CN109503414B - Nitrogenous ring nerolidine type sesquiterpene derivative and preparation and application thereof - Google Patents
Nitrogenous ring nerolidine type sesquiterpene derivative and preparation and application thereof Download PDFInfo
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Abstract
The invention relates to the field of algae inhibitors, in particular to a nitrogenous ring nerolidne type sesquiterpene derivative derived from algae endophytic fungi, a preparation method thereof and application thereof in algae inhibition. The structure of the nitrogenous ring nerolidine type sesquiterpene derivative is shown in the formula (I), the preparation method comprises the steps of inoculating seaweed endophytic fungus Trichoderma asperellum A-YMD-9-2 into a fungus culture medium for fermentation culture, and separating and purifying the fermentation product to obtain the nitrogenous ring nerolidine type sesquiterpene derivative shown in the formula (I). The half inhibitory concentration of the compound on microalgae obtained by the nitrogenous ring nerolidine sesquiterpene derivative through a microalgae inhibition activity experiment can reach 1.1 microgram/milliliter.
Description
Technical Field
The invention relates to the field of algae inhibitors, in particular to a nitrogenous ring nerolidne type sesquiterpene derivative derived from algae endophytic fungi, a preparation method thereof and application thereof in algae inhibition.
Background
Worldwide, offshore red tide disasters are increasingly aggravated, and the development of marine fishery, offshore tourism and marine economy is seriously hindered. After 2000, China enters the high-incidence period of red tide, and the incidence frequency and the harm degree of the red tide are obviously increased. The main harm forms of red tide are four, namely, the ecological balance of the ocean is destroyed; secondly, marine fishery resources are damaged; thirdly, the health of human beings is harmed; and fourthly, the development of marine tourism industry is influenced. Statistically, the economic loss caused by red tide is more than 10 billion yuan each year. There are about 300 species of microalgae in the ocean that can trigger red tide, and among them, there are about 80 species of toxic red tide algae. The scientific and effective prevention and treatment of red tide is one of the worldwide problems.
At present, the prevention and treatment strategy of red tide is to prevent the eutrophication of seawater, and also to inhibit the development of red tide organisms, namely red tide algae, and the method for inhibiting the development of the red tide algae is mainly chemical treatment. Although chemical agents such as copper sulfate, chlorine gas, etc. rapidly and effectively kill or inhibit harmful algae or inhibit their growth and reproduction, there are problems of harm to non-red tide organisms, drug residues, secondary pollution to the environment, etc.
Compared with the traditional chemical agents used in the treatment of the red tide, the marine organism-derived natural drug has the advantages of strong pertinence, high safety, obvious activity and environmental friendliness, and provides a new idea for solving the problem of prevention and treatment of the red tide caused by red tide algae at present
Disclosure of Invention
The invention aims to provide a nitrogenous ring nerolidne type sesquiterpene derivative and preparation and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a nitrogenous ring nerolidine type sesquiterpene derivative has a structure shown in formula (I)
A method for preparing nitrogen-containing ring nerolidine type sesquiterpene derivative comprises inoculating Trichoderma asperellum A-YMD-9-2 into fungus culture medium, fermenting, and purifying the fermentation product to obtain nitrogen-containing ring nerolidine type sesquiterpene derivative shown in formula (I); the Trichoderma asperellum A-YMD-9-2 is preserved in a China Center for Type Culture Collection (CCTCC) in 2018, 6 months and 27 days, and the preservation number is CCTCC M2018405.
The method specifically comprises the following steps:
1) inoculating Trichoderma asperellum A-YMD-9-2 into a fungus culture medium, fermenting for 10-60 days, extracting with an organic solvent, and concentrating to obtain a crude extract;
2) subjecting the crude extract obtained in the step 1) to silica gel column chromatography, performing gradient elution by eluent, collecting eluted components, and detecting the eluted components by thin layer chromatography;
3) collecting the eluted components in the step 2), and sequentially carrying out reversed phase silica gel column chromatography, gel column chromatography and preparative thin layer chromatography for separation and purification to obtain the nitrogenous ring nerolidne type sesquiterpene derivative shown in the formula (I).
The fungus culture medium in the step 1) is a rice solid culture medium, a jerusalem artichoke glucose liquid culture medium or a potato glucose liquid culture medium.
The organic solvent is one or more of ethyl acetate, petroleum ether, n-hexane, cyclohexane, dichloromethane, methanol, ethanol, propanol or isopropanol.
