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(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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • (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...

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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

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Application Information

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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
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