Method for the production of steroidal glycosides series furostana, increases germination, seed vigor and yield of eggplant
(57) Abstract:Usage: as a means of improving germination, seed vigor and yield of eggplant. The inventive product steroidal glycoside series furostana (somelongozid), yield 0.9% on dry raw materials. Reagent 1: the roots of eggplant. Reagent 2: 70% aqueous ethanol. Reagent 3: Sephadex G-50 column, eluent - distilled water. Seed germination is increased by 11-22%, biomass increased by 15%. The invention relates to Bioorganic chemistry, in particular to methods for the production of steroidal glycosides from plant material.The known method for the production of steroidal glycosides which have an antimicrobial effect, from the flowers and seeds of onions, which consists in degreasing plant materials and extraction with methanol concentration of the methanol extract, dilute the residue with water and extraction with butyl alcohol, the process of evaporation of the obtained extract to the dry residue, which was dissolved in methanol and the desired product precipitated with acetone 
However, the known method is rather time-consuming.The closest technical solution to the present invention is a method of obtaining a steroid of glycothermal water, the resulting aqueous extract is then repeatedly treated with butanol, butanolide extract was concentrated in vacuo and the residue is washed with acetone and dried 
The disadvantage of this method is that it is necessary to use in the extraction of large amounts of water and therefore large amounts of butyl alcohol, which is difficult to extract concentrated in vacuo. In addition, butanol-1, along with the number of furostana glycosides, steroid glycosides extracted several spirostana that strongly inhibit the growth-promoting processes in plants.The purpose of the invention to simplify the process for the production of steroidal glycosides series furostana from the roots of eggplant with a higher growth promoting activity compared with the structural analogs.This goal is achieved by the method lies in the fact that steroid glycosides extracted from the roots of eggplant (Solanum Melongena L.) with 70% alcohol. The extract obtained was concentrated in vacuo to an aqueous residue, which chromatographic on a column of Sephadex G-50 using distilled water as eluent.Dedicated control desired product in a thin layer of silica gel in the systems of the reagents Sanya and Ehrlich.P R I m e R 1. 1 kg of freshly ground roots eggplant, pour 2 liters of 70% aqueous ethanol, extracted by heating for 4 h, the extraction was repeated three times. The extract obtained was concentrated in vacuo to an aqueous residue, which chromatographic on a column of Sephadex G-50 using distilled water as eluent. Control of the division performed by TLC in the solvent system chloroform-methanol-water 65:35:10 (bottom layer) and 65:35:7 (volume ratio), showing the chromatogram reagents San and Ehrlich.The result is 9 g amount of steroid glycosides series furostana called somelongozid, representing 0.9% of the weight of the feedstock. The content of glycosides to the absolute dry weight of roots of eggplant is 2.2%
Somelongozid is the sum of a number of glycosides chetyrehsteroidnyh furostana.In the IR spectrum of the drug is present broad absorption band at 900 cm-1characteristic of glycosides of this type.Somelongozid a powder, light brown, non-hygroscopic, non-volatile, easily soluble in water, ethanol, methanol. Not soluble in acetone, chloroform, discemi methods identified tigogenin and diosgenin, in oligosaccharide part glycosides paper and gas-liquid chromatography identified glucose, rhamnose, galactose.For presowing treatment of seeds eggplant drug dissolved in distilled water in concentrations of 0.001, 0.005, 0.01, and 0.05% Concentration of 0.01% was the most effective.At the same time experiencing structural analogues: tomatozide  kapsikozid  melongozid  in the same concentrations. Experienced the growth regulators: Ivin, succinic acid, IAA.Served as control seeds, soaked in water.P R I m m e R 2. Eggplant seeds varieties "Dnestrovsc" in gauze bags hurt in the resulting solution of the glycoside for 24 h and left at room temperature. Thus treated seeds are placed in a Petri dish filled with sand, covered with filter paper, and incubated at a temperature of 20-30aboutC. After 5 days determine vigor, after 10 days, germination of seeds. Experiment was repeated 4 times in each case. In one relearn 100 seeds. The results of these studies are presented in table. 1.Seeds treated with 0.01% solution of steroidal glycosides, and control, soaked in water, is the cue parameters of seedlings (20 days after sowing) and expected growth relative to the control. Data on the increase in the basic biometric measurements are given in table. 2.For comparison, the results made by the same method, where the seeds were soaked in a 0.005% solution of a known stimulator of succinic acid.As can be seen from the table, somelongozid provides maximum positive effect for germination energy and germination of eggplant in a concentration of 0.005-0.01% it increases germination to 11-22% germination by 20-24% compared with control. Seedling biomass increased by 15% Structural analogues and growth stimulants had a weak positive effect, and the biometrics of seedlings even a negative effect.Seedlings obtained from treated biologically active substances seed (somelongozid 0.01% succinic acid 0.005%) and control (seeds treated water) were planted in the field. Take into account the yield of eggplant. The data presented in table. 3.The drug was tested in field conditions of the farm "Nistru" Novo-Ann's area of Moldova in the area of 7 hectaresThe seeds before sowing is soaked in a 0.01% solution of somelongozid within 24 hours the Control of the new seedlings in the experiment compared to control was 27% higher. The term yield seedlings decreased by 13 days. Yields in the experimental apparatus was 210 kg/ha, whereas in the control 165 kg/ha, yield increase of 27% compared to control.Therefore, the amount of steroid glycosides series furostana (somelongozid) stimulates germination, seed vigor eggplant, stimulates the growth and development of plants in the early season, increases the yield of eggplant on 14-27% METHOD for the production of STEROIDAL GLYCOSIDES SERIES furostana, INCREASES GERMINATION, SEED vigor AND YIELD of EGGPLANT, extraction of roots of eggplant, characterized in that, to increase the growth-promoting activity, extraction was carried out with 70% aqueous ethanol, the extract was concentrated to an aqueous residue with subsequent chromatographytandem on a column of Sephadex G-50 using distilled water as eluent.
