Terpenoid dihydroquinolone alkaloid compound as well as crystal, preparation method and application thereof as marine anti-fouling agent

A technology of dihydroquinolinone and compound is applied to terpenoid dihydroquinolinone alkaloid compound and crystal, preparation and application field as marine antifouling agent, and achieves the effect of broad application prospect and strong inhibitory activity

Active Publication Date: 2014-02-05
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of terpenoid dihydroquinolinone alkaloid compounds with important antifouling activity as antifouling agents has not been seen in recent years.

Method used

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  • Terpenoid dihydroquinolone alkaloid compound as well as crystal, preparation method and application thereof as marine anti-fouling agent
  • Terpenoid dihydroquinolone alkaloid compound as well as crystal, preparation method and application thereof as marine anti-fouling agent
  • Terpenoid dihydroquinolone alkaloid compound as well as crystal, preparation method and application thereof as marine anti-fouling agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1) Strain culture of gorgonian endophytic fungus Scopulariopsis sp. (TA01-33)

[0018] The culture medium used for bacterial culture contains 1.0% glucose (weight percentage, the same below), 0.2% yeast extract, 0.2% peptone, 1.0% agar, 3.0% sodium chloride, and the rest is water; when used, it is made into a test tube slope, fungus The strain was cultured at 30°C for 5 days.

[0019] (2) Fermentation of gorgonian endophytic fungus Scopulariopsis sp. (TA01-33)

[0020] The culture medium used for fermentation culture contains 1.0% glucose (weight percentage, the same below), 0.2% yeast extract, 0.2% peptone, 3.0% sodium chloride, and the rest is water; the fungal strain is cultured at 28°C for 60 days.

[0021] (3) Extraction and separation of compounds of formula I

[0022] Take 10L of the fermentation broth obtained in step (2) and filter to remove the bacteria. After the filtrate is concentrated, it is extracted with an equal volume of ethyl acetate for 5 times; the extract ...

Embodiment 2

[0025] (1) Strain culture of gorgonian endophytic fungus Scopulariopsis sp. (TA01-33)

[0026] The culture medium used for strain culture contains glucose 0.1%-5.0% (weight percentage, the same below), yeast extract 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium chloride 0.05%- 5%, the rest is water. When used, it is made into a test tube slope, and the fungal strain is cultured at 0-30°C for 3-15 days.

[0027] (2) Fermentation of gorgonian endophytic fungus Scopulariopsis sp. (TA01-33)

[0028] The medium used for fermentation culture contains glucose 0.1%-5.0% (weight percentage, the same below), yeast extract 0.01%-1%, peptone 0.01%-1%, sodium chloride 0.05%-5%, the rest is water, fungus The strain was cultured at 0-30°C for 10-60 days.

[0029] (3) Extraction and separation of compounds of formula I

[0030] Take 5-50L of the fermentation broth obtained in step (2) and filter to remove the bacteria. After the filtrate is concentrated, it is extracted with 1-3 times the volume...

Embodiment 3

[0032] Take 5 mg of the compound of formula I and dissolve it in a vial containing 2 mL of methanol, ethanol, tetrahydrofuran or acetone. After standing at 0° C. for 30 days, slowly crystallize to obtain crystals of the compound of formula I.

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Abstract

The invention provides a terpenoid dihydroquinolone alkaloid compound as well as a crystal, a preparation method and an application thereof as a marine anti-fouling agent. The preparation method is characterized by firstly carrying out strain culture on a fungus Scopulariopsis sp.(TA01-33), then carrying out fermentation culture on the fungus, removing the thallus through filtration and using ethyl acetate for extraction after filtrate concentration; carrying out normal phase silica-gel column chromatography, Sephadex LH-20 gel column chromatography and high performance liquid chromatography (HPLC) in sequence, thus obtaining the compound in the formula I in the specification. The compound in the formula I and pharmaceutically acceptable salts or crystal thereof can be used for preparing a high-efficiency and low-toxicity marine anti-fouling agent.

Description

Technical field [0001] The invention relates to a novel terpenoid dihydroquinolone (terpenoid dihydroquinolone) alkaloid compound and its crystal, preparation method and application thereof, in particular to a kind of marine fouling organism barnacle Balanus amphitrite larvae with strong inhibition Active terpenoid dihydroquinolinone alkaloid compound, crystal, preparation method and application thereof. Background technique [0002] Marine biological fouling is the harmful accumulation of organic molecules, microorganisms, animals, plants, and their by-products on the surface of marine submerged facilities. This hazardous accumulation often occurs on the surface of unprotected marine submerged facilities, including marine and tourist ships, naval warships, heat exchangers, marine sensors, and aquaculture bases. Biological fouling has caused huge economic losses. Taking only the US Navy warships as an example, the annual economic loss in this area is between 1.8 billion and 2.6 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C12P17/16A01N43/42A01P7/00C12R1/645
CPCA01N43/42C07D405/06C12P17/16
Inventor 王长云邵长伦胥汝芳王开玲钱培元徐颖
Owner OCEAN UNIV OF CHINA
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