CN103265550A - Alkaloid compound, preparation method thereof, application thereof in preparing paints resisting marine biofouling and anticancer drugs - Google Patents
Alkaloid compound, preparation method thereof, application thereof in preparing paints resisting marine biofouling and anticancer drugs Download PDFInfo
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- CN103265550A CN103265550A CN2013101351496A CN201310135149A CN103265550A CN 103265550 A CN103265550 A CN 103265550A CN 2013101351496 A CN2013101351496 A CN 2013101351496A CN 201310135149 A CN201310135149 A CN 201310135149A CN 103265550 A CN103265550 A CN 103265550A
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Abstract
The invention discloses alkaloid class compounds and preparation method thereof and the application in preparation marine biofouling prevention coating material and anti-tumor drug. Its structure of alkaloid compound such as formula (I) is shown, wherein compound 1:R1=H, R2=OH, R3=Cl; Compound 2:R1=OH, R2=H, R3=H. Compound 1 and compound 2 are that preparative separation obtains from fungi Aspergillus westerdijkiae DFFSCS013(CCTCC M2013078) fermentation liquid. Alkaloid compound of the invention has anti-ocean Macro-fouling Organismss grass tongue fur worm and kentrogon attachment activity, and the growth of the various tumor cell strains such as malignant myeloid cell lines K562 can be inhibited, therefore have good application prospect in terms of preparation marine biofouling prevention coating material and anti-tumor drug.
Formula (I) wherein compound 1:R1=H, R2=OH, R3=Cl; Compound 2:R1=OH, R2=H, R3=H.
Description
Technical field:
The invention belongs to biological technical field, be specifically related to alkaloid compounds and preparation method thereof and the application in the anti-marine biofouling coating of preparation and antitumor drug.
Background technology:
Fungi can produce the secondary metabolite of the multiple structure type that comprises alkaloids, peptide class, polyketone class, steroidal and terpene etc., wherein much has antitumor, antibacterium, biological activity such as antimycotic, antiviral, pest-resistant.Alkaloid is the nitrogenous alkaline organic compound of a class in the natural product, and great majority have complicated ring texture, are one of effective constituent important in the natural drug.Had at present many alkaloids to be used for clinical example, as the camptothecine in the camplotheca acuminata and the vincristine(VCR) in the Vinca for antitumor etc.In addition, marine biofouling become people take full advantage of oceanic resources one of the matter of utmost importance that will urgently solve.Along with poisonous paint such as TBT are disabled in the whole world, it is urgent to develop efficient, nontoxic, eco-friendly ocean novel antifouling agent demand, and the research of this respect is dashed forward important ecological significance and economic implications.The Marine Natural Product Antifoulants agent belongs to nontoxic (or low toxicity) stain control agent, easily degraded, and do not endanger halobiontic life, be conducive to keep ecological balance, therefore, develop the Marine Natural Product Antifoulants agent and become one of important channel that obtains the high effect nontoxic stain control agent.
Summary of the invention:
First purpose of the present invention provides a class and has antitumor and alkaloid compound anti-fouling activity.
The present invention is by multiple column chromatography and one dimension, two dimensional NMR wave spectrum, from the fermented liquid of fungi Aspergillus westerdijkiae DFFSCS013, separate and obtain the new alkaloid compound of a class, this alkaloid compound has the cytotoxic activity that suppresses multiple growth of cancer cells, can be used for preparing antitumor drug; And also have anti-marine biofouling to adhere to activity, can be used for preparing anti-marine biofouling coating, thereby realized purpose of the present invention.
Alkaloid compound of the present invention, its structure is shown in formula I:
Formula I
Compound 1:R
1=H, R
2=OH, R
3=Cl; Compound 2:R
1=OH, R
2=H, R
3=H.
Second purpose of the present invention provides the preparation method of the alkaloid compound shown in formula I.
