CN101347418A - Use of 8-0-4'type lignan in preparing anticomplement medicament - Google Patents
Use of 8-0-4'type lignan in preparing anticomplement medicament Download PDFInfo
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Abstract
The invention belongs to the field of Chinese traditional medicines and relates to a new use of 8-0-4' lignan in preparing an anti-complement medicine. The compound 8-0-4' lignan is extracted from a Chinese medicinal herb eucommia bark, and in vitro experiments prove that the compound 8-0-4' lignan can inhibit cell hemolysis caused by the activations of classical and alternative pathways of a complement system, and has obvious inhibitory action on the activation of the classical and alternative pathways of the complement system; and the results of pharmacological tests prove that the compound 8-0-4' lignan has obvious anti-complement effect and low effective concentration. The compound 8-0-4' lignan of the invention can be further taken as an active ingredient for preparing a novel anti-complement medicine.
Description
Technical field
The invention belongs to the field of Chinese medicines, relate to the new pharmaceutical usage of 8-O-4 ' type lignanoid, be specifically related to the purposes of 8-O-4 ' type lignanoid in the preparation anticomplement medicament.
Background technology
Complement system is one of immune defense system of wanting of body weight for humans.The normal activation of complement system is being eliminated external microorganism, is being removed damage in the human body or dead cell and tissue and keep in the balance of body and play an important role.Yet the improper activation of complement system can cause human immune system's overreaction, causes the damage and the inflammatory reaction of human body self normal structure, is the important medium of inflammatory reaction.Studies show that the disease relevant with the complement excessive activation relates to rejection after rheumatoid arthritis, alzheimer disease, systemic lupus erythematosus (sle) (SLE), the organ transplantation, multiple organ dysfunction syndrome syndrome, adult respiratory distress syndrome (ARDS) etc.Report is arranged, serious symptom severe acute respiratory syndrome (SARS) and the bird flu that causes by H5N1 type viral infection, can find immune overreaction symptom clinically, as ARDS, it is relevant with cellular immunization, humoral immunization excessive activation that septic shock and Reyes syndrome etc., above-mentioned reaction symptom are considered to.Existingly studies confirm that the excessive activation of SARS and complement system is relevant, though do not prove at present the excessive activation that can cause complement system behind the highly pathogenic H5N1 type avian influenza people as yet on evidence, yet the existing influenza infection activating complement alternative pathway that studies show that plays an important role in the generation of viral respiratory system disease.Therefore, activated inhibition treatment has than the important clinical meaning to complement system.
The Cortex Eucommiae (Eucommia ulmoides Olive.) has another name called " thinking celestial ", " kapok ", " pulling a skin ", " silk gross weight " etc., is the deciduous tree that the Eucommiaceae Cortex Eucommiae belongs to, and is that the Gu that the quaternary glacier motion residual is got off on the geologic history is given birth to the few survivors seeds.China's tradition is used as medicine with the dry bark of the Cortex Eucommiae, is the famous and precious tonic herb of using always.The record the earliest of the relevant Cortex Eucommiae sees the Han dynasty, and the medical inscribed wooden slip that slope, Gansu Wuwei drought beach in 1972 tomb of Han dynasty is unearthed has the record of asthenia internal injury disease due to the kidney