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Preparation method and application of cyclic ether type diaryl heptane in juglans regia

A technology of diarylheptane and Qinglongyi is applied in the field of medicine, which can solve problems such as pollution, and achieve the effects of reducing environmental pollution and improving effective utilization.

Pending Publication Date: 2022-08-02
HEILONGJIANG UNIV OF CHINESE MEDICINE
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Problems solved by technology

[0005] The invention belongs to the technical field of medicine, relates to a new diaryl heptane compound extracted from Qinglongyi, and discloses a method for preparing the compound and its application, so as to further improve the utilization rate of Qinglongyi and solve environmental pollution The problem

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  • Preparation method and application of cyclic ether type diaryl heptane in juglans regia
  • Preparation method and application of cyclic ether type diaryl heptane in juglans regia
  • Preparation method and application of cyclic ether type diaryl heptane in juglans regia

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Experimental program
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Embodiment 1

[0027] 3',4''-Epoxy-1-(4'-methoxyphenyl)-7-(2'',6''-dihydroxy-3''-methoxyphenyl)-3- The preparation method of heptanone:

[0028] (1) Alcohol extraction method: dry fresh Qinglongyi at low temperature, take 10 kg and pulverize it into coarse powder, add 8 times the volume of 95% ethanol, extract by heating under reflux for 3 times, combine the obtained extracts, recover the solvent, and reduce the pressure. After drying, 688.8 g of extract was obtained;

[0029] (2) Organic solvent extraction method: dilute the extract obtained in step (1) by adding 5 times the amount of pure water, and then extract the diluted solution 5 times with the same volume of dichloromethane as the diluent, and combine the dichloromethane. The methane extract was concentrated and dried to obtain 238.6 g of dichloromethane extract;

[0030] (3) Purification and enrichment of Girard reagent: take the dichloromethane extract obtained in step (2), repeatedly knead and dissolve it in 5000 mL of acetic ac...

Embodiment 2

[0034] The mass spectrum and NMR spectrum data of the compound of the present invention are as follows:

[0035] HR-ESI-MS m / z: 371.1495 [M-H] - , indicating that the molecular weight of this compound is 372. 1 H-NMR (CD 3 OD, 600 MHz) δ: 1.48 (2H, m, H-5), 1.63 (1H, m, H-6a), 1.71 (1H, m, H-4a), 1.77 (1H, m, H-6b) , 2.18 (1H, dt, J = 19.4, 8.2 Hz, H-4b), 2.28 (1H, m, H-2a), 2.33 (1H,m, H-7a), 2.35 (1H, m, H-2b), 2.61 (1H, dd, J = 16.0, 8.2 Hz, H-1a), 2.92 (1H,dd, J = 16.0, 10.2 Hz, H-1b), 3.13 (1H, dt, J = 13.0, 5.2 Hz, H-7b), 3.80 (3H,s, H-7'), 3.86 (3H, s, H-7''), 5.50 (1H, d, J = 1.6 Hz, H-2'), 6.03 (1H, s , H-5''), 6.62 (1H, dd, J = 8.0, 1.6 Hz, H-6'), 6.83 (1H, d, J = 8.0 Hz, H-5'); 13 C-NMR (CD 3 OD, 150 MHz) δ: 18.7 (C-5), 23.9 (C-6), 26.5 (C-1), 29.8 (C-7), 40.6 (C-2), 45.7 (C-4), 55.4 (C-7') , 60.3 (C-7''), 112.3 (C-5'), 112.8 (C-2'), 114.4 (C-5''), 121.1 (C-6'), 125.6 (C-1'' ), 134.2 (C-1'), 140.7 (C-3''), 146.5 (C-4'), 146.6 (C-4''), 148.5 (C-...

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Abstract

The invention belongs to the technical field of medicines, relates to a novel diaryl heptane compound extracted from cortex juglandis mandshuricae, and discloses a method for preparing the compound and application. The specific preparation process comprises the following steps: performing alcohol extraction method, organic solvent extraction method, purification and enrichment of a Girard reagent, silica gel column chromatography separation, preparative HPLC separation and the like on cortex juglandis mandshurica to obtain one cyclic ether type diaryl heptane compound named as 3 ', 4'-epoxy-1-(4 '-methoxyphenyl)-7-(2' ', 6'-dihydroxy-3 ''-methoxyphenyl)-3-heptanone, and further comprises the following steps of: performing column chromatography on the cyclic ether type diaryl heptane compound to obtain the 3 ', 4'-epoxy-1-(4 '-methoxyphenyl)-7-(2' ', 6'-dihydroxy-3 ''-methoxyphenyl)-3-heptanone. The molecular formula of the compound is C21H24O6. In-vitro anti-tumor activity research shows that the compound has a certain inhibition effect on human cervical cancer cells Hela and human liver cancer cells HepG-2. The method for preparing the diaryl heptane compound is clear and controllable in operation, and the obtained compound is few in impurity and high in purity and has the application prospect of being developed into anti-tumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a cyclic ether-type diarylheptane compound separated from Qinglongyi, a preparation method thereof, and an application in the preparation of antitumor drugs. Background technique [0002] Malignant tumors have become a major common disease that seriously endangers human health. Liver cancer is the third largest malignant tumor in the world, and cervical cancer is the fourth most common cancer in women. burden. Traditional Chinese medicine has more obvious advantages in exerting synergistic and attenuating effects, improving clinical symptoms of tumor patients, improving quality of life, and stabilizing tumor lesions. [0003] Qinglongyi is a walnut tree of the Jugaceae family Juglans mandshurica The immature outer peel of Maxim., also known as green walnut peel, walnut green peel. Qinglongyi contains various chemical components such as quinones, terpenes, flavonoids, organic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/00A61P35/00
CPCC07D313/00A61P35/00Y02P20/582
Inventor 周媛媛刘源张雪柔孙朝
Owner HEILONGJIANG UNIV OF CHINESE MEDICINE
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