Cephalotaxus fortunei norditerpenoid compounds as well as pharmaceutical composition and application to pharmacy thereof

A technology of cloverleaf and compounds, applied in the field of medicine, can solve the problems of compound activity mining, less research on mechanism of action, and less quantity

Inactive Publication Date: 2017-05-17
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

Norditerpene is another class of components with significant anti-tumor activity in the genus of cloverwood, and it is only found in the genus of cloverleaf, and the amount is small. The activity excavation and mechanism of action of this compound There are few studies on

Method used

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  • Cephalotaxus fortunei norditerpenoid compounds as well as pharmaceutical composition and application to pharmacy thereof
  • Cephalotaxus fortunei norditerpenoid compounds as well as pharmaceutical composition and application to pharmacy thereof
  • Cephalotaxus fortunei norditerpenoid compounds as well as pharmaceutical composition and application to pharmacy thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0053] Extraction and Separation

[0054] Dried alpine clover (39kg) and Gongshan clover branches and leaves (19kg) were crushed and soaked in methanol 3 times for 2 days each time, the extracts were combined, the solvent was distilled off under reduced pressure, and the extract was diluted with water. Add 1% (v / v) hydrochloric acid aqueous solution to adjust the pH to 2–3 and stir, extract with petroleum ether to remove impurities such as chlorophyll and fatty acids, and extract the aqueous layer with ethyl acetate to obtain crude extract A 1 (510g) and B 1 (292g), the pH of the aqueous layer was adjusted to pH 7–8 with 10% ammonia (v / v) solution, and then extracted with ethyl acetate to obtain the crude extract A 2 (198g) and B 2 (39g).

[0055] Take the crude extract of Alpine cloverleaf A 1 (252g) was mixed with 250g normal phase silica gel, 3kg silica gel column chromatography, chloroform-methanol (1:0–1:1, v / v) gradient elution, detected by thin layer chromatography,...

preparation Embodiment 2

[0062] Chemical transformation:

[0063] Under alkaline conditions, the lactone ring can be opened. For example: adding the cephalus triterpene compound containing the lactone ring to the sodium methoxide / methanol solution, stirring at room temperature, filtering, and drying to prepare the lactone ring. Similar compounds.

[0064] Obtain unsubstituted diterpenes through dehydroxylation reactions such as: adding pyridine and phenyl thiochloroformate ( PhOCSCl) after 7–14 hours of reaction, add tri-n-butyl tin hydrogen (n‐Bu 3 SnH) was stirred for 4 hours, purified, and dried to obtain dehydroxylated cephalotaxin norditerpene. The chemical conversion process of the tricuspid norditerpenoids is shown below.

[0065]

[0066] The chemical structure of Gongshan harringtonide I (1) is:

[0067]

[0068] The physical and chemical properties of Gongshan harringtonide I are as follows: light yellow powder; molecular formula C 19 h 20 o 3 ; UV (MeOH) λ max 243, 325nm; hydrog...

preparation Embodiment 1

[0172] Prepare the above-mentioned compound of the present invention according to the method of Preparation Example 1, and use ethanol, glycerin, polyethylene glycol and other cosolvents to dissolve, and make oral preparations; or add water for injection according to routine, fine filter, potting and sterilization preparation into injection.

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PUM

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Abstract

The invention relates to cephalotaxus fortunei norditerpenoid compounds expressed as formula (I), pharmacologically acceptable salts thereof, a pharmaceutical composition taking the cephalotaxus fortunei norditerpenoid compounds as active components and application of the cephalotaxus fortunei norditerpenoid compounds to preparation of anti-tumor medicines. A series of novel cephalotaxus fortunei norditerpenoid compounds are discovered in cephalotaxus plants; extracorporeal activity screening shows that the compounds has significant cytotoxic activity and anti-inflammatory activity; mechanism research shows that the cephalotaxus fortunei norditerpenoid compounds are different from colchicines containing cycloheptenone, have no influence on microtubule polymerization and are relevant with inhibition of NF-kB signal channels; in-vivo transplantation tumor activity evaluation shows that the cephalotaxus fortunei norditerpenoid compounds have significant anti-tumor activity and have good pharmacy prospects.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of medicine, and specifically relates to an antineoplastic drug whose active ingredients are cloverleaf norditerpenoids, derivatives thereof, organic and inorganic acid salts, pharmaceutical compositions containing them and plant extracts of the genus cloverleaf , and their application in the preparation of medicines for treating or preventing cancer. [0003] Background technique: [0004] Malignant tumor (cancer) is a serious disease that endangers human health. In China, there are 1.6 million new cancer patients every year, and 1.3 million cancer patients die every year. The current methods of cancer treatment mainly include surgery, chemotherapy, radiotherapy, tumor biological immunotherapy, and traditional Chinese medicine treatment. Although localized cancers can be successfully treated with surgery and radiation therapy, chemotherapy remains the conventional treatment of choice for advanced or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C07D493/18C07C69/757C07C67/48A61K31/366A61K31/215A61P35/00A61P35/02
CPCC07C69/757C07D493/08C07D493/18
Inventor 蔡祥海倪玲钟秀虹保梅芬
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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