CN116235856A - Application of crocin-1 and crocin-2 - Google Patents
Application of crocin-1 and crocin-2 Download PDFInfo
- Publication number
- CN116235856A CN116235856A CN202310024976.1A CN202310024976A CN116235856A CN 116235856 A CN116235856 A CN 116235856A CN 202310024976 A CN202310024976 A CN 202310024976A CN 116235856 A CN116235856 A CN 116235856A
- Authority
- CN
- China
- Prior art keywords
- nmr
- saffron
- glycoside
- cdcl
- crocin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- SEBIKDIMAPSUBY-ARYZWOCPSA-N Crocin Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)OC(=O)C(C)=CC=CC(C)=C\C=C\C=C(/C)\C=C\C=C(C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SEBIKDIMAPSUBY-ARYZWOCPSA-N 0.000 title claims description 10
- CZSBHMFVVLYIQQ-RDVATZJHSA-N Crocin 2 Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C=CC=C(/C)C(=O)OC3OC(CO)C(O)C(O)C3O CZSBHMFVVLYIQQ-RDVATZJHSA-N 0.000 title claims description 9
- CZSBHMFVVLYIQQ-DRVLGOCHSA-N beta-D-gentiobiosyl beta-D-glucosyl crocetin Chemical compound O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1)O)C(=O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CZSBHMFVVLYIQQ-DRVLGOCHSA-N 0.000 title claims description 9
- 244000124209 Crocus sativus Species 0.000 claims abstract description 24
- 235000015655 Crocus sativus Nutrition 0.000 claims abstract description 24
- 235000013974 saffron Nutrition 0.000 claims abstract description 24
- 239000004248 saffron Substances 0.000 claims abstract description 24
- 241000723873 Tobacco mosaic virus Species 0.000 claims abstract description 16
- 229930014626 natural product Natural products 0.000 claims abstract description 9
- 239000000575 pesticide Substances 0.000 claims abstract description 7
- 150000002611 lead compounds Chemical class 0.000 claims abstract description 5
- 238000005556 structure-activity relationship Methods 0.000 claims abstract description 3
- 230000000694 effects Effects 0.000 description 19
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 14
- 241000700605 Viruses Species 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PANKHBYNKQNAHN-JTBLXSOISA-N Crocetin Natural products OC(=O)C(\C)=C/C=C/C(/C)=C\C=C\C=C(\C)/C=C/C=C(/C)C(O)=O PANKHBYNKQNAHN-JTBLXSOISA-N 0.000 description 8
- PANKHBYNKQNAHN-JUMCEFIXSA-N carotenoid dicarboxylic acid Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)O)C=CC=C(/C)C(=O)O PANKHBYNKQNAHN-JUMCEFIXSA-N 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 5
- -1 diester derivatives of crocetin Chemical class 0.000 description 5
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 5
- 229960000329 ribavirin Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 229940126543 compound 14 Drugs 0.000 description 4
- PANKHBYNKQNAHN-MQQNZMFNSA-N crocetin Chemical compound OC(=O)C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)C(O)=O PANKHBYNKQNAHN-MQQNZMFNSA-N 0.000 description 4
- 239000000287 crude extract Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000001972 Gardenia jasminoides Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 2
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 244000111489 Gardenia augusta Species 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
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- 150000001555 benzenes Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
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- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000009627 gardenia yellow Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002796 natural product derivatives Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 229930010796 primary metabolite Natural products 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention belongs to the technical field of pesticides, and provides application of saffron glycoside-1 and saffron glycoside-2, wherein natural products of saffron glycoside-1 and saffron glycoside-2 are used as active lead compounds, and a pesticide for resisting tobacco mosaic virus is synthesized through a structure-activity relationship or is directly used for resisting the tobacco mosaic virus, so that the pesticide is used for preventing and treating the tobacco mosaic virus.
Description
Technical Field
The invention relates to application of crocin-1 and crocin-2, and belongs to the technical field of pesticides.
Background
With the increasing population of the world and the changing dietary structure of people, the pressure of grain production is increasing. And diseases, insects and grasses bring great threat to the production of grains, and continuous and effective control is required. Meanwhile, the environmental, toxicological and management requirements of the application of the agrochemical products are continuously strict, and the requirements on pest control products are also continuously increased. And the sustained development of disease and pest control agent resistance further limits the application of the medicine. Therefore, there is a continuous need to discover and develop new, effective, economical pest control agents to increase crop yield and to supply an increasing number of humans.
