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Preparation and application of amide compound of ginkgolic acid

A technology of ginkgo phenolic acid amide and amide compound, which is applied in the field of natural product chemistry, can solve the problems of ginkgo toxicity, death, allergic reaction and the like, and achieves the effects of low toxicity, low toxicity, anticancer activity, and low product toxicity

Active Publication Date: 2021-03-23
INST OF BOTANY JIANGSU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[Lepoittevin J P, Benezra C, Asakawa Y. Allergic contact dermatitis to Ginkgo biloba L.: relationship withurushiol[J]. Archives of Dermatological Research, 1989, 281(4): 227-230.] "Ginkgo biloba is poisonous", raw food or excessive consumption can cause allergic reactions, and even lead to death. Due to ginkgolic acids in ginkgo biloba

Method used

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  • Preparation and application of amide compound of ginkgolic acid
  • Preparation and application of amide compound of ginkgolic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation method of ginkgolic acid amide compound: using DCC-HoBt condensation method, 0.04 mmol ginkgolic acid (C13:0) and 0.04 mmol HoBt were dissolved in 10 mL ethyl acetate, stirred at 0°C for 30 minutes, and then 0.04 mmol DCC was added. React at 0°C for 2.5 h. Then 2 mL of 0.04 mmol dehydroabietylamine in ethyl acetate solution was added dropwise, the reaction was tracked by TLC, and stirred in an ice bath for 30 minutes, so that DCU was fully separated. DCU was removed by filtration, and after rotary evaporation under reduced pressure, the product was separated and purified by column chromatography (V ethyl acetate: V n-hexane = 1:3), and finally a light brown oil was obtained, 0.014 g, with a yield of 60%.

[0026] Said steps have a molar ratio of ginkgolic acid (C13:0) to dehydroabietylamine of 1:1.0.

[0027] The test results are as follows: m.p. 38-39°C; IR (neat) ν max 3416, 2924, 2852, 1630,1534, 1454, 1375, 1280, 1216, 819, 739, 628; 1H NMR (DMSO- d6...

Embodiment 2

[0030] Preparation method of ginkgolic acid amide compound: using DCC-HoBt condensation method, 0.04 mmol ginkgolic acid (C13:0) and 0.04 mmol HoBt were dissolved in 10 mL ethyl acetate, stirred at 0°C for 30 minutes, and then 0.04 mmol DCC was added. React at 0°C for 2.5 h. Add 2 mL of 0.044 mmol of dehydroabietylamine solution in ethyl acetate dropwise, follow the reaction by TLC, and then stir in an ice bath for 30 minutes, so that DCU is fully separated. DCU was removed by filtration, and the product was separated and purified by column chromatography (V ethyl acetate: V n-hexane = 1:3) after rotary evaporation under reduced pressure, and finally a light brown oil was obtained, 0.015 g, with a yield of 64%.

[0031] The molar ratio of ginkgolic acid (C13:0) to dehydroabietylamine in the described steps is 1:1.1. The test result shows that it is the same as that of Example 1.

Embodiment 3

[0033] Preparation method of ginkgolic acid amide compound: using DCC-HoBt condensation method, 0.04 mmol ginkgolic acid (C13:0) and 0.04 mmol HoBt were dissolved in 10 mL ethyl acetate, stirred at 0°C for 30 minutes, and then 0.04 mmol DCC was added. React at 0°C for 2.5 h. Then 2 mL of 0.048 mmol dehydroabietylamine in ethyl acetate was added dropwise, the reaction was tracked by TLC, and then stirred in an ice bath for 30 minutes, so that DCU was fully separated. DCU was removed by filtration, and after rotary evaporation under reduced pressure, the product was separated and purified by column chromatography (V ethyl acetate: V n-hexane = 1:3), and finally a light brown oil was obtained, 0.014 g, with a yield of 60%.

[0034] Said step is that the molar ratio of ginkgolic acid (C13:0) to dehydroabietylamine is 1:1.2. The test result shows that it is the same as that of Example 1.

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Abstract

The invention discloses a specific modified product of ginkgolic acid (C13: 0) and dehydroabietylamine with anti-cancer activity, namely a preparation method of an amide compound of ginkgolic acid andapplication of the amide compound of ginkgolic acid in the aspect of anti-cancer activity. The preparation method of the amide compound is easy to operate. According to the invention, active compounds in two economic forest species are combined, so the amide compound is good in innovation. The IC50 value of the amide compound to Hela cells is 1.83 [mu]M, the IC50 value of the amide compound to HepG2 cells is 3.31 [mu]M, the IC50 value of the amide compound to MCF-7 cells is 9.98 [mu]M, and the IC50 value of the amide compound to A549 cells is 5.80 [mu]M. The amide compound has good anti-Helacell, anti-HepG2 cell, anti-MCF-7 cell and anti-A549 cell activity, has low toxicity, changes the traditional concept that ginkgo biloba is toxic and causes the phenomena of anaphylactic reactions, even death and the like if eaten without cooking or eaten excessively, and provides a new idea for the development of anticancer drugs. The compound is novel in structure, contains a long-chain electrondonating group (-C13H27), has low toxicity and unique anti-cancer activity, is an anti-cancer drug with an excellent prospect, creates conditions for researching the relationship between the anti-cancer activity and the structure of the compound, and lays a foundation for research and development of new drugs.

Description

technical field [0001] The invention belongs to the field of natural product chemistry, and specifically relates to a preparation method of an amide compound, a modified product of ginkgolic acid (C13:0) and dehydroabietylamine, and its application in anticancer activity. Background technique [0002] Many studies in recent years have shown that a variety of ginkgo extracts have significant anticancer activity against many human and mouse tumor strains. Itokawa et al. studied the anticancer activity of long-chain phenolic acids in the outer testa of Ginkgo biloba, and the results showed that these compounds can inhibit the mouse sarcoma S 180 and Chinese rat V-79 cells. [Itokawa H, Totsuka N, Nakahara K, Takeya K, Lepoittevin J P, Asakawa Y. Anticancer principles from Ginkgo biloba L.[J]. Chem Pharm Bull, 1987, 35(7): 3016-3020.] Lee et al. isolated ginkgolic acid from the extract of Ginkgo biloba testa, and found its extremely strong phosphatidylinositol exclusive Inh...

Claims

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Application Information

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IPC IPC(8): C07C235/46C07C231/02C07C231/24A61P35/00
CPCC07C235/46C07C231/02C07C231/24A61P35/00C07C2603/26
Inventor 赵俸艺徐莉吴文龙王未凡曹福亮李维林
Owner INST OF BOTANY JIANGSU PROVINCE & CHINESE ACADEMY OF SCI
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