CN104478982B - The luxuriant and rich with fragrance ester B of furancarboxylic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use - Google Patents

The luxuriant and rich with fragrance ester B of furancarboxylic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use Download PDF

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CN104478982B
CN104478982B CN201410772144.9A CN201410772144A CN104478982B CN 104478982 B CN104478982 B CN 104478982B CN 201410772144 A CN201410772144 A CN 201410772144A CN 104478982 B CN104478982 B CN 104478982B
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chloroform
ester
phenanthrene
furoate
cyclopentane
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CN104478982A (en
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赵岩
张连学
唐国胜
郜玉钢
许永华
张爱华
何忠梅
刘学周
祝洪艳
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Jilin Agricultural University
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Jilin Agricultural University
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    • 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

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Abstract

The present invention relates to a kind of furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester B of many hydrogen and extracting method thereof and its pharmaceutical use.Belong to new compound and pharmaceutical use thereof.With Stem and leaf of Radix Ginseng or stem and leaf of Radix Panacis Quinquefolii and mushroom for raw material, through pulverizing, high temperature high pressure process, drying, chloroform extraction, silica gel column chromatography, recrystallization method, obtain furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester B of many hydrogen, its chemical name is: furans-2-formic acid (3S, 10R, 13R)-10,13-dimethyl-17-((2R, E)-5,6-dimethyl-g-3-alkene-2-base)-2,3,4,9,10,11,12,13,14,15,16,17-ten dihydro-1H-ring penta [a] phenanthrene-3-ester.The application of the luxuriant and rich with fragrance ester B of furancarboxylic acid pentamethylene many hydrogen in the hypertensive medicine of preparation treatment.