FIELD: organic chemistry, steroids, pharmacy.
SUBSTANCE: invention relates to a new type of selective estrogens comprising steroid structure of the general formula (I) with nonaromatic ring A and free of bound hydroxyl group at carbon atom 3 wherein R1 means hydrogen atom (H), (C1-C3)-alkyl or (C2-C3)-acyl; R2 means hydrogen atom (H), α-(C1-C4)-alkyl, α-(C2-C4)-alkenyl or α-(C2-C4)-alkynyl; R3 means hydrogen atom (H) or (C1-C4)-alkyl at position 16 of steroid structure; R4 means ethynyl; R5 means hydrogen atom (H), (C1-C3)-alkyl or (C2-C3)-acyl; R6 means (C1-C5)-alkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl being each of that is substituted optionally with chlorine or fluorine atom; dotted line means the optional double bond. Compounds of the formula (I) elicit the selective affinity to ERα-receptors.
EFFECT: valuable properties of compounds and composition.
4 cl, 3 sch, 1 tbl, 8 ex
FIELD: organic chemistry, chemical technology, pharmacy.
SUBSTANCE: invention describes the improved method for preparing flumetasone (6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione), flumetazone 21-acetate or its 17-carboxyl-androstene analogue of the formula (I) . Method involves interaction of benzoyl chloride with compound of the formula (II) in pyridine medium of its mixture with N,N'-dimethylacetamide to prepare 3-enol ester of the formula (IIIa) and it's the following interaction with 1-(chloromethyl)-4-fluoro-1,4-diazonium-bicyclo[2.2.2]octane-bis(tetrafluoroborate) in acetonitrile medium and water to prepare compound of the formula (IIIb) and the following removing the protective group in compound of the formula (IIIb) at the position C3 in medium of aqueous metabisulfite and ammonia to prepare compound of the formula (IV) . After the fluorination reaction of 9,11-epoxy group in compound of the formula (IV) using HF flumetasone 21-acetate is prepared followed by the selective hydrolysis with KOH in methanol (CH3OH) medium in the presence or absence of H2O2 to prepare compound of the formula (I) or flumetasone, respectively.
EFFECT: improved preparing method.
3 cl, 5 ex
SUBSTANCE: invention relates to methods for isolation and purification of triterpene glucosides from vegetable raw, in particular, saponins from beet and waste in sugar manufacturing, in particular, from beet pulp. Method involves alkaline extraction of raw at temperature 80°C for 8 h followed by settling. Granulated anion-exchange resin AV-17-2P in OH-form is used as a sorbent, and desorption process of sorbent is carried out with 70% ethanol. Invention can be used in food, pharmaceutical and cosmetic industry.
EFFECT: improved preparing method.
2 cl, 1 ex
FIELD: organic chemistry, steroids, chemical technology.
SUBSTANCE: invention describes a method for preparing 3-keto-7α-alkoxycarbonyl-substituted ▵4,5-steroid of the formula (I): wherein is taken among or R3 means hydrogen atom (H), lower alkyl, lower alkoxy-group or cyano-group (CN); R21 means hydrogen atom (H) or alkyl; R26 means (C1-C4)-alkyl; R8 and R9 form in common heterocyclic ring system. Method involves interaction of an alkylating agent with 4,5-dihydro-5,7-lactone steroid of the formula (II): wherein R18 means (C1-C4)-alkyl or R18O-group taken in common form O,O-oxyalkylene bridge or keto-group and R3, R8 and R9 have above given values in the presence of a base. Compounds of the formula (I) are used as intermediate compounds in improved methods for synthesis of epoxymexerone.
EFFECT: improved preparing method.
56 cl, 42 tbl, 30 sch, 5 dwg, 89 ex
FIELD: organic chemistry, medicine, pharmacy.
SUBSTANCE: invention relates to compounds of the formula (I): wherein R represents (C3-C6)-cycloalkyl possibly substituted with (C1-C4)-alkyl, or benzofuranyl, naphthyl, benzothiophenyl, benzooxadiazolyl, or phenyl possibly substituted with one or some substitutes. Also, invention describes methods for preparing compound of the formula (I). Indicated compounds are useful as pharmaceutical preparations possessing with anti-inflammatory properties.