The organic solvent in the step 2) is one or more of petroleum ether-ethyl acetate, petroleum ether-ethanol, petroleum ether-propanol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, dichloromethane-methanol, dichloromethane-ethanol, dichloromethane-propanol and dichloromethane-isopropanol in a volume ratio of 50-0: 1.
The reverse phase silica gel column chromatography eluent in the step 3) is water-methanol or water-ethanol with the volume ratio of 5-0: 1; the eluent of the gel column chromatography is dichloromethane-methanol or dichloromethane-ethanol with the volume ratio of 2-0: 1; the thin layer chromatography developing solvent is prepared from dichloromethane-methanol or petroleum ether-ethanol with the volume ratio of 30-0: 1.
The application of the nitrogenous ring nerolidine sesquiterpene derivative in preparing the algistat for the microalgae is provided.
The microalgae are marine dunaliella anatipestifer causing red tide hazards.
The invention has the following advantages: the invention obtains the nitrogen-containing cyclonerolidine type sesquiterpene derivative through fermentation, extraction and separation of Trichoderma asperellum A-YMD-9-2 separated from the marine red algae gracilaria, and the half inhibition concentration of the compound on marine dunaliella caused by red tide is 1.1 microgram/milliliter through a microalgae inhibition activity experiment.
The specific implementation mode is as follows:
the invention is further illustrated below with reference to the examples of embodiment.
Example 1
The structure of the nitrogen-ring nerolidine type sesquiterpene derivative derived from the seaweed endophytic fungi is shown as a formula (I).
The compound has the following physicochemical and spectral characteristics:
colorless oil; specific optical rotation [ alpha ]]20 D-22(c 0.30, MeOH); hydrogen nuclear magnetic resonance spectrum (solvent is deuterated chloroform) deltaH1.03d (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; nuclear magnetic resonance carbon spectrum (solvent is deuterated chloroform) deltaC 14.4CH3,44.7CH,81.6C,40.5CH2,24.4CH2,53.8CH,74.3C,43.4CH2,123.3CH,140.3CH,53.8C,27.5CH3,26.0CH3,25.0CH3,28.1CH3,166.4C,121.4CH,150.0C,43.8CH2,60.0CH2,18.2CH3(ii) a High resolution mass spectrometry [ M ]]+m/z 367.2714, calculated 367.2723.
Example 2
The preparation method of the nitrogenous ring nerolidne type sesquiterpene derivative shown in the formula (I) comprises the following steps:
a Trichoderma asperellum A-YMD-9-2 strain growing well on a plate is taken, cut into small pieces and inoculated into a rice solid culture medium, 50 g of the rice solid culture medium is put into each 1L triangular flask, 200 bottles in total are statically fermented for 40 days at room temperature, then ethyl acetate is used for extraction for three times, reduced pressure concentration is carried out, and 212.4 g of crude extract is obtained after concentration.
The rice solid medium comprises 500 g of rice, 6 g of peptone, 500 ml of distilled water and 500 ml of aged seawater per liter.
Trichoderma asperellum A-YMD-9-2 strain was preserved in the China center for type culture Collection CCTCC at 2018, 6 months and 27 days, address: the preservation number of the university of Wuhan, China is CCTCC M2018405, the classification name is Trichoderma asperellum, and the plant number is A-YMD-9-2.
Subjecting the crude extract to 100-mesh 200-mesh silica gel column chromatography, performing gradient elution sequentially with petroleum ether-ethyl acetate and dichloromethane-methanol at volume ratios of 50:1, 20:1, 10:1, 5:1, 2:1, 1:1 to 0:1, and 20:1, 10:1, 5:1, 2:1 to 0:1, respectively collecting eluates, detecting the collected components by Thin Layer Chromatography (TLC) (dichloromethane-methanol development at volume ratio of 50-1: 1, anisaldehyde-sulfuric acid color development or 254nm ultraviolet light detection), judging and combining the same or similar parts according to Rf value to obtain 8 components (1-8).
