MD1192Y - Glycoside preparation from Veronica officinalis L. plants with fungicidal action on Alternaria alternata - Google Patents
Glycoside preparation from Veronica officinalis L. plants with fungicidal action on Alternaria alternata Download PDFInfo
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- MD1192Y MD1192Y MDS20170010A MDS20170010A MD1192Y MD 1192 Y MD1192 Y MD 1192Y MD S20170010 A MDS20170010 A MD S20170010A MD S20170010 A MDS20170010 A MD S20170010A MD 1192 Y MD1192 Y MD 1192Y
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- veronica officinalis
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- 240000005592 Veronica officinalis Species 0.000 title claims abstract description 18
- 229930182470 glycoside Natural products 0.000 title claims abstract description 17
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 17
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 11
- 241000223602 Alternaria alternata Species 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000284 extract Substances 0.000 claims abstract description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 10
- 241000196324 Embryophyta Species 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 5
- 239000004952 Polyamide Substances 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920002647 polyamide Polymers 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 3
- 238000010828 elution Methods 0.000 claims abstract description 3
- 235000010465 Veronica officinalis Nutrition 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 241000209140 Triticum Species 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 229930182486 flavonoid glycoside Natural products 0.000 description 2
- 150000007955 flavonoid glycosides Chemical class 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- JBFOLLJCGUCDQP-ZFORQUDYSA-N Apigenin 7-glucuronide Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 JBFOLLJCGUCDQP-ZFORQUDYSA-N 0.000 description 1
- KMOUJOKENFFTPU-UHFFFAOYSA-N Apigenin-7-glucosid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 KMOUJOKENFFTPU-UHFFFAOYSA-N 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000983759 Linaria genistifolia Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- LFYKLMBWGAMUQU-UHFFFAOYSA-N apigenin 7-O-glucuronide Natural products OC1OC(C(O)C(O)C1O)C(=O)Oc2cc(O)c3C(=O)C=C(Oc3c2)c4ccc(O)cc4 LFYKLMBWGAMUQU-UHFFFAOYSA-N 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930193997 cynaroside Natural products 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229930182489 iridoid glycoside Natural products 0.000 description 1
- 150000008145 iridoid glycosides Chemical class 0.000 description 1
- PEFNSGRTCBGNAN-QNDFHXLGSA-N luteolin 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 PEFNSGRTCBGNAN-QNDFHXLGSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- PEFNSGRTCBGNAN-UHFFFAOYSA-N nephrocizin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 PEFNSGRTCBGNAN-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JBFOLLJCGUCDQP-UHFFFAOYSA-N scutellarin A Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 JBFOLLJCGUCDQP-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Invenţia se referă la preparatele fungicide, şi anume la un preparat glicozidic din plante de Veronica officinalis L. cu acţiune fungicidă asupra Alternaria alternata.Preparatul, conform invenţiei, conţine o soluţie apoasă de extract sumar de glicozide din plante de Veronica officinalis L. cu concentraţia de 5 x (10-4…10-2)%, obţinut din partea aeriană a plantei prin extragere triplă cu soluţie hidrometanolică, concentrarea extractului prin distilare în vid, extragerea dublă cu benzen a substanţelor balast, cromatografierea extractului purificat pe coloană cu poliamidă cu eluarea în sistemul apă-metanol în raport de 4:1 şi concentrarea ulterioară a eluatelor până la reziduu uscat.The invention relates to fungicidal preparations, namely to a glycosidic preparation of plants of Veronica officinalis L. with fungicidal action on Alternaria alternata.The preparation, according to the invention, contains an aqueous solution of glycoside extract of plants of Veronica officinalis L. with concentration 5 x (10-4 ... 10-2)%, obtained from the aerial part of the plant by triple extraction with hydromethanolic solution, the concentration of the extract by vacuum distillation, the double extraction with benzene of the ballast substances, the chromatography of the purified extract on the column with polyamide with elution in the 4: 1 water-methanol system and subsequent concentration of the eluates to the dry residue.