Description

Cyclopentahydrophenanthrene furoate B, and extraction method and pharmaceutical application thereof
Technical Field
The invention relates to a furoic acid cyclopentane multi-hydrogen phenanthrene ester B, an extraction method and a pharmaceutical application thereof. Belongs to a new compound and the pharmaceutical application thereof.
Background
Ginseng radixPanaxgisengC.A.Mey., American ginsengPanaxquinquefoliumL. are all (A) of AraliaceaeAraliaceae) Ginseng of the genus (Panax) A plant. 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.
Mushroom (Lentinus edodes)Lentinusedodes(Berk.) sing, also known as flower mushroom, Lentinus edodes, and Balanophora latifolia, is the fruit body of Lentinus edodes of the family Pleurotaceae. The mushroom is the second edible mushroom in the world and is also ChinaOne of the specialty products is called mountain delicacies in folk. It is a fungus that grows on wood. Has delicious taste, pleasant fragrance and rich nutrition. The shiitake mushroom is rich in vitamin B group, ferrum, potassium, provitamin D (converted into vitamin D after being sun-cured), sweet in taste and neutral in nature. It can be used for treating anorexia, hypoqi, and asthenia.
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 and American ginseng processed products, the research and development process finds that products obtained by processing ginseng stems and leaves or American ginseng stems and leaves and mushrooms together (at high temperature and high pressure) 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: furan-2-carboxylic acid (3S,10R,13R) -10, 13-dimethyl-17- ((2R, E) -5,6-dimethylhept-3-en-2-yl) -2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [ a ] a]Phenanthrene-3-ester [ (3S,10R,13R) -17- ((2R, E) -5,6-dimethylhept-3-en-2-yl) -10, 13-dimethylol-2, 3,4,9,10,11,12,13,14,15,16, 17-dodecahydro-1H-cycleopenta[a]phenanthren-3-ylfuran-2-carboxylate]Called as furoic acid cyclopentane multi-hydrogen phenanthrene ester B for short, and the half inhibition rate (IC) of the compound to ACE is determined50) 30.5. mu.g/mL was reached. And further analyzing the source of the furoic acid cyclopentane multi-hydrogen phenanthrene ester B, wherein the compound is not detected in ginseng stem leaves, American ginseng stem leaves, shiitake mushrooms, high-temperature and high-pressure processed products of ginseng stem leaves, American ginseng stem leaves and high-temperature and high-pressure processed products of shiitake mushrooms, and the compound is generated after the ginseng stem leaves or American ginseng stem leaves and shiitake mushrooms are processed at high temperature and high pressure. The furoic acid cyclopentane multi-hydrogen phenanthrene ester B is expected to become a new medicine for reducing blood pressure.
Disclosure of Invention
The invention provides a furoic acid cyclopentane multi-hydrogen phenanthrene ester B, an extraction method and a pharmaceutical application thereof.
A cyclopentanoperhydrophenanthrene furoate B of formula:
furan-2-carboxylic acid (3S,10R,13R) -10, 13-dimethyl-17- ((2R, E) -5,6-dimethylhept-3-en-2-yl) -2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [ a ] phenanthren-3-yl [ (3S,10R,13R) -17- ((2R, E) -5, 6-dimethylhep-3-en-2-yl) -10, 13-dimethylene-2, 3,4,9,10,11,12,13,14,15,16, 17-dodecahydro-1H-cyclopentha [ a ] phenoanthen-3-furanyl-2-carboxylate ]
The invention also aims to prepare a new substance with stronger biological activity by using ginseng stem leaves or American ginseng stem leaves and shiitake mushroom as raw materials and carrying out crushing, high-temperature and high-pressure treatment, drying, chloroform extraction, silica gel column chromatography and recrystallization methods.
In order to achieve the above object, the following processes are required:
(1) processing: taking 1 part of ginseng stem leaves or American ginseng stem leaves and 2-5 parts of shiitake mushrooms, shearing into pieces, adding 1 time of water, carrying out high-temperature and high-pressure treatment for 4-8 hours, and filtering to obtain filtrate and dregs respectively;
(2) extraction: extracting the filtrate obtained in the step (1) with chloroform for 1-3 times, adding equal volume of chloroform each time, and combining chloroform extracts; extracting the residue obtained in the step (1) with chloroform for 1-3 times, adding 5-10 times of chloroform each time, and combining chloroform extracting solutions; mixing the chloroform extractive solution and chloroform extractive solution, and recovering solvent to obtain chloroform extract;
(3) separation: and (3) taking the chloroform extract obtained in the step (2), performing repeated column chromatography by taking silica gel as an adsorbent, performing gradient elution by using petroleum ether-dichloromethane (20: 1-1: 1), collecting the eluent of the part B of the cyclopentane-polyhydrophenanthrene furoate, recovering the solvent to obtain a crude product of the cyclopentane-polyhydrophenanthrene furoate B, and recrystallizing by using petroleum ether-acetone to obtain the cyclopentane-polyhydrophenanthrene furoate B.
The invention relates to application of furoic acid cyclopentane multi-hydrogen phenanthrene ester B 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 furoic acid cyclopentane multi-hydrogen phenanthrene ester B can be used for preparing the antihypertensive drug, has the characteristic of obvious curative effect and can inhibit IC of ACE50Can reach 30.5 mu g/mL.
Detailed Description
Example 1:
collecting 100g of ginseng stem leaves and 200g of shiitake mushrooms, cutting into pieces, adding 300mL of water, performing high-temperature and high-pressure treatment for 8h, and filtering to obtain filtrate and dregs respectively; extracting the above filtrate with chloroform for 3 times, adding 300mL of chloroform each time, and mixing chloroform extracts; extracting the above residue with chloroform for 3 times, adding 300mL of chloroform each time, and mixing chloroform extractive solutions; mixing the chloroform extractive solution and chloroform extractive solution, and recovering solvent to obtain chloroform extract; and (2) taking the chloroform extract, performing repeated column chromatography by taking silica gel as an adsorbent, performing gradient elution by using petroleum ether-acetone (50: 1-1: 1), collecting the eluent of the part B of the cyclopentane and polyhydrophenanthrene furoate, recovering the solvent to obtain a crude product of the cyclopentane and polyhydrophenanthrene furoate B, and recrystallizing by using petroleum ether-acetone to obtain the cyclopentane and polyhydrophenanthrene furoate B.
