CN104402961B - The luxuriant and rich with fragrance ester A of tetrahydrochysene furoic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use - Google Patents
The luxuriant and rich with fragrance ester A of tetrahydrochysene furoic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use Download PDFInfo
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- CN104402961B CN104402961B CN201410773419.0A CN201410773419A CN104402961B CN 104402961 B CN104402961 B CN 104402961B CN 201410773419 A CN201410773419 A CN 201410773419A CN 104402961 B CN104402961 B CN 104402961B
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- ester
- tetrahydrofurfuryl
- taking
- impatiens balsamina
- chloroform
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 239000002253 acid Substances 0.000 title claims abstract description 21
- 239000001257 hydrogen Substances 0.000 title claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 8
- 150000002148 esters Chemical class 0.000 title abstract description 18
- 239000003205 fragrance Substances 0.000 title abstract 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 title abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims abstract description 19
- 235000003140 Panax quinquefolius Nutrition 0.000 claims abstract description 19
- 235000008434 ginseng Nutrition 0.000 claims abstract description 19
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 4
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 35
- 244000018716 Impatiens biflora Species 0.000 claims description 27
- 235000015912 Impatiens biflora Nutrition 0.000 claims description 27
- 241000208340 Araliaceae Species 0.000 claims description 19
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 14
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 13
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000003480 eluent Substances 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 12
- 239000002026 chloroform extract Substances 0.000 claims description 8
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002386 leaching Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000005520 cutting process Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003463 adsorbent Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000002791 soaking Methods 0.000 claims description 4
- 238000010025 steaming Methods 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 3
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 206010020772 Hypertension Diseases 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 1
- 244000131316 Panax pseudoginseng Species 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000001631 hypertensive effect Effects 0.000 abstract 1
- 238000010298 pulverizing process Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 16
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 13
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 13
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 150000003431 steroids Chemical class 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- VTGUMPUFLSYIEV-UHFFFAOYSA-N oxolan-2-ylmethyl furan-2-carboxylate Chemical compound C=1C=COC=1C(=O)OCC1CCCO1 VTGUMPUFLSYIEV-UHFFFAOYSA-N 0.000 description 6
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- 239000012085 test solution Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 229940127088 antihypertensive drug Drugs 0.000 description 3
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- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 3
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 3
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- 102000005862 Angiotensin II Human genes 0.000 description 2
- 101800000733 Angiotensin-2 Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229950006323 angiotensin ii Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
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- 239000005541 ACE inhibitor Substances 0.000 description 1
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- 101800004538 Bradykinin Proteins 0.000 description 1
- 102400000967 Bradykinin Human genes 0.000 description 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
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- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 241001495448 Impatiens <genus> Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 235000002791 Panax Nutrition 0.000 description 1
- 241000208343 Panax Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 206010001584 alcohol abuse Diseases 0.000 description 1
- 208000025746 alcohol use disease Diseases 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
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- 230000004071 biological effect Effects 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 235000019425 dextrin Nutrition 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
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- JAOVOFHFEAKFIQ-UHFFFAOYSA-N formic acid;oxolane Chemical compound OC=O.C1CCOC1 JAOVOFHFEAKFIQ-UHFFFAOYSA-N 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to a kind of tetrahydrochysene furoic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen and extracting method thereof and its pharmaceutical use.Belong to new compound and pharmaceutical use thereof.With ginseng and northeast Flower of Garden Balsam for raw material, through pulverizing, high temperature high pressure process, drying, chloroform extraction, silica gel column chromatography, recrystallization method, obtain tetrahydrochysene furoic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen, its chemical name is: tetrahydrofuran (THF)-2-formic acid 17-(5-ethyl-6-methyl-2-in heptan base)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-ten tetrahydrochysene-1H-ring penta [a] phenanthrene-3-ester.The application of the luxuriant and rich with fragrance ester A of tetrahydrochysene furoic acid pentamethylene many hydrogen in the hypertensive medicine of preparation treatment.
Description
Technical Field
The invention relates to a tetrahydrofurfuryl acid cyclopentanoperhydrophenanthrene ester A, an extraction method and a pharmaceutical application thereof. Belongs to a new compound and the pharmaceutical application thereof.
