Method of rickardine c obtaining

FIELD: medicine; pharmacology.

SUBSTANCE: perform processing of an elevated part and roots of the primrose plant (Primula macrocalyx Bge.) with an organic dissolvent - ligroin or hexane with the subsequent extraction with acetone and allocation of a target product using chromatography.

EFFECT: increase of output of the product.

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The invention relates to pharmaceutical industry and relates to retrieve riccardino With connection lesbiandildo type structural formula I:

The specified connection can be used as pharmaceuticals.

The compound (I) was first isolated from moss Reboulia hemispherica in 1982 [Asakawa, Y. and Matsuda, R. Riccardin C, a novel cyclic bibenzyl derivative from Reboulia hemispherica. / Phytochemistry. 1982. N21. P.2143-1244]. From literature data it is known that Riccardi (I) (Riccardin C) and similar bisbenzimide system (Perrottetins, Marchantins, Plagiochins), which is a phenolic compound that was previously only observed from bryophytes - mosses-liverworts (from genus Riccardia, Marchantia, Plagiochila and others) [Wu, C., Lin, H. Labdanoids and bis(bibenzyls) from Jungermannia species / Phytochemistry. - 1995. - V.44. - N1. - P.101-105; Martini, U., wireless connection, J., Becker, H.. Chlorinated macrocyclic bis(bibenzyls) from the liverwort Bazzania trilobata / Phytochemistry. - 1998. - V.47. - N1. - P.89-96; Toyota, M., Yoshida, T., Matsunam, J., Asakawa, Y. Sesquiterpene and other constituents of the liverwort Dumortiera hirsuta // Phytochemistry. - 1997. - V.44. - N2. - P.293-298], and in higher plants, algae and fungi, were not found.

From literature data it is known that these compounds exhibit a wide range of cytotoxic, antibacterial and antifungal activity and are used as inhibitors of 5-lipoxygenase [Zinsmeister, H.D.; Becker, H.; Eicher, T... Bryophytes, a source of biologically active, naturally occuring material. / Angew. Chem. 1991, 103, 134-151; Asakawa, Y. Progress in the Chemistry of Natural Oganic Products / Eds.: Herz, E., Kirby, G.W., Moore, R. E., Steglich, W., Tamm, C. - New York: Springer, Wien, 1995. - P.5]. In addition, we discovered that Riccardi (I) and close to him on the structure of the compounds are inhibitors of the inducible NO-synthase [Harinantenaina, D.N. Quang, N. Takeshi et. al. Bis(bibenzyls) from liverworts inhibit lipopolysaccaharide-induced inducible NOS in RAW 264.7 cells: a study of structure-activity relartionships and molecular mechanism // J. L. Nat. Prod. - 2005. - N6. - P.1779-1781]. The selection of the substances responsible for the inhibition of NO-synthase, the creation of new products appropriate action is one of the most important problems in medicine, as excessive release of NO leads to a number of different, often severe pathological conditions. These include septic shock, neurodegenerative diseases, Parkinson's disease and Alzheimer's disease, various inflammatory processes [hranik, V.G., Grigoriev, NB synthase Inhibitors of nitric oxide - biology and chemistry // Izvestiya an. ser. chem. - 2002. - N11 - S-1841].

A method of obtaining riccardino With low output (0.0015%) by allocations from the moss-liverwort [Anton, H., Shoeneborn, R., Mues, R. Bibenzils and bisbibenzyls from a neotropical Plagiochila species. / Phytochemistry. 1999. The N8. P.1639-1645]. The method consists in the extraction of air-dried raw materials consistently methylene chloride and 80%aqueous methyl alcohol and subsequent fractionation of the methanol extract on solid-phase extractor with phase RP-18, and then, twice chromatography of the corresponding fractions in sefad the CNS LH-20 chromatography on a preparative HPLC column.

As a prototype the selected method of obtaining riccardino by extraction With moss-liverwort Reboulia hemispherica the ethyl acetate and methanol, followed by separation of the extract column chromatography on silica gel and thin-layer chromatography [Asakawa, Y. and Matsuda, R. Riccardin C, a novel cyclic bibenzyl derivative from Reboulia hemispherica. / Phytochemistry. 1982. N21. P.2143-1244], the output of the substances (I) - 0.00153%.

The drawback of both methods is the low output riccardino With and inaccessible raw materials used to obtain Japanese moss liverworts, plants having a small area and difficult in the introduction.

Object of the invention is to create a simple manufacturable method of obtaining riccardino With high yield from the available raw materials.

The problem is solved by allocating riccardino (I) of flowering plants, namely primrose krupnokuskovoy (Primula macrocalyx Bge.) sequential extraction of the aerial parts and roots of the plants with an organic solvent (petroleum ether, hexane, acetone), followed by separation of the target product by chromatography was carried out. Primrose, krupnotsvetkova - a perennial herb with a thick rootstock, bearing numerous lobe roots and up to 10 or more canopies. The plant is found in the Crimea, the Caucasus, southern Urals, widespread in the South of Western Siberia and the Krasnoyarsk territory. Kul is evermedia in the Central Siberian Botanical garden (Novosibirsk). The proposed method can extract richardin With (I) high yield from both aerial parts and roots of evening primrose oil, both from wild plants and introduced.

Raw materials: we used aerial parts and rhizomes primrose krupnokuskovogo (Primula macrocalyx Bge.), collected by the expedition to the Altai mountains in the vicinity of the village Amos, Chemal district, in August 2004, and introduced the primrose grown on portions of the Central Siberian Botanical garden, SB RAS. Choosing the type of evening primrose and the introduction was conducted by staff of the laboratory of medicinal plants of the Botanical garden, SB RAS.

A General method of allocating riccardino C.

For the most complete removal of lipophilic substances, whose presence in the extracts significantly complicates chromatographic selection of individual compounds, the extraction is carried out by the insistence of the air-dried plant materials in hexane or petroleum ether at room temperature. Insisting carried out repeatedly until the discoloration of the solvent. It is the insistence, not boiling solvent, allows to separate pigments, wax and other lipophilic substances from raw materials, and richardin With cold hexane or petroleum ether is removed.

Further processing of vegetable raw materials carried out by the insistence in ACE the Ohe at room temperature. In the processing of vegetable raw materials in acetone receive a fairly simple composition of the extract containing one main ingredient - Riccardi (peak 15, figure 1).

The acetone extract is divided into a column of silica gel (ratio extract:adsorbent 1:40), receive a fraction enriched with riccardino C. Or pre - acetone extract sequentially treated with chloroform and ethanol, all of richardin With separated chloroform. Then the enriched substance (I) divide fractions on silica gel and the column with reversed phase (Art. 9334 LiChrosorb RP-18, 10 μm, Merck), receive Riccardi (figure 2).

By comparing the obtained spectral data with the literature [Anton, H., Shoeneborn, R., Mues, R. Bibenzils and bisbibenzyls from a neotropical Plagiochila species. / Phytochemistry. 1999. The N8. P.1639-1645.] a dedicated connection has been attributed to the structure of riccardia (I).

The invention is illustrated by the following examples.

Example 1. In a column 5 cm in diameter with a faucet at the bottom of the load 94.24 g plant materials (air-dry crushed leaves and stems), six-pour 0.5 liters of hexane and insist a total of 48 hours to colorless extract. The weight of the hexane extract of 0.65 g (0.7% by weight of raw materials), the extract discarded. Then raw insist acetone 4 times in 24 hours, the weight of the extract - 2.11 g (2.24% by weight of raw materials).

2.11 g of acetone extract share nakaloke silica gel (100/160 multiplesμ the ratio of substance: adsorbent ˜ 1:40, eluent - chloroform with a gradient of ethyl alcohol from 1%), allocate the amount of 0.045 g fractions enriched substance (I).

Fractions enriched substance (I) (0.045 g; 2.13% by weight acetone extract) are divided by reversed phase. In a glass filter fill 3 g SiO2(L 60/200 μ), 10 g of inverted phases (Art. 9334 LiChrosorb RP-18, 10 μm, Merck), washed several times with distilled water, methanol, causing the fraction of compound (I) in methanol and elute the substance (I) 90% methanol. Mass selected pure substance (I) is 0.020 g (0.95% - by weight of the extract; 0.021% - by weight of dry material).

The IR spectrum of the compound (I) (C28H24O4; νcm-1, CHCl3): 3597, 3550, 2928, 2860, 1740, 1706, 1606, 1566, 1506, 1482, 1433, 1333, 1269, 1188, 1105, 1050, 978, 914.

The UV spectrum of the compound (I) (methanol): 279 nm.

An NMR spectrum1N compounds (I) DMSO-d6, +55°, δ, ppm (J, Hz): 5.34 (H3I , J3,52.0), 6.65 DD (H5I , J5,68.0 J5,32.0), 6.77 (H6I , J6,58.0), 6.77 (N6I , J6,58.0), 2.61 (m 2N7), 2.55 m (2N8), 6.32 (H10I , J10,141.7), 6.70 d (H13I , J13,147.6), 6.09 DD (N14I , J14,137.6 J14,101.7), 6.68 SD (N2'N6'), 6.82 SD (N3'N5'I , J3',2'7.7), 2.80 sh (2N7'2N8'), 6.80 (N10'I , J10',12'2.6), 6.63 DD (N12'I , J12',13'8.3 J12',102.6), 6.85 (H13'I , J 13',12'8.3), 8.65 (With11-HE), 8.78 sh (1-HE), 9.09 sh (11'-HE).

