CN108484363B - Sesquiterpene triol compound and preparation and application thereof - Google Patents
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Abstract
The invention relates to the field of algae inhibitors, in particular to a sesquiterpene triol compound derived from algal epiphytic fungi, a preparation method thereof and application thereof in inhibiting microalgae. The preparation method comprises inoculating Trichoderma viride (Trichoderma virens) Y13-3 of algal epiphytic fungus to a fungus culture medium for fermentation culture, and separating and purifying the fermentation product to obtain the sesquiterpene triol compound shown in formula (I). According to the sesquiterpene triol compound obtained by the invention, the half inhibition concentration of the compound on microalgae can reach 0.27 microgram/ml through a microalgae inhibition activity experiment.
Description
Technical Field
The invention relates to the field of algae inhibitors, in particular to a sesquiterpene triol compound derived from algal epiphytic fungi, a preparation method thereof and application thereof in inhibiting microalgae.
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 for the red tide is to inhibit the development of red tide organisms, namely red tide algae besides preventing the eutrophication of seawater, and the method for inhibiting the development of the red tide algae is mainly chemical agent 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 medicine 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 sesquiterpene triol compound and preparation and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a sesquiterpene triol compound has a structure shown in formula (I)
A method for preparing sesquiterpene triol compound comprises inoculating Trichoderma viride (Trichoderma virens) Y13-3 in fungus culture medium, fermenting, and purifying the fermentation product to obtain sesquiterpene triol compound shown in formula (I); the Trichoderma viride (Trichoderma virens) Y13-3 is preserved in the China Center for Type Culture Collection (CCTCC) in 2018, 1 month and 10 days, and the preservation number is CCTCC M2018016;
the preparation method comprises the following specific steps:
1) inoculating Trichoderma viride (Trichoderma virens) Y13-3 into a fungus culture medium, fermenting for 10-60 days, extracting by 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 using an organic solvent, collecting eluent, and detecting the eluent 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 thin layer chromatography for separation and purification to obtain the sesquiterpene triol compound shown in the formula (I).
The fungus culture medium in the step 1) is a potato glucose liquid culture medium, a rice solid culture medium, a wort culture medium or a jerusalem artichoke glucose liquid culture medium; preferably: potato dextrose liquid medium.
The organic solvent extract is one or more of dichloromethane, ethyl acetate, methanol, ethanol, propanol or isopropanol; preferably: and (3) ethyl acetate.
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 gel column chromatography is dichloromethane-methanol or dichloromethane-ethanol with volume ratio of 2-0: 1; the thin layer chromatography developing solvent is petroleum ether-ethyl acetate, petroleum ether-ethanol or dichloromethane-ethyl acetate with volume ratio of 10-0: 1.
And 3) detecting by TLC after each chromatography in the step 3), and collecting components with red spots.
The application of the sesquiterpene triol compound in preparing the algistat for microalgae is disclosed.
The microalgae are marine dunaliella, prorocentrum donghaiense, red tide heterocurvula and virulent Carlsberg which cause marine red tide.
The invention has the following advantages: the sesquiterpene triol compound obtained by fermenting and separating Trichoderma viride (Trichoderma virens) Y13-3 separated from the surface of the marine red algae gracilaria is subjected to microalgae activity inhibition experiments to obtain the compound with half inhibition concentrations of 0.27,3.6,4.2 and 5.0 micrograms/ml for marine kappaphycus, east-sea prototheca, red-tide isocurvularia and virulent kappaphycus respectively.
Detailed Description
The invention is further illustrated below with reference to the examples of embodiment.
Example 1
The structure of the sesquiterpene triol compound derived from the epiphytic fungi of the seaweed is shown as a formula (I).
The compound has the following physicochemical and spectral characteristics:
colorless oil; specific optical rotation [ alpha ]]20 D7.2(c0.16, MeOH); nuclear magnetic resonance hydrogen spectrum (deuterium substituted chloroform as solvent)H1.66(d, 14.0), 1.57(dd, 14.1, 7.5), 4.19(d, 7.2), 1.53(dd, 11.6, 0.7), 1.85(m), 1.46(tdd, 11.2, 13.8, 2.9), 2.09(ddd, 15.2, 5.1, 2.8), 2.03(m), 5.34(br d, 8.4), 2.02(dd, 14.8, 8.7), 1.81(m), 1.21(s), 1.26(s), 1.75(br s), 1.02(s), 3.30(s); nuclear magnetic resonance carbon spectrum (deuterated chloroform as solvent)C42.9(C)，49.9(CH2)，73.4(CH)，85.6(C)，57.3(CH)，22.2(CH2)，34.7(CH2)，139.2(CH)，122.2(CH)，43.0(CH2)，75.8(CH)，25.0(CH3)，25.7(CH3)，27.6(CH3)，21.4(CH3) (ii) a High resolution mass spectrometry [ M ]]+m/z254.1881, calculated 254.1882.