invigorating Drug therapys " seven kinds of impairments " such as adopting the Cortex Eucommiae; The early stage record of another of the Cortex Eucommiae sees Shennong's Herbal, and it classifies the Cortex Eucommiae as one of top grade 120 kinds, and " Cortex Eucommiae acrid in the mouth is flat in record.Main waist and knee, invigorating middle warmer benefit vital essence, hard muscles and bones, strong will.Wet except that itching under cloudy, urine Yu drop.Clothes are made light of one's life by commiting suicide anti-old for a long time.Think celestial for one." main active is lignanoid and iridoids in the known Cortex Eucommiae; the pinoresinol diglucoside is that main antihypertensive compositions, Deyama etc. have studied various lignanoids in the Cortex Eucommiae and glucosides thereof the inhibitory action to the cAMP phosphodiesterase in the lignanoid; find the inhibition effect of cAMP phosphodiesterase is followed successively by: lignanoid's bioside＞lignanoid's monomer＞lignanoid's monoglycosides, and neolignan bioside, neolignan do not have this effect.The geniposide of iridoid apoplexy due to endogenous wind has discharge function, and aglycon can promote bile secretion; The aucubin antibacterial action is stronger, can stimulate the parasympathetic nervous maincenter, accelerates uric acid and shifts and discharge, and diuresis is obvious; Iridoid such as Geniposidic acid and aucubin can promote that collagen is proteic synthetic in the aged mouse body, promotes the metabolism of skeleton and muscle, and the effect of bone and muscle strengthening is arranged.8-O-4 ' type neolignan is the important natural Lignanoids compounds of a class, comprise Semen Myristicae (Myristica frag-rans) and the cool wood of Su Lilanweiluo (virolasurinamensis) and V.carinata, V.pavonis, have effects such as antifungal, leukemia, inhibition silkworm class larval growth, anti-cercaria intrusion, antitumor, anti-liver poison.Have in the report Cortex Eucommiae and contain 8-O-4 ' type neolignan, but take a broad view of report both domestic and external, there is no the anticomplementary drug effect of such compound monomer and the complement suppressive drug of preparation thereof.
Summary of the invention
The purpose of this invention is to provide the new pharmaceutical usage of 8-O-4 ' type lignanoid, be specifically related to the purposes of 8-O-4 ' type lignanoid in preparation complement inhibition medicine.
8-O-4 ' type of the present invention lignanoid comprises red-guaiacyl glycerol-β-silver maple aldehyde ether (erythro (+)-guaiacylglycerol-8-O-4 '-(sinapyl aldehyde) ether), red-guaiacyl glycerol-β-the silver maple alcohol ether (erythro (+)-guaiacylglycerol-8-O-4 '-(sinapyl alcohol) ether), (±)-guaiacyl glycerol-β-coniferyl aldehyde ether (Erythro and threo-guaiacylglycerol-8-O-4 '-coniferylaldehyde) ether), the plain D (Hedytol D) of Auricled Hedyotis Herb, the plain C (Hedytol C) of Auricled Hedyotis Herb.The plain D of preferred compound Auricled Hedyotis Herb, the plain C of Auricled Hedyotis Herb and red-guaiacyl glycerol-β-silver maple aldehyde ether
The above-claimed cpd monomer has the anticomplementary drug effect through experiment confirm, can prepare the complement suppressive drug.
8-O-4 ' type neolignan of the present invention has the chemical constitution of formula (I):
Wherein,
R
2＝OMe、H；
R3＝OH、α-OH、β-OH；
When
R
2=OMe, R
3During=OH chemical compound 1 (red-guaiacyl glycerol-β-silver maple aldehyde ether);
When
R
2When=OMe, R3=OH chemical compound 2 (red-guaiacyl glycerol-β-the silver maple alcohol ether);
When
R
2When=H, R3=OH chemical compound 3 ((+)-guaiacyl glycerol-β-coniferyl aldehyde ether);
When
R
2=OMe, R
3During=α-OH chemical compound 4 (the plain D of Auricled Hedyotis Herb);
When
R
2=OMe, R
3During=β-OH chemical compound 5 (the plain C of Auricled Hedyotis Herb).