The preparation method of the alkaloid compound shown in formula I of the present invention is characterized in that, may further comprise the steps:
(1) fermented liquid of preparation fungi Aspergillus westerdijkiae DFFSCS013;
(2) fermented liquid that step (1) is obtained concentrates and obtains ethyl acetate extract, dichloromethane extract or chloroform extract with ethyl acetate, methylene dichloride or chloroform solvent extraction;
(3) with the described ethyl acetate extract of step (2), dichloromethane extract or chloroform extract are through the normal pressure silica gel column chromatography, with chloroform-methanol, chloroform-acetone, chloroform-ethyl acetate, sherwood oil-acetone or petroleum ether-ethyl acetate solvent systems are eluent, carry out gradient elution from volume ratio 100:0 to 0:100, follow the trail of the merging component with thin-layer chromatography, the component that on thin-layer chromatography, can launch with the chloroform-methanol solvent systems in volume ratio 95:5 to the 90:10 scope, obtain crude product through gel filtration chromatography, purified, obtain the alkaloid compound 1 and 2 shown in formula I.
The fermented liquid of fungi Aspergillus westerdijkiae DFFSCS013 described in the step (1) can be inoculated into fungi Aspergillus westerdijkiae DFFSCS013 in the suitable substratum of aspergillus fungi, makes under common fermentation condition.Preferred manufacturing procedure is that fungi Aspergillus westerdijkiae DFFSCS013 is inoculated in the PDA nutrient agar, cultivated 3 days for 26 ℃, obtain cultivating the flat board that bacterial classification is arranged, then bacterial classification inoculation in the flat board is gone in the PDB liquid nutrient medium, cultivated 2 days for 26 ℃ in rotating speed 200rpm shaking table, temperature, obtain seed liquor, seed liquor is inoculated in the rice solid medium again, leave standstill cultivation 26 days in 26 ℃ of temperature, obtain fermented liquid.The composition of above-mentioned PDA nutrient agar is potato 200g, glucose 20g, sea salt 30g, agar 20g and 1L water; The composition of PDB liquid nutrient medium is potato 200g, glucose 20g, sea salt 30g and 1L water; The composition of rice solid medium is rice 400g, yeast extract 2g, glucose 2g, sea salt 18g and water 600mL.
The most handy ethyl acetate of the described extraction of step (2), described concentrating can be adopted conventional method such as concentrating under reduced pressure.
The described purifying of step (3) can adopt chromatographic column to separate or recrystallization.
Adhere to active testing by the large-scale fouling organism grass tongue worm larva in anti-ocean and kentrogon and find that compound 1 and compound 2 suppress the EC that careless tongue worm larva adheres in the formula I of the present invention
50Value is respectively 13.51 μ g/mL and 28.12 μ g/mL, and suppresses the EC that kentrogon adheres to
50Value is less than 25 μ g/mL, when measured maximum concentration 200 μ g/mL, larva is not shown toxicity, has good anti-marine biofouling activity, can be for the preparation of anti-marine biofouling coating, as it being infiltrated alone or in combination or being spread in the film forming natural resin, polyethylene ethyl acetate copolymer and other hydrolyzable, in the polymkeric substance such as solvable or insoluble resin, make fouling resistance coating, effective constituent to the surface that fouling resistance coating can discharge q.s reaches antifouling effect, and these compounds are active skull cap components, and all not soluble in water, very easily be dissolved in chloroform, low polar organic solvent such as ethyl acetate has good lipophilicity, therefore can be applied to alone or in combination prepare in the marine antifoulant, have a good application prospect.
By the anti tumor activity in vitro screening experiment, the result shows: the compound 1 shown in the formula I of the present invention and 2 suppresses the IC of human leukemia cell line K562 growth
50Value is respectively 44.2 and 52.8 μ M, and the effect of certain inhibition malignant melanoma cell strain A375, lung cancer cell line A549, cervical cancer cell strain HeLa, breast cancer cell line mcf-7, laryngeal cancer cell strain Hep-2, hepatoma cell strain HepG2, colon-cancer cell strain SW-620 growth is arranged.
Therefore, the 3rd purpose of the present invention provides the alkaloid compound shown in the formula I or the application of its salt in the anti-marine biofouling coating of preparation and antitumor drug.
Described antitumor drug is preferably anti-human white blood medicine.