1. And (3) structural identification:
MS: the peak of molecular ion is 490.3 by mass spectrum measurement, and the binding IR,1HNMR、13CNMR determines the molecular formula as C33H46O3。
IR spectrum: 3081cm-1Is a double-bond hydrocarbon stretching vibration peak (upsilon)CH），2988-2873cm-1Stretching vibration peak (upsilon) of carbon-hydrogen bond of saturated alkaneCH) Proving saturated alkanyl radicalsThe presence of a cluster; 1728cm-1Is a stretching vibration peak (. nu.) of carbonylC=O) Indicating the presence of a carbonyl group in the compound; 1709cm-1Is upsilonC=CIndicating the presence of a carbon-carbon double bond; 1381cm-1、1370cm-1Deformation vibration peak of methyl group ( CH3）。
1HNMR(300MHz,CDCl3)ppm：7.504(dd,1H,J=0.9,1.8Hz) is the alkene hydrogen signal at position 5 of furan-2-carboxylic acid group, 7.111(dd,1H,J=0.9,3.6Hz) is the alkene hydrogen signal at position 3 of furan-2-carboxylic acid group, 6.441: (dd,1H,J=1.8,3.6Hz) are alkene hydrogen signals at the 4-position of the furan-2-carboxylic acid group, and together form the furan-2-carboxylic acid group; 5.542(d,1H,J=5.7Hz)、5.334(d,1H,J=5.7Hz)、5.151(dd,1H,J=4.2,7.2Hz)、5.137(dd,1H,J=4.2,7.2Hz) signals for olefinic hydrogen at 6, 7, 3 ', 4' positions of steroid parent nucleus, 4.883: (m1H) is the steroid nucleus 3-position oxygen-linked carbon hydrogen signal, 0.982: (d,3H,J=6.6Hz)、0.916(s,3H)、0.860(d,3H,J=6.9Hz)、0.781(d,3H,J=6.9Hz)、0.766(d,3H,J=6.9Hz)、0.565(sAnd 3H) are signals of 6 methyl hydrogens on the steroid parent nucleus and the 17-site side chain, and 2.588-0.479 are signals of hydrogen on other saturated carbons of the steroid parent nucleus and the 17-site side chain, and the data indicate the existence of a steroid structure and furoic acid.
13CNMR(75MHz,CDCl3) The carbon spectrum data shows 33 carbon signals, specifically, 157.18 is carbonyl carbon signal, 145.07, 144.06, 116.68 and 110.74 together form furan-2-carboxylic acid group, 137.28, 119.38, 115.28, 140.60, 134.54 and 130.96 are steroid mother nucleus C5, C6, C7, C8, C3 'and C4' unsaturated carbon signal, 72.53 is oxygen-linked carbon signal at position 3 of steroid mother nucleus, 54.69, 53.50, 45.02 and 41.80 (× 2), 39.42, 38.00, 36.90, 36.10, 35.67, 32.07, 27.26, 27.15, 21.97, 20.09, 20.01, 18.93, 18.63, 16.59, 15.16 and 11.04 are steroid mother nucleus and other saturated carbon signals at position 17.
Bonding of1HNMR、13CNMR and IFurther analysis of the R spectrum comprehensively determines that the compound is furan-2-carboxylic acid (3S,10R,13R) -10, 13-dimethyl-17- ((2R, E) -5,6-dimethyl hept-3-en-2-yl) -2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [ a ] a]Phenanthrene-3-ester [ (3S,10R,13R) -17- ((2R, E) -5,6-dimethylhept-3-en-2-yl) -10, 13-dimethylol-2, 3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [ a ] a]phenanthren-3-ylfuran-2-carboxylate]The furoic acid cyclopentane multi-hydrogen phenanthrene ester B is short, and the compound is a novel compound which is not reported in documents through literature search. The specific NMR signals for this compound are assigned as follows:
1HNMR(300MHz,CDCl3)ppm：7.504(dd,1H,J=0.9,1.8Hz,5’’-H)，7.111(dd,1H,J=0.9,3.6Hz,3’’-H)，6.441(dd,1H,J=1.8,3.6Hz,4’’-H)，5.542(d,1H,J=5.7Hz,6-H)、5.334(d,1H,J=5.7Hz,7-H)、5.151(dd,1H,J=4.2,7.2Hz,3’-H)、5.137(dd,1H,J=4.2,7.2Hz,4’-H)，4.883(m,1H,3-H)，0.982(d,3H,J=6.6Hz,2’-CH3)、0.916(s,3H,10-CH3)、0.860(d,3H,J=6.9Hz,5’-CH3)、0.781(d,3H,J=6.9Hz,6’-CH3)、0.766(d,3H,J=6.9Hz,7’-H)、0.565(s,3H,13-CH3) 2.588-0.479 is the signal of hydrogen on steroid parent nucleus and 17-position side chain other saturated carbon.
13CNMR(75MHz,CDCl3)ppm：157.18(C=O)、145.07(C5’’)、144.06(C2’’)、140.60(C8)、137.28(C5)、134.54(C3’)、130.96(C4’)、119.38(C6)、116.68(C3’’)、115.28(C7)、110.74(C4’’)、72.53(C3)、54.69(C17)、53.50(C14)、45.02(C9)、41.80(C13,5’)、39.42(C2’)、38.00(C12)、36.90(C1)、36.10(C4)、35.67(C10)、32.07(C6’)、27.26(C2)、27.15(C16)、21.97(C15)、20.09(C11)、20.01(C7’)、18.93(6’-CH3)、18.63(C1’)、16.59(5’-CH3)、15.16(10-CH3)、11.04(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 antihypertensive activity of a new compound, namely cyclopentane-phenanthrene furoate B and a known compound, namely ergosterol, 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 ergosterol) was prepared as 5 different concentration extract solutions. 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-C18Chromatography column (4.6 mm × 250mm, 5 μm) (dajongshen separation science and technology), mobile phase methanol:trifluoroacetic acid water (0.01%), 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 of 228nm, flow rate of 1.0mL/min, column temperature of 25 deg.C, sample injection amount of 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 above experiment is adopted to obtain the new compound of furoic acid cyclopentane multi-hydrogen phenanthrene ester B and the known compound of ergosterol IC for ACE inhibitory activity50The value is obtained. IC of novel compound furoic acid cyclopentane multi-hydrogen phenanthrene ester B to ACE50= 30.5. mu.g/mL, IC for ACE of the known compound ergosterol50=892 μ g/mL. Experimental results show that the novel compound furoic acid cyclopentane multi-hydrogen phenanthrene ester B has stronger ACE inhibitory activity, and the inhibitory effect on ACE is nearly 30 times of that of the known compound ergosterol. The new compound furoic acid cyclopentane multi-hydrogen phenanthrene ester B is expected to become a new blood pressure lowering medicine.
Example 2:
taking 100g of American ginseng stem leaves and 400g of lentinus edodes, cutting into pieces, adding 500mL of water, treating at high temperature and high pressure for 6h, and filtering to respectively obtain filtrate and dregs; extracting the filtrate with 500mL of chloroform for 1 time to obtain chloroform extract; extracting the above residue with 500mL chloroform for 1 time to obtain chloroform extractive solution; mixing the chloroform extractive solution and chloroform extractive solution, and recovering solvent to obtain chloroform extract; and (2) taking the chloroform extract, performing repeated column chromatography by taking silica gel as an adsorbent, performing gradient elution by using petroleum ether-acetone (50: 1-1: 1), collecting the eluent of the part B of the cyclopentane and polyhydrophenanthrene furoate, recovering the solvent to obtain a crude product of the cyclopentane and polyhydrophenanthrene furoate B, and recrystallizing by using petroleum ether-acetone to obtain the cyclopentane and polyhydrophenanthrene furoate B.

