CN103478149A - Application of nigericin in preparing algicide - Google Patents
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Abstract
The invention provides application of nigericin in preparing algicide, relating to alga killing compounds. The molecular formula of nigericin is C40H68O11, and the relative molecular mass is 742. Nigericin is an effective alga inhibiting active compound, and can be applied to preparation of algicide. The production strain of nigericin is Streptomyces malaysiensis O4-6, and is collected in the China Center for Type Culture Collection (CCTCC) on February 28, 2011 with the collection number of CCTCC NO: M2011051.
Description
Technical field
The present invention relates to kill the algae compound, the particularly application of a kind of nigericin in preparing algae-inhibiting agent.
Background technology
In recent years, along with being widely used of molecular ecology method, the huge progress that the actinomycetic Study on Diversity in marine actinomycete Study on Diversity, especially deep-sea obtains.Increasing marine actinomycete is found (1, Prof.Alan Claude, W., Diversity and biogeography of marine actinobacteria[J] .2006.9(3): 279-286.), comprise new 16S rDNA sequence cluster (2, Liesack, W.and E.Stackebrandt, Occurrence of novel groups of the domain Bacteria as revealed by analysis of genetic material isolated from an Australian terrestrial environment.J.Bacteriol.[J], 1992.174 (15): 5072-5078.3, Rheims, H., et al., Molecular biological evidence for the occurrence of uncultured members of the actinomycete line of descent in different environments and geographical locations.Microbiology[J], 1996.142 (10): 2863-2870.), actinomycetic kind and quantity constantly increase, 170 genus have been increased to by 3 initial genus.Yet, actinomycetic known species with its quantity existed at natural world, compare remain inappreciable (4, Bull, A.T., et al., Marine actinobacteria:perspectives, challenges, future directions.Antonie Van Leeuwenhoek International Journal of General and Molecular Microbiology[J], 2005.87 (3): 259-262; 5, Jensen, P.R., et al., Marine actinomycete diversity and natural product discovery.Antonie van Leeuwenhoek[J], 2005.87 (1): 43-48).
Due to the particularity of marine environment, marine microorganism has unique metabolic way, and the metabolic chemistry structure of generation has great complexity and diversity.Over nearly 20 years, relevant marine microorganism produces the new report with bioactive secondary metabolite to be increased gradually, finds that from marine actinomycete the probability of new biological activity material even surpasses the Lu Sheng actinomycetes.The part active substance obtained from marine actinomycete has griseorhodin A, salt spore amine A, salt spore amine B, the blue element of smoked clothing cyanines, salt amine, tetraodotoxin, ocean mycin A, B, four and mycin D1, chromomycin A3, enterococcin, echinomycin, antimycin A, bar bifilomycin, Antibiotic U-5956, lipomycin, the lagosin, Deng (6, Xu Lihua etc., actinomycetes phylogeny---principle, method and put into practice [M]. Beijing: Science Press, 2007.).These results of study show, marine environment is the precious resources storehouse of finding and screening new actinomycetes species and metabolite, are wherein containing a large amount of actinomycetes resources and are awaiting development and utilize.
Since 20th century, be accompanied by the coastal area explosive population growth, the developing rapidly of industrial or agricultural, the serious organic contamination of inner bay, river mouth and the stretch of coastal water and eutrophication.Harmful algae wawter bloom (Harmful algae blooms, HABs) be sharply ascendant trend in Chinese generation scale and frequency, to China coast caused serious ecology, Environmental and resource issue and great economic loss (7, Qin, S., et al., Two New Metabolites, Epoxydine A and B, from Phoma sp.Helvetica Chimica Acta[J], 2010.93 (1): 169-174).Research red-tide control method, formulate the environmental practice that relevant Preventing Countermeasures has become the task of top priority of many countries and regions.Because the physics and chemistry method is administered red tide and is existed and be difficult to that large tracts of land is used and easily cause the weak point such as secondary pollution, utilize biological Ecology Action each other administer red tide become the current research focus (8, Skerratt, J.H., et al., Algicidal bacteria associated with blooms of a toxic dinoflagellate in a temperate Australian estuary.Marine Ecology-Progress Series[J], 2002.244:1-15.).