Above-claimed cpd of the present invention prepares by following method:
Cortex Eucommiae is pulverized, with 95% soak with ethanol, and filtration, merging filtrate, decompression recycling ethanol gets ethanol extraction to there not being the alcohol flavor.Ethanol extraction adds the water suspendible, with isopyknic petroleum ether, ethyl acetate, n-butanol extraction three times, obtains petroleum ether part, ethyl acetate extract and n-butanol portion respectively.Activity is carried out at three positions detect, show that the ethyl acetate extract activity is the strongest, get ethyl acetate extract, successively with petroleum ether-ethyl acetate (20: 1,10: 1,8: 1,5: 1,5: 2,1: 1,1: 2, ethyl acetate) gradient elution, obtain 8 streams part (I-VIII).Stream part V (15.4g) is with petroleum ether/acetone (5: 1,4: 1,2: 1,1: 1) eluting, obtains four streams part: Fr.5A-Fr.5D; Fr.5A preparation of silica gel thin layer (F
254,Petroleum ether/acetone=3: 1) chromatographic isolation obtains chemical compound 1 and chemical compound 3; Fr.5B obtains chemical compound 2 by reversed phase column chromatography (10%-60% methanol gradient elution).Stream part VI is with petroleum ether/acetone (5: 1,4: 1,3: 1,2: 1,1: 1,1: 2) silica gel column chromatography, and obtain six streams part: Fr.6A-Fr.6F, Fr.6D is by preparation thin layer (F
254,Petroleum ether/acetone=3: 1) separation obtains chemical compound 4 and chemical compound 5.
The present invention confirms that through experiment in vitro red-guaiacyl glycerol-β-silver maple aldehyde ether, red-guaiacyl glycerol-β-the silver maple alcohol ether, (±)-guaiacyl glycerol-β-coniferyl aldehyde ether, the plain D of Auricled Hedyotis Herb, the plain C of Auricled Hedyotis Herb have inhibition to activating the cell haemolysis that is caused at the classics of complement system and alternative pathway, and the classics of complement system and alternative pathway are activated obvious inhibitory action.
8-O-4 ' type neolignan of the present invention is through pharmacological testing, and result's proof has significant anticomplementary action, and valid density low (table 1).The neolignan of surveying the classical pathway of complement activation or alternative pathway are shown certain inhibitory action, and majority of compounds is better than effect to alternative pathway to the effect of classical pathway.Wherein red-guaiacyl glycerol-β-silver maple aldehyde ether, red-guaiacyl glycerol-β-the silver maple alcohol ether, (±)-guaiacyl glycerol-β-coniferyl aldehyde ether, the plain D of Auricled Hedyotis Herb have identical configuration, and they all have stronger inhibitory action to the activation of classical pathway, wherein the plain D activity of Auricled Hedyotis Herb is the strongest, and its 503nhibiting concentration to classical pathway can reach 38 ± 18 μ g/ml.The plain C of the Auricled Hedyotis Herb only configuration at 7-OH is opposite with the plain D of Auricled Hedyotis Herb, and its activity is also on the contrary, and it is 113 ± 27 μ g/ml to the effective 503nhibiting concentration of the alternative pathway of complement, to the almost unrestraint effect of activation of classical pathway.
Description of drawings
Fig. 1 is a complement inhibition component separating flow chart of the present invention.
The specific embodiment
Embodiment 1 preparation 8-O-4 ' type neolignan
Cortex Eucommiae 9kg pulverizes, with 95% soak with ethanol (50L * 3), and filtration, merging filtrate, decompression recycling ethanol gets ethanol extraction 1.4Kg to there not being the alcohol flavor.Ethanol extraction adds water (3000ml) suspendible, with isopyknic petroleum ether, ethyl acetate, n-butanol extraction three times, obtains petroleum ether part (200g), ethyl acetate extract (420g) and n-butanol portion (600g) respectively.Activity is carried out at three positions detect, find that the ethyl acetate extract activity is the strongest, get ethyl acetate extract (200g), successively with petroleum ether-ethyl acetate (20: 1,10: 1,8: 1,5: 1,5: 2,1: 1,1: 2, ethyl acetate) gradient elution, obtain 8 streams part (I-VIII).Stream part V (15.4g) is with petroleum ether/acetone (5: 1,4: 1,2: 1,1: 1) eluting, obtains four streams part: Fr.5A-Fr.5D; Fr.5A preparation of silica gel thin layer (F
254,Petroleum ether/acetone=3: 1) chromatographic isolation obtains chemical compound 1 (5mg) and chemical compound 3 (3mg); Fr.5B obtains chemical compound 2 (6mg) by reversed phase column chromatography (10%-60% methanol gradient elution).Stream part VI (20.5g) is with petroleum ether/acetone (5: 1,4: 1,3: 1,2: 1,1: 1,1: 2) silica gel column chromatography, and obtain six streams part: Fr.6A-Fr.6F, Fr.6D is by preparation thin layer (F
254,Petroleum ether/acetone=3: 1) separation obtains chemical compound 4 (10mg) and chemical compound 5 (8mg).
