CN101921280A - Seaweed polyether compound and preparation method and application thereof - Google Patents
Seaweed polyether compound and preparation method and application thereof Download PDFInfo
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- CN101921280A CN101921280A CN2009100162240A CN200910016224A CN101921280A CN 101921280 A CN101921280 A CN 101921280A CN 2009100162240 A CN2009100162240 A CN 2009100162240A CN 200910016224 A CN200910016224 A CN 200910016224A CN 101921280 A CN101921280 A CN 101921280A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 41
- 229920000570 polyether Polymers 0.000 title claims abstract description 20
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 19
- 241001474374 Blennius Species 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 241000195493 Cryptophyta Species 0.000 claims abstract description 11
- 241001338998 Laurencia saitoi Species 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 238000004809 thin layer chromatography Methods 0.000 claims description 24
- 239000000284 extract Substances 0.000 claims description 17
- 239000000287 crude extract Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 235000014666 liquid concentrate Nutrition 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 8
- 239000013535 sea water Substances 0.000 abstract description 5
- 238000013375 chromatographic separation Methods 0.000 abstract description 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 3
- 238000001035 drying Methods 0.000 abstract 1
- 238000002386 leaching Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical group ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001641 gel filtration chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 241001247197 Cephalocarida Species 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 208000031513 cyst Diseases 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 231100000225 lethality Toxicity 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IFHPYSVGNHWKDY-UHFFFAOYSA-N (+)-Thyrsiferol Natural products O1C(C(C)(O)C)CCC1(C)C(O)CCC(C)(O)C1OC2(C)CCC(C3(C)OC(C)(C)C(Br)CC3)OC2CC1 IFHPYSVGNHWKDY-UHFFFAOYSA-N 0.000 description 1
- IFHPYSVGNHWKDY-JXHBSGSUSA-N (1s,4s)-4-[(2r,4as,6r,8ar)-2-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-4a-methyl-3,4,6,7,8,8a-hexahydro-2h-pyrano[3,2-b]pyran-6-yl]-1-[(2r,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]pentane-1,4-diol Chemical compound O1[C@@H](C(C)(O)C)CC[C@]1(C)[C@@H](O)CC[C@](C)(O)[C@@H]1O[C@@]2(C)CC[C@H]([C@@]3(C)OC(C)(C)[C@H](Br)CC3)O[C@@H]2CC1 IFHPYSVGNHWKDY-JXHBSGSUSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000422392 Laurencia Species 0.000 description 1
- 241000206640 Rhodomelaceae Species 0.000 description 1
- 241000206572 Rhodophyta Species 0.000 description 1
- 238000005276 aerator Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical class OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 210000001136 chorion Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CFIPFJIKZAGWFH-UHFFFAOYSA-N thyrsifenyl 23-acetate Natural products O1C(C(C)(C)OC(=O)C)CCC1(C)C(O)CCC(C)(O)C1OC2(C)CCC(C3(C)OC(C)(C)C(Br)CC3)OC2CC1 CFIPFJIKZAGWFH-UHFFFAOYSA-N 0.000 description 1
- KIRZKILDCHMWNV-UHFFFAOYSA-N thyrsiferol Natural products CC(C)(O)C1CCC(C)(C1)C(O)CCC(C)(O)C2CCC3OC(CCC3(C)O2)C4(C)CCC(Br)C(C)(C)O4 KIRZKILDCHMWNV-UHFFFAOYSA-N 0.000 description 1
- CFIPFJIKZAGWFH-WMYXADBDSA-N thyrsiferyl 23-acetate Chemical compound O1[C@@H](C(C)(C)OC(=O)C)CC[C@]1(C)[C@@H](O)CC[C@](C)(O)[C@@H]1O[C@@]2(C)CC[C@H]([C@@]3(C)OC(C)(C)[C@H](Br)CC3)O[C@@H]2CC1 CFIPFJIKZAGWFH-WMYXADBDSA-N 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the field of insecticidal drugs, in particular to a seaweed polyether compound and a preparation method and an application thereof. The seaweed polyether compound is as shown in the specific structural formula (I), and the preparation method comprises the steps of washing laurencia saitoi perestenko of marine red alga clean with seawater, removing gravels and miscellaneous algae attached on the surface, drying in the shade, smashing, then leaching, carrying out solvent distribution and repeated chromatographic separation and obtaining a monomer compound. The obtained compound can be used as the drug which is used as a pesticide. Furthermore, the natural structure of the polyether compound extracted, separated and purified from the laurencia saitoi perestenko of the marine red alga belongs to a micromolecular natural organic compound, and the seaweed polyether compound is easily prepared, has significant insecticidal activity and can be used as the insecticidal drug. In the structural formula (I), R is equal to OH or OAc.