Description
Invenţia se referă la preparatele fungicide, şi anume la un preparat glicozidic din plante de Veronica officinalis L. cu acţiune fungicidă asupra Alternaria alternata. The invention relates to fungicidal preparations, namely to a glycoside preparation from Veronica officinalis L. plants with fungicidal action on Alternaria alternata.
Este cunoscut extractul sumar de glicozide iridoidice (genistifoliozide), obţinut prin extragere cu soluţie hidrometanolică la fierbere din plante de Linaria genistifolia L. Mill, pentru tratarea plantelor de grâu în faza de înfrăţire [1]. The summary extract of iridoid glycosides (genistifoliosides), obtained by extraction with boiling hydromethanolic solution from Linaria genistifolia L. Mill plants, is known for treating wheat plants in the twinning phase [1].
Dezavantajul produsului constă în accesibilitatea limitată a materiei prime, totodată acesta a fost testat pe grâul de primăvară faţă de agenţii fitopatogeni Pyrenophora teres Drechsler şi Fusarium spp. The disadvantage of the product lies in the limited accessibility of the raw material, however, it has been tested on spring wheat against the phytopathogenic agents Pyrenophora teres Drechsler and Fusarium spp.
Problema pe care o rezolvă invenţia constă în lărgirea sortimentului de substanţe naturale, cu activitate fungicidă sporită, ecologic inofensive şi accesibile pentru combaterea Alternaria alternata la culturile legumicole. The problem solved by the invention consists in expanding the range of natural substances with increased fungicidal activity, ecologically harmless and accessible for combating Alternaria alternata in vegetable crops.
Invenţia soluţionează problema prin aceea că se propune un preparat glicozidic din plante de Veronica officinalis L. cu acţiune fungicidă asupra Alternaria alternata, care conţine o soluţie apoasă de extract sumar de glicozide din plante de Veronica officinalis L. cu concentraţia de 5 x (10-4…10-2)%, obţinut din partea aeriană a plantei prin extragere triplă cu soluţie hidrometanolică, concentrarea extractului prin distilare în vid, extragerea dublă cu benzen a substanţelor de balast, cromatografierea extractului purificat pe coloană cu poliamidă cu eluarea în sistemul apă-metanol în raport de 4:1 şi concentrarea ulterioară a eluatelor până la reziduu uscat. The invention solves the problem by proposing a glycoside preparation from Veronica officinalis L. plants with fungicidal action on Alternaria alternata, which contains an aqueous solution of a summary extract of glycosides from Veronica officinalis L. plants with a concentration of 5 x (10-4…10-2)%, obtained from the aerial part of the plant by triple extraction with hydromethanol solution, concentration of the extract by vacuum distillation, double extraction with benzene of the ballast substances, chromatography of the purified extract on a polyamide column with elution in the water-methanol system in a ratio of 4:1 and subsequent concentration of the eluates to a dry residue.
Rezultatul tehnic al invenţiei constă în lărgirea sortimentului de substanţe biologic active obţinute din materie primă vegetală accesibilă, cu acţiune fungicidă, inofensive pentru organismele vii, utilizate pentru reducerea răspândirii bolilor provocate de fungii Alternaria alternata la culturile legumicole. The technical result of the invention consists in expanding the assortment of biologically active substances obtained from accessible plant raw material, with fungicidal action, harmless to living organisms, used to reduce the spread of diseases caused by the fungus Alternaria alternata in vegetable crops.
