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Lanoline alkane type triterpenoid sexangulic acid, derivative thereof and preparation and use thereof

A technology of triterpene compound and lanolin, which is applied in the field of medicine, can solve the problems of no galenic acid and achieve obvious anti-tumor effect

Inactive Publication Date: 2009-06-24
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But, in existing literature, do not see any report of niloic acid and its derivatives and its activity

Method used

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  • Lanoline alkane type triterpenoid sexangulic acid, derivative thereof and preparation and use thereof
  • Lanoline alkane type triterpenoid sexangulic acid, derivative thereof and preparation and use thereof
  • Lanoline alkane type triterpenoid sexangulic acid, derivative thereof and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of lanolin-type triterpenoid lanolinic acid

[0037] (1) Extraction: The dry weight of the Chinese mangrove plant Neptonia chinensis is 3.1kg, and it is extracted 4 times by percolation with 5L of methanol. The extracts are combined and then concentrated under reduced pressure. The suspension was repeatedly extracted 3 times, and the obtained extracts were combined and concentrated under reduced pressure to obtain 41 g of ethyl acetate extract.

[0038] (2) Separation: 41g of ethyl acetate extract was subjected to 200-300 mesh silica gel column chromatography, and petroleum ether / ethyl acetate 100:0→90:10→80:20→50:50→20:80→10: 90→0:100 gradient elution, the amount of each gradient is 1000ml; among them, petroleum ether / ethyl acetate 10:90 eluted part 421mg, after 200-300 mesh silica gel column chromatography, chloroform / methanol 100:0→95: 5→90:10 gradient elution, the amount of each gradient is 200ml; 107mg of chloroform / methanol 95:5 eluted part was purifi...

Embodiment 2

[0045] Preparation of Hailianic Acid Derivatives

[0046] 1. Methyl galenic acid (R 1 for hydrogen, R 2 For the preparation of methyl)

[0047] Weigh 2.0 mg of laminic acid into a 25 mL round bottom flask, add 1 mg of CH 2 N 2 2 mL of diethyl ether solution, reacted at room temperature for 18 h, removed diethyl ether and CH under reduced pressure 2 N 2 , to get methyl heliolate (R 1 = H, R 2 =CH 3 ).

[0048] 2. 3-Acetoxypiplenic acid (R 1 for Ac, R 2 for the preparation of hydrogen)

[0049] Weigh 2.0 mg of niporinic acid in a 25 mL round-bottomed flask, add 1.5 mL each of anhydrous pyridine and acetic anhydride, react at room temperature for 18 h, remove pyridine and acetic anhydride under reduced pressure to obtain 3-acetoxypicillinic acid (R 1 =Ac,R 2 = H).

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Abstract

The invention relates to the medicine technical field, in particular to lanostane triterpenoid compound sexangulic acid extracted and separated from a Chinese mangrove plant Bruguiera sexangula, derivatives, a preparation method and a use thereof. The structural formula of the sexangulic acid and the derivative thereof are shown in the following formula, when R1 and R2 are simultaneously hydrogen, the compound is the sexangulic acid. A plurality of in vitro anti-tumor activity tests prove that the compound and the derivative thereof can obviously inhibit tumor cell activity and are expected to be applied to preparing anti-cancer drugs. The invention can provide a lead compound for developing new medicines for treating various common multiple cancers, and plays an important role in developing and utilizing living marine resources in China.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to a new lanolin-type triterpene compound sexangulic acid (sexangulic acid) isolated from the mangrove plant Bruguiera sexangula in the South China Sea, its derivatives and its preparation Methods and uses. This type of compound has a significant inhibitory effect on two tumor cell lines A-549 human lung adenocarcinoma cell line and HL-60 human leukemia cell line, and can be used as a class of lead compounds for the development of new anti-tumor drugs, and can also be used as a therapeutic agent. Drugs for various clinically common multiple cancers. Background technique [0002] Mangroves are plants that include the mangrove family and some other different families but grow exclusively in the intertidal zone of tropical and subtropical coasts. Due to the particularity of the growth environment, mangrove plants are rich in novel structures and biologically active compounds...

Claims

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Application Information

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IPC IPC(8): C07J9/00A61K31/575A61P35/00A61P35/02
Inventor 郭跃伟黄才国李亮冯波王国飞
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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