Background
Ginseng radixPanaxgisengC.a.mey. is a plant of the genus panax of the family araliaceae. Wherein,Panaxgreek is the meaning of "universal drug", and the full-language pronunciation of ginseng is "Aoerga", which is the meaning of "king of Baicao". As a traditional medicinal material, the traditional Chinese medicine has a history of thousands of years and is widely applied in various countries in the world. Ginseng is effective in invigorating primordial qi, restoring pulse, relieving depletion, invigorating spleen, benefiting lung, promoting fluid production, and tranquilizing mind.
Impatiens balsamina L.Var.Dc.Var.DcImpatiensfurcillataHemsl is plant of impatiens of Balsaminaceae. The plants are distributed in Russian far east areas, Korea and inner Mongolia, Hebei, Liaoning, Jilin and other places in Chinese continent, and grow in areas with the altitude of 700 m to 1,000 m, and are seen in forest borders, valley edges or grass clusters.
Hypertension is a clinical syndrome mainly manifested by increased systemic arterial pressure, and is the most common cardiovascular disease. The primary hypertension has two main types of pathogenesis factors, one is internal cause, such as heredity; another category is external causes such as mental stress, salt overload, smoking, obesity, alcohol abuse, lack of exercise, etc. Long-term hypertension can affect the function of the heart, brain, kidney, etc., and ultimately lead to failure of the function of these organs. Hypertension is a frequently encountered disease, and the incidence rate of hypertension in China is 7.7% in the last 80 th century; by the beginning of this century, the temperature rapidly increased to 18.8%; in recent 10 years, the prevalence of hypertension has increased by 31%. At present, the number of hypertension patients in China is estimated to exceed 2 hundred million, and the trend still continues to be continued and reversion is unlikely to occur in a short period of time. If not controlled any more, it will grow 50% in the next 15 years. The antihypertensive drug mainly comprises diuretics, beta receptor blocker, calcium channel blocker, angiotensin converting enzyme inhibitor and angiotensin II receptor blocker. These drugs have certain side effects such as cardiac suppression, metabolic abnormalities, renal damage, and the like. And the number of the antihypertensive drugs with the independent intellectual property rights in China is less.
In the research and development process of ginseng processed products, the subject group discovers that products obtained by the common processing treatment (high temperature and high pressure) of impatiens balsamina by people have a strong Angiotensin Converting Enzyme (ACE) inhibition effect, active ingredients are further tracked, and a new compound is obtained by separation, wherein the chemical name of the compound is as follows: tetrahydrofuran-2-carboxylic acid 17- (5-ethyl-6-methylhept-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a ] a]Phenanthrene-3-ester [17- (5-ethyl-6-methylheptan-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a ] a]phenanthren-3-yltetrahydrofuran-2-carboxylate]Tetrahydrofurfuroic acid cyclopentanoHydrophenanthrene ester A, and the half inhibition rate (IC) of the compound to ACE is determined50) 10. mu.g/mL was reached. Further analyzing the source of the tetrahydrofurfuryl and polyhydrophenanthrene ester A, the compound is not detected in ginseng, impatiens balsamina, a high-temperature and high-pressure processed product of ginseng and impatiens balsamina, and the high-temperature and high-pressure processed product of impatiens balsamina indicates that the compound is generated by the ginseng and the impatiens balsamina which are prepared by the formula and are processed at high temperature and high pressure. The tetrahydrofurfuryl acid cyclopentanoperhydrophenanthrene ester A is expected to become a new blood pressure reducing medicine.
Disclosure of Invention
The invention provides a tetrahydrofurfuryl acid cyclopentanoperhydrophenanthrene ester A, an extraction method and a pharmaceutical application thereof.
A tetrahydrofurfuryl and polyhydrophenanthrene furoate ester a of the formula:
tetrahydrofuran-2-carboxylic acid 17- (5-ethyl-6-methylhept-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a ] phenanthrene-3-ester [17- (5-ethyl-6-methylheptan-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a ] phenothran-3-yltetrahydrofu-2-carboxylate ]
The invention also aims to prepare a novel substance with stronger biological activity by using ginseng and impatiens balsamina as raw materials and carrying out crushing, high-temperature and high-pressure treatment, drying, chloroform extraction, silica gel column chromatography and recrystallization.