Natural products are primary or secondary metabolites produced by living cells. Historically, natural products have been an important component of medicine and a major tool in agriculture for the control of weeds, pathogens and pests. Most natural products are unstable in the environment or have toxicity, insecticidal spectrum, light stability or production problems, especially in today's strict regulatory environments, which need to be solved by structural modification prior to commercialization. The synthesis of natural product derivatives also provides tools for the study of chemical biology, and can determine the relationship between structure and biological activity, and understand the action mode of natural products and biological targets.
Crocin-1 and crocin-2 are diester derivatives of crocetin and sugar, exist in traditional Chinese medicines of gardenia and saffron, have the effects of resisting apoptosis, hyperlipidemia, atherosclerosis and oxidization, and can also grow various cancer cells. In the agricultural biological activity research process of gardenia yellow in gardenia, the crocin-1 and crocin-2 have good tobacco mosaic virus resistance activity.
Disclosure of Invention
The invention aims to provide a preparation method of saffron glycoside-1 and saffron glycoside-2 and an application thereof in plant protection.
The invention provides application of saffron glycoside-1 and saffron glycoside-2, wherein natural products of saffron glycoside-1 and saffron glycoside-2 are used as active lead compounds, and pesticides for resisting tobacco mosaic virus are synthesized through a structure-activity relationship.
The invention provides application of crocin-1 and crocin-2, which are directly used for resisting tobacco mosaic virus and preventing and treating tobacco mosaic virus.
The invention discovers that the natural products saffron glycoside-1 and saffron glycoside-2 show higher anti-plant virus activity level than commercial variety ribavirin for the first time, and can be used as novel plant source pesticides or can be developed as lead compounds.
Detailed Description
The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples.
Example 1
Preparation and structural characterization of saffron glycoside-1 and saffron glycoside-2:
150g of cape jasmine fruit powder is soaked in 1200ml of methanol for 72 hours, and the solution is continuously stirred during the soaking. Suction filtering, and spin drying the filtrate to obtain 33.7g of fructus Gardeniae crude extract. Separating the crude extract with macroporous adsorbent resin, eluting with water and ethanol to obtain five components (1-5). The component 4 was separated by silica gel column chromatography to obtain six components (4.1-4.6). And recrystallizing the component 4.6 to obtain the crocin-1. The component 4.5 is further separated by preparative chromatography to obtain the crocin-2.