Up to now, the algal control microorganism that great majority screen is to have carried out the algal control effect by secreting the special material with algistatic activity.The algistatic activity material of having reported comprises: protein (containing extracellular enzyme), polypeptide, amino acid, antibiotic, nitrogen-containing compound etc. other not yet qualitatively the algal control compound (9, Yoshikawa, K., et al., beta-cyanoalanine production by marine bacteria on cyanide-free medium and its specific inhibitory activity toward cyanobacteria.Applied and Environmental Microbiology[J], 2000.66 (2): 718-722).Become by screening efficient, single-minded algistatic activity material the new approaches that the exploitation algae-inhibiting agent is administered for red tide.
Summary of the invention
The purpose of this invention is to provide the application of a kind of nigericin in preparing algae-inhibiting agent.
The molecular formula of described nigericin (Nigericin) is C
40h
68o
11, relative molecular mass is 742, structural formula is:
Described nigericin is a kind of potent algistatic activity compound, and nigericin can be applied in preparing algae-inhibiting agent.The production bacterial strain of described nigericin is Streptomyces malaysiensis O4-6, this bacterial strain has been preserved in Chinese Typical Representative culture collection center on February 28th, 2011, preservation center deposit number is: CCTCC NO:M2011051, address: China. Wuhan. and Wuhan University.
The preparation method of described nigericin comprises the following steps:
1) separation of ruling on flat board of the inoculation that will produce nigericin is cultivated 5～7d at 28～37 ℃ of temperature; Picking list colony inoculation is in the Gause I liquid nutrient medium, and in 28～37 ℃, 180～250rpm obtains zymotic fluid after cultivating 5～7d; The gained zymotic fluid is carried out centrifugal, collect supernatant; The bacterial strain of described production nigericin is Streptomyces malaysiensis O4-6, this bacterial strain has been preserved in Chinese Typical Representative culture collection center on February 28th, 2011, preservation center deposit number is: CCTCC NO:M2011051, address: China. Wuhan. and Wuhan University;
2) be extracted with ethyl acetate step 1) gained supernatant, reduced pressure concentration, drying, obtain acetic acid ethyl ester extract;
3) acetic acid ethyl ester extract is dissolved in to ethyl acetate, then joins in silicagel column and carry out wash-out, collect eluent and carry out thin layer chromatography analysis, according to launching collection of illustrative plates, merge the eluent of collecting;
4) by step 3) gained eluent in 30～45 ℃ of lower evaporated in vacuo, product carries out the mensuration of algistatic activity, but obtains the active component of algal control;
5) but the active component of gained algal control is carried out to the high performance liquid chromatography wash-out, collect eluent, obtain nigericin.
In step 1), described centrifugal condition can be: speed 10000～12000g, time 10～20min.
In step 3), the specification of described silicagel column can be 170mm * 30mm, 200～300 orders; The eluant, eluent of described wash-out can be the mixture of n-hexane and ethyl acetate etc.; The program of described wash-out is: with n-hexane and the ethyl acetate volume ratio mixture wash-out 20min of 1: 2, then use n-hexane and the ethyl acetate volume ratio mixture wash-out 30min of 1: 1, finally use n-hexane wash-out 30min; The flow velocity of wash-out can be 1mL/min; The solvent of described thin layer chromatography analysis can be ethyl acetate etc., and the developer of described thin layer chromatography analysis is the chloroformic solution containing 0.5% iodine etc.
In step 5), the program of described wash-out can be:
0～7.5min, 85% methanol/water (v/v);
7.5～10.5min 85% methanol/water～100% methyl alcohol;
10.5～22.5min 100% methyl alcohol.