In order to achieve the above object, the following processes are required:
(1) processing: taking northeast impatiens balsamina, cutting into pieces, adding 5-10 times of water, treating at high temperature and high pressure for 2-4 h, and filtering to obtain the northeast impatiens balsamina leaching solution; crushing sun-dried ginseng, soaking the sun-dried ginseng in the impatiens balsamina leach liquor, steaming at high temperature and high pressure for 4-8 hours, taking out, and drying to obtain a high-temperature and high-pressure processed product of the impatiens balsamina of ginseng;
(2) extraction: taking the product of the impatiens balsamina in the step (1) after high-temperature and high-pressure treatment, leaching the product with chloroform for 1-3 times, adding 5-10 times of chloroform each time, combining chloroform extracting solutions, and evaporating to dryness to obtain a chloroform extract;
(3) separation: and (3) taking the chloroform extract obtained in the step (2), performing column chromatography by taking silica gel as an adsorbent, performing gradient elution by using petroleum ether-dichloromethane (20: 1-1: 1), collecting partial eluent of the cyclopentane and polyhydrophenanthrene ester A tetrahydrofurfuryl acid, recovering the solvent to obtain a crude product of the cyclopentane and polyhydrophenanthrene ester A tetrahydrofurfuryl acid, performing silica gel column chromatography, eluting by using petroleum ether-acetone (10: 1) as an eluent, collecting partial eluent of the cyclopentane and polyhydrophenanthrene ester A tetrahydrofurfuryl acid, recovering the solvent, and recrystallizing by using petroleum ether-acetone to obtain the cyclopentane and polyhydrophenanthrene ester A tetrahydrofurfuryl acid.
The invention relates to application of cyclopentane hydrofuran and polyhydrophenanthrene ester A tetrahydrofurfuryl furoate in preparing a medicine for treating hypertension.
When the invention is used for preparing the medicine for treating hypertension, the medicine is safe to be taken orally or parenterally. In the case of oral administration, it may be administered in any conventional form, such as powders, granules, tablets, capsules, pills, solutions, suspensions, syrups, buccal tablets, sublingual tablets, and the like; when the drug is administered parenterally, it may take any conventional form, such as intravenous injections, ointments, suppositories, inhalants and the like.
The medicine for treating hypertension according to the present invention is composed of an effective ingredient monomer or an effective ingredient together with a solid or liquid excipient, which is well known in the art, and the powder is an internal powder having, as specific examples, lactose, starch, dextrin, calcium carbonate, synthetic or natural aluminum sulfate, magnesium oxide, magnesium stearate, sodium bicarbonate, dried yeast, etc.; the excipient of the solution agent comprises water, glycerol, 1, 2-propylene glycol, simple syrup, ethanol, ethylene glycol, polyethylene glycol, sorbitol, etc.; the excipient of ointment can be fatty oil, hydrophobic agent or hydrophilic agent composed of aqueous lanolin, vaseline, glycerol, beeswax, wood wax, liquid paraffin, resin, and high grade wax.
The invention has the beneficial effects that the new compound of the tetrahydrofurfuryl acid cyclopentanoperhydrophenanthrene ester A can be used for preparing the antihypertensive drug, has the characteristic of obvious curative effect and can inhibit IC of ACE (angiotensin converting enzyme)50Can reach 10 mug/mL.
Detailed Description
Example 1:
taking 200g of northeast impatiens balsamina, cutting into pieces, adding 2L of water, treating at high temperature and high pressure for 4h, and filtering to obtain leaching solution of the northeast impatiens balsamina; taking 1000g of sun-dried ginseng, crushing, soaking with the impatiens balsamina extract, steaming at high temperature and high pressure for 4h, taking out, and drying to obtain a high-temperature and high-pressure processed product of the impatiens balsamina of ginseng; extracting the product of the obtained impatiens balsamina at high temperature and high pressure with chloroform for 3 times (5L each time), mixing chloroform extractive solutions, and evaporating to obtain chloroform extract; and performing column chromatography on the obtained chloroform extract by using silica gel as an adsorbent, performing gradient elution by using petroleum ether-dichloromethane (20: 1-1: 1), collecting partial eluent of the cyclopentane and phenanthrene ester A tetrahydrofurfuryl furoate, recovering the solvent to obtain a crude product of the cyclopentane and phenanthrene ester A tetrahydrofurfuroate, performing silica gel column chromatography, eluting by using petroleum ether-acetone (10: 1) as an eluent, collecting partial eluent of the cyclopentane and phenanthrene ester A tetrahydrofurfuroate, recovering the solvent, and recrystallizing by using petroleum ether-acetone to obtain the cyclopentane and phenanthrene ester A tetrahydrofurfuroate.