Compound 1: saffron glycoside-1: mp 229-231 ℃; 1 H NMR(400MHz,DMSO)δ7.36(d,J＝10.8Hz,2H),6.90–6.79(m,4H),6.72–6.63(m,2H),6.54(d,J＝10.2Hz,2H),5.42(d,J＝7.6Hz,2H),5.33(d,J＝4.2Hz,2H),5.20(s,2H),5.10(d,J＝3.1Hz,2H),4.98–4.83(m,6H),4.46(t,J＝5.7Hz,2H),4.17(d,J＝7.8Hz,2H),3.99(d,J＝10.4Hz,2H),3.70–3.54(m,4H),3.46–3.39(m,4H),3.28–3.19(m,6H),3.14–3.09(m,2H),3.05(s,4H),2.95(td,J＝8.3,4.4Hz,2H),1.99(d,J＝10.0Hz,12H)； 13 C NMR(100MHz,DMSO)δ166.16,144.59,139.88,136.91,135.95,131.98,125.27,123.90,103.07,94.52,76.86,76.75,76.27,76.25,73.44,72.44,69.96,69.22,67.92,60.97,12.67,12.55；HRMS(MALDI)calcd for C 44 H 64 NaO 24 [M+Na] + 999.3680,found 999.3677。
compound 2: saffron glycoside-2: mp is 201-203 ℃; 1 H NMR(400MHz,DMSO)δ7.36(d,J＝11.2Hz,1H),6.90–6.84(m,2H),6.81(d,J＝2.9Hz,1H),6.72–6.63(m,2H),6.54(d,J＝8.3Hz,1H),5.42(d,J＝7.7Hz,2H),5.31(dd,J＝11.3,4.8Hz,2H),5.19(d,J＝3.4Hz,1H),5.14–5.08(m,2H),5.03(d,J＝5.1Hz,1H),4.94(d,J＝4.5Hz,1H),4.90(d,J＝1.8Hz,1H),4.86(d,J＝4.7Hz,1H),4.59(t,J＝5.9Hz,1H),4.46(t,J＝5.9Hz,1H),4.18(d,J＝7.8Hz,1H),3.99(d,J＝10.4Hz,1H),3.79(d,J＝11.3Hz,1H),3.68–3.62(m,3H),3.59(dd,J＝11.2,5.2Hz,1H),3.47–3.41(m,3H),3.27–3.21(m,6H),3.19–3.10(m,3H),3.06(s,2H),2.96(td,J＝8.3,4.8Hz,1H),1.99(d,J＝9.5Hz,12H)； 13 C NMR(100MHz,DMSO)δ166.15,144.56,144.49,139.84,139.74,136.87,135.91,131.95,125.34,125.27,123.87,103.06,94.57,94.52,77.82,76.84,76.74,76.44,76.26,73.44,72.51,72.44,72.42,69.96,69.50,69.23,67.92,60.96,60.54,12.64,12.53；HRMS(MALDI)calcd for C 38 H 54 NaO 19 [M+Na] + 837.3152,found 837.3149。
example 2
Synthesis and structural characterization of crocetin:
saffron glycoside-1 (2.00 g,2.05 mmol) was dissolved in 100mL of water, an aqueous solution of sodium hydroxide (2.00 g,50 mmol) was added, and the mixture was heated to 100deg.C with stirring to react for three hours; after cooling, 2M hydrochloric acid was added to adjust the pH of the reaction solution to approximately 2. Suction filtration and water washing of the filter cake to obtain crude crocetin (0.60 g,1.83 mmol) mp>320℃； 1 H NMR(400MHz,DMSO)δ7.20(d,J＝10.5Hz,1H),6.83(d,J＝6.6Hz,1H),6.72(d,J＝14.7Hz,1H),6.63(d,J＝11.5Hz,1H),6.49(d,J＝5.5Hz,1H),1.97(s,3H),1.92(s,3H)； 13 C NMR(100MHz,DMSO)δ169.65,143.64,138.31,137.08,135.68,132.04,127.68,124.58,13.28,13.00。
Example 3
Synthesis and structural characterization of crocetin diester:
the crude crocetin (0.20 g,0.61 mmol) was dissolved in DMF (50 mL), DBU (0.37 g,2.44 mmol) and bromohydrocarbon (2.44 mmol) were then added, stirred at room temperature for 24-96h, water and dichloromethane were added, the aqueous phase was washed twice with dichloromethane, the organic phases were combined, washed three times with water, washed once with saturated saline, dried over anhydrous magnesium sulfate, suction filtered, desolventized and silica gel column chromatography to give the target product (3-19).
