MD636Z - Process for producing flavonoid glycosides from Linaria vulgaris Mill. - Google Patents
Process for producing flavonoid glycosides from Linaria vulgaris Mill. Download PDFInfo
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- MD636Z MD636Z MDS20120181A MDS20120181A MD636Z MD 636 Z MD636 Z MD 636Z MD S20120181 A MDS20120181 A MD S20120181A MD S20120181 A MDS20120181 A MD S20120181A MD 636 Z MD636 Z MD 636Z
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- methanol
- temperature
- glycosides
- concentrated
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- 229930182486 flavonoid glycoside Natural products 0.000 title claims abstract description 19
- 150000007955 flavonoid glycosides Chemical class 0.000 title claims abstract description 19
- 241000167860 Linaria vulgaris Species 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000010828 elution Methods 0.000 claims abstract description 6
- 239000000284 extract Substances 0.000 claims abstract description 6
- 229930182470 glycoside Natural products 0.000 claims abstract description 6
- 150000002338 glycosides Chemical class 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000004952 Polyamide Substances 0.000 claims abstract description 5
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920002647 polyamide Polymers 0.000 claims abstract description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000035784 germination Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000208822 Lactuca Species 0.000 description 4
- 235000003228 Lactuca sativa Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 241000013557 Plantaginaceae Species 0.000 description 1
- 108010016634 Seed Storage Proteins Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Pyrane Compounds (AREA)
Abstract
Description
Invenţia se referă la chimia bioorganică şi poate fi utilizată pentru obţinerea glicozidelor flavonoide din Linaria vulgaris Mill. The invention relates to bioorganic chemistry and can be used to obtain flavonoid glycosides from Linaria vulgaris Mill.
Este cunoscut procedeul de obţinere a linarozidelor din plante de Linaria vulgaris Mill. uscate la aer liber prin extragerea cu butanol saturat cu apă şi percolarea extractului concentrat pe coloană cu silicagel [1]. The process of obtaining linarosides from Linaria vulgaris Mill. plants dried in the open air by extraction with water-saturated butanol and percolation of the concentrated extract on a silica gel column is known [1].
Dezavantajul procedeului cunoscut constă în aceea că se obţine o cantitate mică de glicozide, conţine un număr mai mare de operaţii costisitoare, extracţia cu butanol saturat cu apă duce la o diminuare a glicozidelor. The disadvantage of the known process is that a small amount of glycosides is obtained, it contains a larger number of expensive operations, extraction with butanol saturated with water leads to a decrease in glycosides.
Problema pe care o soluţionează invenţia propusă constă în sporirea extracţiei, adică a cantităţii şi calităţii de glicozide flavonoide din Linaria vulgaris Mill. The problem solved by the proposed invention consists in increasing the extraction, i.e. the quantity and quality of flavonoid glycosides from Linaria vulgaris Mill.
Esenţa invenţiei constă în aceea că materia primă proaspăt colectată se mărunţeşte şi se supune extracţiei cu metanol de 3 ori, a câte 5 ore, la temperatura de 35…40°C, după care extractele se unesc şi se concentrează în vid la temperatura de 40°C până la un volum constant, apoi se extrag cu benzen substanţele balast, iar fracţiile obţinute se cromatografiază pe coloană de poliamidă cu eluarea în sistemul apă-metanol în raport de 4:1 şi se analizează în strat subţire de silicagel cu cloroform-metanol în raport de 3:1, respectiv, după care fracţiile ce conţin glicozide se unesc şi se concentrează în vid la temperatura de 40°C în prezenţa butanolului. The essence of the invention is that the freshly collected raw material is crushed and subjected to extraction with methanol 3 times, for 5 hours each, at a temperature of 35…40°C, after which the extracts are combined and concentrated in vacuo at a temperature of 40°C to a constant volume, then the ballast substances are extracted with benzene, and the obtained fractions are chromatographed on a polyamide column with elution in the water-methanol system in a ratio of 4:1 and analyzed in a thin layer of silica gel with chloroform-methanol in a ratio of 3:1, respectively, after which the fractions containing glycosides are combined and concentrated in vacuo at a temperature of 40°C in the presence of butanol.