Wherein, red-guaiacyl glycerol-β-silver maple aldehyde ether (1) C
21H
24O
8, faint yellow solid.Specific rotatory power
(c=0.04, methanol).Ultraviolet (methanol): λ max (log ε): 212 (3.97), 283 (3.55), 319 (3.51).Infrared (KBr tabletting): 3441,3056,2926,2852,1671,1623,1582,1516,1464,1424,1335,1266,1126,1034,738.Nuclear-magnetism (deuterated acetone):
1H-NMR, 400,000,000) δ ppm:7.05 (d, J=2Hz, H-2), 6.78 (d, J=8Hz, H-5), 6.85 (dd, J=2,8Hz, H-6), 5.01 (dd, J=4.7,4.3Hz, H-7), 4.29 (m, H-8), 3.50,3.87 (m, H-9), 7.15 (s, H-2 '), 7.15 (s, H-6 '), (7.63 d J=15.6Hz, H-7 '), 6.80 (dd, J=15.6,7.8Hz, H-8 '), (9.69 d, J=7.8Hz, H-9 '), 3.84 (s, 3-OMe), 3 ' 5 '-OMe.
13C-NMR (100,000,000) δ ppm:133.68 (1), 110.83 (2), 147.93 (3), 146.48 (4), 115.17 (5), 120.04 (6), 73.43 (7), 88.05 (8), 60.98 (9), 131.06 (1 '), 106.97 (2 '), 154.49 (3 '), (139.23 4 '), 154.49 (5 '), 106.97 (6 '), (153.44 7 '), 129.11 (8 '), 193.82 (9 '), 56.15 (3-OMe), 56.70 (3 ', 5 '-OMe).HR-ESI-MS：m/z?427.1366(M+Na)(Calc.Mass：427.1369).
Wherein, red-guaiacyl glycerol-β-silver maple alcohol ether (2) C
21H
26O
8, weak yellow liquid.Specific rotatory power
(c=0.14, methanol).Nuclear-magnetism (deuterated acetone):
1H-NMR (400,000,000) δ ppm:7.05 (d, J=2Hz, H-2), 6.78 (d, J=8Hz, H-5), 6.83 (dd, J=2,8Hz, H-6), 4.99 (dd, J=4.7,4.3Hz, H-7), 4.18 (m, H-8), 3.65,3.92 (m, H-9), 6.82 (s, H-2 '), 6.82 (s, H-6 '), 6.55 (brd J=15.6Hz, H-7 '), 6.39 (dt J=15.6,5.1Hz, H-8 ') 4.24 (2H, m, H-9 '), 3.84 (s, 3-OMe), 3.89 (6H, s, 3 ' 5 '-OMe).
13C-NMR (100,000,000) δ ppm:133.69 (1), 110.80 (2), 147.95 (3), 146.41 (4), 115.19 (5), 119.94 (6), 73.26 (7), 87.94 (8), 60.84 (9), 134.354 (1 '), 104.53 (2 '), 154.25 (3 '), (135.91 4 '), 154.25 (5 '), 104.53 (6 '), (130.84 7 '), 129.80 (8 '), 63.1 (9 '), 56.17 (3-OMe), 56.67 (3 ', 5 '-OMe).
