CN103333176A - Norlignan compounds and method of separating and verifying norlignan compounds from pouzolzia zeylanica var. microphylla - Google Patents
Norlignan compounds and method of separating and verifying norlignan compounds from pouzolzia zeylanica var. microphylla Download PDFInfo
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Abstract
The invention discloses norlignan compounds and a method of separating and verifying norlignan compounds from pouzolzia zeylanica var. microphylla. The norlignan compounds have a structure as shown in formula (I), and the norlignan compounds can be separated from the pouzolzia zeylanica var. microphylla and have certain antibacterial activity, thereby capable of being used for preparing antibacterial medicament. The formula (I) is as shown in the specification.
Description
Technical field
The invention belongs to natural product active ingredient and extract the field, specifically disclose a kind of norlignan compounds and separation and authentication method from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang.
Background technology
Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang
Pouzolzia zeylanica(L.) Benn. Var. microphylla (Wedd.) W.T.Wang. has another name called Shi Zhu, stone pearl son, be born in moist mountain region, limes marginis and roadside or the low mountain shrubbery or in the sparse woods, mainly be distributed in ground such as China Jiangxi, Fujian, Taiwan, Guangdong, Guangxi, Yunnan, it is distributed more widely in China to be that Sri Lanka Pouzolzia Herb belongs in the medicinal plant, uses more a kind of.Its main effect is detoxify and promote the subsdence of swelling, synthetism, and it is swollen to be used for carbuncle, syphilis, pulmonary tuberculosis, fracture.There are " sobbing purulence cream ", " purulence see disappear ", " grass of drawing out the pus " etc. to be commonly called as.
Few to the research report of Sri Lanka Pouzolzia Herb platymiscium both at home and abroad, mainly be the fragmentary report of, expelling parasite antibiotic about it, antitumor and hypoglycemic application.The chemical constitution study aspect, foreign literature has reported that Sri Lanka Pouzolzia Herb contains Quercetin (quercetin), Vitexin (vitexin), isovitexin (isovitexin), phylanthin, methyl-stearate (metyl-stearate), β-daucosterol and two norlignan's compounds, difference called after pouzoligan A and pouzoligan B, its structure is 2-hydroxyl-4-[hydroxy phenyl-(4-hydroxyl-3-methoxy-benzyl)]-3-(3, the 5-dihydroxy phenyl) tetrahydrofuran (THF) and 1,4-dihydroxyl-3-[4-hydroxy phenyl-(4-hydroxyl-3-methoxy-benzyl)]-2-(3,5 – dihydroxy phenyl) butane.Domestic rarely seen Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang total flavones, total alkaloid extracting technique patent do not see that other are about the research report of Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang Lignanoids compounds.
Summary of the invention
The object of the present invention is to provide a kind of novel norlignan compounds that is extracted by Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, it has certain antibacterial and tumors inhibition activity.
Another order of the present invention is to provide the method by isolating described novel norlignan compounds in the Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang.
The present invention also has a purpose to be to provide the authentication method of this new compound simultaneously.
Above-mentioned purpose of the present invention is achieved by following technical solution:
A kind of norlignan compounds, described norlignan compounds has structure shown in formula I:
（Ⅰ）。
The English called after of compound shown in the formula I: 2,5-bis (4-methoxy-3-epoxylphenyl)-3, and 4-bis (3,5-dihydroxyphenyl)-tetrahydrofuran, its structure is explained by wave spectrum and is determined.
The method that described compound separates from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang comprises the steps:
S1. Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang is pulverized, added ethanol, refluxing extraction, united extraction liquid is condensed into medicinal extract liquid, and is standby;
S2. the medicinal extract liquid that S1. is obtained adopts sherwood oil, chloroform, ethyl acetate extraction successively, collects acetic acid ethyl acetate extract and concentrated, obtains acetic acid ethyl ester extract;
S3. acetic acid ethyl ester extract is carried out column chromatography, with the mixed solution gradient elution of methylene dichloride and methyl alcohol, the volume ratio of methylene dichloride and methyl alcohol is followed successively by: 80:1,40:1,20:1,10:1,5:1,1:1,0:1; Every 500mL collects a elutriant, and elutriant is known through the tlc inspection, and the thin out concentration of namely changing elutriant of principal spot color merges the 60th ~ 80 part of effluent liquid;
S4. the effluent liquid that S3. is merged separates with the dextrane gel column chromatography that is of a size of 1cm * 150cm, be the mixed solution wash-out of 1:1 with chloroform and methyl alcohol volume ratio, 5mL collects a elutriant, knows colour developing through the tlc inspection, collect the 35th ~ 45 part of effluent liquid, be designated as Fr.4;
S5. S4. gained Fr.4 is carried out column chromatography, carry out wash-out with the mixed solution of chloroform and methyl alcohol, know through the tlc inspection, merge the colour developing component;
S6. S5. gained colour developing component is carried out the ODS column chromatography, with the methanol-eluted fractions of 30 volume %, elutriant is known through the tlc inspection, merges the colour developing component, concentrates and obtains compound shown in the formula I;
Described thin-layer chromatography inspection is known with 5% sulfuric acid Vanillin solution as developer.
Preferably, among the S1., used ethanol is 75% aqueous ethanolic solution.
Preferably, among the S1, the temperature of described extraction is being carried out below 70 ℃.