Claims (1)

1. A process for the extraction of cyclopentanoperhydrophenanthrene furoate ester B, having the chemical name furan-2-carboxylic acid (3S,10R,13R) -10, 13-dimethyl-17- ((2R, E) -5,6-dimethylhept-3-en-2-yl) -2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta [ a ] phenanthrene-3-ester, characterized in that it comprises the following steps:
(1) processing: taking 1 part of ginseng stem leaves or American ginseng stem leaves and 2-5 parts of shiitake mushrooms, shearing into pieces, adding 1 time of water, carrying out high-temperature and high-pressure treatment for 4-8 hours, and filtering to obtain filtrate and dregs respectively;
(2) extraction: extracting the filtrate obtained in the step (1) with chloroform for 1-3 times, adding equal volume of chloroform each time, and combining chloroform extracts; extracting the residue obtained in the step (1) with chloroform for 1-3 times, adding 5-10 times of chloroform each time, and combining chloroform extracting solutions; mixing the chloroform extractive solution and chloroform extractive solution, and recovering solvent to obtain chloroform extract;
(3) separation: taking the chloroform extract in the step (2), performing repeated column chromatography by taking silica gel as an adsorbent, and performing repeated column chromatography by using petroleum ether-dichloromethane 20: 1-1: 1, performing gradient elution, collecting partial eluent of the cyclopentane-phenanthrene furoate B, recovering the solvent to obtain a crude product of the cyclopentane-phenanthrene furoate B, and recrystallizing with petroleum ether-acetone to obtain the cyclopentane-phenanthrene furoate B;
the high temperature and high pressure in the step (1) are temperature of 110-135 ℃, or pressure of 0.05-0.22 MPa.
CN201410772144.9A 2014-12-16 2014-12-16 The luxuriant and rich with fragrance ester B of furancarboxylic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use Expired - Fee Related CN104478982B (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1370179A (en) * 1999-06-21 2002-09-18 福布斯医药技术股份有限公司 Aromatic and heterocyclic derivatives of phytosterols and/or phytosanols for use in treating or preventing cardiovascular disease
CN102766184A (en) * 2012-08-01 2012-11-07 南通大学 Protopanoxadiol peroxide derivatives as well as preparation method and application thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1370179A (en) * 1999-06-21 2002-09-18 福布斯医药技术股份有限公司 Aromatic and heterocyclic derivatives of phytosterols and/or phytosanols for use in treating or preventing cardiovascular disease
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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