Wherein, (±)-guaiacyl glycerol-β-coniferyl aldehyde ether (3) C
20H
22O
7, the weak yellow liquid specific rotatory power
(c=0.95, methanol) nuclear-magnetism (deuterated acetone):
1H-NMR (400,000,000) δ ppm:6.8-7.5 (6H, and Ar-H) 4.91 (1H, dd, J=4.7,4.3Hz, H-7), 4.52 (1H, m, H-8), 3.6-4.0 (2H, m, H-9), 6.64 with 6.66 (1H, 2 * dd J=8,16Hz, H-7 '), 7.53 and 7.55 (1H, 2 * d, J=16Hz, H-8 '), 9.57 and 9.6 (1H, 2 * d, J=8Hz, H-9 '), 3.8 (3H, s, 3-OMe), and 3.86, (3H, 2 * s, 3 '-OMe), 3.91 (3H, 2 * s, 5 '-OMe).
13C-NMR (100,000,000) δ ppm:133.68,134.05 (1), 111.50,111.32 (2), 147.99,147.88 (3), 146.83,146.70 (4), 115.17,115.03 (5), 120.56,120.41 (6), 73.78,73.64 (7), 86.98,85.47 (8), 62.00,61.94 (9), 129.03, (128.85 1 '), 112.12,112.06 (2 '), 153.57,153.57 (3 '), 152.64, (152.64 4 '), 117.66,117.24 (5 '), 124.08,124.00 (6 '), 151.60,151.60 152.16,152.16 (7 '), 129.03, (128.85 8 '), 193.87,193.87 (9 '), 56.15 (3-OMe), 56.70 (3 ', 5 '-OMe).
Wherein, plain D (4) C of Auricled Hedyotis Herb
31H
36O
11, colourless liquid.Nuclear-magnetism (deuterochloroform):
1H-NMR (400,000,000) δ ppm:6.5-6.9 (8H, m, Ar-H), 3.16 (2H, m, H-7,7 '), 3.16,3.5 (2H, H-9 "), 3.88 (3H, s; OMe), 3.90 (6H, s, 2 * OMe), 3.92 (3H, s; OMe) 4.06 (1H, m, H-8 "), 4.13 (2H, m, H-9,9 '), 4.29 (2H, m, H-9,9 '), 4.76 (2H, m, H-7,7 '), 5.0 (1H, brs, H-7 ")
13C-NMR (100,000,000) δ ppm:131.22 (1), 108.57 (2), 146.71 (3), 145.28 (4), 114.29 (5), 118.9 (6), 86.02 (7), 54.46 (8), 72.13 (9), (134.17 1 '), 102.74 (2 '), 153.41 (3 '), (1137.80 4 '), 153.41 (5 '), 102.74 (6 '), (85.67 7 '), 54.03 (8 '), 71.52 (9 '), 132.65 (1 "), 108.28 (2 "), 146.58 (3 "); 144.80 (4 "), 114.13 (5 "), 118.69 (6 "), 72.48 (7 "), 87.05 (8 "), 60.54 (9 "); 55.96 (2OMe), 56.22 (3OMe).
Wherein, plain C (5) C of Auricled Hedyotis Herb
31H
36O
11, colourless liquid.Nuclear-magnetism (deuterochloroform):
1H-NMR (400,000,000) δ ppm:6.5-6.9 (8H, m, Ar-H), 3.16 (2H, m, H-7,7 '), 3.32 (2H, H-9 "), 3.88 (3H; s, OMe), 3.90 (6H, s, 2 * OMe); 3.92 (3H, s, OMe) 4.06 (1H, m, H-8 "), 4.13 (2H, m, H-9,9 '), 4.29 (2H, m, H-9,9 '), 4.76 (2H, m, H-7,7 '), 5.0 (1H, d, J=9.0Hz, H-7 ") 13C-NMR (100,000,000) δ ppm:131.86 (1), 109.74 (2), 146.72 (3), 145.37 (4), 114.29 (5); 118.9 (6), 85.87 (7), 54.52 (8), 72.06 (9); 134.55 (1 '), 102.69 (2 '), 153.12 (3 '), 137.86 (4 '); 153.12 (5 '), 102.69 (6 '), 85.71 (7 '), 54.00 (8 '); 71.53 (9 '), 132.64 (1 "), 108.57 (2 "), 146.45 (3 "), 145.29 (4 "), 114.26 (5 "), 120.34 (6 "), 74.07 (7 "), 89.06 (8 "), 60.51 (9 "), 55.96 (2OMe), 56.22 (3OMe).