The present invention is from fungi Aspergillus westerdijkiae DFFSCS013(CCTCC M2013078) the fermented liquid preparation separate and obtained alkaloid compounds-compound 1 and compound 2.Compound 1 and compound 2 have the large-scale fouling organism grass tongue worm in anti-ocean and kentrogon adheres to activity, and can suppress growth of various tumor cell strains such as leukemia cell line K562, therefore have a good application prospect aspect the anti-marine biofouling coating of preparation and the antitumor drug.
Fungi Aspergillus westerdijkiae DFFSCS013 of the present invention is preserved in Chinese typical culture collection center (CCTCC), address on March 12nd, 2013: China, Wuhan, Wuhan University, preserving number CCTCC M2013078.
Description of drawings:
Fig. 1 is the NOESY coherent signal of compound 1 and 2, wherein 1 representation compound, 1,2 representation compound 2.
Embodiment:
Following examples are to further specify of the present invention, rather than limitation of the present invention.
Embodiment 1: alkaloid compound 1 and 2 preparation
The PDA nutrient agar is like this preparation: with 200 gram potatoes, and 20 gram glucose, 30 gram sea salt, 20 gram agar mix, and add 1 premium on currency and fully dissolve, 121 ℃ of high pressure steam sterilizations 25 minutes.
The PDB liquid nutrient medium is like this preparation: with 200 gram potatoes, and 20 gram glucose, 30 gram sea salt mix, and add after 1 premium on currency fully dissolves, and are sub-packed in the Erlenmeyer flask of 500mL again, and every bottle of about 150mL was 121 ℃ of high pressure steam sterilizations 25 minutes.
The rice solid medium is like this preparation: 400 gram rice, 2 gram yeast extracts, 2 gram glucose, 18 gram sea salt are mixed, add after 600 ml waters fully dissolve, in the Erlenmeyer flask of the 5000mL that packs into, 121 ℃ of high pressure steam sterilizations 25 minutes.
With aseptic bamboo let with fungi Aspergillus westerdijkiae DFFSCS013 bacterial classification inoculation on the PDA nutrient agar, cultivated 3 days for 26 ℃, obtain cultivating the flat board that bacterial classification is arranged, choosing about 3 microlitre bacterial classification inoculations with aseptic bamboo let from flat board then goes into to contain in the Erlenmeyer flask of the above-mentioned PDB of the being equipped with liquid nutrient medium of 150mL, cultivated 2 days for 26 ℃ in shaking table (rotating speed 200rpm) temperature, obtain seed liquor, in the triangular flask of above-mentioned every bottle of rice solid medium, inoculate the 50mL seed liquor again, leave standstill cultivation after 26 days in 26 ℃ of temperature, obtain fermented liquid.
To cultivate the fermented liquid that obtains through rice solid medium (2kg rice altogether) extracts 3 times with acetone-water (volume ratio 80:20), it is residual then this extracting solution to be evaporated to no acetone, with water equal-volume ethyl acetate extraction 3 times after concentrating, concentrating under reduced pressure obtains ethyl acetate extract 30g.After ethyl acetate extract is mixed sample with purification on normal-phase silica gel (200-300 order) dry method, the glass chromatography column (containing the about 500g of 200-300 purpose purification on normal-phase silica gel) of packing into, carry out the normal temperature column chromatography, with chloroform-methanol as eluent, carry out gradient elution from volume ratio 100:0 to 0:100, according to thin-layer chromatography (GF
254Silica-gel plate) situation merges each cut, reclaims eluting solvent, and the evaporate to dryness cut shifts with methyl alcohol.The component that to can launch with the chloroform-methanol solvent systems in volume ratio 95:5 to the 90:10 scope on thin-layer chromatography is through gel filtration chromatography (diameter 18mm, column length 1600mm, gel is sephedex LH-20, moving phase is the chloroform-methanol of volume ratio 1:1) separate, collect cut, separate out crude product, crude product adopts high performance liquid phase half preparation, and (the detection wavelength is 254nm, flow velocity is 3mL/min, chromatographic column is Phenomenex Gemini 5 μ C18110A column (250 * 10mm, 5 μ m), moving phase is that volume ratio is the methanol-water of 65:35) be 25 to separate purifying during with 33 minutes and obtain compound 1 and 2 at appearance time respectively.