Description
Technical field
The present invention relates to the insecticidal materials field, is a kind of seaweed polyether compound and its production and application specifically.
Background technology
In recent years, because people are more and more higher to the requirement of environmental quality, and some common insecticides side effect occurs because of residue problem, and the insect resistance that constantly produces or the like, eco-friendly sterilant more and more is subject to people's attention, wherein, plant insecticide has efficiently, low toxicity and easy advantage such as degraded, its research and development are especially noticeable, demonstrate good ecology, economic and social benefit, show vast potential for future development.
Summary of the invention
The purpose of this invention is to provide a kind of seaweed polyether compound and its production and application.
For achieving the above object, the technical solution used in the present invention is:
Seaweed polyether compound: shown in the structural formula (I),
Structural formula (I), wherein: R=OH or OAc.
The preparation method of seaweed polyether compound:
1) marine red alga is risen together concave crown algae (Laurencia saitoi) and wash, dry in the shade, pulverize, then extract 2-5 time with organic solution, united extraction liquid concentrates, and obtains crude extract;
2) water of getting 10-15 times of volume of gained crude extract in the step 1) adds in the crude extract of step 1), then uses volume of water 1-1.5 ethyl acetate extraction doubly 2-5 time, extract concentrated extract, standby;
3) get step 2) in extract carry out silica gel column chromatography, carry out wash-out with organic solvent, collect elutriant, elutriant detects through thin-layer chromatography;
Described machine solvent is 100: 0-0: the petroleum ether-ethyl acetate of 100 gradients or sherwood oil-acetone;
4) with in the step 3) with 0-10: the component under 100 gradient elutions carries out gel column and the thin-layer chromatography separation and purification gets structural formula (I) target compound.
Organic solution in the step 1) can be in chloroform, acetone, ethyl acetate, ethanol or the methyl alcohol one or more.
The used elutriant of silica gel column chromatography can be petroleum ether-ethyl acetate or sherwood oil-acetone in the described step 4); During the described thin-layer chromatography separation and purification of described step 4), developping agent is an ethyl acetate, and Rf is the component of 0.45-0.5, and structural formula (I) R that is behind the purifying is the target compound of OH; Developping agent is an ethyl acetate, and Rf is the component of 0.65-0.7, and structural formula (I) R that is behind the purifying is the target compound of OAc.
Described compound can be made the medicine of sterilant.
The present invention has the following advantages:
The marine red alga that the present invention relates to is risen concave crown algae (Laurencia saitoi) together and is belonged to rhodophyta, Rhodomelaceae, Laurencia marine alga, be distributed widely in the areas such as China, Japan and the Korea peninsula of West Pacific Ocean bank, generally be grown on the rock of tideland.The present invention rises the concave crown algae together by marine red alga and belongs to the small molecules natural organic-compound through extracting, separate the polyethers natural compounds that obtains, prepare easily, our experiments show that their lethality rates to the halogen worm when 10 mcg/ml are 100%, have significant insecticidal activity, can be used as insecticidal materials.
Embodiment:
Below in conjunction with embodiment the present invention is further elaborated.