Embodiment 2 classical pathway complement inhibition tests
Get guinea pig serum, with VBS
2+(barbitol buffer solution, pH=7.4 contain 0.5mM Mg to buffer
2+With 0.15mM Ca
2+) dilution is 1: 80, as the complement of classical pathway source.With the antibody of the anti-sheep red blood cell of rabbit with VBS
2+Buffer dilution be 1: 1000 as hemolysin; The sheep red blood cell (SRBC) that is stored in the Alsever liquid is configured to 2%SRBC.Precision weighing sample 1mg adds VBS
2+Buffer dissolving (the DMSO hydrotropy of adding 1%) is diluted to 8 concentration.The sample solution 200 μ l of variable concentrations and 1: 80 complement 200 μ l are behind 37 ℃ of preincubate 10min, add 100 μ l hemolysins (1: 1000) and 100 μ l 2%SRBC successively, behind 37 ℃ of water-bath 30min, put into the low-temperature and high-speed centrifuge, centrifugal 10min under 5000rpm, 4 ℃ of conditions.Get every pipe supernatant 200 μ l respectively in 96 orifice plates, measure absorbance at 405nm.Experiment is provided with the blank group (sample solution of 200 μ l respective concentration+400 μ l VBS simultaneously
2+), complement control group (200 μ lVBS
2+Buffer+200 μ l complements+100 μ l hemolysins+100 μ lSRBC) and full haemolysis group (100 μ l 2%SRBC+500 μ l H
2O).The sample sets absorbance of each concentration deducted calculate the haemolysis suppression ratio behind the corresponding matched group absorbance.As X-axis, the haemolysis suppression ratio is mapped as Y-axis with the logarithm of sample concentration, and the fitting a straight line that obtains is calculated CP
50Value (table 1).
Embodiment 3 alternative pathway complement inhibition tests
Get the volunteer of NAM serum, (barbitol buffer solution, pH=7.4 contain 5mM Mg with the VBS-Mg-EGTA buffer
2+With 8mM EGTA) dilution is 1: 10, as the complement of alternative pathway source.The rabbit erythrocyte that is stored in 3.8% liquor sodii citratis is configured to 2% rabbit erythrocyte with the VBS-Mg-EGTA buffer.Each sample 1mg of precision weighing adds VBS-Mg-EGTA buffer (the DMSO hydrotropy of adding 1%), is diluted to 8 concentration.The sample solution 150 μ l of variable concentrations and 1: 10 complement 150 μ l add 200 μ l, 2% rabbit erythrocyte behind 37 ℃ of preincubate 10min, put into the low-temperature and high-speed centrifuge behind 37 ℃ of water-bath 30min, centrifugal 10min under 5000rpm, 4 ℃ of conditions.Get every pipe supernatant 200 μ l respectively in 96 orifice plates, measure absorbance at 405nm.Experiment is provided with sample simultaneously according to group (sample solution of 150 μ l respective concentration+350 μ l VBS-Mg-EGTA), complement control group (150 μ l VBS-Mg-EGTA buffer+150 μ l complements+200 μ l2% rabbit cells) and full haemolysis group (200 μ l, 2% rabbit erythrocyte+300 μ l H
2O).Calculate the haemolysis suppression ratio behind the sample sets absorbance deduction respective sample matched group absorbance with each concentration.As X-axis, the haemolysis suppression ratio is mapped as Y-axis with the logarithm of sample concentration, and the fitting a straight line that obtains is calculated AP
50Value (table 1).
Table 1 is that the complement of chemical compound 1-5 suppresses active.
