Synthesis method for natural jolkinolide A and B

A technology of spurge lactone and Euphorbia serrata, applied in the field of spurge lactone compounds, can solve the problems of low total yield, low content and the like

Inactive Publication Date: 2014-05-28
CHINA PHARM UNIV
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  • Abstract
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Problems solved by technology

[0010] The content of rock euphorbia lactones in native plants is relatively low (the content in general Chinese medicinal materials is <0.01%). Many scholars at home and abroad have used ionone and abietic acid as raw materials to synthesize them through a series of reactions. route leads to lower overall yield

Method used

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  • Synthesis method for natural jolkinolide A and B
  • Synthesis method for natural jolkinolide A and B
  • Synthesis method for natural jolkinolide A and B

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Compound 1 (2g, 6.57mmol) was put into a reaction flask, dissolved in THF (20ml), added 60% sodium hydride (0.47g, 19.71mol), heated to reflux for 3-5h, cooled to room temperature, added carbon disulfide (0.44 ml, 7.23mmol), kept at 50-60°C for 1h, cooled to room temperature, added iodomethane (0.45ml, 7.23mmol), and reacted at room temperature for 30min. Under ice-bath conditions, water was added dropwise to quench the reaction, part of the solvent was evaporated, extracted with ethyl acetate, dried, and column chromatography (petroleum ether:ethyl acetate (V / V)=10:1) gave 15.5g of white solid compound 2. The yield is 81%. mp: 103-105℃.IR(KBr,cm -1 ): 3470, 3302, 2982, 2925, 2849, 2359, 1708, 1695, 1444, 1230, 1070, 1057, 960, 874, 749; 1 H-NMR (CDCl 3 , 300MHz) δ: 4.98(s, 1H), 4.82(s, 1H), 4.76-4.76(d, J=11, 1H), 4.41-4.38(d, J=10.9, 1H), 2.56(s, 3H ), 2.18-2.10(m,3H), 1.88-1.81(m,5H), 1.77-1.73(m,3H), 1.63-1.42(m,9H), 1.26-1.22(d, J=9.5,1H) , 1.01(s, 6H). 13 C-...

Embodiment 2

[0045] Put compound 2 (3.1g, 7.86mmol) into the reaction flask, add toluene (100ml) to dissolve, add the catalyst, and use a syringe to add tributyltin hydride (3.7mL, 13.35mmol) to the reaction solution within 3h under nitrogen protection , maintain the reaction temperature at 80-100°C. Part of the solvent was evaporated, extracted with ethyl acetate, dried, and column chromatographed (petroleum ether: ethyl acetate (V / V) = 15:1) to obtain 3.9 g of white solid compound 3 with a yield of 88%. mp: 117-119℃.IR(KBr,cm -1 ): 3111, 2994, 2946, 2992, 2846, 2842, 2360, 2354, 1400, 1367, 1112, 1088,877; 1 H-NMR (CDCl 3 , 300MHz) δ: 4.98(s, 1H), 4.82(s, 1H), 2.19-2.11(m, 3H), 1.85-1.764(m, 3H), 1.66-1.65(m, 2H), 1.62-1.59( m,2H)1.58-1.49(m,6H), 1.45-1.42(m,2H), 1.39-1.30(m,2H), 1.28-1.13(m,7H), 1.03(s,3H,); 13 C-NMR (300MHz, CDCl 3 )δ: 156.3, 102.7, 80.4, 56.2, 54.7, 47.6, 47.1, 42.0, 41.7, 41.3, 40.3, 39.4, 39.1, 33.6, 33.3, 23.4, 21.2, 20.2, 18.6, 17.5; ESI-MS m / z: 311[M+Na] +...

Embodiment 3

[0047] Compound 3 (2.6g, 9.01mmol)) was put into the reaction flask, THF (30ml) was added to dissolve, selenium dioxide (0.6g, 5.41mmol) and tert-butyl hydroperoxide (1mL) were added successively, and the reaction was carried out at room temperature for 10-24h . It was diluted with water, extracted with ethyl acetate, dried, and column chromatographed (petroleum ether: ethyl acetate (V / V) = 3: 1) to obtain 32.2 g of white solid compound 4 with a yield of 80%. mp: 244-246°C; IR(KBr,cm -1 ): 3551, 3474, 3227, 3115, 2932, 1370, 1363, 1004, 562; 1 H-NMR (CDCl 3 , 300MHz) δ: 5.30(s, 1H), 5.26(s, 1H), 3.82(s, 1H), 2.10-2.06(d, J=11.1, 1H), 1.88-1.76(m, 4H), 1.75- 1.49(m, 5H), 1.44-1.37(m, 4H), 1.31-1.25(m, 3H), 1.18-1.11(m, 2H), 1.02(s, 3H), 0.95-0.92(m, 1H), 0.87(s, 3H), 0.82(s, 3H). 13 C-NMR (300MHz, CDCl 3 )δ: 161.6, 107.1, 80.8, 78.1, 56.2, 53.5, 45.6, 43.4, 42.0, 40.8, 40.5, 39.1, 35.5, 33.9, 33.3, 21.9, 19.9, 19.5, 18.6, 17.8; ESI-MSm / z: 327 [M+Na] + ;HRMS: m / z[M+Na] ...

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Abstract

The invention provides a method for synthesizing a jolkinolide A component and a jolkinolide B component which serve as main active components of a traditional Chinese medicine euphorbia fischeriana. The natural jolkinolide A and B is obtained by simple and high-efficiency synthesis through a series of chemical reactions by taking low-cost and readily-available p-13,19-dyhydroxyl kaurene; a preparation condition, a preparation process and important spectral structures and physical property data of all midbodies and target compounds are supplied.

Description

technical field [0001] The invention relates to a method for preparing Jolkinolide A and Jolkinolide B, the main active components of the traditional Chinese medicine Euphorbia chamaejasmin, from stevioside. technical background [0002] Chamaejasma chamaejasma is a traditional Chinese medicinal material in my country. It is the root of Euphorbia fischeriana Steud, a plant of Euphorbia (Euphorbiaceae) Euphorbia. It has a long history of using chamaejasma root as medicine to treat cancer, edema and ascites in my country. (Ogura, M., Koike, K., Cordell, G.A., Farnsworth, N.R., 1978. Planta Medica. 33, 128-143; Wang, H.B., Chu, W.J., Wang, Y., Ji, P., Wang, Y.B., Yu, Q., Qin, G.W., 2010.J Asian Nat Prod Res.12, 1038-1043.). Modern medical and traditional Chinese medicine studies have found that rock euphorbia lactone compounds have a variety of biological activities, such as: Anti-tumor, anti-bacterial, anti-inflammatory and deworming activities, among which the anti-tumor act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C07D493/20
CPCC07D493/10C07D493/20
Inventor 张大永朱昶臻吴晓明
Owner CHINA PHARM UNIV
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