Embodiment 1
The preparation method of seaweed polyether compound:
1) will gather the fresh concave crown algae (Laurencia saitoi) that rises together and clean through seawater, and remove the grit and the assorted algae of surface attachment, shady and cool place airing is standby.Get sample 70 grams behind the airing, extract at normal temperatures three times with about 300 milliliters of chloroform-methanols (volume ratio is 2: 1) after being crushed to the 60-80 order, each 48 o'clock, united extraction liquid was at 40 ℃ of left and right sides of temperature concentrating under reduced pressure acquisition crude extract.
2) water of getting 10 times of volumes of gained crude extract in the step 1) adds in the crude extract of step 1), then uses the ethyl acetate extraction 3 times of 1 times of volume of water, extract concentrate extract, standby;
3) ethyl acetate extract after will concentrating (1.1 gram) carries out silicagel column (200-300 order) chromatography, carry out wash-out with petroleum ether-ethyl acetate with 100: 0,100: 1,30: 1,10: 1,4: 1 to 0: 100 gradient, collect elutriant respectively, elutriant detects with thin-layer chromatography (TLC), judge, merge identical or similar portions according to the Rf value, when detecting, thin-layer chromatography (TLC) use aubepine-sulfuric acid as developer, developping agent is a petroleum ether-ethyl acetate (100: 0-0: 100), obtain six components (I-VI).
4) with component VI, Rf=0.2-0.9 (ethyl acetate is a developping agent), promptly carrying out gel filtration chromatography again with the component under the pure ethyl acetate wash-out separates, TLC detects, collecting Rf is the component of 0.45-0.5 and the component of displaing yellow spot, and by thin layer (developping agent is chloroform-ethyl acetate 4: 3) chromatographic separation, the target compound that promptly gets structural formula (I) R behind the purifying and be OH is 8.5 milligrams, Rf is the component of 0.65-0.7, promptly get structural formula (I) R behind the purifying and be 31.7 milligrams of the target compounds of OAc, detect through TLC, all be single, evenly yellow spotting is defined as pure compound.
Through Spectrum Analysis, its structure is accredited as shown in (I), and R is respectively OH (thyrsiferol) or OAc (thyrsiferyl 23-acetate).
Physico-chemical property when R is OH or OAc:
Structural formula (I) R is the target compound of OH: clear crystal, proton nmr spectra data: 1.09 (s), 1.12 (s), 1.15 (s), 1.18 (s), 1.19 (s), 1.21 (s), 1.26 (s), 1.39 (s), 3.04 (dd, 11.5,2.1Hz), 3.45 (brd, 9.7), 3.57 (dd, 11.0,7.2Hz), 3.70 (dd, 12.8,2.5Hz), 3.75 (dd, 9.8,6.2Hz), 3.89 (dd, 12.3,4.0Hz) ppm; Carbon-13 nmr spectra data: 31.0 (q), 75.0 (s), 59.0 (d), 28.3 (t), 37.0 (t), 74.4 (s), 86.6 (d), 23.0 (t), 38.6 (t), 72.0 (s), 76.4 (d), 21.2 (t), 20.7 (t), 76.1 (d), 73.3 (s), 33.6 (t), 25.5 (t), 77.7 (d), 86.1 (s), 32.5 (t), 26.6 (t), 87.5 (d), 70.5 (s), 24.0 (q), 23.7 (q), 20.1 (q), 21.4 (q), 22.9 (q), 23.4 (q), 27.6 (q) ppm.
Structural formula (I) R is the target compound of OAc: clear crystal, proton nmr spectra data: 1.08 (s), 1.15 (s), 1.17 (s), 1.18 (s), 1.26 (s), 1.38 (s), 1.43 (s), 1.47 (s), 1.98 (s), 3.03 (dd, 11.5,2.5Hz), 3.44 (dd, 10.1,1.76Hz), 3.56 (dd, 11.0,7.2Hz), 3.69 (dd, 12.8,2.8Hz), 3.88 (dd, 12.3,4.1Hz), 4.00 (dd, 9.7,6.1Hz) ppm; Carbon-13 nmr spectra data: 31.0 (q), 75.0 (s), 58.9 (d), 28.2 (t), 37.0 (t), 74.4 (s), 86.5 (d), 23.0 (t), 38.5 (t), 71.9 (s), 76.3 (d), 21.2 (t), 20.7 (t), 76.1 (d), 73.2 (s), 33.6 (t), 25.4 (t), 77.5 (d), 86.3 (s), 31.9 (t), 26.8 (t), 85.8 (d), 82.5 (s), 22.1 (q), 23.7 (q), 20.1 (q), 21.4 (q), 22.9 (q), 23.2 (q), 22.4 (q), 22.0 (q), 170.4 (s) ppm.
Embodiment 2
The preparation method of seaweed polyether compound:
1) will gather the fresh concave crown algae (Laurencia saitoi) that rises together and clean through seawater, and remove the grit and the assorted algae of surface attachment, shady and cool place airing is standby.Get the sample behind the airing, extract at normal temperatures five times with acetone-ethyl acetate (volume ratio is 2: 1) after being crushed to the 60-80 order, each 48 o'clock, united extraction liquid obtained crude extract at 40 ℃ of left and right sides of temperature concentrating under reduced pressure.
2) water of getting 15 times of volumes of gained crude extract in the step 1) adds in the crude extract of step 1), then uses the ethyl acetate extraction 5 times of 1.5 times of volume of water, extract concentrate extract, standby;
3) ethyl acetate extract after will concentrating carries out silicagel column (200-300 order) chromatography, carry out wash-out with petroleum ether-ethyl acetate with 100: 0,100: 1,30: 1,10: 1,4: 1 to 0: 100 gradient, collect elutriant respectively, elutriant detects with thin-layer chromatography (TLC), judge, merge identical or similar portions according to the Rf value, when detecting, thin-layer chromatography (TLC) use aubepine-sulfuric acid as developer, developping agent is a petroleum ether-ethyl acetate (100: 0-0: 100), obtain six components (I-VI).
4) with component VI, Rf=0.2-0.9 (ethyl acetate is a developping agent), promptly carrying out gel filtration chromatography again with the component under the pure ethyl acetate wash-out separates, TLC detects, collecting Rf is the component of 0.45-0.5 and the component of displaing yellow spot, and by thin layer (developping agent is chloroform-ethyl acetate 4: 3) chromatographic separation, structural formula (I) R that promptly gets behind the purifying is the target compound of OH, Rf is the component of 0.65-0.7, structural formula (I) R that promptly gets behind the purifying is the target compound of OAc, detect through TLC, all be single, even yellow spotting, be defined as pure compound.
Embodiment 3
The preparation method of seaweed polyether compound:
1) will gather the fresh concave crown algae (Laurencia saitoi) that rises together and clean through seawater, and remove the grit and the assorted algae of surface attachment, shady and cool place airing is standby.Get the sample behind the airing, extract secondary at normal temperatures with ethanol after being crushed to the 60-80 order, each 48 o'clock, united extraction liquid obtained crude extract at 40 ℃ of left and right sides of temperature concentrating under reduced pressure.
2) water of getting 12 times of volumes of gained crude extract in the step 1) adds in the crude extract of step 1), then uses the ethyl acetate extraction 2 times of 1.2 times of volume of water, extract concentrate extract, standby;
3) ethyl acetate extract after will concentrating carries out silicagel column (200-300 order) chromatography, carry out wash-out with petroleum ether-ethyl acetate with 100: 0,100: 1,30: 1,10: 1,4: 1 to 0: 100 gradient, collect elutriant respectively, elutriant detects with thin-layer chromatography (TLC), judge, merge identical or similar portions according to the Rf value, when detecting, thin-layer chromatography (TLC) use aubepine-sulfuric acid as developer, developping agent is a petroleum ether-ethyl acetate (100: 0-0: 100), obtain six components (I-VI).
4) with component VI, Rf=0.2-0.9 (ethyl acetate is a developping agent), promptly carrying out gel filtration chromatography again with the component under the pure ethyl acetate wash-out separates, TLC detects, collecting Rf is the component of 0.45-0.5 and the component of displaing yellow spot, and by thin layer (developping agent is chloroform-ethyl acetate 4: 3) chromatographic separation, structural formula (I) R that promptly gets behind the purifying is the target compound of OH, Rf is the component of 0.65-0.7, structural formula (I) R that promptly gets behind the purifying is the target compound of OAc, detect through TLC, all be single, even yellow spotting, be defined as pure compound.
