(1S, 2S, 4S)-beta-elemene and preparation method and application thereof

An elemene and vinyl technology, applied in the field of medicine, can solve the problem of not further reducing the side effects of β-elemene, β-elemene activity and the like, and achieve a quality control, anti-tumor activity and high safety. Effect

Active Publication Date: 2019-03-08
YUAN INT GROUP
View PDF6 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research of this patent mainly focused on the derivatives of β-elemene and whether it has the effect of treating atherosclerosis, and did not further reduce the side effects of β-elemene and improve the efficacy of β-elemene itself. active

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • (1S, 2S, 4S)-beta-elemene and preparation method and application thereof
  • (1S, 2S, 4S)-beta-elemene and preparation method and application thereof
  • (1S, 2S, 4S)-beta-elemene and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1β-elemene stereoisomer 1R-methyl-1-vinyl-2R, the preparation of 4R-diisopropenyl cyclohexane

[0036] (1) Crude products containing β-elemene stereoisomers (from plant extracts containing β-elemene such as zedoary oil, citronella oil, and Eupatorium volatile oil, or from fermentation products obtained by yeast fermentation One or more), dissolved and loaded in n-hexane, separated by high performance preparative liquid chromatography, and eluted with a mixed solvent system of 90% acetonitrile and water as the mobile phase, flow rate: 15mL / min, detection wavelength: 210nm, chromatographic column: YMC-pack ODS-A 10μM, 20×250mm, at the peak time of about 17min, collect β-elemene and its stereoisomer 1R-methyl-1-vinyl-2R, 4R-diisopropenylcyclohexane 5.05g; (2) the sample obtained in step (1) is dissolved and loaded in n-hexane, and then separated by high-efficiency preparative liquid chromatography, with a mixed solvent system of 80% acetonitrile and water Eluti...

Embodiment 2

[0037] Example 2 Physical and chemical properties and structural identification of β-elemene stereoisomer 1R-methyl-1-vinyl-2R, 4R-diisopropenylcyclohexane

[0038] The β-elemene stereoisomer 1R-methyl-1-vinyl-2R,4R-diisopropenylcyclohexane prepared in Example 1 was used for physical and chemical property analysis.

[0039] Ultraviolet Spectrum: The maximum absorption wavelength of the β-elemene stereoisomer is 205nm.

[0040] Infrared spectrum: The β-elemene stereoisomers are at 3082, 2968, 2935, 2871, 1639, 1448, 1373, 889cm -1 moderate to strong peak intensity.

[0041] Specific rotation: Take the β-elemene stereoisomer, weigh it accurately, add absolute ethanol to dissolve, the concentration is 14mg / mL, and measure the specific rotation at 20°C to be 36.24.

[0042] Mass Spectrum: The high-resolution mass spectrum of the β-elemene stereoisomer shows that the molecular weight of the compound is [M] + =204.1877, molecular formula is C 15 h 24 .

[0043] NMR: 13 C NMR ...

experiment example 3

[0054] Experimental example 3 β-elemene stereoisomer 1R-methyl-1-vinyl-2R, 4R-diisopropenyl cyclohexane and β-elemene acute toxicity comparison

[0055] Samples tested: β-elemene stereoisomer 1R-methyl-1-vinyl-2R, 4R-diisopropenylcyclohexane, β-elemene, all produced by CSPC Yuanda (Dalian ) Pharmaceutical Co., Ltd., in liquid form, stored at 4°C.

[0056] Preparation method: Accurately weigh the sample, dissolve it with DMF, then add Tween 80 (TW80) to aid dissolution, and finally dissolve it in normal saline (NS), DMF:TW80:5%NS=10:2:88 (V:V: V), ultrasound for 5 minutes, ready to use.

[0057] Test animals: ICR mice, provided by Shanghai Lingchang Biotechnology Co., Ltd.; experimental animal quality certificate: SCXK (Shanghai) 2013-0016; certificate number: 2013001828818 2013001828481; experimental animal use license: SYXK (Su) 2012 -0004; body weight: 18-22g; number of animals: 100; sex: half male and half male.

[0058] Laboratory environment: room temperature 24±2°C, r...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
absorption wavelengthaaaaaaaaaa
weightaaaaaaaaaa
Login to view more

Abstract

The invention provides (1S, 2S, 4S)-beta-elemene. The (1S, 2S, 4S)-beta-elemene is characterized in that a novel beta-elemene stereisomer is successfully separated from a crude product containing beta-elemene; the novel beta-elemene stereisomer is subjected to physicochemical property analysis and structural identification and is identified as beta-elemene stereisomer 1R-methyl-1-vinyl-2R, R4-diisopropyl cyclohexane, and the specific structure is identified as (1S, 2S, 4S)-beta-elemene. The compound has the same planar structure as beta-elemene. The pharmacological toxicological activity testshows that the side effect of the beta-elemene stereisomer 1R-methyl-1-vinyl-2R, R4-diisopropyl cyclohexane is less than that of the beta-elemene, and the antitumor activity of the beta-elemene stereisomer 1R-methyl-1-vinyl-2R, R4-diisopropyl cyclohexane is beyond that of the beta-elemene. Therefore, a new research direction is supplied to research antitumor drugs, and meanwhile, the configurational isomer of the beta-elemene is enriched.

Description

technical field [0001] The invention relates to the field of medicine, in particular to β-elemene stereoisomers, more specifically to the structure, preparation and application of β-elemene stereoisomers. Background technique [0002] In recent years, in the field of anti-cancer natural medicine research, many researchers have devoted themselves to studying the anti-cancer activities of paclitaxel, elemene various isomers, turmeric extract, warm curcuma extract and various preparation forms of these drugs. [0003] Elemene is a class of sesquiterpenoids present in some plants. The Latin name is Elemenum, the English name is Elemene, and the chemical name is 1-methyl-1-vinyl-2,4-diisopropenyl Cyclohexane, molecular formula C 15 h 24 . There are many isomers of elemene, among which β-elemene, δ-elemene and γ-elemene have been confirmed to have anticancer activity. [0004] β-elemene is the main component of elemene, which exists in many natural plants, such as zedoary, cit...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/19C07C7/12A61K31/015A61P35/00
CPCA61P35/00C07B2200/07C07C13/19C07C2601/14
Inventor 史跃满王若研冯雪陈晓彤李建何爱琳石佳袁一鸣王翼超刘爽
Owner YUAN INT GROUP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap