Method for preparing oleanolic acid

FIELD: chemical technology.

SUBSTANCE: invention relates to methods for preparing oleanolic acid used as a standard sample (comparison samples) in carrying out standardization of medicinal vegetable raw and phytopreparations comprising triterpene saponins - derivatives of oleanolic acid. For preparing oleanolic acid method involves sum of saponins extracted by alkaline extraction from sugar or table beet root crops followed by reprecipitation in acid medium and extraction of precipitate with ethanol, chloroform. Method provides preparing oleanolic acid of high purity degree from inexpensive and available raw.

EFFECT: improved preparing method.

2 cl, 3 ex

 

The present invention relates to methods for oleanolic acid used as a standard sample (comparison samples) when conducting the standardization of medicinal plants and herbal remedies containing triterpene saponins derived oleanolic acid.

Known methods for producing oleanolic acid from the roots of Aralia Manchu [1] or medicinal drug Caporal [2], obtained from the roots of Aralia Manchu. This plant grows only in the far East, Primorye, and is a relic. The known method is based on the formation of oleanolic acid in the hydrolytic cleavage of molecules saponins, which is the active principle of the drug Separal during their prolonged heating in an acidic environment. The resulting oleanolic acid is separated by filtration, washed with water, purified by recrystallization, dried and used for quantitative analysis in the form of alcohol solution.

The main disadvantage of this method is the low availability of plant materials from which to allocate Caporal.

The present invention is the extension used resource base at the expense of cheap and widespread plant materials - the dining room or sugar beets.

The task R is agrees, however, in a known method of obtaining oleanolic acid, which consists in the hydrolytic cleavage in the acidic environment of the source material, separation by filtration of oleanolic acid and purification by recrystallization, according to the invention as starting material used amount of saponins extracted by alkaline extraction from crushed roots dining room or sugar beets, or sugar beet pulp with subsequent presidenial saponins in acidic media and their extraction from the precipitate with ethanol, filtered the precipitate containing oleanolic acid, is subjected three times to extraction with chloroform, distilled chloroform to dryness and purification by recrystallization is conducted three times: once from chloroform and then from ethanol.

Example 1.

1 kg (1000 g) of crushed roots dining room or sugar beet, containing 0.20 to 0.32 per cent of saponins, boiled for one hour with 5 DM30.01 M aqueous NaOH solution (ratio of raw materials:extract 1:5), was cooled to room temperature and separating the slurry by filtration through a fabric filter. The filtrate was acidified by adding 100 cm3concentrated HCl and advocated for 5 hours until complete precipitation of saponins. The precipitate, containing saponins, was filtered through a glass filter PS-4, washed from sugar 100 cm3(for sugar beet - 300 cm3) podcas the military to pH 1.0 in water, slightly dried and subjected to circulation extraction of 80% ethanol to conventional Soxhlet extractions (number of cycles is not less than 8). The resulting alcoholic solution of saponins 100 DM3poured into a tenfold volume (1 DM3) 0.1 M aqueous solution of HCl, the precipitate containing 50-60% saponins were separated by filtration, was transferred to a flask, equipped with reflux condenser, was added 80 cm3a mixture of Kiliani (acetic acid - hydrochloric acid - water in the ratio of 35:10:55) and hydrolyzed by boiling for 8 hours. Upon completion of the hydrolysis the reaction mixture was diluted to twice the volume of water, the precipitation of oleanolic acid was separated by filtration through a glass filter PS-4, washed on the filter with water until no acid and was extracted with chloroform three times with volumes of 30, 20 and 10, see Chloroform extract was combined chloroform drove to dryness. The precipitate weighing between 0.46 and 0.75 g contains 80-85% of oleanolic acid. The resulting oleanolic acid addition thrice purified by recrystallization: I times from chloroform, II and III times - their ethanol. At the end of treatment was received 0.24-0,37 g oleanolic acid content of the basic substance is not less than 97%.

Example 2.

250 g of dried powdered roots dining room or sugar beet (fraction 5-7 mm, humidity 11-13%)containing 0.8-1.3% of saponins, pour 20-Crat the m displacement (5 DM 3) 0.01 M aqueous NaOH solution and insisted for swelling of raw materials for 4 hours, then the solution was heated to boiling and maintained for 12 hours, then cooled to room temperature and separating the slurry by filtration through a fabric filter. Next, the process carried out as described in Example 1. in this example was obtained between 0.30 and 0.46 g of oleanolic acid with a basic substance content not less than 97%.

Example 3.

1 kg sugar beet pulp, containing 0.2-0, 26% saponins, filled three volumes (3 DM3) 0.01 M aqueous NaOH solution and insisted for 1 hour at room temperature. Then, the solution was heated to boiling and kept for 1 hour, then cooled to room temperature and separating the slurry by filtration through a fabric filter. Next, the process carried out as described in Example 1. Received 0,28 at 0.42 g of oleanolic acid with a purity of at least 97%.