1. And (3) structural identification:
MS: the peak of molecular ion is 512.4 by mass spectrum measurement, and the binding IR,1HNMR、13CNMR determines the molecular formula as C34H56O3。
IR spectrum: 2964 and 2888cm-1Stretching vibration peak (upsilon) of carbon-hydrogen bond of saturated alkaneCH) Confirming the presence of a saturated alkane group; 1738cm-1Is a stretching vibration peak (. nu.) of carbonylC=O) Indicating the presence of a carbonyl group in the compound; 1629cm-1Is upsilonC=CIndicating the presence of a carbon-carbon double bond; 1384cm-1、1372cm-1Deformation vibration peak of methyl group ( CH3）。
1HNMR(300MHz,CDCl3)ppm：5.377(d,1H,J=4.8Hz) is steroid parent nucleus 6-site alkene hydrogen signal, 4.681: (m1H) is the 2-position hydrogen signal of tetrahydrofuran-2-carboxylic acid, 4.433: (m1H) is the steroid nucleus 3-position oxygen-linked carbon hydrogen signal, 4.025: (dd,1H,J=7.2,14.4Hz)、3.940(m1H) signals for two hydrogens in position 5 of the tetrahydrofuran-2-carboxylic acid radical, 1.010: (s,3H)、0.922(d,3H)、0.859(t,3H)、0.813(d,6H)、0.668(sAnd 3H) is a steroid parent nucleus and 6 methyl hydrogen signals on a 17-site side chain, and 2.343-0.753 is a steroid parent nucleus and a 17-site side chain and hydrogen signals on other saturated carbons of tetrahydrofuran-2-formic acid, and the data indicate the existence of a steroid structure and tetrahydrofuran formic acid.
13CNMR(75MHz,CDCl3) 172.67 is carbonyl carbon signal, 139.41, 122.68 is steroid mother nucleus C5, C6 unsaturated carbon signal, 76.79, 74.33, 69.17 are oxygen linked carbon signal at 2 position of tetrahydrofuran-2-formic acid, 3 position of steroid mother nucleus, 5 position of tetrahydrofuran-2-formic acid, 56.63, 56.01, 49.99, 45.82, 42.25, 39.67, 37.95, 36.89, 36.51, 36.06, 33.91, 31.81, 30.12 (× 2), 29.16, 28.13, 27.63, 26.13, 24.20, 23.04, 20.96, 19.70, 19.20, 18.98, 18.70, 11.89, 11.76 are saturated carbon signal of steroid mother nucleus and 17 position side chain and two methines of tetrahydrofuran-2-formyl group.
Bonding of1HNMR、13Further comprehensive analysis of CNMR and IR spectrum confirms that the compound is tetrahydrofuran-2-formic acid 17- (5-ethyl)-6-methylhept-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a]Phenanthrene-3-ester [17- (5-ethyl-6-methylheptan-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a ] a]phenanthren-3-yltetrahydrofuran-2-carboxylate]The compound is a novel compound which is not reported in documents by the literature search. The specific NMR signals for this compound are assigned as follows:
1HNMR(300MHz,CDCl3)ppm：5.377(d,1H,J=4.8Hz,6-H)，4.681(m,1H,2’’-H)，4.433(m,1H,3-H)，4.025(dd,1H,J=7.2,14.4Hz,5’’-Ha)、3.940(m,1H,5’’-Hb)，1.010(s,3H,10-CH3)、0.922(d,3H,2’-CH3)、0.859(t,3H,5’-CH3)、0.813(d,6’,6’-CH3)、0.668(s,3H,13-CH3) Is a steroid parent nucleus and 6 methyl hydrogen signals on a 17-site side chain, and 2.343-0.753 are the steroid parent nucleus and the 17-site side chain as well as hydrogen signals on other saturated carbons of tetrahydrofuran-2-formic acid.