Wherein the structure elucidation of compound 1 is as follows:
The steric configuration of compound 1 is identified H-4, H-10 and CH by NOESY spectrum (Fig. 1)
3NOE coherent signal between-24 shows H-10 and CH
3-24 is beta comfiguration, and H-10 and CH
3-24 be positioned at the pentamethylene ring the surface and towards H-4, the relative configuration of deducibility C-3 is shown in formula I thus; Simultaneously, H-19 and NH-21/CH
3-23 have NOE is correlated with, and shows H-19 and CH
3-23 is the α configuration.Hence one can see that, relative configuration and the sclerotiamide of compound 1 are identical, again because the absolute configuration of sclerotiamide by identifying with the method for analog paraherquamide contrast, therefore the absolute configuration of compound 1 is accredited as (3R too, 10S, 11R, 17S, 19S).The concrete structure of compound 1 shown in formula I, R wherein
1=H, R
2=OH, R
3=C1.
Table 1. compound 1 and 2 NMR data (500and125MH
z, respectively, in DMSO-d6, δ ppm)
asignals?overlapping
Formula I.
Embodiment 2: the anti-careless tongue worm larva of the alkaloid compound shown in the formula (I) adheres to active testing
The active testing model adopts the inhibition test of adhering to of one of the most frequently used marine fouling organism model in present laboratory multicell grass tongue worm larva (Bugula neritina).The multicell grass tongue worm of the maturation that collects is placed in the seawater with 0.22 μ m membrane filtration, stimulates with illumination, collect ripe multicell grass tongue worm through the larva of light stimulation generation.Larva is placed in the watch-glass that fills with the seawater of 0.22 μ m membrane filtration.Do active test with the larva that careless tongue worm produces through illumination.The anti-larva of adopting 24 hole polystyrene plates to measure compound adheres to activity.Formula (I) compound (compound 1 or compound 2) is dissolved in DMSO respectively, is diluted to different concentration solution (60 –, 140 μ g/mL) as test fluid with the sterile filtration seawater.The careless tongue worm larva that adds 1mL test fluid and 20 ± 2 maturations in each hole, each concentration are established 5 and repeat sample, and the sterile filtration seawater is done blank.Place 28 ℃ of incubators to place 3 hours 24 porocyte culture plates.Larva number in that the microscopically statistics is adhered to carries out statistical study with spss11.0 software, calculates EC
50Value.
Embodiment 3: the anti-kentrogon of alkaloid compound shown in the formula (I) adheres to active testing
The active testing model is the inhibition test of adhering to that adopts one of the most frequently used marine fouling organism model in present laboratory line barnacle worm cyprids (Barnacles larvae).Adult barnacle is food with very thin Chaetoceros (Chaetoceros gracilis Schutt), in 0.22 μ m filtering sea the nauplius larva of barnacle is cultivated the cypris larva stage, every milliliter of 2 larvas, 28 ℃ of culture temperature.Carry out activity test with the Venus stage young that produces.The anti-larva of adopting 24 hole polystyrene plates to measure compound adheres to activity.Formula (1) compound (compound 1 or compound 2) is dissolved in DMSO respectively, is diluted to different concentration solution (60 –, 140 μ g/mL) as test fluid with the sterile filtration seawater.The kentrogon that adds 1mL test fluid and 20 ± 2 maturations in each hole, each concentration are established 5 and repeat sample, and the sterile filtration seawater is done blank.Place 30 ℃ of incubators to place 24 hours 24 porocyte culture plates.Add up the larva number that adheres at microscopically.
Experimental result shows, compound 1 and 2 suppresses the inhibiting rate that kentrogon adheres to and is respectively 70% and 64%, its EC in the formula (I) when starting point concentration 25 μ g/mL
50Value should not have further test less than 25 μ g/mL(owing to sample size is limited), when measured maximum concentration 200 μ g/mL, larva is not shown toxicity, alkaloid compound shown in the formula (I) has anti-kentrogon and adheres to activity thus, can be for the preparation of in the anti-marine biofouling coating.
