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Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant

A technology of marine organisms and antifouling agents, applied in biocides, plant growth regulators, chemicals for biological control, etc., can solve problems such as damage to the marine environment, poisoning, and immune system damage

Active Publication Date: 2015-02-04
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These anti-fouling materials have also seriously damaged the marine environment while playing an anti-fouling role. For example, organotin oxide (TBTO) has damaged the immune system of many fish and marine organisms, and pesticides have fouled the target. Both biological and non-target organisms produce toxicity and directly endanger human health

Method used

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  • Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant
  • Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant
  • Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Weigh out 10 mg compound 1 Dissolve in 5mL CH 3 OH / CH 2 Cl 2 (volume ratio 1:1), adding a catalytic amount of 10% Pd / C, at 1 atm H 2 After 10 h of reaction at room temperature, the reaction was complete by TLC. After filtration to remove Pd / C, after concentration, 9.9 mg of oil was obtained, with a yield of 98.4%. The purity by HPLC was above 96%, and ESI-MS m / z: 373.2 [M+Na] ＋ .

Embodiment 2

[0032]

[0033] Weigh out 20 mg compound 3 Dissolve in 5 mL CH 2 Cl 2 , adding a catalytic amount of PtO 2 , at 1 atm H 2 Under the action, after reacting at room temperature for 4 hours, TLC detected that the reaction raw materials almost completely disappeared and formed two spots with low polarity, which were filtered to remove PtO 2 , after concentration, the compound was obtained by silica gel column chromatography (eluent: EtOAc / petroleum ether=10:1 ~ 8:1) 4 (13.5 mg), yield 67.2%, compound 5 (4.8 mg), yield 23.9%, HPLC purity above 98%, ESI-MS m / z: 371.2 [M+Na] ＋ ,through 1 Comparison of H NMR spectra to identify compounds 4 , 5 structure, compound 4 There are no two Hs around δ5.4 (double-bonded hydrogen at the 5' and 6' positions), but there are two single peaks and three Hs around 1.7 ((C H 3 ) 2 C=C-), compound 5 On the contrary, there are two H around δ5.4 (double-bonded hydrogen at the 5' and 6' positions), two CH 3 ((C H 3 ) 2 CH-) moves upfie...

Embodiment 3

[0035]

[0036] Weigh out 10 mg compound 6 Dissolve in 5 mL THF, add 5 mg Na 2 CO 3 , after stirring at room temperature for half an hour, add 5 μL EtBr, 30 o After reacting at C for 5 h, TLC detected that the reaction raw materials almost completely disappeared. After concentration, the compound was obtained by silica gel column chromatography (eluent: EtOAc / petroleum ether=15:1 ~ 10:1). 7 (9 mg), the yield was 83.3%, the purity of the compound by HPLC was 98.6%, ESI-MS m / z: 397.2 [M+Na] ＋ .

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PUM

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Abstract

The invention relates to a marine fungi secondary metabolite derivative and an application of the marine fungi secondary metabolite derivative as a marine biological antifoulant. The derivative has the structure represented by a formula I as shown in the specification, wherein R1 and R2 are independently H, a group as shown in the specification, a group as shown in the specification or a group as shown in the specification and one of R1 and R2 is H; R3 and R4 are independently H and OCH3 and one of R3 and R4 is H; R5 and R6 are independently H, C1-C4 alkyl, C2-C4 alkylacyl, C1-C4 haloalkyl, C1-C4 alkylsulfonyl, C2-C4 alkenyl, C3-C8 cycloalkyl and C7-C12 arylalkyl, wherein alkyl, alkylacyl, haloalkyl, alkylsulfonyl, alkenyl, cycloalkyl and arylalkyl are optionally substituted with one or more hydroxy, mercapto, amino, halo, C1-C4 alkyl groups; '-----' represents a single bond or absence; and the prerequisite is that at least one of R5 and R6 is not H when '-----' represents a single bond.

Description

technical field [0001] The invention belongs to the field of marine antifouling, and in particular relates to a derivative of isocoumarin compounds derived from marine fungi that can be used as a marine biological antifouling agent and a preparation method thereof. Background technique [0002] Marine biofouling means that the larvae of marine fouling organisms such as barnacles, mussels, and bryozoans attach and grow on the surface of marine facilities such as hulls, fish tanks, oil wells, or other marine organisms to form communities, thereby causing huge damage to the attached objects. Damage, such as accelerating metal corrosion, reducing the performance of marine facilities, affecting the output and quality of aquaculture, etc. Among marine fouling organisms, barnacles are the most widely distributed and most harmful. The economic loss caused by marine biofouling is huge every year all over the world. Taking ships as an example, fouling organisms adhere to the bottom ...

Claims

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Application Information

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IPC IPC(8): C07D311/76A01N43/16A01P7/00
CPCA01N43/16C07D311/76
Inventor 陈敏其他发明人请求不公开姓名
Owner YANGZHOU UNIV
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