Preparatul se obţine în felul următor: masa vegetală proaspătă de planta Veronica officinalis L. (partea aeriană), în cantitate de 400 g, se mărunţeşte şi se extrage cu soluţie de metanol (4 litri) de 3 ori la încălzire (35…40°C). Extractele se unifică, se concentrează prin distilare în vid la temperatura de 40°C, până la reziduu apos. Reziduul se extrage cu benzen de 2 ori câte 300 ml pentru eliminarea substanţelor de balast. Restul apos se concentrează în vid până la volumul de 100 ml, după care se aplică pe coloana 4x50 cm cu poliamidă (Woelm). Coloana este eluată cu apă-metanol în raport de 4:1. Eluatele sunt combinate conform mobilităţii cromatografice şi concentrate prin distilare în vid până la uscat. Ca rezultat se obţin 3,25 g de praf amorf de culoare maro. Extractul este analizat cu ajutorul cromatografiei în strat subţire pe plăci Silufol. Reacţiile calitative (cu reagenţii Sahnie şi proba Shinod) au confirmat prezenţa glicozidelor flavonoidice în extractul din Veronica officinalis. Constantele fizico-chimice şi datele spectrale înregistrate pentru compuşii obţinuţi coincid cu datele respective din literatură pentru: 6-hidroxiluteolin-7-O-glucopiranozidă, cinarozidă, apigenin-7-O-glucopiranozidă şi apigenin-7-O-glucuronidă. The preparation is obtained as follows: the fresh plant mass of Veronica officinalis L. (aerial part), in an amount of 400 g, is crushed and extracted with methanol solution (4 liters) 3 times with heating (35…40°C). The extracts are unified, concentrated by vacuum distillation at a temperature of 40°C, until an aqueous residue. The residue is extracted with benzene 2 times 300 ml each to eliminate ballast substances. The aqueous residue is concentrated in vacuo to a volume of 100 ml, after which it is applied to a 4x50 cm column with polyamide (Woelm). The column is eluted with water-methanol in a ratio of 4:1. The eluates are combined according to chromatographic mobility and concentrated by vacuum distillation to dryness. As a result, 3.25 g of brown amorphous powder is obtained. The extract is analyzed using thin layer chromatography on Silufol plates. Qualitative reactions (with Sahnie reagents and Shinod sample) confirmed the presence of flavonoid glycosides in the extract of Veronica officinalis. The physicochemical constants and spectral data recorded for the obtained compounds coincide with the respective data in the literature for: 6-hydroxyluteolin-7-O-glucopyranoside, cynaroside, apigenin-7-O-glucopyranoside and apigenin-7-O-glucuronide.
Pentru identificarea sumei de glicozide a fost înregistrat spectrul FT-IR (KBr), unde valorile νmax [cm-1] corespund unui amestec, în care predomină glicozidele flavonoidice: 3362, 3339 (-OH); 2924, 2854 (-CH- şi -CH2 din zaharide); 1706 (˃C=O cetona aromatică); 1629, 1602, 1515 (C=C cicluri aromatice); 1447, 1374 (-OH din fenoli), 1260 (grupa =C-O-C din flavonol), 1159, 1062, 1033, 918 (C-O-C din zaharide), 813, 782, 687, 613 (cicluri aromatice substituite) (vezi figura 1). To identify the amount of glycosides, the FT-IR spectrum (KBr) was recorded, where the νmax [cm-1] values correspond to a mixture, in which flavonoid glycosides predominate: 3362, 3339 (-OH); 2924, 2854 (-CH- and -CH2 from saccharides); 1706 (˃C=O aromatic ketone); 1629, 1602, 1515 (C=C aromatic cycles); 1447, 1374 (-OH from phenols), 1260 (=C-O-C group from flavonol), 1159, 1062, 1033, 918 (C-O-C from saccharides), 813, 782, 687, 613 (substituted aromatic cycles) (see figure 1).
Exemplu de realizare a invenţiei Example of embodiment of the invention
În condiţii de laborator (in vitro), pentru aprecierea proprietăţilor fungicide ale extractului sumar (Σ) de glicozide din Veronica officinalis L. a fost aplicat procedeul discurilor de hârtie. Mediul nutritiv agar cartof-glucoză a fost topit şi inoculat cu Alternaria alternata. Câte 20 ml de mediu inoculat a fost turnat în ceşti Petri sterile. După solidificare, pe suprafaţa mediului au fost plasate discuri de hârtie de filtru îmbibate cu soluţii apoase de Σ de glicozide din Veronica officinalis L. cu diferite pârti de masă: 5x10-6%, 5x10-5%, 5x10-4%, 5x10-3%, 5x10-2% (invenţia) şi cu soluţie de genistifoliozide în concentraţie de 5x10-4% (cea mai apropiată soluţie). Discurile îmbibate cu apă au servit ca martor. Experimentul a fost efectuat în trei replici. Ceştile Petri au fost ţinute în termostat la temperatura de 25°С timp de 7 zile. Diametrul zonelor de inhibiţie a fungilor a fost măsurat cu ajutorul unei rigle. Under laboratory conditions (in vitro), to assess the fungicidal properties of the summary extract (Σ) of glycosides from Veronica officinalis L., the paper disc method was applied. The potato-glucose agar nutrient medium was melted and inoculated with Alternaria alternata. 20 ml of the inoculated medium was poured into sterile Petri dishes. After solidification, filter paper discs soaked with aqueous solutions of Σ glycosides from Veronica officinalis L. with different mass fractions were placed on the surface of the medium: 5x10-6%, 5x10-5%, 5x10-4%, 5x10-3%, 5x10-2% (the invention) and with genistifolioside solution in a concentration of 5x10-4% (the closest solution). The discs soaked with water served as a control. The experiment was performed in three replicates. The Petri dishes were kept in a thermostat at 25°C for 7 days. The diameter of the fungal inhibition zones was measured using a ruler.