13CNMR(75MHz,CDCl3)ppm：172.67(C=O)、139.41(C5)、122.68(C6)、76.79(C2’’)、74.33(C3)、69.17(C5’’)、56.63(C14)、56.01(C17)、49.99(C9)、45.82(C5’)、42.25(C13)、39.67(C12)、37.95(C4)、36.89(C1)、36.51(C10)、36.06(C2’)、33.91(C3’)、31.81(C3’’)、30.12(C7,8)、29.16(C6’)、28.13(C2)、27.63(C4’)、26.13(C15)、25.09(C4’’)、24.20(C16)、23.04(5’-CH2)、20.96(C11)、19.70(C7’)、19.20(6’-CH3)、18.98(C1’)、18.70(10-CH3)、11.89(5’-CH3)、11.76(13-CH3)。
ACEI inhibition Activity test
The renin-angiotensin-aldosterone system (RAS) plays an important role in the development and progression of hypertension, with angiotensin ii being the major effector peptide. ACEI inhibits the conversion of angiotensin I to angiotensin II without inactivating bradykinin, resulting in a hypotensive effect. The experiment adopts an in vitro ACE inhibitory activity experiment to evaluate the blood pressure lowering activity of a new compound of cyclopentane-polyhydrophenanthrene tetrahydrofurfuryl furoate A and a known compound of beta-sitosterol which is obtained by simultaneous separation and has a structure similar to that of the new compound. Specific experimental methods and results are as follows.
2.1 preparation of ACE
Washing fresh pig lung with 0.9% NaCl solution in cold condition, washing to remove trachea and fat, cutting into small pieces, removing a certain amount of pig lung tissue, homogenizing with 5 times volume of cold buffer solution containing pH8.3 and 0.1mol/L borate, and leaching the homogenate in refrigerator for 5 hr. Centrifuging at 4 deg.C (8000 rmp) for 15min to obtain crude extractive solution (supernatant). And (5) freeze-drying for later use.
2.2 preparation of test solutions
10mg of sample (new compound or. beta. -sitosterol) was prepared into 5 extract solutions of different concentrations. Adding the solution according to the following sequence, preserving heat at 37 ℃ for 5min, adding 5 mu LACE solution to start reaction, preserving heat at 37 ℃ for 30min, adding 300 mu L of 1mol/LHCl solution to stop reaction, centrifuging at 10000r/min for 10min, and absorbing the supernatant as a test solution.
HHL solution: taking a proper amount of HHL, and adding borate buffer solution to prepare HHL solution with the concentration of 5 mmol/L.
2.3 assay of hippuric acid
Chromatographic conditions are as follows: LC3000-C18Chromatographic column (4.6 mm × 250mm, 5 μm) (Dalianjiang Shen separation science and technology Co.), mobile phase methanol (0.01%) trifluoroacetic acid water, mobile phase gradient (0 min, 60% B; 3min, 60% B; 3.01min, 100% B; 6min, 100% B; 6.01min, 60% B; 8min, 60% B), detection wavelength 228nm, flow rate 1.0mL/min, column temperature 25 deg.C, and sample injection amount 20 μ L.
Hippuric acid control solution: taking a proper amount of hippuric acid, and adding borate buffer solution to prepare hippuric acid reference solution with the concentration of 0.1 mmol/L.
Respectively and precisely absorbing the test solution and the hippuric acid reference solution, injecting the test solution and the hippuric acid reference solution into a high performance liquid chromatograph, recording a chromatogram, and calculating the content of hippuric acid by an external standard one-point method.
2.4 calculation of ACE inhibition
The calculation formula is as follows: r = (A-B)/A × 100%
In the formula, A and B are the peak areas of hippuric acid of a blank control group and a test group respectively.
IC for ACE inhibitory activity50Value representation, IC50Values were calculated using SPSS software.