EFFECT: valuable medicinal properties of compounds and preparations.
12 cl, 1 tbl, 107 ex
FIELD: organic chemistry, steroids, labeled compounds.
SUBSTANCE: invention relates to highly labeled analog of physiologically active compound, i. e. to 9α-fluoro-16α-hydroxyprednisolon [3H]-acetonide highly labeled with tritium of the formula (I): . The highly tritium-labeled compound of the formula (I) is necessary for investigation of active non-labeled analog.
EFFECT: valuable properties of compound.
2 cl, 1 ex
FIELD: organic chemistry, steroids, medicine, pharmacy.
SUBSTANCE: invention describes compounds of the formula (I) , their pharmaceutically acceptable salts, solvates, stereoisomers wherein in each case R1 and R2 mean independently hydrogen atom, possibly substituted alkyl, aryl, heteroalkyl wherein heteroatom means nitrogen atom, heteroaryl wherein a heteroatom means nitrogen, oxygen or sulfur atom; or R1 and R2 in common with N-atom to which they are bound can form a heterocyclic structure as a moiety of organic group comprising 6-12 carbon atoms and comprising optionally 1-6 heteroatoms chosen from nitrogen and oxygen atoms; R3 and R4 mean hydrogen atom or a protective group under condition that R and/or R4 represents part of the hydroxyl protective group; № from 1 to 17 mean carbon atoms wherein C-atoms at № 1, 2, 4, 11, 12, 15 and 16 can be substituted with two from R5 groups; C17-atom can be substituted with one of the following groups: =C(R5)(R5), =C=C(R5)(R5) or two from groups - R5 and -OR6; C-atoms at № 5, 8, 9, 10, 13 and 14 can be substituted with group R5 wherein R means hydrogen atom (H), (C1-C6)-alkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-halogenalkyl; R6 means H, protective group, such as -OR6-protected OH-group wherein the group -OR6 can form cyclic protective structure for vicinal -OH groups. Proposed compounds can be components of pharmaceutical composition and useful in treatment and/or prophylaxis of different states including inflammation, asthma, allergic disease, chronic obstructive pulmonary disease, allergic dermatitis, solid neoplasms, ischemia and cardiac arrhythmia.
EFFECT: improved treatment method, valuable medicinal properties of substances and pharmaceutical composition.
53 cl, 10 tbl, 24 ex
FIELD: organic chemistry, steroids, chemical technology.
SUBSTANCE: invention relates to novel effective methods for synthesis of 9,11-epoxy-17α-hydroxy-3-oxopregn-4-ene-7α,21-dicarboxylic acid, γ-lactone, methyl ester (eplerenone). Also, invention describes novel intermediate compounds of the general formula (I): wherein R1 means hydrogen atom (H), -COR4 wherein R4 means (C1-C6)-alkyl, (C1-C6)-alkoxy-group; R3 means (C1-C)-alkyl; Z1 means compound of the formula wherein -O-COR4 is at α-position; Z2 means -CH-, or Z1 and Z2 form in common a double bond; Q means compounds of formulas .
EFFECT: improved methods of synthesis.
28 cl, 3 sch, 17 ex
FIELD: organic chemistry, steroids.
SUBSTANCE: invention discloses derivatives of steroid sapogenins of the general formula (I): wherein R means alkylcarbonyl, alkoxycarbonyl substituted possibly with amino-group and others under condition that R is not acetyl and R is not ethoxycarbonyl if C3 is in S and C25 in R-configurations simultaneously; R is nor succinyl if C3 and C25 are in S-configuration simultaneously, or C3 R(α) or S(β), and C25 in R-configuration. Also, invention discloses using these compounds in treatment of cognitive dysfunction, noncognitive neurodegeneration, noncognitive neuromuscular degeneration and loss of receptors in absence of cognitive, nervous and neuromuscular insufficiency. Also, invention discloses methods for synthesis of these compounds, treatment and pharmaceutical composition containing thereof.
EFFECT: improved method of synthesis, valuable medicinal properties of compounds and pharmaceutical compositions.
30 cl, 2 tbl, 5 dwg, 16 ex
SUBSTANCE: invention discovers derivatives of 5β-sapogenin and pseudo sapogenin of general formula or , where in general formula I or II: R1 R2, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R15 if available-H, independently R1 and R13-OH or R3-OH, =O or OR, where R - optionally substituted alkyl; lower acyl optinally substituted with carbamonyl or amino or lower alkoxycarbamonyl; lower alkoxycarbamonyl; R14 lower alkyl, optionally double bond with the exception of smylagenin and those compounds of formula I where simultaneously R1= R2= R4= R5= R6= R7= R8=R9= R10= R11= R12= R13=H, R3=β OH, R14=CH3, and methyl in C20 condition has α-orientation and C25 has S-configuration.
EFFECT: compounds increases muscarine receptor number and are useful for enhancement of human or animal cognitive function.
12 cl, 17 ex, 5 dwg, 21 tbl