Rezultatul invenţiei constă în obţinerea glicozidelor flavonoide din Linaria vulgaris Mill. în cantităţi şi de calitate sporite faţă de cea mai apropiată soluţie. The result of the invention consists in obtaining flavonoid glycosides from Linaria vulgaris Mill. in increased quantities and quality compared to the closest solution.
Avantajul constă în aceea că în cea mai apropriată soluţie din 2 kg de masă vegetală se obţin 0,22 g/masă uscată, iar în procedeul revendicat din 0,5 kg de materie primă proaspăt colectată se obţin 3,75 g/masă uscată. Procedeul revendicat conţine un număr redus de etape faţă de cea mai apropiată soluţie, reactivele utilizate sunt mai ieftine, iar glicozidele flavonoide obţinute sunt mai pure şi într-o cantitate mai mare. Prin utilizarea reagentului universal, şi anume a metanolului se obţine o cantitate mai mare de glicozide flavonoide şi spectrul activităţii biologice a lor este mai larg. The advantage is that in the most appropriate solution from 2 kg of plant mass 0.22 g/dry mass is obtained, and in the claimed process from 0.5 kg of freshly collected raw material 3.75 g/dry mass is obtained. The claimed process contains a reduced number of steps compared to the closest solution, the reagents used are cheaper, and the flavonoid glycosides obtained are purer and in a larger quantity. By using the universal reagent, namely methanol, a larger quantity of flavonoid glycosides is obtained and the spectrum of their biological activity is wider.
Glicozidele flavonoide au fost obţinute din plante de Linaria vulgaris Mill. (fam. Scrophulariaceae) colectate în perioada înfloririi (iunie - iulie). Materia primă vegetală proaspătă se extrage la temperatura de 35…40°C cu metanol de 3 ori, a câte 5 ore. Extractul obţinut se concentrează în vid până la uscare, restul uscat obţinut se extrage cu benzen, iar fracţiile liofile se cromatografiază consecutiv pe coloane de poliamidă - Woelm cu eluarea în sistemul apă-metanol în raport de 4:1. Controlul asupra extragerii complete a produsului finit se efectuează prin cromatografiere în strat subţire de silicagel - Silufol cu ajutorul unui reactiv specific. Fracţiile obţinute unite conţin 6 glicozide flavonoide, ceea ce a fost confirmat cu ajutorul cromatografiei în strat subţire de silicagel în prezenţa martorilor autentici. Flavonoid glycosides were obtained from plants of Linaria vulgaris Mill. (family Scrophulariaceae) collected during the flowering period (June - July). The fresh plant raw material is extracted at a temperature of 35…40°C with methanol 3 times, 5 hours each. The extract obtained is concentrated in vacuo to dryness, the dry residue obtained is extracted with benzene, and the lyophilized fractions are chromatographed consecutively on polyamide columns - Woelm with elution in the water-methanol system in a ratio of 4:1. Control over the complete extraction of the finished product is carried out by thin-layer chromatography of silica gel - Silufol using a specific reagent. The obtained fractions combined contain 6 flavonoid glycosides, which was confirmed by thin-layer chromatography of silica gel in the presence of authentic controls.