Conform rezultatelor înregistrate, cea mai înaltă activitate fungicidă o manifestă soluţia de Σ de glicozide din Veronica officinalis cu concentraţia de 5x10-2%. Diametrul zonei de inhibiţie a fungilor Alternaria alternata este de 5,4 ori mai mare comparativ cu varianta martor şi de 1,47 ori mai mare comparativ cu cea mai apropiată soluţie (vezi tabelul, figura 2). According to the recorded results, the highest fungicidal activity is exhibited by the Σ solution of glycosides from Veronica officinalis with a concentration of 5x10-2%. The diameter of the inhibition zone of the fungi Alternaria alternata is 5.4 times larger compared to the control variant and 1.47 times larger compared to the closest solution (see table, figure 2).
Tabel Table
Influenţa glicozidelor asupra dezvoltării fungilor Alternaria alternata The influence of glycosides on the development of Alternaria alternata fungi
Varianta Concentraţia, % Diametrul zonei de inhibiţie a fungilor mm comparativ cu martorul comparativ cu cea mai apropiată soluţie 1. Σ de glicozide din V.officinalis 5x10-6 5,6±0,9 <1,12 0,3 2. Σ de glicozide din V.officinalis 5x10-5 5,00±0 0 0,27 3. Σ de glicozide din V.officinalis 5x10-4 24,6±0,9 <4,9 1,34 4. Σ de glicozide din V.officinalis 5x10-3 22,0±2,0 <4,4 1,20 5. Σ de glicozide din V.officinalis 5x10-2 27,0±0,7 <5,4 1,47 6. Σ de genistifoliozide 5x10-4 18,3±1,8 <3,6 7. Martor H2O - 5,00±0 Variant Concentration, % Diameter of the fungal inhibition zone mm compared to the control compared to the closest solution 1. Σ of glycosides from V.officinalis 5x10-6 5.6±0.9 <1.12 0.3 2. Σ of glycosides from V.officinalis 5x10-5 5.00±0 0 0.27 3. Σ of glycosides from V.officinalis 5x10-4 24.6±0.9 <4.9 1.34 4. Σ of glycosides from V.officinalis 5x10-3 22.0±2.0 <4.4 1.20 5. Σ of glycosides from V.officinalis 5x10-2 27.0±0.7 <5.4 1.47 6. Σ of genistifoliosides 5x10-4 18.3±1.8 <3.6 7. Control H2O - 5.00±0
1. MD 902 Y 2015.05.31 1. MD 902 Y 2015.05.31
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| Application Number | Priority Date | Filing Date | Title |
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| MDS20170010A MD1192Z (en) | 2017-02-06 | 2017-02-06 | Glycoside preparation from Veronica officinalis L. plants with fungicidal action on Alternaria alternata |
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| MDS20170010A MD1192Z (en) | 2017-02-06 | 2017-02-06 | Glycoside preparation from Veronica officinalis L. plants with fungicidal action on Alternaria alternata |
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| MD1192Z MD1192Z (en) | 2018-04-30 |
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| MD767Z (en) * | 2013-11-07 | 2014-12-31 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | Process for treating vines |
| MD902Z (en) * | 2014-09-03 | 2015-12-31 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | Process for treatment of spring wheat |
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