Sources of information

1. Elm Of Dasta, Athanasian, Effec. Sequential control of the production of tinctures Manchurian Aralia. Pharmacy, No. 6, 1981.

2. Muravyova D.A., samylina I.A. Yakovlev G.P. Pharmacognosy. M: Medicine. 2002, s-329.

The method of obtaining oleanolic acid, which consists in the hydrolytic cleavage in the acidic environment of the source material, separation by filtration of oleanolic acid and cleansing it is rekristallizatsiei, characterized in that as starting material used amount of saponins extracted by alkaline extraction from crushed roots dining room or sugar beets, or sugar beet pulp with subsequent presidenial saponins in acidic media and their extraction from the precipitate with ethanol, filtered the precipitate containing oleanolic acid, is subjected three times to extraction with chloroform, distilled chloroform to dryness and purification by recrystallization is conducted three times: once from chloroform and then from ethanol.



 

Same patents:

FIELD: chemical technology, natural materials, medicine, pharmacy.

SUBSTANCE: invention relates to the improved method for preparing betulin from betulinic acid that can be used in preparing anti-tumor and anti-HIV medicinal preparations. Method for preparing betulinic acid involves oxidation of betulin with chrome (VI) oxide in acetic acid to betulonic acid and reduction with sodium boron hydride to betulinic acid. Betulonic acid sodium salt is reduced to betulinic acid and reduction reaction is carried out at room temperature at the concentration of sodium boron hydride 1.0-6.0 wt.-%. Invention provides simplifying method for preparing betulinic acid, reducing its cost and enhancing ecological safety of the process of it producing.

EFFECT: improved preparing method.

1 cl, 4 ex

The invention relates to new biologically active compounds, namely diglyceride glycyrrhizic acid methyl ester L-valine of formula (I), stimulating primary immune response

The invention relates to new chemical substance, specifically to biologically active compounds having immunostimulatory and antiviral activity (anti-HIV and anti-herpes), - N'-{N-[3-oxo-20(29)-lupen-28-oil] -9-aminopentanoic} -3-amino-3-phenylpropionic acid of the formula I

The invention relates to methods of isolating biologically active substances from waste wood, namely the allocation method Betulinol of the outer layer of birch bark (bark)

The invention relates to new chemical compounds, in particular saponin glycyrrhetic acid - 6',6"-di--D-galactopyranosyl 3-O-[2'-O-(-D - glucuronidase)--D-glucuronidase) methyl ester of glycyrrhetic acid of formula IIB, showing antiulcer activity

The invention relates to new chemical compound, namely the amide glycyrrhizic acid with 5-aminouracil formula I exhibiting anti-HIV activity in cell culture MT-4, with high efficiency by inhibiting the accumulation of virousspecificakih protein P24 (ID50= 55 ág/ml or 52,8 μm), the total viral antigen (ID50= 75 μg/ml or 72,0 μm), which reduces the activity of the reverse transcriptase (reverts) (RT) (ID50= 55 ág/ml or 52,8 μm)

The invention relates to new chemical compounds, specifically to glycopeptide glycyrrhizic acid S-benzyl-L-cysteine [I]: 3-O-{2-O-[N-(-D-glucopyranosyloxy)-L-cysteine(S-benzyl)-N-(-D-glucopyranosyloxy)-L-cysteine(S-benzyl)]}-(3,20)-11-oxo-Olean-12-EN-30-(N-carbonyl-L-cysteine(S-benzyl)-3-yl of the formula (IB), exhibiting anti-HIV activity
The invention relates to an improved method of obtaining Betulinol acid

The invention relates to new inclusion complexes of derivatives of 1,2,5-oxadiazol-2-oxide of General formula I, where1=R2=CN or together with the adjacent carbon atoms form annelirovannymi 3,6-bis(lower alkyl)pyridazin-1,2-dioxideis cycle, polycyclic derivatives of glucopyranose General formula II, where if n= 1, R3fragment 11-oxo-18, 20-Olean-12-EN-29-OIC acid of the formula III, R4=H, R5--D-glucuronidase, R6=R7=H and R8= C(O)OH, or, if n= 7, R3=N, R4and R7- simple connection, R5and R6= H or (CH2CH(CH3)O)mH, where m=1 to 14, and R8=CH2OH or CH2O(CH2CH(CH3)O)mH, where m=1-14, generating nitric oxide and activating the soluble form of guanylate cyclase (RGC), antispasmodic, vasodilator and hypotensive means quick action and platelet aggregation inhibitors, method for their production and pharmaceutical compositions based on

FIELD: organic chemistry, steroids, medicine, pharmacy.

SUBSTANCE: invention relates to steroid compounds of the formula (1)

wherein --- means optional double bonds; R6 means hydrogen atom (H), =CH, -CH3 or -CH2-CH3; R7 means hydrogen atom (H), (C1-C4)-alkyl, (C2-C5)-alkenyl, or (C2-C5)-alkynyl; R11 means hydrogen atom (H), (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkylidene; E means 5-7-memberd ring formed with 16 and 17 carbon atoms at α,cis-position relatively to steroid structure and comprising possibly up to two double bonds. Compounds can be used in therapy and in methods for selective modification of activity of estrogen receptors.