Collect 10.5～12.5min eluent and be dissolved in DMSO checking algistatic activity in 30 ℃ of lower evaporated in vacuo of Rotary Evaporators.
The potent algistatic activity compound of gained is through algistatic activity component thin layer chromatography (Thin Layer Chromatography, TLC) detect, usining ethyl acetate, carrene and chloroform launches on silica gel thin-layer plate as solvent to be a spot, is defined as pure compound, and warp
1h-NMR detects, and determines the structural formula of potent algistatic activity compound, and described potent algistatic activity compound can effectively be killed the phaeocystis globosa cell, and it has huge application potential in the preparation of algae-inhibiting agent.
The present invention uses the conventional method screening to obtain a strain Streptomyces malaysiensis O4-6, pass through fermented and cultured, the zymotic fluid that acquisition contains strong algistatic activity compound, described zymotic fluid is centrifugal, collect supernatant, then described supernatant is carried out to separation and purification, obtain the compound with strong algistatic activity.The compound of described strong algistatic activity can be killed frustule efficient, single-mindedly, has the potential that is developed to algae-inhibiting agent, at aspects such as biological degradation algae and improvement red tides, has a wide range of applications.
The accompanying drawing explanation
The high efficiency liquid phase collection of illustrative plates that Fig. 1 is potent algistatic activity compound.In Fig. 1, abscissa is time (min), and ordinate is absorbance (mAU); Respectively compose from left to right peak and be respectively 2.948,10.491,10.910,12.042.
Embodiment
Following examples are to further illustrate of the present invention, but the invention is not restricted to following embodiment.
The separation screening of embodiment 1 marine streptomyces Streptomyces malaysiensis O4-6
One, the separation screening concrete steps of Streptomyces malaysiensis O4-6 are:
1) (particular location is Fujian sky Mangrove Wetlands: 117 ° 24 '-117 ° 30 ' E, 23 ° 53 '-23 ° 56 ' N) sediments, in room temperature, place dry 1 month, get the dry soil sample of 10g, be dissolved in autoclaved 90mL Gause I medium, be placed in 150rpm shaking table concussion 20min, make soil sample dispersed;
2), by 10 times of dilutions of step 1) gained sample, coat Gause I (20g soluble starch, 1g NaNO
3, 0.5gK
2hPO
4, 0.5g MgSO
47H
2o, 0.01g FeSO
47H
2o, 75 μ g K
2cr
2o
7, 10g agar, 1L seawater) and solid plate, be placed at 28 ℃ of temperature and cultivate 5d;
3) the dissimilar single bacterium colony of picking lines the Gause I solid plate, is placed under 28 ℃ and cultivates 5d, verifies whether pure culture, repeats this step until obtain pure culture;
4) inoculate isolated pure culture list bacterium colony in 4mL Gause I liquid nutrient medium, be placed in 28 ℃ of shaking tables, 5d is cultivated in the 180rpm concussion, gets culture centrifugal 10min under the centrifugal force of 10000g, removes bacterial sediment, and supernatant is saved to the 4.5mL centrifuge tube;
5) the 1mL supernatant is joined in 20mL exponential phase phaeocystis globosa culture fluid, in 20 ± 1 ℃, 12h illumination, 12h dark, 50 μ mol photons m
-2s
-1cultivate 2d under the intensity of illumination condition, the Gause I medium for the contrast add in algae liquid, arrange respectively 3 parallel; Observe the whether sedimentation of phaeocystis globosa cell, if sedimentation represent in the 7d culture supernatant of thalline and contain the algistatic activity material, thus filter out the algistatic activity bacterial strain.
