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Eriocalyxin A and Eriocalyxin B and preparation method thereof

A technology for calyx lactones and lactones, which is applied in the field of organic synthesis of natural products, can solve the problems such as no reports on the preparation methods of calyxolactone A and calyxolide B, and achieves a novel synthetic route. Effect

Pending Publication Date: 2022-07-29
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no report on the preparation method of calycilactin A and calycilactin B in the prior art

Method used

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  • Eriocalyxin A and Eriocalyxin B and preparation method thereof
  • Eriocalyxin A and Eriocalyxin B and preparation method thereof
  • Eriocalyxin A and Eriocalyxin B and preparation method thereof

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Effect test

Embodiment 1

[0064] The novel enantio-kaurane diterpenoid compound prepared by the present invention is maoelactone A, which is isolated from medicinal plants, and is named maoelactone A in English. Taking calyxin A as the starting material, the chemical synthesis of calyxolactone A is realized by chemical reaction. Using oridonin as raw material, the structural modification precursor calyxolide B was constructed by Wolff rearrangement tandem lactonization reaction. The structural formula of the above compound is as follows:

[0065]

[0066] The preparation method of the novel enantio-kaurine diterpenoids tricolide A and the structure modification precursor tricolide B of the present invention is as follows:

[0067] (1) Preparation of Intermediate B: Compound A (0.01-100 g) was dissolved in dichloromethane (1-100 mL), and diisopropylethylamine (1-100 mL) was added. SEM-Cl (1-100 mL) was slowly added dropwise in an ice bath at 0°C. The reaction was then placed at room temperature fo...

Embodiment 2

[0098] (1) Preparation of Intermediate B: Compound A (20.0 g, 58 mmol, 1.0 equiv) was dissolved in 30 mL of dichloromethane, and diisopropylethylamine (11.5 mL, 87 mmol, 1.5 equiv) was added. SEM-Cl (15.0 mL, 87 mmol, 1.5 equiv) was slowly added dropwise under an ice bath at 0°C. The reaction was then placed at room temperature for 4 hours. After the completion of the reaction was detected by TLC, saturated NaHCO 3 (30 mL) quenched, extracted with EtOAc (3×300 mL), washed with saturated brine (50 mL), and anhydrous MgSO 4 After drying, filtration, and purification by column chromatography after concentration, eluent: petroleum ether / ethyl acetate=12:1, amorphous solid compound B was obtained. Data for B:R f = 0.41(silica, petroleum ether / acetone 4:1); (MeOH, c 0.07); 1 H NMR (600MHz, CDCl 3 )δ=6.71(d, J=10.1, 1H), 6.29(s, 1H), 5.86(d, J=10.1, 1H), 5.82(s, 1H), 5.25(d, J=1.4, 1H), 5.02 (d, J=7.1, 1H), 4.77 (d, J=7.1, 1H), 4.34 (dd, J=10.3, 1.3, 1H), 4.07 (ddd, J=12.6, ...

Embodiment 3

[0118] Cell-level antitumor activity test of the compounds of the present invention.

[0119] 1. Experimental purpose

[0120] The antitumor activity test of the compounds of the present invention was carried out, and the in vitro antitumor activity of the compounds was evaluated by measuring the growth inhibitory activity of the compounds on human tumor cells.

[0121] 2. Experimental materials

[0122] Human non-small cell lung cancer cell line A549, human liver cancer cell HepG2, human chronic myeloid leukemia cell K562 and human acute promyelocytic leukemia cell HL60 are all gifts from the research group of researcher Li Jia, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, human breast cancer cells MDA-MB-435 was purchased from the Cell Resource Center, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences.

[0123] 3. Test principle

[0124] Cell proliferation was detected by MTS colorimetry. MTS is a new analog of MTT, the full n...

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Abstract

The invention discloses eriocalyxin A and B and a preparation method thereof, and belongs to the technical field of organic synthesis of natural products and the technical field of medicines. The invention provides a novel pentacyclic enantiomer-kaurane diterpenoid compound (eriocalyxin A and eriocalyxin B) and a preparation method of the novel pentacyclic enantiomer-kaurane diterpenoid compound (eriocalyxin A and eriocalyxin B). The compound is synthesized for the first time, the synthesis route is novel, the synthesis method can provide an effective means for structure optimization based on oridonin, and the compound has important research value and application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis of natural products and the technical field of medicine, and in particular relates to a novel enantio-kaurine diterpenoid compound calyxolide A and calyxolide B, a pharmaceutical composition and a preparation method thereof . Background technique [0002] Natural product backbones provide useful templates for medicinal chemistry studies of active molecules. For example, the natural spirolactone type and the enantio-kaurine type diterpenes of the eulongin type provide a reference for the structural modification of oridonin. Calyxolide A was discovered from Isodon eriocalyx with a novel 1,10-cleavage-2,20-cyclization-1,20lactonation-enantio-kaurine-type skeleton. Due to the small sample size of calyxolide A, it was impossible to determine its absolute configuration and conduct biological activity studies. In the present invention, it is hoped that calyxolide A can be obtained by semi-sy...

Claims

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Application Information

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IPC IPC(8): C07D307/94A61K31/365A61P35/00
CPCC07D307/94A61P35/00C07B2200/07
Inventor 普诺·白玛丹增孙汉董周元飞颜秉超杨谦杜雪胡坤
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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