CN104402960A - 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]phenanthren-3-yl furan-3-carboxylate and extraction method and medicine application thereof - Google Patents

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]phenanthren-3-yl furan-3-carboxylate and extraction method and medicine application thereof Download PDF

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CN104402960A
CN104402960A CN201410772137.9A CN201410772137A CN104402960A CN 104402960 A CN104402960 A CN 104402960A CN 201410772137 A CN201410772137 A CN 201410772137A CN 104402960 A CN104402960 A CN 104402960A
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luxuriant
rich
chloroform
furancarboxylic acid
many hydrogen
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赵岩
张连学
唐国胜
郜玉钢
许永华
蔡恩博
刘双利
杨鹤
刘学周
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Jilin Agricultural University
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    • 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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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin

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Abstract

The invention relates to 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]phenanthren-3-yl furan-3-carboxylate as well as an extraction method and medicine application thereof, and belongs to a new compound and medicine application thereof. Ginseng stem and leaves and artemisias tolonifera are taken as raw materials and are subjected to pulverization, high temperature high pressure treatment, drying, chloroform extraction, silica-gel column chromatography and recrystallization, and then the 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]phenanthren-3-yl furan-3-carboxylate is obtained. The 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]phenanthren-3-yl furan-3-carboxylate is applied to preparation of medicines for treating the hypertension.

Description

The luxuriant and rich with fragrance ester A of furancarboxylic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use
Technical field
The present invention relates to a kind of furancarboxylic 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.
Background technology
Ginseng panax gisengc.A.Mey. be araliaceae ginseng plant.Wherein, panaxthe implication of Greek is " panacea ", and the full language pronunciation of ginseng is " Ao Er is thick to be reached ", is the meaning of " kings of hundred grass ".As traditional medicine, there is the history of thousands of years, in countries in the world widespread use.Ginseng reinforces vital energy, and multiple arteries and veins takes off admittedly, reinforces the spleen to benefit the lung, promotes the production of body fluid, calm the nerves.
Wide leaf mountain wormwood artemisia ( artemisias tolonifera), another name temmoku wormwood artemisia, for composite family artemisia ( artemisia) per nnial herb.Stem is upright, hollow, and leaf is green, and be distributed widely in the provinces and regions such as China northeast, North China, East China, southwest, in addition, also there is distribution Korea, Japan and the Far East Area.In Korea S, wide leaf mountain wormwood artemisia is often used as diuretic(s), febrifuge, and treatment eye disease.Its chemical composition comprises volatile oil, terpene, flavonoid, coumarins, chromogen ketone etc.
Hypertension increases clinical syndrome for main manifestations with systemic arterial pressure, is modal cardiovascular disorder.The pathogenic factors of essential hypertension mainly contains two large classes, and a class is internal cause, as heredity; Another kind of is external cause, as nervous, salt too much, smoking, obesity, excessive drinking, shortage motion etc.Long-term hypertension can have influence on the function of the organs such as the heart, brain, kidney, finally causes the exhaustion of these organ dysfunctions.Hypertension belongs to frequently-occurring disease, the eighties in last century, and Chinese Hypertension incidence is 7.7%; To the beginning of this century, rise to 18.8% rapidly; And nearly 10 years, hypertensive morbidity increases 31%.At present, China hypertensive patient estimates more than 200,000,000, and this trend still can continue continuity, unlikely occurs reversing in short duration.If or else controlled, will 50% be increased in 15 from now on year.Antihypertensive drugs kind mainly comprises hydragog(ue), beta-blockers, calcium channel blocker, angiotensin converting enzyme inhibitor, angiotensin-ii receptor retarding agent.These medicines have certain side effect, as Cardiac depression, metabolic disturbance, kidney damage etc.And the Altace Ramipril with China's independent intellectual property right is less.
Seminar is in processing of Panax ginseng Chemical Agent Research and Development process, find that the product after Stem and leaf of Radix Ginseng and the common processing treatment of wide leaf mountain wormwood artemisia (High Temperature High Pressure) has stronger angiotensin-converting enzyme (ACE) restraining effect, carry out activeconstituents tracking further, separation obtains a new compound, its chemical name is: furans-3-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 [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] phenanthren-3-yl furan-3-carboxylate], be called for short furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen, this compound is to the half inhibiting rate (IC of ACE after measured 50) reach 38 μ g/mL.The source of the luxuriant and rich with fragrance ester A of further analysis furancarboxylic acid pentamethylene many hydrogen, this compound is all undetected in Stem and leaf of Radix Ginseng, wide leaf mountain wormwood artemisia, Stem and leaf of Radix Ginseng high temperature high pressure process product, wide leaf mountain wormwood artemisia high temperature high pressure process product, illustrates that this compound is Stem and leaf of Radix Ginseng, wide leaf mountain wormwood artemisia prescription producing after high temperature high pressure process.The luxuriant and rich with fragrance ester A of furancarboxylic acid pentamethylene many hydrogen is expected to become new Altace Ramipril.
Summary of the invention
The invention provides a kind of furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen and extracting method thereof and its pharmaceutical use.
A kind of as shown in the formula furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen:
Furans-3-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 [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] phenanthren-3-yl furan-3-carboxylate]
The present invention also aims to utilize Stem and leaf of Radix Ginseng and wide leaf mountain wormwood artemisia to be raw material, through pulverizing, high temperature high pressure process, drying, chloroform extraction, silica gel column chromatography, recrystallization method, prepare a kind of novel substance had compared with strong biological activity.
For achieving the above object, need following technique to realize:
(1) process: get Stem and leaf of Radix Ginseng 2 ~ 5 parts and wide leaf mountain wormwood artemisia 1 part, shred, add 1 times of water gaging, high temperature high pressure process 4 ~ 8h, filter, obtain filtrate and the dregs of a decoction respectively;
(2) extract: get the filtrate in step (1), with chloroform extraction 1 ~ 3 time, add isopyknic chloroform, combined chloroform extraction liquid at every turn; Separately get the dregs of a decoction in step (1), with chloroform lixiviate 1 ~ 3 time, add 5 ~ 10 times amount chloroforms, combined chloroform extracting solution at every turn; Merge above-mentioned chloroform extraction liquid and chloroform extracted solution, recycling design, obtains chloroform extract;
