dd, J=9.6, 1.6), 7.56 (1H, s), 6.43 (1H, d, J=9.6), 3.55 (1H, m) , 2.17(1H, d, J=5.6), 0.78(1H, s), etc.; 13 CNMR (CD 3 OD, 100MHz) δ: 210.2, 167.9, 155.4, 145.1, 133.2, 117.5, 86.2, 70.8, 69.3, 55.7, 51.2, 47.3, 43.2, 42.5, 35.7, 36.8, 31.2, 31.6, 26.3, 25.2, 23.9, 22.4, 19.7.
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Abstract
The invention provides a hellebore petunidin space isomer compound and preparation and application thereof. The hellebore petunidin space isomer compound is prepared from the conventional Chinese medicinal toad skin by using macroporous resin and a two-dimensional preparation chromatographic separation technology. The compound is prepared by mainly comprising the following steps of: cutting the toad skin into pieces; extracting with ethanol; separating a total extract by using the macroporous resin to obtain a toad bufadienolides extract; and performing two-dimensional preparation chromatographic separation and purification to obtain the compound. An in-vitro experiment proves that the compound has a good tumor cell suppression effect.
Description
technical field [0001] The present invention relates to diene lactone compounds, specifically a novel compound of helleboregenin space isomers and a preparation method thereof, which is a kind of process developed from traditional Preparation of new compounds isolated from traditional Chinese medicine toad skin. Background technique [0002] Toad is an earlier drug in the clinical application of traditional Chinese medicine, and has a history of clinical application in my country for thousands of years. Its medicinal parts are: skin, toad venom, dry whole. Toad skin has the effect of clearing away heat and detoxifying, diuresis and reducing swelling. It is pungent, cool and slightly poisonous. Acta Pharmaceutica Sinica, 2007, 42(8): 858-861). [0003] Dienolactone compounds are the main active ingredients in toad skin, and modern pharmacological studies have shown that they have cardiotonic, antibacterial, and antitumor effects (Jia Caiyun et al. Chinese Herbal Medicine, ...
Claims
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Patent Type & Authority Patents(China)
IPC IPC(8): C07J19/00A61K31/585A61P35/00
Inventor 梁鑫淼刘艳芳张秀莉丰加涛肖远胜薛兴亚
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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