Embodiment 4
The insecticidal activity experiment:
Halogen worm toxicity test can be used to the power of assessing compound insecticidal activity, and is easy and simple to handle, favorable reproducibility.
Experimental technique:
The hatching of artemia cysts: get artemia cysts and place 500 ml beakers for 100 milligrams, add 400 milliliters of artificial seawaters, slowly inflate with a little aerator pump, chorion and unhatched ovum are removed in room temperature hatching 24 hours, and halogen worm larva continues to cultivate 24 hours, and is standby.
The biological method that causes death of halogen worm: according to the improved method of Solis, get 96 porocyte culture plates, every hole adds the artificial seawater liquid that 195 microlitres contain 10 left and right sides halogen worm larvas, makes the test cultures plate.The sample sets of blank group and each concentration is respectively established three parallel holes, and the blank group adds 5 microlitre solvent DMSO, and sample sets adds the polyether compound testing sample in 5 microlitre the foregoing descriptions.Specimen is dissolved in DMSO, and concentration is 0.4 mg/ml.After the incubated at room temperature 24 hours, under the binocular anatomical lens, detect the dead individual number of counting halogen worm.
The biological activity that causes death of halogen worm represents that with corrected mortality calculation formula is as follows:
Corrected mortality=(control group survival rate-treatment group survival rate)/control group survival rate * 100%
Experimental result: the polyether compound of the acquisition in the foregoing description lethality rate to the halogen worm when 10 mcg/ml is 100%.
Claims (5)
1. seaweed polyether compound is characterized in that: shown in the structural formula (I),
Structural formula (I), wherein: R=OH or OAc.
2. preparation method by the described seaweed polyether compound of claim 1 is characterized in that:
1) marine red alga is risen together concave crown algae (Laurencia saitoi) and wash, dry in the shade, pulverize, then extract 2-5 time with organic solution, united extraction liquid concentrates, and obtains crude extract;
2) water of getting 10-15 times of volume of gained crude extract in the step 1) adds in the crude extract of step 1), then uses volume of water 1-1.5 ethyl acetate extraction doubly 2-5 time, extract concentrated extract, standby;
3) get step 2) in extract carry out silica gel column chromatography, carry out wash-out with organic solvent, collect elutriant, elutriant detects through thin-layer chromatography;
Described machine solvent is 100: 0-0: the petroleum ether-ethyl acetate of 100 gradients or sherwood oil-acetone;
4) with in the step 3) with 0-10: the component under 100 gradient elutions carries out gel column and the thin-layer chromatography separation and purification gets structural formula (I) target compound.
3. by the preparation method of the described polyether compound of claim 2, it is characterized in that: the organic solution in the step 1) can be in chloroform, acetone, ethyl acetate, ethanol or the methyl alcohol one or more.
4. by the described preparation method of claim 2, it is characterized in that: the used elutriant of silica gel column chromatography can be petroleum ether-ethyl acetate or sherwood oil-acetone in the described step 4); During the described thin-layer chromatography separation and purification of described step 4), developping agent is an ethyl acetate, and Rf is the component of 0.45-0.5, and structural formula (I) R that is behind the purifying is the target compound of OH; Developping agent is an ethyl acetate, and Rf is the component of 0.65-0.7, and structural formula (I) R that is behind the purifying is the target compound of OAc.
5. application by the described seaweed polyether compound of claim 1, it is characterized in that: described compound can be made the medicine of sterilant.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021249545A1 (en) * | 2020-06-12 | 2021-12-16 | 南开大学 | Method for one-step preparation of polyether having trans-fused polycyclic ether framework structure |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2021249545A1 (en) * | 2020-06-12 | 2021-12-16 | 南开大学 | Method for one-step preparation of polyether having trans-fused polycyclic ether framework structure |
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