(3) be separated: get the chloroform extract in step (2), be that sorbent material carries out column chromatography repeatedly with silica gel, gradient elution is carried out with sherwood oil-methylene dichloride (20:1 ~ 1:1), collect furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester part A elutriant, recycling design, obtain furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester A crude product, with sherwood oil-acetone recrystallization, obtain furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen.
The application of the luxuriant and rich with fragrance ester A of furancarboxylic acid pentamethylene of the present invention many hydrogen in the hypertensive medicine of preparation treatment.
When the present invention is for the preparation of the hypertensive medicine for the treatment of, its oral or parenteral admin is all safe.In oral situation, it can any conventionally form administration, as powder, granula, tablet, capsule, pill, solution, suspension, syrup, buccal tablets, sublingual lozenge etc.; When this drugs for parenteral delivery, any conventionally form can be taked, such as intravenous injection agent, ointment, suppository and inhalation etc.
It is form together with vehicle by effective constituent monomer or effective constituent and solid or liquid that the present invention prepares the hypertensive medicine for the treatment of, the vehicle of solid used herein or liquid is well known in the art, lift several object lesson below, powder is powder agent for oral administration, its vehicle has lactose, starch, paste essence, calcium carbonate, synthesis or puritan filler aluminium, magnesium oxide, Magnesium Stearate, sodium bicarbonate, dry yeast etc.; The vehicle of solution has water, glycerine, 1,2-propylene glycol, simple syrup, ethanol, ethylene glycol, polyoxyethylene glycol, Sorbitol Powder etc.; The vehicle of ointment can use fatty oil, hydrous wool, Vaseline, glycerine, honeybee is cured, wood is cured, white oil, resin, the senior hydrophobizing agent that is combined into such as cured or hydrophilizing agent.
Beneficial effect of the present invention is, the luxuriant and rich with fragrance ester A of new compound furancarboxylic acid pentamethylene many hydrogen can be used for preparing Altace Ramipril, has feature evident in efficacy, its IC suppressed ACE 5038 μ g/mL can be reached.
Embodiment
embodiment 1:
Get Stem and leaf of Radix Ginseng 200g and wide leaf mountain wormwood artemisia 100g, shred, add 300mL water, high temperature high pressure process 8h, filter, obtain filtrate and the dregs of a decoction respectively; Get above-mentioned filtrate, with chloroform extraction 3 times, add 300mL chloroform, combined chloroform extraction liquid at every turn; Separately get the above-mentioned dregs of a decoction, with chloroform lixiviate 3 times, add 300mL chloroform, combined chloroform extracting solution at every turn; Merge above-mentioned chloroform extraction liquid and chloroform extracted solution, recycling design, obtains chloroform extract; Get above-mentioned chloroform extract, be that sorbent material carries out column chromatography repeatedly with silica gel, gradient elution is carried out with sherwood oil-acetone (50:1 ~ 1:1), collect furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester part A elutriant, recycling design, obtain furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester A crude product, with sherwood oil-acetone recrystallization, obtain furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen.
1. Structural Identification:
MS: its molecular ion peak of mass spectroscopy is 508.2, in conjunction with IR, 1h NMR, 13c NMR determines that its molecular formula is C 34h 52o 3.
IR spectrum: 3082 cm -1for the hydrocarbon stretching vibration peak (υ of double bond in furans-3-formic acid group cH), 2952-2884 cm -1for the stretching vibration peak (υ of saturated alkane C-H bond cH), prove the existence of saturated alkane group; 1726 cm -1for the stretching vibration peak (υ of carbonyl c=O), illustrate in this compound to there is carbonyl; 1707 cm -1for υ c=C, the existence of carbon-carbon double bond is described; 1383 cm -1, 1371 cm -1for methyl formation vibration peak ( δ cH3).
1h NMR (300 MHz, CDCl 3) δ ppm:7.491 ( s, 1H) and be furans-3-formic acid group 2 alkene hydrogen signals, 7.097 ( d, 1H, j=3.6Hz) be furans-3-formic acid group 4 alkene hydrogen signals, 6.428 ( d, 1H, j=3.6Hz) be furans-3-formic acid group 5 alkene hydrogen signals, 5.344 ( d, 1H, j=4.5Hz) be steroidal parent nucleus 6 alkene hydrogen signals, 4.808 ( m, 1H) and be hydrogen signal on steroidal parent nucleus 3 even oxygen carbon, 0.980 ( s, 3H), 0.864 ( d, 3H), 0.798 ( t, 3H), 0.753 ( d, 6H), 0.613 ( s, 3H) and be 6 methyl hydrogen signals on steroidal parent nucleus and 17 side chains, 2.386 ~ 0.692 is hydrogen signal in steroidal parent nucleus and 17 other saturated carbon of side chain, the existence of above data declaration steroidal structure and furancarboxylic acid.
13c NMR (75 MHz, CDCl 3) δ ppm: carbon modal data provides 34 carbon signals altogether, specific as follows.157.13 is carbonyl carbon signals, and 144.95,138.49,116.50,110.65 together constitute furans-3-formic acid group; 138.66,121.86 is steroidal parent nucleus C5, C6 unsaturated carbon signal, 73.68 is steroidal parent nucleus 3 even oxygen carbon signal, 55.70,55.09,49.08,44.89,41.33,38.75,37.16,36.01,35.62,35.14,32.98,30.89(× 2), 28.24,27.21,26.84,25.21,23.28,22.11,20.05,18.77,18.31,18.05,17.78,10.97,10.84 be the saturated carbon signal of steroidal parent nucleus and 17 side chains and furans-3-formic acid group two methynes.
In conjunction with 1h NMR, 13c NMR and IR spectrum are comprehensively analyzed further and are determined that this compound is furans-3-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 [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] phenanthren-3-yl furan-3-carboxylate], be called for short furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen, by literature search, this compound is the new compound having no bibliographical information.The concrete NMR signals assignment of this compound is as follows:
1h NMR (300 MHz, CDCl 3) δ ppm:7.491 ( s, 1H, 2 ' ' and-H), 7.097 ( d, 1H, j=3.6Hz, 4 ' '-H), 6.428 ( d, 1H, j=3.6Hz, 5 ' '-H), 5.344 ( d, 1H, j=4.5Hz, 6-H), 4.808 ( m, 1H, 3-H), 0.980 ( s, 3H, 10-CH 3), 0.864 ( d, 3H, 2 '-CH 3), 0.798 ( t, 3H, 5 '-CH 3), 0.753 ( d, 6 ', 6 '-CH 3), 0.613 ( s, 3H, 13-CH 3) be 6 methyl hydrogen signals on steroidal parent nucleus and 17 side chains, 2.386 ~ 0.692 is hydrogen signal in steroidal parent nucleus and 17 other saturated carbon of side chain.
13C NMR (75 MHz, CDCl 3) δppm：157.13 (C=O)、144.95 (C5’’)、138.66 (C5)、138.49 (C2’’)、121.86 (C6)、116.50 (C3’’)、110.65 (C4’’)、73.68 (C3)、55.70 (C14)、55.09 (C17)、49.08 (C9)、44.89 (C5’)、41.33 (C13)、38.75 (C12)、37.16 (C4)、36.01 (C1)、35.62 (C10)、35.14 (C2’)、32.98 (C3’)、30.89 (C7,8)、28.24 (C6’)、27.21 (C2)、26.84 (C4’)、25.21 (C15)、23.28 (C16)、22.11 (5’-CH 2)、20.05 (C11)、18.77 (C7’)、18.31 (6’-CH 3)、18.05 (C1’)、17.78 (10-CH 3)、10.97 (5’-CH 3)、10.84 (13-CH 3)。
2.ACEI inhibit activities is tested
Renin-angiotensin-aldosterone system (RAS) plays an important role in hypertension generation, development, and its angiotensin I is main effector peptide.ACEI suppresses angiotensinⅠ to be converted to angiotensinⅡ, not deactivation bradykinin, produces pressure reduction effect.This experiment adopt external ACE inhibitory activity experimental evaluation new compound furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen and being simultaneously separated obtain, with this new compound structure similar, the hypotensive activity of a known compound β-sitosterol.Specific experiment method and result as follows.
The preparation of 2.1 ACE
Fresh pig lung is met cold 0.9%NaCL solution rinse well, wash away tracheae, fat, be cut into small pieces, go a certain amount of pig lung tissue, carrying out homogenate with meeting cold PH 8.3, the 0.1 mol/L borate buffer solution 5 times of volumes that contain, homogenate being placed in refrigerator lixiviate 5 hours.Centrifugal at 4 DEG C (8000rmp) centrifugal 15 min, obtain crude extract (supernatant liquor).Lyophilize is stand-by.
The preparation of 2.2 need testing solutions
Get the extract solution that 10mg sample (new compound or β-sitosterol) is mixed with 5 different concns.According to the form below order adds solution, after 37 DEG C of insulation 5 min, add 5 μ L ACE solution and start reaction, after 37 DEG C of insulation 30 min, add 1 mol/L HCl solution 300 μ L termination reaction, centrifugal 10 min of 10 000 r/min, draw supernatant as need testing solution.
HHL solution: get appropriate HHL, adds borate buffer solution and is mixed with the HHL solution that concentration is 5 mmol/L.
2.3 urobenzoic acid assays
Chromatographic condition: LC 3000-C 18chromatographic column (4.6 mm × 250 mm, 5 μm) (Shen, large Liaanjiang county separation science technology company), mobile phase methanol: trifluoroacetic acid water (0.01%), eluent gradient is (0 min, 60 %B; 3 min, 60%B; 3.01 min, 100%B; 6 min, 100%B; 6.01 min, 60%B; 8 min, 60%B), determined wavelength 228 nm, flow velocity 1.0 mL/min, column temperature 25 DEG C, sample size 20 μ L.
Urobenzoic acid contrast liquid: get urobenzoic acid appropriate, add borate buffer solution and be mixed with the urobenzoic acid reference substance solution that concentration is 0.1 mmol/L.
Accurate absorption need testing solution and urobenzoic acid reference substance solution inject high performance liquid chromatograph respectively, and record color atlas, calculates the content of urobenzoic acid by one point external standard method.
The calculating of 2.4 ACE inhibiting rates
Calculation formula is as follows: R=(A-B)/A × 100%
In formula, A and B is respectively the peak area of blank group and test group urobenzoic acid.
To ACE inhibitory activity IC 50value represents, IC 50value adopts SPSS computed in software to obtain.
2.5 ACE inhibit activities result and conclusions
Adopt above experiment to obtain new compound furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A and known compound β-sitosterol of many hydrogen to the IC of ACE inhibitory activity 50value.The luxuriant and rich with fragrance ester A of new compound furancarboxylic acid pentamethylene many hydrogen is to the IC of ACE 50=38 μ g/mL, and known compound β-sitosterol is to the IC of ACE 50=771 μ g/mL.Experimental result shows new compound furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen has stronger ACE inhibitory activity, and it is more than 20 times of known compound β-sitosterol to the restraining effect of ACE.The luxuriant and rich with fragrance ester A of this new compound furancarboxylic acid pentamethylene many hydrogen becomes new Altace Ramipril by being expected to.
embodiment 2:
Get Stem and leaf of Radix Ginseng 400g and wide leaf mountain wormwood artemisia 100g, shred, add 500mL water, high temperature high pressure process 6h, filter, obtain filtrate and the dregs of a decoction respectively; Get above-mentioned filtrate, with 500mL chloroform extraction 1 time, obtain chloroform extraction liquid; Separately get the above-mentioned dregs of a decoction, with 500mL chloroform lixiviate 1 time, obtain chloroform extracted solution; Merge above-mentioned chloroform extraction liquid and chloroform extracted solution, recycling design, obtains chloroform extract; Get above-mentioned chloroform extract, be that sorbent material carries out column chromatography repeatedly with silica gel, gradient elution is carried out with sherwood oil-acetone (50:1 ~ 1:1), collect furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester part A elutriant, recycling design, obtain furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester A crude product, with sherwood oil-acetone recrystallization, obtain furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen.