An NMR spectrum13With the compound (I) (DMSO, δC, ppm): 34.8 t (7'), 36.1 t (7), 37 (To8), 37.3 (C8'), 112.7 (With12'), 115.6 (With10), 116 d (6), 116.03 d (10'), 116.6 (With3), 119.5 (With14), 121.5 (With5), 121.5 (With2'With6'), Was 125.6 (With12), 129 d (3'With5'), 129.2 (With14'), 131.7 (With4), 132 d (13'), 132 d (13), 139.1 (With4'), 139.9 (With9'), 142.7 (With9), 144.1 (With1), 147 (With2), 152.7 (With1'), 153.4 (With11), 156.3 (With11').

MS; m/z(%): 424 (100), 225 (7.6), 212 (46), 211 (93.5), 197 (8), 152 (4), 120 (7), 107 (18), 941 (14), 77 (8), 56 (5).

Example 2. From 100 g of air dry raw material (the above-ground part of evening primrose oil, crushed leaves and stems) obtain 2.23 g (2.23% by weight of raw materials) acetone extract as described in example 1. The extract is separated by solvent - chloroform extracted 1.56 g of the extract (70%), ethanol - 0.67 g (30%). Column chromatography of the chloroform extract (SiO2The voltage of 100/160μ, the ratio of the substance:adsorbent ˜1:40; column diameter 1.0 cm, eluent - chloroform with a gradient of ethyl alcohol from 1 to 10%) allocate 0.049 g of the fraction of the substance (I). The course chromatography monitored using TLC plates in the solvent system of 5% ethanol in chloroform. Enriched fractions of the substance (I) (0.049 g; 2.20% by weight acetone e is stricta). In a glass filter fill 3 g SiO2(L 60/200 μ), 10 g of inverted phases (Art. 9334 LiChrosorb RP-18, 10 μm, Merck), washed several times with distilled water, methanol, causing the combined fraction of compound (I) in methanol and elute the substance (I) 90% methanol. Mass selected pure substance (I) is 0.022 g (0.97% - by weight of the extract; 0.022% - by weight of dry material).

Example 3. The air-dried powdered roots of evening primrose krupnokuskovoy weight 199 g insist in the flask in 1.5 l of petroleum ether 3 times in two days to colorless extract. The extracts discarded. Further insist raw materials in 1.5 l of acetone (5 times in two days before the complete removal of riccardia With control by HPLC). Obtain 3.85 g of extract (1.93% by weight of dry material). Extract chromatographic on a column of silica gel (100/160 multiplesμ, the ratio of the substance:adsorbent ˜ 1:40, eluent - chloroform with a gradient of ethyl alcohol from 1 to 10%), isolated in the amount of 0.45 g of fractions enriched substance (I). Spend rechromatography on a column of silica gel (100/160 multiplesμ, the ratio of the substance:adsorbent ˜ 1:80, eluent - chloroform with a gradient of ethyl alcohol from 1 to 10%), allocate the amount of 0.046 g of substance (I) (0.023% by weight of dry material).

Example 4. Air-dry the instances of the whole plant primroses are crushed, the sample mass 100 g is soaked in a flask, 1.0 l of petroleum ether 3 RA is but two days. The extracts discarded. Further insist raw materials in 1.0 l of acetone (5 times in two days before the complete removal of riccardia With control by HPLC). Obtain 2.02 g of extract (2.02% by weight of dry material). Extract chromatographic on a column of silica gel (100/160 multiplesμ, the ratio of the substance:adsorbent ˜1:40, eluent - chloroform with a gradient of ethyl alcohol from 1 to 10%), isolated in the amount of 0.22 g of fractions enriched substance (I). Spend rechromatography on a column of silica gel (100/160 multiplesμ, the ratio of the substance:adsorbent ˜ 1:80, eluent - chloroform with a gradient of ethyl alcohol from 1 to 10%), allocate the amount of 0.022 g of substance (I) (0.022% by weight of dry material).

Thus, the proposed method for riccardia With allows you to get pure substance (I) of the available renewable raw materials with a sufficiently high yield after extraction with organic solvents by maceration at room temperature and sequential chromatography on silica gel and reversed-phase or two-column chromatography on silica gel. He has a number of advantages in comparison with known methods:

extraction of the desired product is carried out of the available raw material is the highest flowering plants primrose krupnokuskovoy, which can be fairly easily harvested in the wild, and cultural venues in contrast to the t collection of moss liverworts, used in the prototype;

- to retrieve riccardino used With various solvents; distilled from the extract, the solvent does not require additional purification or regeneration for use in the re-extraction, which is very scientific;

the solvents and the extraction method selected so that extracted from the raw richardin With out with out greater than in ways analogous. The yield of the target product of the proposed method is 0.021-0.023%, against 0.00153% by a known method prototype.

The method of obtaining riccardino With formulas I:

from plant material by extraction with an organic solvent, followed by separation of the target product by chromatography, characterized in that the feedstock used primrose krupnotsvetkova (Primula macrocalyx Bge.), as the organic solvent is acetone, and extraction is carried out at room temperature with advanced materials processing hexane or petroleum ether.



 

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