Compound 3:
Yield:65.3％；mp 214–216℃； 1 H NMR(400MHz,CDCl 3 )δ7.29(d,J＝10.6Hz,2H),
6.76–6.66(m,2H),6.66–6.50(m,4H),6.42–6.31(m,2H),3.77(s,6H),2.00(d,J＝4.2Hz,12H)； 13 C NMR(100MHz,CDCl 3 )δ168.90,143.73,138.86,136.70,135.32,131.31,126.44,123.80,51.79,12.88,12.77；HRMS(MALDI)calcd for C 22 H 28 O 4 [M]+356.1988,found 356.1980。
compound 4:
Yield:58.5％；mp 205–207℃； 1 H NMR(400MHz,CDCl 3 )δ7.29(d,J＝10.9Hz,2H),
6.73–6.51(m,6H),6.37(d,J＝7.6Hz,2H),4.22(dd,J＝14.0,7.0Hz,4H),2.00(s,12H),1.32(t,J＝7.0Hz,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.60,143.71,138.70,136.85,135.37,131.41,126.93,124.00,60.68,14.49,13.01,12.93；HRMS(MALDI)calcd for C 24 H 32 O 4 [M] + 384.2301,found 384.2293。
compound 5:
Yield:42.4％；mp 152–153℃； 1 H NMR(400MHz,CDCl 3 )δ7.28(d,J＝11.7Hz,2H),6.70
(dd,J＝7.8,2.2Hz,2H),6.65–6.50(m,4H),6.37(d,J＝7.6Hz,2H),4.17(t,J＝6.5Hz,4H),2.00(s,12H),1.67(dd,J＝14.5,6.9Hz,4H),1.43(dd,J＝14.7,7.5Hz,4H),0.96(t,J＝7.3Hz,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.52,143.56,138.53,136.69,135.21,131.26,126.86,123.86,64.47,30.84,19.28,13.76,12.87,12.78；HRMS(MALDI)calcd for C 28 H 40 O 4 [M] + 440.2927,found 440.2919。
compound 6:
Yield:29.9％；mp 190–192℃； 1 H NMR(400MHz,CDCl 3 )δ7.35(d,J＝11.1Hz,2H),
6.75–6.51(m,6H),6.38(d,J＝8.1Hz,2H),4.52(dd,J＝12.5,2.4Hz,2H),4.01(dd,J＝12.3,6.3Hz,2H),3.31–3.26(m,2H),2.88(t,J＝4.4Hz,2H),2.71–2.67(m,2H),2.02(s,6H),2.00(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.14,144.29,139.68,136.87,135.71,131.56,125.99,123.83,65.25,49.73,44.82,12.98,12.90；HRMS(MALDI)calcd for C 26 H 32 O 6 [M] + 440.2199,found440.2191。
compound 7:
Yield:45.3％；mp 231–232℃； 1 H NMR(400MHz,CDCl 3 )δ7.37(d,J＝11.2Hz,2H),
6.77–6.66(m,4H),6.58(d,J＝11.6Hz,2H),6.42(d,J＝6.6Hz,2H),4.82(s,4H),2.02(s,6H),2.01(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ166.70,145.59,141.62,137.04,136.50,131.96,124.21,123.58,114.92,48.71,12.94,12.88；HRMS(MALDI)calcd for C 24 H 26 N 2 O 4 [M] + 406.1893,found 406.1885。
compound 8:
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Yield:49.8％；mp 158–160℃； 1 H NMR(400MHz,CDCl 3 )δ7.24(d,J＝4.4Hz,2H),6.68(d,
J＝8.0Hz,2H),6.63–6.48(m,6H),6.36(d,J＝8.1Hz,2H),3.84(s,4H),1.98(s,6H),1.98(s,6H),0.09(s,18H)； 13 C NMR(100MHz,CDCl 3 )δ169.40,143.65,138.53,136.82,135.32,131.39,127.08,123.97,57.91,13.14,12.93,-2.81；HRMS(MALDI)calcd for C 28 H 44 O 4 Si 2 [M] + 500.2778,found 500.2770。
compound 9:
Yield:42.5％；mp 162–163℃； 1 H NMR(400MHz,CDCl 3 )δ7.39(d,J＝10.8Hz,2H),
6.75–6.52(m,6H),6.38(d,J＝6.6Hz,2H),4.72(s,4H),3.78(s,6H),2.04(s,6H),2.00(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.62,167.62,144.46,140.20,136.79,135.70,131.50,125.38,123.70,60.84,52.16,12.82,12.77；HRMS(MALDI)calcd for C 26 H 32 O 8 [M] + 472.2097,found472.2089。
compound 10:
Yield:24.04％；mp 175–177℃； 1 H NMR(400MHz,CDCl 3 )δ7.37(d,J＝10.4Hz,2H),
6.79–6.50(m,6H),6.40(s,2H),5.85(s,4H),2.12(s,6H),2.01(s,12H)； 13 C NMR(100MHz,CDCl 3 )δ169.79,166.87,144.82,140.65,136.83,135.94,131.61,125.18,123.65,79.51,20.81,12.77,12.70；HRMS(MALDI)calcd for C 26 H 32 O 8 [M] + 472.2097,found 472.2089。
