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Triterpenoid glycoside compounds from glechoma longituba, and extraction separation method thereof

A compound and composition technology, applied in the field of medicine, can solve the problems of no triterpene glycoside components, reports, complex chemical components, etc.

Active Publication Date: 2019-06-14
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

[0003] The chemical composition contained in Lily saliva is complex and has various structures. The triterpenoids that have been isolated from Lily saliva include oleanolic acid, ursolic acid, betulin, and betulinic acid, but there is no research on the triterpenoids. Glycoside composition report

Method used

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  • Triterpenoid glycoside compounds from glechoma longituba, and extraction separation method thereof
  • Triterpenoid glycoside compounds from glechoma longituba, and extraction separation method thereof
  • Triterpenoid glycoside compounds from glechoma longituba, and extraction separation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1: Extraction and Separation of Triterpenoid Glycosides A and B in Lisiana

[0063] 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)

[0064] The extraction and separation steps of the triterpene glycosides dichrysalis saponin A and B are as follows in sequence:

[0065] (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;

[0066] (2) Concentrating 75% ethanol extract: 75% ethanol extract (EYELA ...

Embodiment 2

[0071] Example 2: Structural identification of triterpene glycosides dichrysside A and B

[0072] Two new triterpene glycosides were identified, both of which have the molecular formula C 48 h 78 o 20 , named as styrenin A and styrenin B, and their chemical structural formulas are respectively:

[0073]

[0074] Table 1 is the NMR data (Varian UNITY INOVA 600 type superconducting nuclear magnetic resonance instrument (U.S. Varian Co., Ltd.)) of these two new triterpene glycoside compounds: 1 H-NMR with 13C-NMR in pyridine-d 5 middle.

[0075] Table 1: NMR data of the triterpenoid glycosides styrenin A and styrenin B of the present invention.

[0076]

[0077]

[0078] Recorded in pyridine-d 5 .

[0079] For the structural identification and derivation of Limoside A please refer Figure 2-9 .

[0080] Lithium saponin A: white powder, soluble in methanol. The melting point is 219-221°C measured by RY-IG melting point analyzer (Tianjin Tianguang Optical Instru...

Embodiment 3

[0093] Example 3: In vitro anti-tumor activity test of triterpene glycosides dichrysside A and B

[0094] Tumor cell growth inhibition rate (%)=(measured value of test well / measured value of control well)×100%

[0095] 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-purple crystalline formazan (Formazan) and deposited in cells, death This enzyme disappears in cells, and MTT is not reduced. After dissolving formazan with dimethylsulfoxide (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.

[0096] The cell lines used are: BGC-823 (human gastric cancer cells), Bel (human liver cancer...

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Abstract

The invention discloses triterpenoid glycoside compounds from glechoma longituba, and an extraction separation method thereof, and belongs to the technical field of medicine. And more specifically, two novel triterpenoid glycoside compounds are obtained through extraction and separation of glechoma longituba medicinal material, and are named as glechoma longituba saponin A and glechoma longituba saponin B respectively. The molecular formulas of glechoma longituba saponin A and glechoma longituba saponin B are determined to be C48H78O20, molecular weight is 974, and chemical structural formulasare represented by formula I and formula II respectively through a plurality of detection methods including superconductive nuclear magnetic resonance spectrum detection and mass spectrum detection.The invention also discloses the physical and chemical properties and optical activities of glechoma longituba saponin A and glechoma longituba saponin B; MTT method is adopted for in vitro activity screening, the results show that glechoma longituba saponin A and glechoma longituba saponin B possess inhibition effects on human stomach cancer cells, human liver cancer cells, human colorectal carcinoma cells, human ovary cancer cells, and human lung cancer cells, can be taken as lead compounds in development of novel antitumor drugs, and can be used for development of medicines used for a plurality of common clinical cancers.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a triterpene glycoside compound isolated for the first time by using 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 standards are recorded in the 2015 edition of the Pharmacopoeia of the People's Republic of China. Spicy, slightly bitter, slightly cold in nature, returns to the liver, kidney, and bladder meridians; has the effects of clearing heat and detoxifying, diuretic and calculi, dispelling blood stasis and reducing swelling, and is clinically used for hot stranguria, stone st...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P35/00A61K31/7024
Inventor 周国平钟瑞建袁铭铭陈伟康郑洋滨胡寿荣潘蕾易路遥万林春
Owner 江西省药品检验检测研究院
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