Component 6 with Rf value of 0.6-0.7 (volume ratio of 7:1 dichloromethane-methanol development, 254nm ultraviolet detection), that is, component eluted with volume ratio of 10:1 dichloromethane-methanol gradient, is sequentially subjected to reversed phase C18Silica gel column, Sephadex LH-20 gel column and preparative thin layer chromatography. Inverse phase C18Performing silica gel column chromatography with water-methanol at volume ratio of 1:1, performing TLC detection (dichloromethane-methanol at volume ratio of 7:1 is developed, and ultraviolet light at 254nm is detected, and anisaldehyde-sulfuric acid is developed), and collecting component with fluorescence under ultraviolet light at 254nm and anisaldehyde-sulfuric acid is developed into red; collecting eluate of the fraction by Sephadex LH-20 gel column chromatography, detecting by TLC (dichloromethane-methanol development at volume ratio of 7:1, ultraviolet detection at 254nm, and anisaldehyde-sulfuric acid color development), and collecting anisaldehyde-sulfuric acid red component; collecting components, performing thin layer chromatography, using dichloromethane-methanol with volume ratio of 7:1 as developing agent, and collecting components which have fluorescence under 254nm ultraviolet light and Rf value of 0.6-0.7, i.e. compound (8.7 mg) shown in formula (I). And detecting by thin layer chromatography (volume ratio of 7:1 dichloromethane-methanol development, 254nm ultraviolet detection, anisaldehyde-sulfuric acid color development), wherein the compound shows single, uniform fluorescence and red spots, and is determined to be a pure compound. The structure is identified as a nitrogenous ring nerolidne type sesquiterpene derivative through spectral analysis, and the structural formula is shown as (I).
Example 3
The difference from the embodiment 2 is that
A Trichoderma asperellum A-YMD-9-2 strain growing well on a flat plate is taken, cut into small pieces and inoculated into a jerusalem artichoke glucose liquid culture medium, 300 ml of the culture medium is put into each 1L triangular flask, 200 bottles in total are statically fermented for 40 days at room temperature, then dichloromethane is used for extraction for three times, reduced pressure concentration is carried out, and 200 g of crude extract is obtained after concentration.
The jerusalem artichoke glucose liquid culture medium comprises 500 ml of boiling juice containing 200 g of jerusalem artichoke tubers per liter, 20 g of glucose, 5 g of peptone and 500 ml of aged seawater.
Subjecting the crude extract to 200-mesh 300-mesh silica gel column chromatography, sequentially performing gradient elution with petroleum ether-ethanol at volume ratio of 50:1, 30:1, 15:1, 10:1, 5:1, 2:1, 1:1 to 0:1, respectively collecting eluates, detecting by thin layer chromatography (petroleum ether-ethanol at volume ratio of 50-0:1 is developed, anisaldehyde-sulfuric acid is developed or 254nm ultraviolet light is detected), and judging and combining the same or similar parts according to Rf value to obtain 8 components (1-8).
Developing the component 6 with Rf value of 0.6-0.7 (petroleum ether-ethanol ratio of 3:1, detecting with 254nm ultraviolet light, and developing with anisaldehyde-sulfuric acid), and sequentially eluting with petroleum ether-ethanol gradient of volume ratio of 5:1 by reversed phase C18Silica gel column, Sephadex LH-20 gel column and preparative thin layer chromatography. Inverse phase C18Performing silica gel column chromatography with water-ethanol at volume ratio of 1:1, performing TLC detection (petroleum ether-ethanol at volume ratio of 3:1 is developed, ultraviolet detection at 254nm is performed, and anisaldehyde-sulfuric acid is developed), and collecting anisaldehyde-sulfuric acid red component; collecting eluate after Sephadex LH-20 gel column chromatography, detecting by TLC (petroleum ether-ethanol development at volume ratio of 3:1, ultraviolet detection at 254nm, and anisaldehyde-sulfuric acid color development), and collecting anisaldehyde-sulfuric acid red component; collecting components, performing thin layer chromatography with petroleum ether-ethanol as developer at volume ratio of 3:1, and collecting components with Rf value of 0.6-0.7 to obtain the product shown in formula (I)The nitrogen-containing ring nerolidine type sesquiterpene derivative.
Example 4
Microalgae inhibition activity experiment:
specifically, the method comprises activating microalgae to be tested, collecting microalgae in logarithmic growth phase, and diluting with sterilized f/2 culture medium to a certain cell concentration (about 5 × 10)4One/ml), take 96-well plate, add 195 microliter algae solution per well as test culture plate. The sample group and the control group were each set in triplicate, the sample group was added 5. mu.l of a 4 mg/ml compound solution in dimethyl sulfoxide (DMSO) as the solvent, the blank group was added 5. mu.l of a solvent, and the positive control group was added 5. mu.l of K in 4 mg/ml concentration2Cr2O7And (3) solution. The culture temperature is 20 ℃, the illumination intensity is 2000Lux, and the light-dark ratio is 14:10 (h), and the culture is carried out for 24 h. Wherein the microalgae to be tested is marine dunaliella anata.