compound 11:
Yield:45.4％；mp 189–191℃； 1 H NMR(400MHz,CDCl 3 )δ7.33(d,J＝10.7Hz,2H),
6.74–6.50(m,6H),6.37(d,J＝7.7Hz,2H),5.99(ddt,J＝16.2,10.7,5.5Hz,2H),5.35(d,J＝17.2Hz,2H),5.25(d,J＝10.4Hz,2H),4.68(d,J＝5.2Hz,4H),2.02(s,6H),1.99(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.18,143.98,139.16,136.87,135.52,132.79,131.49,126.59,123.95,117.92,65.37,13.02,12.93；HRMS(MALDI)calcd for C 26 H 32 O 4 [M] + 408.2301,found 408.2293。
compound 12:
Yield:62.3％；mp 157–159℃； 1 H NMR(400MHz,CDCl 3 )δ7.35(d,J＝10.7Hz,2H),
6.75–6.51(m,6H),6.38(d,J＝7.1Hz,2H),4.78(s,4H),2.48(s,2H),2.02(s,6H),2.00(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ167.54,144.35,139.88,136.80,135.67,131.50,125.67,123.72,78.19,74.58,52.11,12.84,12.80；HRMS(MALDI)calcd for C 26 H 28 O 4 [M] + 404.1988,found404.1980。
compound 13:
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Yield:41.9％；mp 183–185℃； 1 H NMR(400MHz,CDCl 3 )δ7.37–7.27(m,4H),6.98(d,J＝
7.4Hz,2H),6.94(s,2H),6.87(d,J＝8.2Hz,2H),6.70(d,J＝10.4Hz,2H),6.59(dd,J＝21.2,12.8Hz,4H),6.36(d,J＝7.7Hz,2H),5.19(s,4H),3.82(s,6H),2.03(s,6H),1.99(s,6H)； 13 CNMR(100MHz,CDCl 3 )δ168.32,159.87,144.08,139.34,138.15,136.87,135.57,131.50,129.72,126.49,123.92,120.34,113.69,113.60,66.32,55.39,13.08,12.92；HRMS(MALDI)calcd for C 36 H 40 O 6 [M] + 568.2825,found 568.2816。
compound 14:
Yield:41.5％；mp 167–169℃； 1 H NMR(400MHz,CDCl 3 )δ7.24–7.17(m,6H),7.00(t,J＝
8.6Hz,4H),6.71(dd,J＝7.9,2.4Hz,2H),6.63–6.49(m,4H),6.38(d,J＝7.8Hz,2H),4.34(t,J＝6.8Hz,4H),2.97(t,J＝6.8Hz,4H),1.99(s,6H),1.97(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.28,162.93,160.51,143.85,138.97,136.73,135.43,133.82,133.79,131.38,130.42,130.34,126.46,123.79,115.38,115.17,65.03,34.50,12.85,12.79；HRMS(MALDI)calcd for C 36 H 38 F 2 O 4 [M] + 572.2738,found 572.2729。
compound 15:
Yield:30.3％；mp 164–165℃； 1 H NMR(400MHz,CDCl 3 )δ7.58(d,J＝7.8Hz,4H),7.37(d,
J＝7.8Hz,4H),7.24(d,J＝10.5Hz,2H),6.72(dd,J＝7.9,2.3Hz,2H),6.63–6.48(m,4H),6.38(d,J＝7.4Hz,2H),4.40(t,J＝6.7Hz,4H),3.06(t,J＝6.6Hz,4H),1.99(s,6H),1.97(s,6H)； 13 CNMR(100MHz,CDCl 3 )δ168.21,143.96,142.35,139.12,136.72,135.49,131.41,129.29,126.28,125.45,125.42,125.38,125.34,123.73,64.46,35.10,29.70,12.83,12.78；HRMS(MALDI)calcd for C 38 H 38 F 6 O 4 [M] + 672.2674,found 672.2665。
compound 16:
Yield:47.9％；mp 186–188℃； 1 H NMR(400MHz,CDCl 3 )δ8.60(d,J＝4.3Hz,2H),7.71
(td,J＝7.7,1.3Hz,2H),7.42–7.38(m,4H),7.26–7.21(m,2H),6.71(dd,J＝7.9,2.7Hz,2H),6.59(dt,J＝15.0,12.9Hz,4H),6.38(d,J＝8.7Hz,2H),5.34(s,4H),2.06(s,6H),2.00(s,6H)； 13 CNMR(100MHz,CDCl 3 )δ167.98,156.42,149.40,144.15,139.55,136.76,136.74,135.55,131.42,126.08,123.76,122.72,121.64,66.94,12.95,12.79；HRMS(MALDI)calcd for C 32 H 34 N 2 O 4 [M+H] + 511.2591,found 511.2588。
compound 17:
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Yield:47.3％；mp 183–184℃； 1 H NMR(400MHz,CDCl 3 )δ7.27(d,J＝9.1Hz,2H),7.08(s,
