Diterpenoid glycoside compound in glechoma longituba and extraction and separation method thereof

A compound and composition technology, applied in the field of medicine, can solve problems such as the lack of diterpene and its glycoside components, reports, complex chemical components, etc.

Active Publication Date: 2019-07-19
江西省药品检验检测研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The chemical constituents contained in Lily chrysalis are complex and diverse in structure. The terpenoids that have been isolated from Lily chrysalis include triterpenoids oleanolic acid, ursolic acid, betulin, betulinic acid, etc., as well as monoterpenoids and Sesquiterpenoids, but no reports on diterpenes and their glycosides

Method used

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  • Diterpenoid glycoside compound in glechoma longituba and extraction and separation method thereof
  • Diterpenoid glycoside compound in glechoma longituba and extraction and separation method thereof
  • Diterpenoid glycoside compound in glechoma longituba and extraction and separation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1: Extraction and separation of the diterpenoid glycosides diclairoside A and B in Dichrysalis:

[0064] Lianqian herbal medicine was collected from Huoshan County, Lu'an City, Anhui Province on June 12, 2016. It was identified as Glechoma longituba (Nakai) Kupr, a plant of the Labiatae family, by Wan Linchun, deputy director of the Jiangxi Provincial Institute of Drug Inspection and Testing. of whole grass. The specimen is kept in the Jiangxi Provincial Drug Inspection and Testing Research Specimen Laboratory (specimen number JXSYJY2016012)

[0065] The extraction and separation steps of the diterpene glycosides Dilimoside A and B are as follows:

[0066] (1) Heating and reflux extraction with ethanol: Dried Dilimocarpis in the shade and then pulverized, 50.0Kg of the pulverized Herba Lisiana, heated and refluxed with 75% ethanol for 3 times, filtered to obtain a 75% ethanol extract;

[0067] (2) Concentrating 75% ethanol extract: 75% ethanol extract (EYELA S...

Embodiment 2

[0072] Example 2: Structural Identification of Diterpenoid Glycosides Dicarinaside A and B:

[0073] Two new diterpene glycosides were identified with molecular formulas of C 33 h 50 o 15 and C 33 h 48 o 15 , named as liancaoside A and liancaoside B, and its chemical structural formula is:

[0074]

[0075] Table 1 is the NMR data (Varian UNITY INOVA 600 type superconducting NMR instrument (Varian Co., Ltd., U.S.)) of these two new diterpene glycoside compounds: 1 H-NMR with 13 C-NMR on CD 3 OD.

[0076]Table 1: NMR data of the diterpene glycosides diluciside A and diluciside B of the present invention.

[0077]

[0078]

[0079]

[0080] Please refer to Figure 2-8 .

[0081] Limoside A: Pale yellow powder, soluble in methanol. The melting point is 225-227°C measured by RY-IG melting point analyzer (Tianjin Tianguang Optical Instrument Co., Ltd., China), and measured by Perkin-Elmer 341 polarimeter (PERKIN ELMER Co., Ltd., USA)[α] 20 D -4.0 (c 0.025,...

Embodiment 3

[0090] Example 3: In vitro anti-tumor activity test of diterpenoid glycosides dicarinaside A and B:

[0091] Tumor cell growth inhibition rate (%)=(measured value of test well / measured value of control well)×100%

[0092] Test principle: MTT method: There is a dehydrogenase related to NAPP (nicotinamide adenine dinucleotide phosphate, coenzyme II) in the mitochondria of living cells, and succinate dehydrogenase can make exogenous yellow thiazolium blue MTT ( 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) is reduced to water-insoluble blue-violet crystalline formazan (Formazan) and deposited in cells, dead cells During this enzyme disappears, MTT is not reduced. After dissolving formazan with dimethyl sulfoxide (DMSO), the absorbance can be detected at 570nm and 630nm with a microplate reader, and the optical density value is proportional to the number of viable cells.

[0093] The cell lines used are: BGC-823 (human gastric cancer cells), Bel (human liver canc...

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Abstract

The invention discloses a diterpenoid glycoside compound in a glechoma longituba and extraction and separation method thereof, which relate to the technical field of medicine. Specifically, two novelditerpenoid glycosides are isolated from a glechoma longituba herbal material by certain extraction, which are named as glechoma longituba glucoside A and glechoma longituba glucoside B. After the superconducting nuclear magnetic resonance spectroscopy, mass spectrometry and other tests of glechoma longituba glucoside A and glechoma longituba glucoside B, the molecular formulas are determined to be C33H50O15 and C33H48O15, the molecular weights are 686 and 684, respectively, and the chemical structural formulas are respectively (I) and (II). The compound discloses the physicochemical properties and optical activity of glechoma longituba glucoside A and glechoma longituba glucoside B, and adopts a MTT method for in-vitro activity screening, and the results show that the compound has inhibitory effects on human gastric cancer cells, human liver cancer cells, human colon cancer cells, human ovary Both cancer cells and human lung cancer cells. The compound can be used as the lead compoundfor the development of new anti-tumor drugs, and can also be used as a drug for the development and treatment of a variety of clinically common multiple cancers.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a diterpene glycoside compound isolated for the first time from Dilimocarpa as a raw material, an extraction method and application thereof. The above-mentioned compound has inhibitory effect on tumor cell lines, and can be used as a lead compound for developing new anti-tumor drugs, and can also be used as drugs for developing and treating various common clinical multiple cancers. Background technique [0002] Glechoma longituba (Nakai) Kupr is the aerial part of Glechoma longituba (Nakai) Kupr. The quality standard is recorded in the "Pharmacopoeia of the People's Republic of China" 2015 edition. It tastes pungent, slightly bitter, and slightly cold in nature. It belongs to the liver, kidney, and bladder channels; For hot stranguria, stone stranguria, damp-heat jaundice, sore carbuncle swelling and pain, bruises. Modern pharmacology shows that Lisianthus has diuretic and cho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/256C07H1/08A61P35/00A61K31/704
CPCA61P35/00C07H1/08C07H15/256
Inventor 袁铭铭周国平钟瑞建郑洋滨陈伟康胡寿荣潘蕾万林春易路遥
Owner 江西省药品检验检测研究院
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