Exemplu de realizare a invenţiei Example of embodiment of the invention
O cantitate de 0,5 kg de Linaria vulgaris Mill., materie primă proaspăt colectată (plantă întreagă) în timpul înfloririi, se mărunţeşte şi se extrage la temperatura de 35…40°C cu metanol în raport de 1:1, procedura repetându-se de 3 ori, a câte 5 ore. Extractele unificate se concentrează în vid la temperatura de 40°C până la volum apos constant. Rămăşiţa se extrage cu benzen de 2 ori câte 400 ml pentru îndepărtarea substanţelor de balast. Restul apos se concentrează în vid până la volumul de 100 ml şi se aplică pe coloană de poliamidă - Woelm (4 x 50 cm). A quantity of 0.5 kg of Linaria vulgaris Mill., freshly collected raw material (whole plant) during flowering, is crushed and extracted at a temperature of 35…40°C with methanol in a ratio of 1:1, the procedure being repeated 3 times, 5 hours each. The unified extracts are concentrated in vacuo at a temperature of 40°C until a constant aqueous volume. The residue is extracted with benzene 2 times 400 ml each to remove ballast substances. The aqueous residue is concentrated in vacuo to a volume of 100 ml and applied to a polyamide column - Woelm (4 x 50 cm).
Eluarea se efectuează în sistemul apă-metanol în raport de 4:1. Fracţiile colectate câte 10 ml se analizează în strat subţire de silicagel pe plăci de Silufol în amestecul de solvenţi cloroform-metanol în raport de 3:1. Cromatogramele se developează cu reactivul benzidinic, care constă din benzidină - 0,5 g, acid acetic - 20 ml, etanol - 80 ml şi reactivul Ehrlich ce conţine p-dimetilaminobenzaldehidă - 1 g, acid clorhidric - 2 ml, etanol - 98 ml, după care plăcile se încălzesc până la 100°C. Eluarea se efectuează până la manifestarea reacţiei negative la prezenţa glicozidelor. Fracţiile cu conţinut de glicozide flavonoide se unesc şi se concentrează în vid la temperatura de 40°C, în prezenţa butanolului. Produsul final obţinut este suma glicozidelor flavonoide de 3,75 g care constă din 6 substanţe (glicozide flavonoide) cu următoarele valori ale fracţiilor pe plăci de Silufol: 0,27; 0,37; 0,45; 0,46; 0,48; 0,67 în sistemul de solvenţi cloroform:metanol în raport de 3:1. Suma glicozidelor flavonoide se testează cu privire la determinarea activităţii biologice pentru cultura de salată verde. Pentru aceasta, se tratează seminţele cu soluţie de glicozide flavonoide şi se determină capacitatea germinativă a seminţelor necondiţionate sau cu termen îndelungat de păstrare. Cu acest scop, seminţele de salată verde înmuiate în soluţii de glicozide flavonoide de diferite concentraţii (10-1…10-5%) timp de 2 ore, apoi spălate dublu cu apă, se usucă timp de 20…60 min şi se plasează pe foi de hârtie de filtru înmuiate cu apă distilată. Pentru încolţire se utilizează metoda de role de hârtie. Capacitatea de germinare s-a determinat la ziua a 10-a, iar energia de germinaţie la ziua a 4-a. Rezultatele testării sunt prezentate în tabel. Elution is carried out in the water-methanol system in a ratio of 4:1. The collected fractions of 10 ml are analyzed in a thin layer of silica gel on Silufol plates in the chloroform-methanol solvent mixture in a ratio of 3:1. The chromatograms are developed with the benzidine reagent, which consists of benzidine - 0.5 g, acetic acid - 20 ml, ethanol - 80 ml and the Ehrlich reagent containing p-dimethylaminobenzaldehyde - 1 g, hydrochloric acid - 2 ml, ethanol - 98 ml, after which the plates are heated to 100°C. Elution is carried out until the negative reaction to the presence of glycosides is manifested. The fractions containing flavonoid glycosides are combined and concentrated in vacuo at a temperature of 40°C, in the presence of butanol. The final product obtained is the sum of flavonoid glycosides of 3.75 g which consists of 6 substances (flavonoid glycosides) with the following values of the fractions on Silufol plates: 0.27; 0.37; 0.45; 0.46; 0.48; 0.67 in the solvent system chloroform:methanol in a ratio of 3:1. The sum of flavonoid glycosides is tested for determining the biological activity for the lettuce crop. For this, the seeds are treated with a solution of flavonoid glycosides and the germination capacity of the unconditioned or long-term stored seeds is determined. For this purpose, the lettuce seeds are soaked in solutions of flavonoid glycosides of different concentrations (10-1…10-5%) for 2 hours, then washed twice with water, dried for 20…60 min and placed on sheets of filter paper soaked with distilled water. The paper roll method was used for germination. Germination capacity was determined on day 10, and germination energy on day 4. The test results are presented in the table.