Two, the separation screening concrete steps of Streptomyces malaysiensis O4-6 can be:
1) Fujian sky Mangrove Wetlands (117 ° 24 '-117 ° 30 ' E, 23 ° 53 '-23 ° 56 ' N) sediments, in room temperature, place dry 1 month, get the dry soil sample of 10g, be dissolved in autoclaved 90m L Gause I medium, be placed in 200rpm shaking table concussion 30min, make soil sample dispersed;
2), by 10 times of dilutions of step 1) gained sample, coat Gause I (20g soluble starch, 1g NaNO
3, 0.5gK
2hPO
4, 0.5g MgSO
47H
2o, 0.01g FeSO
47H
2o, 75 μ g K
2cr
2o
7, 10g agar, 1L seawater) and solid plate, be placed under 37 ℃ and cultivate 7d;
3) the dissimilar single bacterium colony of picking lines the Gause I solid plate, is placed under 37 ℃ and cultivates 7d, verifies whether pure culture, repeats this step until obtain pure culture;
4) inoculate isolated pure culture list bacterium colony in 4mL Gause I liquid nutrient medium, be placed in 37 ℃ of shaking tables, 7d is cultivated in the 250rpm concussion, gets culture centrifugal 20min under the centrifugal force of 12000g of 7d, removes bacterial sediment, and supernatant is saved to the 4.5mL centrifuge tube;
5) the 1mL supernatant is joined in 20mL exponential phase phaeocystis globosa culture fluid, in 20 ± 1 ℃, 12h illumination, 12h dark, 50 μ mol photons m
-2s
-1cultivate 2d under the intensity of illumination condition, the Gause I medium for the contrast add in algae liquid, arrange respectively 3 parallel; Observe the whether sedimentation of phaeocystis globosa cell, if sedimentation represent in the supernatant of thalline 7d culture and contain the algistatic activity material, thus filter out the algistatic activity bacterial strain.
The computational methods of embodiment 2 algal control rates
1) phaeocystis globosa is at 20 ± 1 ℃, 12h illumination, 12h dark, 50 μ mol photons m
-2s
-1under the intensity of illumination condition, be cultured to exponential phase in triangular flask, then divide and install in 24 porocyte culture plates, every hole packing 2mL frustule suspension, Adaptable growth 1d;
2) 100 μ L culture to be measured adds 24 orifice plates, cultivates 2d;
3) get the phaeocystis globosa culture fluid, 200 μ L samples, in 24 orifice plates, detect the fluorescence intensity at 680nm place under the 460nm excitation by microplate reader, according to following formula, calculate the algal control rate, observe the frustule metamorphosis simultaneously:
Algal control rate=(F
c-F
t)/F
c* 100%
In formula, F
cmean the control group fluorescence intensity, F
tmean the experimental group fluorescence intensity.
Embodiment 3 algistatic activity physical properties are identified
1) marine streptomyces Streptomyces malaysiensis O4-6 is inoculated in 28～37 ℃ of shaking tables of Gause I medium, and 5～7d is cultivated in 180～250rpm concussion.Zymotic fluid is centrifugal 10～20min under the centrifugal force of 10000～12000g, obtains streptomycete Streptomyces malaysiensis O4-6 culture fluid supernatant; Be extracted with ethyl acetate the gained supernatant, reduced pressure concentration, drying, obtain acetic acid ethyl ester extract.
2) Temperature Treatment experimental design: the culture fluid supernatant containing the algistatic activity material is carried out to 40 ℃, 60 ℃, 80 ℃, 100 ℃ and 120 ℃ of high pressure 30min thermal treatment, 3 parallel laboratory test groups are set; The control experiment group is: untreated culture fluid supernatant; Get 100 μ L culture fluid supernatants and add in the 2mL algae culturing liquid, after cultivating 2d, sampling is pressed embodiment 2 and is calculated algal control efficiency.Experimental result (referring to table 1) shows: after this culture fluid supernatant carries out thermograde thermal treatment, its efficiency of algal control to phaeocystis globosa does not vary widely, and illustrates that the algistatic activity material can not tolerate high temperature treatment more than 100 ℃.
