Novel diepoxy lignan compound and preparation method thereof

A technology of diepoxide and compound, applied in the field of medicine, can solve the problems of unclear material basis, unstable variety sources, and difficulty in formulating quality standards.

Inactive Publication Date: 2019-05-10
江西省药品检验检测研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a traditional antitussive and expectorant traditional Chinese medicine, fresh bamboo leek has definite curative effect. It was first recorded in the 1977 edition of "Chinese Pharmacopoeia". Because of its unstable variety source and unclear material basis, it is difficult to formulate its quality standard. In 1985 The "Chinese Pharmacopoeia" after the 2010 edition did not separately record fresh bamboo leek as a medicinal material

Method used

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  • Novel diepoxy lignan compound and preparation method thereof
  • Novel diepoxy lignan compound and preparation method thereof
  • Novel diepoxy lignan compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the extraction and separation method of diepoxy lignan compound fresh bamboo bitumin B in fresh bamboo leek:

[0041] The moso bamboo was collected from Tonggu County, Yichun City, Jiangxi Province, and was identified as the fresh stem of Phyllostachys edulis (Carr.) H. de Lehaie, a plant of the genus Phyllostachys edulis (Carr.) H. de Lehaie, which was identified by Wu Ziping, a senior experimenter of Tonggu County Weisheng Industrial Co., Ltd. The specimens are kept in the herbarium of the Jiangxi Provincial Institute for Drug Inspection and Testing.

[0042] The preparation steps of fresh bamboo pitchin B are as follows:

[0043] (1) Extraction of fresh bamboo leek: after the moso bamboo is cut off, fresh bamboo leek is obtained through dry distillation;

[0044] (2) Concentrating fresh bamboo lek: concentrating the fresh bamboo lek under reduced pressure to obtain extract;

[0045] (3) Extraction: take fresh bamboo leek extract (37.8kg), add 40L of p...

Embodiment 2

[0049] Example 2: Structural identification of the diepoxy lignan compound fresh bamboo bitin B

[0050] The physical and chemical properties of fresh bamboo bitin B are as follows: white powder, easily soluble in organic reagents such as acetone, propylene glycol, pyridine, methanol, etc., with a melting point of 166-168 ° C, UV (CH 3 OH)λ max 240nm and 268nm. UHPLC-quadrupole-time-of-flight mass spectrometry gave the quasi-molecular ion peak m / z 401.1214[M+Na] + (calcd for C 18 h 18 o 6 Na, 401.0849), bound 1 H-NMR and 13 C-NMR spectrum confirms that its molecular formula is C 18 h 18 o 9 . 1 H and 13 The C NMR data are shown in Table 1. At the same time, by measuring two-dimensional H-C correlation spectrum (HSQC), H-C long-distance correlation spectrum (HMBC), CD spectrum, etc., the signal assignments of all carbon atoms and hydrogen atoms and the chemical structure of the compound were determined. The chemical structural formula is as follows:

[0051]

...

Embodiment 3

[0055] Example 3: In vitro anti-tumor activity test of the diepoxylignan compound basalin B

[0056] Tumor cell growth inhibition rate (%)=(1-measured value of experimental well / measured value of control well)×100%

[0057] Test principle: MTT method: There is a dehydrogenase related to NAAP (nicotinamide adenine dinucleotide phosphate, coenzyme II) in the mitochondria of living cells, which can convert yellow thiazolyl blue MTT (3-(4, 5- Aimethylthiazo-2-yl)-2,5-Aiphenyl tetrazolium bromiAe) is reduced to insoluble blue-purple formazan (Formanzan), this enzyme disappears in dead cells, and MTT is not reduced. After dissolving formazan with AMSO (dimethyl sulfoxide), the optical density (OA) can be detected at 570 nm with a microplate reader, and the optical density value is proportional to the number of living cells.

[0058] The cell lines used are: HT-1376 (human bladder cancer cells) and HCT-8 (human colon cancer cells).

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Abstract

The invention discloses a novel diepoxy lignan compound and a preparation method thereof. The novel diepoxy lignan compound is isolated from fresh bamboo juice prepared by dry distilling the gramineous plant Phyllostachys edulis, is named as fresh bamboo juice compound B; detection of the fresh bamboo juice compound B via superconducting nuclear magnetic resonance spectroscopy, mass spectrometry and the like determines that the fresh bamboo juice compound B has a molecular formula of C18H19O9 and molecular weight of 378, and a chemical structural formula thereof is shown as formula (I). The fresh bamboo juice compound B is subjected to in-vitro activity screening, and the results show that the compound herein can evidently inhibit human bladder cancer cells and human colon cancer cells andmay act as an antitumor drug.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a novel diepoxylignan compound fresh bamboo bitumin B obtained by separating and purifying fresh bamboo bitumen and a preparation method thereof. The compound has obvious inhibitory effect on tumor cell lines, and can be used as a lead compound for developing new antitumor drugs, and can also be used as drugs for developing and treating various common clinical multiple cancers. Background technique [0002] Fresh bamboo leek is the liquid naturally drained from the fresh stems of the gramineous plants Phyllostachys glauca McCluve, Phyllostachys nuda McClure and several plants of the same genus. After boiling, add an appropriate amount of preservatives to make it. It has the effect of clearing heat and resolving phlegm. It is used for cough with excessive phlegm due to lung heat, asthma and chest tightness, strong tongue after stroke, phlegm heat and convulsions in children. It i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/20A61K31/357A61P35/00
Inventor 付辉政罗跃华钟瑞建洪挺周志强姚金龙陈伟康易路遥
Owner 江西省药品检验检测研究院
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