Claims (3)

1. one kind as shown in the formula furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen:
Its chemical name is furans-3-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.
2. the extracting method of the luxuriant and rich with fragrance ester A of a furancarboxylic acid pentamethylene as claimed in claim 1 many hydrogen: it is characterized in that comprising the following steps:
(1) process: get Stem and leaf of Radix Ginseng 2 ~ 5 parts and wide leaf mountain wormwood artemisia 1 part, shred, add 1 times of water gaging, high temperature high pressure process 4 ~ 8h, filter, obtain filtrate and the dregs of a decoction respectively;
(2) extract: get the filtrate in step (1), with chloroform extraction 1 ~ 3 time, add isopyknic chloroform, combined chloroform extraction liquid at every turn; Separately get the dregs of a decoction in step (1), with chloroform lixiviate 1 ~ 3 time, add 5 ~ 10 times amount chloroforms, combined chloroform extracting solution at every turn; Merge above-mentioned chloroform extraction liquid and chloroform extracted solution, recycling design, obtains chloroform extract;
(3) be separated: get the chloroform extract in step (2), be that sorbent material carries out column chromatography repeatedly with silica gel, gradient elution is carried out with sherwood oil-methylene dichloride (20:1 ~ 1:1), collect furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester part A elutriant, recycling design, obtain furancarboxylic acid pentamethylene and many hydrogen luxuriant and rich with fragrance ester A crude product, with sherwood oil-acetone recrystallization, obtain furancarboxylic acid pentamethylene and the luxuriant and rich with fragrance ester A of many hydrogen;
High Temperature High Pressure described in step (1) refers to temperature 110 ~ 135 DEG C, or pressure 0.05 ~ 0.22MPa.
3. furancarboxylic acid pentamethylene as claimed in claim 1 the application of the luxuriant and rich with fragrance ester A of many hydrogen in the hypertensive medicine of preparation treatment.
CN201410772137.9A 2014-12-16 2014-12-16 The luxuriant and rich with fragrance ester A of furancarboxylic acid pentamethylene many hydrogen and extracting method thereof and pharmaceutical use Expired - Fee Related CN104402960B (en)

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CN106565641B (en) * 2016-11-14 2019-04-02 中国科学院昆明植物研究所 Furans Ladanum alkane forskolin and its pharmaceutical composition and its application in pharmacy
EP3852765A4 (en) * 2018-09-19 2022-06-22 ModernaTX, Inc. Sterol purification

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