Example 2
A preparation method of sesquiterpene triol compounds shown in formula (I) comprises the following steps:
a Trichoderma viride (Trichoderma virens) Y13-3 strain growing well on a flat plate is taken, cut into small pieces and inoculated into a potato 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 30 days at room temperature, then ethyl acetate is used for extraction for three times, reduced pressure concentration is carried out, and 27.2 g of crude extract is obtained after concentration.
The potato glucose liquid culture medium comprises 500 ml of boiling juice containing 100 g of potatoes per liter, 20 g of glucose, 5 g of peptone, 5 g of yeast extract powder and 500 ml of aged seawater.
Trichoderma viride (Trichoderma virens) strain Y13-3 was stored in the China center for type culture Collection CCTCC 1 month 10 days 2018, address: the preservation number of the university of Wuhan, China is CCTCC M2018016, the classification name is Trichoderma virens, and the strain number is Y13-3.
Subjecting the crude extract to 200-mesh 300-mesh silica gel column chromatography, sequentially eluting with petroleum ether-ethyl acetate at volume ratios of 50: 1, 20: 1, 10: 1, 5: 1, 2: 1 to 1: 1 and dichloromethane-methanol at volume ratios of 20: 1, 10: 1, 5: 1 to 1: 1, respectively collecting eluates, detecting the collected components by Thin Layer Chromatography (TLC) (petroleum ether-ethyl acetate at volume ratio of 20-0: 1 is developed, and anisaldehyde-sulfuric acid is used as color developing agent), and judging and combining the same or similar parts according to Rf value to obtain 10 components (1-10).
Subjecting fraction 6 with Rf value of 0.3-0.4 (developed with ethyl acetate and developed with sulfuric acid-anisaldehyde) to gradient elution with petroleum ether-ethyl acetate at volume ratio of 1: 1, and sequentially subjecting to reversed phase C18Silica gel column, SephadexLH-20 gel column and thin layer chromatography. Inverse phase C18Performing TLC detection (developing with ethyl acetate and developing with sulfuric acid-anisaldehyde) with water-methanol at volume ratio of 1: 1 as eluent, and collecting red spot component; collecting fraction, performing Sephadex LH-20 gel column chromatography with methanol as eluent, detecting by TLC (ethyl acetate development, sulfuric acid-anisaldehyde color development), and collecting red spot fraction; collecting the components, performing thin layer chromatography, using petroleum ether-ethyl acetate as developing agent at volume ratio of 1: 1, collecting the component with Rf value of 0.3-0.4, which is the compound (6.8 mg) shown in formula (I), detecting by TLC (ethyl acetate development, sulfuric acid-anisaldehyde color development), and determining as pure compound. By spectroscopic analysis, its junctionThe structure is identified as a novel sesquiterpene triol compound, and the structural formula is shown in (I).
Example 3
The difference from the embodiment 2 is that
Taking Trichoderma viride (Trichoderma virens) Y13-3 strain growing well on a flat plate, cutting into small pieces, inoculating into Jerusalem artichoke glucose liquid culture medium, putting 300 ml of culture medium into each 1L triangular flask, standing and fermenting for 40 days at room temperature, filtering, and respectively collecting mycelium and fermentation liquid.
The jerusalem artichoke glucose liquid culture medium comprises 500 ml of boiling juice containing 100 g of jerusalem artichoke tubers, 20 g of glucose, 5 g of peptone, 5 g of yeast extract powder and 500 ml of aged seawater per liter.
Collecting about 30L fermentation liquid, extracting with ethyl acetate for three times, and concentrating under reduced pressure; drying and pulverizing mycelium, extracting with ethyl acetate for three times, and concentrating under reduced pressure; the concentrate was subjected to Thin Layer Chromatography (TLC) detection (volume ratio 20-0: 1 petroleum ether-ethyl acetate development, sulfuric acid-anisaldehyde development) to obtain similar results, and the concentrate of the fermentation broth and the mycelium was combined to obtain 18.0 g of crude extract.
Subjecting the crude extract to 200-mesh 300-mesh silica gel column chromatography, sequentially eluting with petroleum ether-ethanol at volume ratio of 50: 1, 30: 1, 15: 1, 10: 1, 5: 1, 2: 1, and 1: 1 to 0: 1, respectively collecting eluates, detecting with thin layer chromatography (petroleum ether-ethyl acetate at volume ratio of 20-0: 1 for development, and sulfuric acid-anisaldehyde for color development), and determining and combining the same or similar parts according to Rf value to obtain 8 components (1-8).