The impact of table 1 Temperature Treatment on algistatic activity material algal control efficiency
3) pH processes experimental design: measure culture fluid supernatant pH value, by culture fluid supernatant pH be adjusted to respectively 1,3,5,7,9 and 11,2h after again its pH is recalled to processing, 3 parallel laboratory test groups are set; Get 100 μ L bacteria-free filtrates and add in the 2mL algae culturing liquid, after cultivating 24h, sampling is pressed embodiment 2 and is calculated algal control efficiency.Experimental result (referring to table 2) shows: after this culture fluid supernatant carries out acidifying and basification, its efficiency of algal control to phaeocystis globosa does not vary widely, and illustrates that the algistatic activity material is all more stable under acid condition and alkali condition.
Table 2pH processes the impact on algistatic activity material algal control efficiency
4) dialysis treatment experimental design: utilize the molecule interception to be about the 1Kd bag filter, the culture fluid supernatant is carried out to dialysis treatment, after PBS buffer solution dialysis 3h, proceed to fresh PBS buffer solution and continue dialysis 3h, 3 parallel laboratory test groups are set; Control group is the culture fluid supernatant of not dialysing; Get 100 μ L culture fluid supernatants and add in the 2mL algae culturing liquid, after cultivating 24h, sampling is pressed embodiment 2 and is calculated algal control efficiency.Experimental result (referring to table 3) shows: after the bag filter dialysis treatment that this culture fluid supernatant is about 1Kd through the molecule interception, its efficiency of algal control to phaeocystis globosa obviously reduces, its algal control efficiency is only on average 21.4%, illustrates that the algistatic activity molecular weight of material is less than 1Kd.
The impact of table 3 dialysis treatment on algistatic activity material algal control efficiency
5) different organic solvents extraction experiments design: select n-butanol, carrene, ethyl acetate as extractant, with 1: 1 volume ratio extraction 500mL culture fluid supernatant, repeat 3 extractions respectively.500mL culture fluid supernatant, in 30 ℃ of lower evaporated in vacuo of Rotary Evaporators, selects the 500mL acetonitrile to dissolve.Various extractive with organic solvent, in 30 ℃ of lower evaporated in vacuo of Rotary Evaporators, obtain the extraction crude extract.5mL DMSO dissolves crude extract, gets 100 μ L DMSO dissolved matters and adds in the 2mL algae culturing liquid, and after cultivating 24h, sampling is pressed embodiment 2 and calculated algal control efficiency, and 3 parallel laboratory test groups are set, and adds DMSO to the algae culturing liquid control group.Experimental result (table 4) shows: this culture fluid supernatant is after the opposed polarity organic solvent extraction, algal control efficiency shows different, acetic acid ethyl ester extract algal control rate is higher, and average out to 87.9% illustrates a little less than algistatic activity material polarity and easily extracted by ethyl acetate.
Table 4 different organic solvents extract algal control efficiency
Embodiment 4 algistatic activity component silica gel column chromatographies
Streptomycete Streptomyces malaysiensis O4-6 is inoculated in 28～37 ℃ of shaking tables of Gause I medium, and 5～7d is cultivated in 180～250rpm concussion.Zymotic fluid is centrifugal 10～20min under the centrifugal force of 10000～12000g, obtains streptomycete Streptomyces malaysiensis O4-6 culture fluid supernatant.Be extracted with ethyl acetate the gained supernatant, reduced pressure concentration, drying, obtain acetic acid ethyl ester extract.
The 100mg acetic acid ethyl ester extract is dissolved in 1mL ethyl acetate, is splined on silicagel column (170 * 30mm, 200-300 order), eluant, eluent: the mixture of n-hexane and ethyl acetate, elution program: volume ratio 1: 2,20min; 1: 1,30min; 1: 0,30min; Elution flow rate: 1mL/min; Collect eluent 2mL/ pipe with collecting pipe.
Embodiment 5 algistatic activity component thin layer chromatographys (Thin Layer Chromatography, TLC) are analyzed
1) as embodiment 4, eluent utilizes TLC to analyze, and solvent is ethyl acetate, developer: the chloroformic solution of 0.5% iodine merges eluent in collecting pipe according to launching collection of illustrative plates.