Tabel Table
Influenţa soluţiei de glicozide flavonoide asupra seminţelor de salată verde (soiul Moskovskii parnikovîi) cu termen îndelungat de păstrare Influence of flavonoid glycoside solution on lettuce seeds (Moskovskii parnikovii variety) with long-term storage
Substanţa Concentraţia substanţei, % Termenul de păstrare a seminţelor (4 ani) Energia de germinare, % Germinarea, % Apă Martor 8 65 Moldstim 0,1 8 59 0,01 25 73 0,001 31 74 0,0001 26 70 0,00001 20 68 Suma glicozidelor flavonoide 0,1 10 67 0,01 31 85 0,001 34 91 0,0001 26 74 0,00001 22 65Substance Substance concentration, % Seed storage period (4 years) Germination energy, % Germination, % Water Control 8 65 Moldstim 0.1 8 59 0.01 25 73 0.001 31 74 0.0001 26 70 0.00001 20 68 Sum of flavonoid glycosides 0.1 10 67 0.01 31 85 0.001 34 91 0.0001 26 74 0.00001 22 65
Analizând datele obţinute se observă că la tratarea înainte de semănat a seminţelor de salată verde cu calităţi reduse de germinare (păstrate timp de 4 ani) cu soluţii apoase de glicozide flavonoide cel mai semnificativ efect se obţine la utilizarea soluţiei cu concentraţia de 0,001%, la care energia germinativă şi germinaţia generală a seminţelor a sporit cu 26% în comparaţie cu martorul. Analyzing the data obtained, it is observed that when treating lettuce seeds with low germination qualities (stored for 4 years) with aqueous solutions of flavonoid glycosides before sowing, the most significant effect is obtained when using the solution with a concentration of 0.001%, at which the germination energy and general germination of the seeds increased by 26% compared to the control.
1. Maschenko N., Kintia P., Guriev A., Marchenko A., Basarello C., Piacente S., Pizza C. Glycosides from Linaria vulgaris Mill. Chemistry Journal of Moldova, v. 3; Nr. 2, 2008, p. 98...100 1. Maschenko N., Kintia P., Guriev A., Marchenko A., Basarello C., Piacente S., Pizza C. Glycosides from Linaria vulgaris Mill. Chemistry Journal of Moldova, v. 3; No. 2, 2008, p. 98...100
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Cited By (1)
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|---|---|---|---|---|
| MD825Z (en) * | 2014-01-22 | 2015-05-31 | Алёна ГЕНДОВ-МОШАНУ | Process for producing polyphenols from grape pomace |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4301C1 (en) * | 2013-06-12 | 2015-03-31 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | 1-epi-5-O-alozilantirinozide for the treatment of lettuce seeds |
| MD844Z (en) * | 2014-05-07 | 2015-07-31 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | Process for growing tobacco plants |
| MD893Z (en) * | 2014-10-08 | 2015-11-30 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | Process for presowing treatment of onion seeds |
| MD1012Z (en) * | 2015-09-09 | 2016-10-31 | Институт Генетики, Физиологии И Защиты Растений Академии Наук Молдовы | Process for treatment of grape-vine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD825Z (en) * | 2014-01-22 | 2015-05-31 | Алёна ГЕНДОВ-МОШАНУ | Process for producing polyphenols from grape pomace |
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| Publication number | Publication date |
|---|---|
| MD636Y (en) | 2013-05-31 |
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