2H),6.98(d,J＝7.8Hz,2H),6.76–6.67(m,4H),6.64–6.50(m,4H),6.42–6.32(m,2H),4.55(t,J＝8.6Hz,4H),4.31(t,J＝6.9Hz,4H),3.19(t,J＝8.6Hz,4H),2.92(t,J＝6.9Hz,4H),1.99(s,12H)； 13 C NMR(100MHz,CDCl 3 )δ168.35,158.82,143.70,138.82,136.72,135.32,131.33,129.95,128.51,127.18,126.66,125.46,123.85,109.08,71.19,65.59,34.73,29.78,12.87,12.79；HRMS(MALDI)calcd for C 40 H 44 O 6 [M] + 620.3138,found 620.3128。
compound 18:
Yield:46.2％；mp 143–145℃； 1 H NMR(400MHz,CDCl 3 )δ7.32–7.26(m,6H),6.95(t,J＝
7.6Hz,2H),6.91(d,J＝8.1Hz,4H),6.70(dd,J＝8.0,2.5Hz,2H),6.64–6.50(m,4H),6.37(d,J＝8.4Hz,2H),4.37(t,J＝6.2Hz,4H),4.09(t,J＝6.1Hz,4H),2.19(p,J＝6.2Hz,4H),2.02–1.96(m,12H)； 13 C NMR(100MHz,CDCl 3 )δ168.48,158.94,143.95,139.02,136.86,135.50,131.47,129.60,126.63,123.92,120.92,114.65,64.58,61.64,28.97,13.03,12.93；HRMS(MALDI)calcd for C 38 H 44 O 6 [M] + 596.3138,found 596.3129。
compound 19:
Yield:48.6％；mp 205–206℃； 1 H NMR(400MHz,CDCl 3 )δ7.84(dd,J＝4.9,3.2Hz,4H),
7.72–7.68(m,4H),7.24(d,J＝10.2Hz,2H),6.72(d,J＝10.0Hz,2H),6.58–6.46(m,4H),6.37(d,J＝8.5Hz,2H),4.23(t,J＝5.9Hz,4H),3.85(t,J＝6.7Hz,4H),2.16–2.08(m,4H),1.99(s,6H),1.97(s,6H)； 13 C NMR(100MHz,CDCl 3 )δ168.24,168.19,143.77,138.91,136.70,135.30,133.93,132.15,131.31,126.39,123.77,123.25,62.10,35.34,27.77,12.78；HRMS(MALDI)calcd for C 42 H 42 N 2 O 8 [M] + 702.2941,found 702.2931。
example 4
Biological activity is exemplified by anti-tobacco mosaic virus (Tobacco mosaic virus, TMV) activity,
1. virus purification and concentration determination:
the virus purification and concentration measurement are carried out by compiling tobacco mosaic virus SOP standard according to a measuring room generated by elements of university of south China. After 2 times of polyethylene glycol centrifugation treatment, the concentration of the virus crude extract is measured, and the virus crude extract is refrigerated at 4 ℃ for standby.
2. Compound solution preparation:
after weighing, adding DMF to dissolve the raw materials to obtain 1×10 5 Mu g/mL mother liquor, and then diluting the mother liquor to the required concentration by using an aqueous solution containing 1 per mill of Tween 80; the ribavirin preparation is directly diluted with water.
3. Living body protecting action:
3-5 She Qishan Xiyan with uniform growth vigor is selected, the whole plant is sprayed and applied, each treatment is repeated for 3 times, and 1 permillage of Tween 80 aqueous solution is used for comparison. After 24h, the leaf surface is spread with silicon carbide (500 meshes), the whole leaf surface is dipped with a virus liquid by a writing brush, the whole leaf surface is lightly rubbed for 2 times along the branch pulse direction, the lower part of the leaf surface is supported by a palm, the virus concentration is 10 mug/mL, and the leaf surface is washed by running water after inoculation. And after 3d, recording the number of the lesions, and calculating the control effect.