EFFECT: improved method for modifying, valuable medicinal properties of compounds.

10 cl, 1 sch, 1 tbl, 1 ex

FIELD: chemical technology, natural materials, medicine, pharmacy.

SUBSTANCE: invention relates to the improved method for preparing betulin from betulinic acid that can be used in preparing anti-tumor and anti-HIV medicinal preparations. Method for preparing betulinic acid involves oxidation of betulin with chrome (VI) oxide in acetic acid to betulonic acid and reduction with sodium boron hydride to betulinic acid. Betulonic acid sodium salt is reduced to betulinic acid and reduction reaction is carried out at room temperature at the concentration of sodium boron hydride 1.0-6.0 wt.-%. Invention provides simplifying method for preparing betulinic acid, reducing its cost and enhancing ecological safety of the process of it producing.

EFFECT: improved preparing method.

1 cl, 4 ex

FIELD: organic chemistry, steroids, pharmacy.

SUBSTANCE: invention describes unsaturated 14,15-cyclopropanoandrostanes of the general formula (I):

wherein R1 means hydrogen atom (H), hydroxy-group (OH); R2 means hydroxy-group (OH), hydrogen atom (H); R3 means hydrogen atom (H), (C1-C10)-alkyl at α- or β-position; R4 means halogen atom (F, Cl, Br) or pseudohalogen group (azide, rhodanide), hydroxy-group (OH), perfluoroalkyl; R5 means (C1-C4)-alkyl; if double bond is at 1,2-position then R4 can mean hydrogen atom (H). Also, invention relates to a method for preparing these compounds and pharmaceutical compositions containing these compounds. Compounds of the formula (I) are compounds eliciting gestagenic and/or androgenic effect.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 1 tbl, 9 ex

The invention relates to steroids of General formula I

where R1- Oh, (H,H), (H,OR), NOR, where R is H1-6alkyl, C1-6acyl; R2- H or C1-6alkyl, R3- H, or R3- C1-6alkyl, C2-6alkenyl,2-6quinil, possibly substituted with halogen, R4- H, C1-6alkyl or C2-6alkenyl; R5- C1-6alkyl, R5- H, R7- H, C1-6alkyl, R8Is H, OH, halogen;

R9and R10independently H, or R9and R10independently C1-6alkyl, possibly substituted C1-4alkoxy or halogen;

R11- H, SO3H1-15acyl, dashed line indicates a possible link from4,5(10)or4,9-diene system

The invention relates to new chemical substance, specifically to biologically active compounds having immunostimulatory and antiviral activity (anti-HIV and anti-herpes), - N'-{N-[3-oxo-20(29)-lupen-28-oil] -9-aminopentanoic} -3-amino-3-phenylpropionic acid of the formula I

The invention relates to methods of isolating biologically active substances from waste wood, namely the allocation method Betulinol of the outer layer of birch bark (bark)
The invention relates to an improved method of obtaining Betulinol acid

The invention relates to new inclusion complexes of derivatives of 1,2,5-oxadiazol-2-oxide of General formula I, where1=R2=CN or together with the adjacent carbon atoms form annelirovannymi 3,6-bis(lower alkyl)pyridazin-1,2-dioxideis cycle, polycyclic derivatives of glucopyranose General formula II, where if n= 1, R3fragment 11-oxo-18, 20-Olean-12-EN-29-OIC acid of the formula III, R4=H, R5--D-glucuronidase, R6=R7=H and R8= C(O)OH, or, if n= 7, R3=N, R4and R7- simple connection, R5and R6= H or (CH2CH(CH3)O)mH, where m=1 to 14, and R8=CH2OH or CH2O(CH2CH(CH3)O)mH, where m=1-14, generating nitric oxide and activating the soluble form of guanylate cyclase (RGC), antispasmodic, vasodilator and hypotensive means quick action and platelet aggregation inhibitors, method for their production and pharmaceutical compositions based on

FIELD: organic chemistry, steroids, pharmacy.

SUBSTANCE: invention describes unsaturated 14,15-cyclopropanoandrostanes of the general formula (I):

wherein R1 means hydrogen atom (H), hydroxy-group (OH); R2 means hydroxy-group (OH), hydrogen atom (H); R3 means hydrogen atom (H), (C1-C10)-alkyl at α- or β-position; R4 means halogen atom (F, Cl, Br) or pseudohalogen group (azide, rhodanide), hydroxy-group (OH), perfluoroalkyl; R5 means (C1-C4)-alkyl; if double bond is at 1,2-position then R4 can mean hydrogen atom (H). Also, invention relates to a method for preparing these compounds and pharmaceutical compositions containing these compounds. Compounds of the formula (I) are compounds eliciting gestagenic and/or androgenic effect.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 1 tbl, 9 ex

Up!