Table 1
Wherein,
aData are the meansigma methods of three experiments
bNon-activity in active testing scope of the present invention
Claims (6)
1. 8-O-4 ' type the lignanoid of formula (I) structure is in the purposes of preparation in the anticomplement medicament,
Wherein,
R
2＝OMe、H；
R3＝OH、α-OH、β-OH。
2. by the described purposes of claim 1, wherein said 8-O-4 ' type lignanoid be chemical compound red-(4-(red 1 for guaiacyl glycerol-β-silver maple aldehyde ether, 3-dihydroxy-2-(4-(3-aldehyde-1-(E)-alkene)-2,6-dimethoxy phenoxy group) propyl group)-the 2-methoxyphenol).
3. by the described purposes of claim 1, wherein said 8-O-4 ' type lignanoid be chemical compound red-(4-(red-1 for guaiacyl glycerol-β-silver maple alcohol ether, 3-dihydroxy-2-(4-(3-hydroxyl-1-(E)-alkene)-2,6-dimethoxy phenoxy group) propyl group)-the 2-methoxyphenol).
4. by the described purposes of claim 1, wherein said 8-O-4 ' type lignanoid is that (4-(red-1 for chemical compound (±)-guaiacyl glycerol-β-coniferyl aldehyde ether, 3-dihydroxy-2-(4-(3-aldehyde-1-(E)-alkene)-2-methoxyl group phenoxy group) propyl group)-the 2-methoxyphenol), 4-(Soviet Union-1,3-dihydroxy-2-(4-(3-aldehyde-1-(E)-alkene)-2-methoxyl group phenoxy group) propyl group)-2-methoxyphenol).
5. by the described purposes of claim 1, wherein said 8-O-4 ' type lignanoid is the plain D of chemical compound Auricled Hedyotis Herb, (4-(4-(4-(1-Alpha-hydroxy, 3-hydroxyl-1-(4-hydroxy 3-methoxybenzene base) propyl group-2-oxygen)-3, the 5-Dimethoxyphenyl)-two tetrahydrochysenes [3,4-c] furan-1-yl)-the 2-methoxyphenol).
6. by the described purposes of claim 1, wherein said 8-O-4 ' type lignanoid is plain C (4-(4-(4-(the 1-beta-hydroxy of chemical compound Auricled Hedyotis Herb, 3-hydroxyl-1-(4-hydroxy 3-methoxybenzene base) propyl group-2-oxygen)-3, the 5-Dimethoxyphenyl)-two tetrahydrochysenes [3,4-c] furan-1-yl)-the 2-methoxyphenol).
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249862A (en) * | 2010-05-19 | 2011-11-23 | 复旦大学 | Application of phenol compounds in preparation of anti-complement medicines |
| CN103467258A (en) * | 2013-08-15 | 2013-12-25 | 华北制药集团新药研究开发有限责任公司 | Lignanoid compound, and preparation method and use thereof |
| CN114409667A (en) * | 2022-01-11 | 2022-04-29 | 西北农林科技大学 | Eucommia ulmoides leaf lignan compound, preparation method and application of eucommia ulmoides leaf lignan compound in neuroprotection |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329204B1 (en) * | 1999-02-10 | 2001-12-11 | E. I. Du Pont De Nemours & Company | Plant caffeic acid 3-0-methyltransferase homologs |
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2007
- 2007-07-20 CN CN2007100440995A patent/CN101347418B/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249862A (en) * | 2010-05-19 | 2011-11-23 | 复旦大学 | Application of phenol compounds in preparation of anti-complement medicines |
| CN103467258A (en) * | 2013-08-15 | 2013-12-25 | 华北制药集团新药研究开发有限责任公司 | Lignanoid compound, and preparation method and use thereof |
| CN114409667A (en) * | 2022-01-11 | 2022-04-29 | 西北农林科技大学 | Eucommia ulmoides leaf lignan compound, preparation method and application of eucommia ulmoides leaf lignan compound in neuroprotection |
| WO2023134240A1 (en) * | 2022-01-11 | 2023-07-20 | 西北农林科技大学 | Lignan compounds from eucommiae folium, preparation method therefor and use in neuroprotection |
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