2) merge eluent in 30 ℃ of lower evaporated in vacuo of Rotary Evaporators, be dissolved in DMSO, press the method validation algistatic activity in embodiment 2, embodiment 3, obtain potent algistatic activity component.
Embodiment 6 algistatic activity component high performance liquid chromatography (High-performance liquid chromatography, HPLC) are analyzed
The potent algistatic activity component of embodiment 5 gained utilizes HPLC to analyze, elution program:
0～7.5min, 85% methanol/water;
7.5min～10.5min 85% methanol/water～100% methyl alcohol;
10.5～22.5min 100% methyl alcohol.
As shown in Figure 1, the eluent of collecting 10.5～12.5min is dissolved in DMSO in 30～45 ℃ of lower evaporated in vacuo of Rotary Evaporators to experimental result, presses embodiment 2, embodiment 3 checking algistatic activities.
The Structural Identification of the potent algistatic activity compound of embodiment 7:
Embodiment 6 algistatic activities detect, and through TLC, detect, with ethyl acetate, carrene and chloroform, on silica gel thin-layer plate, launch to be a spot, and warp
1h-NMR detects, and is defined as pure compound, and structural formula is as follows:
The ESI-MS spectrum of described pure compound is at m/z747.47[M+Na]
+place shows the adduct ion peak of molecule, in conjunction with 13C-NMR(DEPT) spectrum and 1H-NMR spectrum, releasing its molecular formula is C
40h
68o
11, relative molecular mass is 742.The 1H-NMR spectrum shows a large amount of methyl, methylene and 1 methoxyl group signal.13C-NMR spectrum show 40 C, by the trace analysis with DEPT, can obviously obtain: 10 CH
3(δ
cbe respectively 59.53,29.00,22.76,16.98,16.41,16.12,14.38,13.39,13.07,11.48), 10 CH
2(δ
cbe respectively 66.88,41.65,37.08,35.77,32.30,31.99,29.47,26.27,25.86,23.51), 15 CH
1(δ
cbe respectively 85.17,81.39,79.40,76.75,76.43,73.20,68.37,60.38,45.79,39.58,36.69,36.40,35.07,31.80,27.65), 5 quaternary carbon (δ
cbe respectively 183.83,107.49,97.15,84.78,82.31).From the two-dimensional map of HMBC, HSQC, H-H COSY and NOSEY, can determine the relevant ownership of each C and H.Through the Scifinder database retrieval, then compare with corresponding document, then comprehensive its physicochemical property, determine consistent with nigericin.
In sum, to extract the compound with algistatic activity that purifying obtains be nigericin in the present invention.
Claims (1)
1. the application of nigericin in preparing algae-inhibiting agent; The molecular formula of described nigericin is C
40h
68o
11, relative molecular mass is 742; The production bacterial strain of described nigericin is Streptomyces malaysiensis O4-6, and this bacterial strain is preserved in Chinese Typical Representative culture collection center on February 28th, 2011, and preservation center deposit number is: CCTCC NO:M2011051.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113303341A (en) * | 2021-07-16 | 2021-08-27 | 西南大学 | Application of streptomyces malaysiae F913 |
| CN116496923A (en) * | 2022-11-30 | 2023-07-28 | 南京灿辰微生物科技有限公司 | Streptomyces griseoviridis 0728-09 and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20060166343A1 (en) * | 2003-07-07 | 2006-07-27 | Ben Hankamer | Photosynthetic hydrogen production |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113303341A (en) * | 2021-07-16 | 2021-08-27 | 西南大学 | Application of streptomyces malaysiae F913 |
| CN116496923A (en) * | 2022-11-30 | 2023-07-28 | 南京灿辰微生物科技有限公司 | Streptomyces griseoviridis 0728-09 and application thereof |
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