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Bicyclo-orange flower naphthene type sesquiterpene derivative as well as preparation and application thereof

A technology of nerane and sesquiterpene is applied in the field of bicyclic cyclonerane-type sesquiterpene derivatives and their preparation, and can solve the problems of secondary environmental pollution, drug residues, non-red tide biological hazards 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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  • Bicyclo-orange flower naphthene type sesquiterpene derivative as well as preparation and application thereof
  • Bicyclo-orange flower naphthene type sesquiterpene derivative as well as preparation and application thereof
  • Bicyclo-orange flower naphthene type sesquiterpene derivative as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0025]

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

[0027] Colorless oil; specific rotation [α] 20 D -30(c 0.32, MeOH); H NMR spectrum (solvent is deuterated chloroform) δ H 1.02d(6.6),1.71m,1.61m,1.50m,1.80m,1.50m,1.75m,1.70m,1.45ddd(12.1,3.3,3.3),1.67m,3.87ddd(11.5,9.9,4.1), 1.16s, 1.24s, 1.19s, 1.19s, 5.62br s, 2.35br t(5.7), 3.79br t(5.7), 2.16br s, 5.24br d(9.8); C NMR spectrum (solvent is deuterated Chloroform) δ C 15.1 (CH 3 ), 44.0(CH), 81.6(C), 40.6(CH 2 ), 25.1 (CH 2 ), 56.6(CH), 75.8(C), 31.7(CH 2 ),23.6(CH 2 ), 53.3(CH), 73.9(C), 30.3(CH 3 ),26.2(CH 3 ),25.5(CH 3 ),22.9(CH 3 ), 166.3(C), 120.7(CH), 150.4(C), 43.7(CH 2 ),60.2(CH 2 ), 18.3 (CH 3 ); high-resolution mass spectrometry [M] + m / z 367.2725, calculated 367.2723.

Embodiment 2

[0029] The preparation method of the bicyclic ring 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 seawater.

[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, and ...

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 seawater.

[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 elutio...

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PUM

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Abstract

The invention relates to the field of algicides and specifically relates to a bicyclo-orange flower naphthene type sesquiterpene derivative as well as a preparation method thereof and application of the derivative in the aspect of algal inhibition. The structure of the derivative is shown by a formula (I) as shown in the specification; the preparation method of the derivative comprises the following steps: inoculating an endophytic fungi trichoderma asperellum in alga into a fungi medium for fermentation culture and separating and purifying a fermentation product to obtain the bicyclo-orange flower naphthene type sesquiterpene derivative shown by the formula (I). A microalgae inhibition experiment on the obtained bicyclo-orange flower naphthene type sesquiterpene derivative shows that themedian inhibitory concentration of a compound on microalga can reach 0.63mug / ml.

Description

technical field [0001] The invention relates to the field of algae inhibitors, in particular to a bicyclic 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 are about 3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/14A01N43/16A01P13/00C12P17/06C12R1/885
CPCA01N43/16C07B2200/07C07D309/14C12P17/06
Inventor 季乃云宋银平
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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