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Nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative as well as preparation and application thereof

A technology of nerane and sesquiterpene is applied in the field of nitrogen-containing cyclonerane-type sesquiterpene derivatives and their preparation, and can solve the problems of non-red tide biological hazards, secondary environmental pollution, drug residues and the like

Active Publication Date: 2019-03-22
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although chemicals such as copper sulfate and chlorine can quickly and effectively kill or inhibit harmful algae or inhibit their growth and reproduction, there are problems such as harm to non-red tide organisms, drug residues, and secondary pollution to the environment.

Method used

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  • Nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative as well as preparation and application thereof
  • Nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative as well as preparation and application thereof
  • Nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The structure of the nitrogen-containing nerolitan-type sesquiterpene derivative derived from the endophytic fungus of seaweed is shown in formula (I).

[0025]

[0026] The compound has the following physicochemical and spectroscopic properties:

[0027] Colorless oil; specific rotation [α] 20 D -22 (c 0.30, MeOH); H NMR spectrum (solvent is deuterated chloroform) δ H 1.03d(6.8),1.58m,1.66m,1.56m,1.85m,1.63m,1.87m,2.21dd(13.1,7.3),2.15dd(13.1,7.3),5.60dt(15.7,7.3),5.68d (15.7), 1.43s, 1.24s, 1.13s, 1.40s, 5.58br s, 2.29t(6.0), 3.74t(6.0), 2.10d(0.9), 5.50br s; C NMR spectrum (solvent is deuterium Chloroform) δ C 14.4CH 3 ,44.7CH,81.6C,40.5CH 2 ,24.4CH 2 ,53.8CH,74.3C,43.4CH 2 ,123.3CH,140.3CH,53.8C,27.5CH 3 ,26.0CH 3 ,25.0CH 3 ,28.1CH 3 ,166.4C,121.4CH,150.0C,43.8CH 2 ,60.0CH 2 ,18.2CH 3 ; High resolution mass spectrometry [M] + m / z 367.2714, calculated 367.2723.

Embodiment 2

[0029] The preparation method of nitrogen-containing nerolitan-type sesquiterpene derivatives as shown in formula (I):

[0030] Get the Trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 strain that grows well on the plate, cut into small pieces and inoculate in rice solid medium, put 50 grams of rice solid medium in every 1 liter of Erlenmeyer flask , 200 bottles in total, fermented statically at room temperature for 40 days, then extracted three times with ethyl acetate, concentrated under reduced pressure, and obtained 212.4 grams of crude extract after concentration.

[0031] The rice solid medium consists of 500 grams of rice per liter, 6 grams of peptone, 500 milliliters of distilled water, and 500 milliliters of aged sea water.

[0032] Trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 strain was preserved in the China Center for Type Culture Collection CCTCC on June 27, 2018, address: Wuhan University, China, the preservation number is CCTCC M 2018405, a...

Embodiment 3

[0037] The difference from Example 2 is that

[0038] Get the well-grown Trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 bacterial classification on the plate, cut into small pieces and inoculate in Jerusalem artichoke glucose liquid medium, put 300 milliliters of medium in every liter of Erlenmeyer flask, A total of 200 bottles were fermented at room temperature for 40 days, then extracted three times with dichloromethane, concentrated under reduced pressure, and 200 grams of crude extract was obtained after concentration.

[0039]The Jerusalem artichoke glucose liquid medium is composed of 500 milliliters of boiled juice containing 200 grams of Jerusalem artichoke tubers per liter, 20 grams of glucose, 5 grams of peptone, and 500 milliliters of aged sea water.

[0040] The crude extract was subjected to 200-300 mesh silica gel column chromatography, followed by volume ratios of 50:1, 30:1, 15:1, 10:1, 5:1, 2:1, 1:1 to 0:1 Petroleum ether-ethanol for gradient eluti...

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Abstract

The invention relates to the field of algistats, in particular to a nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative as well as a preparation method and application in algaeinhibition. The structure of the nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative is shown in formula (I). The preparation method of the derivative comprises the followingsteps: inoculating seaweed endophytic fungus trichoderma asperellum A-YMD-9-2 into a fungal culture medium for fermentation culture, and separating and purifying a fermentation product to obtain the nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative represented by formula (I). A microalgae inhibition experiment of the nitrogen-containing cyclic flores aurantii labdane sesquiterpene derivative disclosed by the invention shows that the median inhibitory concentration of the compound for microalgae can reach 1.1 [mu]g / ml.

Description

technical field [0001] The invention relates to the field of algae inhibitors, in particular to a nitrogen-containing nerolitan-type sesquiterpene derivative derived from seaweed endophytic fungi, a preparation method thereof and an application in algae inhibition. Background technique [0002] Worldwide, coastal red tide disasters are becoming more and more serious, seriously hindering the development of marine fisheries, near-shore tourism and marine economy. Since 2000, my country has entered a period of high incidence of red tides, and the frequency and degree of damage of red tides have increased significantly. There are four main harmful forms of red tide, one is to destroy the balance of marine ecology; the other is to destroy marine fishery resources; the third is to endanger human health; the fourth is to affect the development of marine tourism. According to statistics, the annual economic losses caused by red tides are as high as more than 1 billion yuan. There ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/28A01N37/36A01P13/00C12P13/02C12R1/885
CPCA01N37/36C07B2200/07C07C235/28C12P13/02C07C2601/08
Inventor 季乃云宋银平
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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