Counting microalgae in each experimental group under a microscope by using a blood counting plate. For the experimental group with the inhibition rate of more than 50%, the half inhibition concentration IC is further calculated50The value is obtained. The prepared compound solutions with final concentrations of 4 mg/ml were sequentially diluted to finally obtain 15 groups of sequentially reduced concentrations of components (1000, 500, 200, 100, 50, 20, 10, 5, 2, 1, 0.5, 0.25, 0.125, 0.0625, 0.03125 μ g/ml). Observing and calculating microalgae inhibition rate of the compound under each concentration gradient, taking at least 5 concentration gradients with the inhibition rate between 0 and 100, and calculating IC50The value is obtained.
The experimental results are as follows: the obtained cyclonerane sesquiterpene derivative has half inhibitory concentration of 1.1 microgram/ml on marine dunaliella and has effect of inhibiting marine dunaliella.
Claims (3)
1. A nitrogenous ring nerolidine type sesquiterpene derivative is characterized in that: the structure of the nerolidine type sesquiterpene derivative containing nitrogen ring is shown as the formula (I)
2. A method for preparing nitrogen-containing cyclonerane-type sesquiterpene derivatives of claim 1, which comprises the following steps: inoculating Trichoderma asperellum A-YMD-9-2 into a fungus culture medium for fermentation culture, and purifying the fermentation product to obtain the nitrogenous cyclic nerolidine type sesquiterpene derivative shown in the formula (I); the Trichoderma asperellum A-YMD-9-2 is preserved in a China Center for Type Culture Collection (CCTCC) in 2018, 6 months and 27 days, and the preservation number is CCTCC M2018405;
the preparation method comprises the following specific steps:
1) inoculating Trichoderma asperellum A-YMD-9-2 into a fungus culture medium, fermenting for 10-60 days, extracting with an organic solvent, and concentrating to obtain a crude extract;
2) subjecting the crude extract obtained in the step 1) to silica gel column chromatography, performing gradient elution by eluent, collecting eluted components, and detecting the eluted components by thin layer chromatography;
3) collecting the eluted components in the step 2), and sequentially carrying out reversed phase silica gel column chromatography, gel column chromatography and preparation thin layer chromatography for separation and purification to obtain the nitrogenous ring nerolidne type sesquiterpene derivative shown in the formula (I);
the fungus culture medium in the step 1) is a rice solid culture medium, a jerusalem artichoke glucose liquid culture medium or a potato glucose liquid culture medium;
the organic solvent is one or more of ethyl acetate, petroleum ether, n-hexane, cyclohexane, dichloromethane, methanol, ethanol, propanol or isopropanol;
the eluent in the step 2) is one or more of petroleum ether-ethyl acetate, petroleum ether-ethanol, petroleum ether-propanol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, dichloromethane-methanol, dichloromethane-ethanol, dichloromethane-propanol and dichloromethane-isopropanol in a volume ratio of 50-0: 1;
the reverse phase silica gel column chromatography eluent in the step 3) is water-methanol or water-ethanol with the volume ratio of 5-0: 1; the eluent of the gel column chromatography is dichloromethane-methanol or dichloromethane-ethanol with the volume ratio of 2-0: 1; the thin layer chromatography developing solvent is prepared from dichloromethane-methanol or petroleum ether-ethanol with the volume ratio of 30-0: 1.
3. Use of the nitrogenous ring nerolidine-type sesquiterpene derivative of claim 1, wherein: the nitrogenous ring nerolidine type sesquiterpene derivative is used for preparing an algistat for marine dunaliella.
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| CN110003041B (en) * | 2019-04-26 | 2021-09-28 | 中国科学院烟台海岸带研究所 | Cyclonerane acylated derivative and preparation and application thereof |
| CN109956883B (en) * | 2019-04-26 | 2021-09-28 | 中国科学院烟台海岸带研究所 | Acetylated nitrogenous ring nerolidine type sesquiterpene derivative and preparation and application thereof |
| CN109988180B (en) * | 2019-04-26 | 2021-09-28 | 中国科学院烟台海岸带研究所 | Diketopiperazine derivative and preparation and application thereof |
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