Subjecting fraction 4 with Rf value of 0.3-0.4 (developed with ethyl acetate and developed with sulfuric acid-anisaldehyde) to gradient elution with petroleum ether-ethanol at volume ratio of 10: 1, and sequentially subjecting to reversed phase C18Silica gel column, Sephadex LH-20 gel column and thin layer chromatography. Inverse phase C18Eluting with silica gel column chromatography with water-ethanol at volume ratio of 1: 1, and detecting by TLC (ethyl acetate development, sulfuric acid-anisaldehyde)Color development), collecting the components of red spots; collecting fraction, performing Sephadex LH-20 gel column chromatography with ethanol as eluent, detecting by TLC (ethyl acetate development, sulfuric acid-anisaldehyde color development), and collecting red spot fraction; collecting the components, performing thin layer chromatography, using petroleum ether-ethanol as developing agent at volume ratio of 8: 1, and collecting the components with Rf value of 0.3-0.4 to obtain sesquiterpene triol compound shown in formula (I).
Example 4
Microalgae inhibition activity experiment:
the method specifically comprises the following steps: activating the microalgae to be tested, taking the microalgae in logarithmic growth phase, diluting to a certain algae cell concentration (about 5 × 10) by using a sterilized f/2 culture medium4One/ml), take 96-well plate, add 95 microliter algae solution per well as test culture plate. The sample group and the control group were each set in triplicate, and 5. mu.l of a solution of the compound of formula (I) at a concentration of 4 mg/ml in dimethyl sulfoxide (DMSO) was added to the sample group, 5. mu.l of dimethyl sulfoxide (DMSO) was added to the blank group, and 5. mu.l of K at a concentration of 4 mg/ml was added to the positive control group2Cr2O7And (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 Cardunaliella, prorocentrum donghaiense, red tide heterocurvula or virulent Carlsberg algae.
Counting microalgae in each experimental group under a microscope by using a blood counting plate, and further calculating half inhibitory concentration IC of the experimental group with the inhibitory rate of more than 50%50The value is obtained. The prepared DMSO solutions of the compound shown in the formula (I) with the final concentration of 4 mg/ml are sequentially diluted by DMSO, and 11 groups of components with sequentially reduced concentrations (2000, 1000, 500, 200, 100, 50, 20, 10, 5, 2, 1 microgram/ml) are finally obtained. 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 sesquiterpene triol compound has half inhibitory concentrations of 0.27 microgram/ml, 3.6 microgram/ml, 4.2 microgram/ml and 5.0 microgram/ml for Scutellaria oceanica, Prorocentrum donghaiensis, Isochrysosporium rubescens or Rhabdophyceae acutifolius respectively, and has the effect of inhibiting Scutellaria oceanica, Prorocentrum donghaiensis, Isochrysosporium rubescens or Rhabdophyceae acutifolius.
Claims (3)
1. A sesquiterpene triol compound, which is characterized in that: the structure of the sesquiterpene triol compound is shown in the formula (I)
2. A method of preparing a sesquiterpene triol compound of claim 1 comprising: 1) inoculating Trichoderma viride (Trichoderma virens) Y13-3 into a fungus culture medium, fermenting for 10-60 days, extracting by 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 using an organic solvent, collecting eluent, and detecting the eluent 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 thin layer chromatography for separation and purification to obtain the sesquiterpene triol compound shown in the formula (I);
the Trichoderma viride (Trichoderma virens) Y13-3 is preserved in the China Center for Type Culture Collection (CCTCC) in 2018, 1 month and 25 days, and the preservation number is CCTCC M2018016;
the fungus culture medium in the step 1) is a potato glucose liquid culture medium, a rice solid culture medium, a malt wort culture medium or a jerusalem artichoke glucose liquid culture medium;
the organic solvent extract is one or more of dichloromethane, ethyl acetate, 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;
step 3), the reverse phase silica gel column chromatography eluent is water-methanol or water-ethanol with the volume ratio of 5-0: 1; the eluent of gel column chromatography is dichloromethane-methanol or dichloromethane-ethanol with volume ratio of 2-0: 1; the thin layer chromatography developing solvent is petroleum ether-ethyl acetate, petroleum ether-ethanol or dichloromethane-ethyl acetate with volume ratio of 10-0: 1;
and 3) detecting by TLC after each chromatography in the step 3), and collecting components with red spots.
3. Use of the sesquiterpene triol of claim 1 in which: the sesquiterpene triol compound is applied to preparing an algistat for microalgae;
the microalgae is marine dunaliella, prorocentrum donghaiense, red tide heterocurvula or virulent karl algae causing marine red tide.
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| CN109232493B (en) * | 2018-11-14 | 2022-08-16 | 中国科学院海洋研究所 | Sesquiterpene compound and preparation method and application thereof |
| CN111606878B (en) * | 2020-05-25 | 2023-02-21 | 中国科学院烟台海岸带研究所 | Cadinane derivative and preparation and application thereof |
| CN111662257B (en) * | 2020-05-25 | 2023-03-14 | 中国科学院烟台海岸带研究所 | Benzencadinane derivative, and preparation and application thereof |
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