Embodiment 4: the alkaloid compound anti tumor activity in vitro test shown in the formula (I)
Collect leukemia cell line K562, malignant melanoma cell strain A375, lung cancer cell line A549, cervical cancer cell strain HeLa, breast cancer cell line mcf-7, laryngeal cancer cell strain Hep-2, hepatoma cell strain HepG2 and the colon-cancer cell strain SW-620 of logarithmic phase respectively, make its suspension with 10% serum, 1640 substratum, be inoculated in 96 well culture plates, every porocyte number is 5000/80 μ L, places 5%CO
237 ℃ of cultivations of incubator.With 10% serum, 1640 substratum compound 1 and 2 in the formula (I) being diluted to concentration is 3.125 μ g/mL, 6.25 μ g/mL, 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL, 100 μ g/mL, the experimental solutions of 200 μ g/mL.Adding concentration next day in the culture plate of different experimental group respectively is 3.125 μ g/mL, 6.25 μ g/mL, 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL, 100 μ g/mL, the experimental solutions 20 μ L of 200 μ g/mL, and make the final concentration in every hole reach test (experimental group concentration adopts the two-fold dilution).10% serum, 1640 substratum that add equivalent in addition in the negative control group.Behind the 48h, inhale the nutrient solution of abandoning in experimental group and the control group, every hole adds MTT20 μ L (2.5mg/mL), continue to cultivate 4h, every hole adds DMSO100 μ L termination reaction again, places 20min for 37 ℃, detect each hole in the absorbance A value at 570nm place with microplate reader, calculate inhibitory rate of cell growth.Cell growth rate=(experimental group OD ÷ control group OD) * 100%.
Experimental result shows that the compound 1 shown in the formula I of the present invention and 2 suppresses the IC of human leukemia cell line K562 growth
50Value is respectively 44.2 and 52.8 μ M, and the effect of certain inhibition malignant melanoma cell strain A375, lung cancer cell line A549, cervical cancer cell strain HeLa, breast cancer cell line mcf-7, laryngeal cancer cell strain Hep-2, hepatoma cell strain HepG2, colon-cancer cell strain SW-620 growth is arranged, IC
50Value is 80～100 μ M.Therefore the alkaloid compound shown in the formula of the present invention (I) can be for the preparation of antitumor drug.
Claims (7)
1. the alkaloid compound shown in the formula I:
Compound 1:R
1=H, R
2=OH, R
3=Cl; Compound 2:R
1=OH, R
2=H, R
3=H.
2. the preparation method of the described alkaloid compound of claim 1 is characterized in that, may further comprise the steps:
(1) fermented liquid of preparation fungi Aspergillus westerdijkiae DFFSCS013;
(2) fermented liquid that step (1) is obtained concentrates and obtains ethyl acetate extract, dichloromethane extract or chloroform extract with ethyl acetate, methylene dichloride or chloroform solvent extraction;
(3) with the described ethyl acetate extract of step (2), dichloromethane extract or chloroform extract are through the normal pressure silica gel column chromatography, with chloroform-methanol, chloroform-acetone, chloroform-ethyl acetate, sherwood oil-acetone or petroleum ether-ethyl acetate solvent systems are eluent, carry out gradient elution from volume ratio 100:0 to 0:100, follow the trail of the merging component with thin-layer chromatography, the component that on thin-layer chromatography, can launch with the chloroform-methanol solvent systems in volume ratio 95:5 to the 90:10 scope, obtain crude product through gel filtration chromatography, purified, obtain the described compound 1 of claim 1 and 2.
3. the preparation method of alkaloid compound according to claim 2, it is characterized in that, the preparation of fermentation liquid method of fungi Aspergillus westerdijkiae DFFSCS013 described in the step (1) is that fungi Aspergillus westerdijkiae DFFSCS013 is inoculated in the PDA nutrient agar, cultivated 3 days for 26 ℃, obtain cultivating the flat board that bacterial classification is arranged, then with the bacterial classification inoculation on the flat board in the PDB liquid nutrient medium, in rotating speed 200rpm shaking table, temperature was cultivated 2 days for 26 ℃, obtain seed liquor, seed liquor is inoculated in the rice solid medium again, leave standstill cultivation 26 days in room temperature, obtain fermented liquid; The prescription of described rice solid medium is: add rice 400g, yeast extract 2g, glucose 2g and sea salt 18g in every 600mL water.