4. In vivo therapeutic action:
3-5 She Qishan Xiyan with uniform growth vigor is selected, the whole leaf of the writing brush is inoculated with virus, the virus concentration is 10 mug/mL, and the whole leaf is washed by running water after inoculation. After leaf surface is dried, spraying and applying the whole plant, repeating for 3 times every treatment, and setting 1%Tween 80 water solution as a control. And after 3d, recording the number of the lesions, and calculating the control effect.
5. In vivo passivation:
selecting 3-5 She Qishan Xie smoke with uniform growth vigor, mixing the medicament with an equal volume of virus juice, inactivating for 30min, performing friction inoculation, wherein the virus concentration is 20 mug/mL, washing with running water after inoculation, repeating for 3 times, and setting 1 milltween 80 water solution for comparison. And counting the number of lesions after 3d, and calculating a result.
Inhibition ratio (%) = [ (control number of dried spots-treated number of dried spots)/control number of dried spots ] ×100%
TABLE 1 results of in vivo tests of crocetin diester against tobacco mosaic Virus (0.5 mg/mL) a
When the in vivo inactivation activity of the tested compound is higher than 40%, the in vivo protection and in vivo therapeutic effect of the compound is tested.
It can be seen from Table 1 that all compounds showed activity against tobacco mosaic virus at a concentration of 0.5 mg/mL. The natural products saffron glycoside-1 and saffron glycoside-2 exhibit activity levels significantly higher than commercial varieties of ribavirin. Most of the synthetic crocetin diester derivatives showed good in vivo anti-TMV activity, and compounds 5,9,13,14 and 15 showed higher levels of activity than ribavirin, in particular compound 14. Compounds 3-5 containing linear alkyl chains have moderate anti-TMV activity, but their passivation effect is less than 40%. The alkyl chain has a greater effect on TMV activity when it is linked to different functional groups (compounds 6-12). Compound 9, bearing methoxy functionality, exhibited a higher level of activity than ribavirin. When substituted benzene ring is introduced into alkyl chain through C-C bond, anti-TMV activity (inhibition rate: compound 13> compound 3; compound 14> compound 15> compound 4) can be improved, and crocetin di (4-fluorobenzene ethyl) ester (compound 14) shows highest anti-TMV activity in the synthesized crocetin diester and is higher than that of the lead compounds safflor-1 and safflor-2. However, the introduction of the heteroaromatic ring does not increase the anti-TMV activity.
Claims (2)
1. The application of the saffron glycoside-1 and the saffron glycoside-2 is characterized in that natural products of the saffron glycoside-1 and the saffron glycoside-2 are used as active lead compounds, and pesticides for resisting tobacco mosaic virus are synthesized through a structure-activity relationship.
2. The application of the crocin-1 and the crocin-2 is characterized in that the crocin-1 and the crocin-2 are directly used for resisting tobacco mosaic virus and preventing and treating the tobacco mosaic virus.
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| CN116617238B (en) * | 2023-05-29 | 2024-08-09 | 中国科学院水生生物研究所 | Application of Chinese herbal medicine saffron glycoside I in fish antiviral |
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| US5763651A (en) * | 1996-06-17 | 1998-06-09 | Roche Vitamins Inc. | Process for manufacturing polyene esters and acids |
| CN103665060B (en) * | 2013-12-23 | 2015-08-19 | 成都普思生物科技有限公司 | The separation purification method of a kind of crocin I monomer, crocin II monomer |
| CN105131052B (en) * | 2015-07-24 | 2018-04-20 | 河南中大恒源生物科技股份有限公司 | A kind of extracting method of crocin I |
| CN105906672B (en) * | 2016-04-29 | 2017-12-29 | 暨南大学 | Safflower red chlorins compound and application thereof |
| CN108651465B (en) * | 2018-07-24 | 2021-04-30 | 江西省科学院应用化学研究所 | Application of iridoid glycoside in preparation of pesticide |
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