2.5ACE inhibitory Activity results and conclusions
The experiment obtains the new compound of the tetrahydrofurfuryl acid cyclopentane multi-hydrogen phenanthrene ester A and the known compound of β -sitosterol IC of ACE inhibitory activity50The value is obtained. IC of novel compound tetrahydrofurfuryl acid cyclopentanoperhydrophenanthrene ester A for ACE50= 10. mu.g/mL, and IC for ACE is known for compound β -sitosterol50The experimental result shows that the new compound tetrahydrofurfuryl acid cyclopentanoperhydrophenanthrene ester A has stronger ACE inhibitory activity, and the inhibitory action to ACE is nearly 80 times of that of the known compound β -sitosterol.
Example 2:
taking 200g of northeast impatiens balsamina, cutting into pieces, adding 1L of water, treating at high temperature and high pressure for 2h, and filtering to obtain leaching solution of the northeast impatiens balsamina; taking 500g of sun-dried ginseng, crushing, soaking with the impatiens balsamina extract, steaming at high temperature and high pressure for 6h, taking out, and drying to obtain the high-temperature and high-pressure processed product of impatiens balsamina of ginseng; extracting the product of the obtained impatiens balsamina at high temperature and high pressure with 10L chloroform for 1 time, and evaporating the extractive solution to dryness to obtain chloroform extract; and repeatedly carrying out column chromatography on the obtained chloroform extract by using silica gel as an adsorbent, carrying out gradient elution by using petroleum ether-dichloromethane (20: 1-1: 1), collecting partial eluent of the cyclopentane and phenanthrene ester A tetrahydrofurfuryl furoate, recovering the solvent to obtain a crude product of the cyclopentane and phenanthrene ester A tetrahydrofurfuryl furoate, carrying out silica gel column chromatography, eluting by using petroleum ether-acetone (5: 1) as an eluent, collecting partial eluent of the cyclopentane and phenanthrene ester A tetrahydrofurfuryl furoate, recovering the solvent, and recrystallizing by using petroleum ether-acetone to obtain the cyclopentane and phenanthrene ester A tetrahydrofurfuroate.
Claims (1)
1. An extraction method of tetrahydrofurfuryl and polyhydrophenanthrene furoate A with the chemical name of tetrahydrofuran-2-formic acid 17- (5-ethyl-6-methylhept-2-yl) -10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta [ a ] phenanthrene-3-ester: the method is characterized by comprising the following steps:
(1) processing: taking northeast impatiens balsamina, cutting into pieces, adding 5-10 times of water, treating at high temperature and high pressure for 2-4 h, and filtering to obtain the northeast impatiens balsamina leaching solution; crushing sun-dried ginseng, soaking the sun-dried ginseng in the impatiens balsamina leach liquor, steaming at high temperature and high pressure for 4-8 hours, taking out, and drying to obtain a high-temperature and high-pressure processed product of the impatiens balsamina of ginseng;
(2) extraction: taking the product of the impatiens balsamina in the step (1) after high-temperature and high-pressure treatment, leaching the product with chloroform for 1-3 times, adding 5-10 times of chloroform each time, combining chloroform extracting solutions, and evaporating to dryness to obtain a chloroform extract;
(3) separation: taking the chloroform extract in the step (2), performing column chromatography by taking silica gel as an adsorbent, and performing column chromatography by using petroleum ether-dichloromethane 20: 1-1: 1, gradient elution is carried out, partial eluent of the tetrahydrofurfuryl acid cyclopentane multi-hydrogen phenanthrene ester A is collected, the solvent is recovered, a tetrahydrofurfuryl acid cyclopentane multi-hydrogen phenanthrene ester A crude product is obtained, silica gel column chromatography is carried out, and the weight ratio of petroleum ether-acetone 10: 1, eluting with an eluent, collecting partial eluent of the tetrahydrofurfuryl acid cyclopentane multi-hydrogen phenanthrene ester A, recovering the solvent, and recrystallizing with petroleum ether-acetone to obtain the tetrahydrofurfuryl acid cyclopentane multi-hydrogen phenanthrene ester A;
the high temperature and high pressure in the step (1) are temperature of 110-135 ℃, or pressure of 0.05-0.22 MPa.
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| CN102766184A (en) * | 2012-08-01 | 2012-11-07 | 南通大学 | Protopanoxadiol peroxide derivatives as well as preparation method and application thereof |
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