4. the preparation method of alkaloid compound according to claim 2 is characterized in that, the described extraction ethyl acetate of step (2), described concentrated employing concentrating under reduced pressure; The described purifying of step (3) adopts chromatographic column to separate or recrystallization.
5. the described alkaloid compound of claim 1 or its salt adhere to application in the coating the anti-marine fouling organism of preparation.
6. the described alkaloid compound of claim 1 or its salt application in the preparation antitumor drug.
7. application according to claim 6 is characterized in that, described antitumor drug is anti-human white blood medicine.
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Cited By (7)
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|---|---|---|---|---|
| CN104031954A (en) * | 2014-06-06 | 2014-09-10 | 中国海洋大学 | Method for preparing monoterpene-dihydro-quinolinone alkaloid compound and crystals thereof as well as application of crystals as marine antifouling agent |
| CN107033221A (en) * | 2017-02-08 | 2017-08-11 | 中国科学院南海海洋研究所 | Two small-molecular peptides and preparation method thereof and the application in antiviral drugs is prepared |
| CN108484628A (en) * | 2018-05-25 | 2018-09-04 | 广西中医药大学 | Application of the kusulactone class compound in preventing marine biofouling |
| CN111228330A (en) * | 2020-03-13 | 2020-06-05 | 广州暨南生物医药研究开发基地有限公司 | Stephanine-containing anti-inflammatory pharmaceutical composition and preparation method thereof |
| CN111234586A (en) * | 2020-02-24 | 2020-06-05 | 中国科学院南海海洋研究所 | Application of pyrazinoquinazolinetrione alkaloid compound in preparation of marine fouling organism control agent |
| CN112225714A (en) * | 2020-09-25 | 2021-01-15 | 中国科学院南海海洋研究所 | Phthalide glycerol ether compound, preparation method thereof and application thereof in marine biofouling resistance |
| CN113265337A (en) * | 2021-06-17 | 2021-08-17 | 华南农业大学 | Marine aspergillus versicolor and isolated culture method and application thereof |
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| CN104031954A (en) * | 2014-06-06 | 2014-09-10 | 中国海洋大学 | Method for preparing monoterpene-dihydro-quinolinone alkaloid compound and crystals thereof as well as application of crystals as marine antifouling agent |
| CN104031954B (en) * | 2014-06-06 | 2017-10-13 | 中国海洋大学 | A kind of preparation method of monoterpene dihydro-quinolinone alkaloid compound and its crystal and the application as marine antifoulant |
| CN107033221A (en) * | 2017-02-08 | 2017-08-11 | 中国科学院南海海洋研究所 | Two small-molecular peptides and preparation method thereof and the application in antiviral drugs is prepared |
| CN108484628A (en) * | 2018-05-25 | 2018-09-04 | 广西中医药大学 | Application of the kusulactone class compound in preventing marine biofouling |
| CN108484628B (en) * | 2018-05-25 | 2020-01-17 | 广西中医药大学 | Application of quassin lactone compounds in preventing marine biofouling |
| CN111234586A (en) * | 2020-02-24 | 2020-06-05 | 中国科学院南海海洋研究所 | Application of pyrazinoquinazolinetrione alkaloid compound in preparation of marine fouling organism control agent |
| CN111234586B (en) * | 2020-02-24 | 2021-01-19 | 中国科学院南海海洋研究所 | Application of pyrazinoquinazolinetrione alkaloid compound in preparation of marine fouling organism control agent |
| CN111228330A (en) * | 2020-03-13 | 2020-06-05 | 广州暨南生物医药研究开发基地有限公司 | Stephanine-containing anti-inflammatory pharmaceutical composition and preparation method thereof |
| CN112225714A (en) * | 2020-09-25 | 2021-01-15 | 中国科学院南海海洋研究所 | Phthalide glycerol ether compound, preparation method thereof and application thereof in marine biofouling resistance |
| CN113265337A (en) * | 2021-06-17 | 2021-08-17 | 华南农业大学 | Marine aspergillus versicolor and isolated culture method and application thereof |
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