Preferably, among the S1., used consumption of ethanol is 10 ~ 20 times of many Sri Lanka Pouzolzia Herbs.
Preferably, among the S1., the number of times of refluxing extraction is 3 times, each 2 hours.
Preferably, S5. is that the mixing solutions of 13:1 carries out wash-out for adopting chloroform and methyl alcohol volume ratio.
Preferably, S5. is the mixing solutions of 13:1 when carrying out wash-out for adopting chloroform and methyl alcohol volume ratio, and every 50mL collects a elutriant, knows through the tlc inspection, and this component is collected in the 6th ~ 10 part of colour developing.
Preferably, among the S6., every 10mL collects a elutriant, knows through the tlc inspection, and this component is collected in the 8th ~ 11 part of colour developing.
Preferably, column chromatography described in S3. and the S5. is silica gel column chromatography.
Preferably, the silica gel among the S3. is 100 ~ 200 orders; S5. the silica gel in is 300 ~ 400 orders.
Compound shown in the resulting formula I, use methylene dichloride: methyl alcohol=12:1, ascending development, (254nm) is viewed as a gray corrosion under the ultraviolet lamp, and the colour developing of 5% sulfuric acid Vanillin solution is single bluish voilet spot.At methylene dichloride: Rf=0.53 in methyl alcohol=12:1 system, at chloroform: Rf=0.41 in acetone=1:1 system, at sherwood oil: Rf=0.28 among ethyl acetate=1:2.
Confirm that through activity experiment compound shown in the formula I has certain biocidal property, can be applied to prepare antibacterial medicines.
Compound shown in the formula I has certain restraining effect to cancer cells, is expected to be applied to prepare cancer therapy drug.
Compared with prior art, the present invention has following beneficial effect:
The present invention discloses a kind of new norlignan's compounds, and it can separate from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang and obtains, and has certain biocidal property, can be applied to prepare antibacterial medicines, and it has certain restraining effect to cancer cells, is expected to be applied to prepare cancer therapy drug.
Description of drawings
Fig. 1 is compound shown in the formula I
1H-NMR figure;
Fig. 2 is compound shown in the formula I
13C-NMR figure;
Fig. 3 is compound shown in the formula I
13C-DEPT-NMR figure;
Fig. 4 is the HMBC spectrogram of compound shown in the formula I;
Fig. 5 is the HMQC spectrogram of compound shown in the formula I;
Fig. 6 is the EI-MS spectrogram of compound shown in the formula I;
Fig. 7 is the HR-EI-MS spectrogram of compound shown in the formula I;
Fig. 8 is the IR spectrogram of compound shown in the formula I.
Embodiment
Below in conjunction with specific embodiment the present invention is further explained explanation, but specific embodiment is not done any restriction to the present invention.Unless stated otherwise, related reagent, method is this area reagent and method commonly used among the embodiment.
The method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating compound shown in the formula I:
(1) extract: take by weighing Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang 10kg, shred, put into extractor, add the ethanol of 15 times of volumes 75%, refluxing extraction three times, each two hours, extracting solution merge concentrate smart crude extract, standby.
(2) liquid-liquid extraction separates: medicinal extract liquid is disperseed with suitable quantity of water, use sherwood oil, chloroform, ethyl acetate extraction to each extraction liquid look shallow successively, acetic acid ethyl acetate extract is evaporated to fluid extract.
(3) silica gel column chromatography separates: acetic acid ethyl ester extract 21g is carried out silicagel column, and (100 ~ 200 orders, 1500g) chromatographic separation are carried out gradient elution with methylene dichloride and methyl alcohol, and the volume ratio of methylene dichloride and methyl alcohol is followed successively by: 80:1,40:1,20:1,10:1,5:1,1:1,0:1.Every 500mL collects a elutriant, and elutriant is known through the tlc inspection, and the thin out gradient of namely changing elutriant of principal spot merges the 60th ~ 80 part of effluent liquid;
(4) sephadex chromatography separates: the 60th ~ 80 part of effluent liquid that step (3) is obtained carries out dextrane gel (Sephadex
TMLH-20) column chromatography separation (1cm * 150cm), be the mixed solution wash-out of 1:1 with chloroform and methyl alcohol volume ratio, 5mL collects a elutriant, knows colour developing through the tlc inspection, collects the 35th ~ 45 part of effluent liquid, is designated as Fr.4;
(5) silica gel column chromatography separates: 0.5g Fr.4 carries out silicagel column, and (300 ~ 400 orders 50g) separate, and chloroform and methyl alcohol volume ratio are the mixed solution wash-out of 13:1, every 50mL collects a, detects the colour developing of 5% sulfuric acid Vanillin through TLC, merge the 5th ~ 10 component, obtain Fr.A.
(6) C18 reverse phase silica gel column purification: with Fr.A process C18 reverse phase silica gel post (20g), 30% methanol-eluted fractions, every 10mL collects a, detect through TLC, the colour developing of 5% sulfuric acid Vanillin merges the 8th ~ 11 component, concentrate, brown crystallization is separated out in placement, and chloroform-methanol (1:1) recrystallization purifying obtains compound shown in the formula I (75mg) after the vacuum-drying.
The outward appearance of compound shown in the formula I is brown tabular crystal (chloroform-methanol), mp.170 ~ 173, specific rotation+3.0., UV
: 280nm, use methylene dichloride: methyl alcohol=12:1, ascending development, (254nm) is viewed as a gray corrosion under the ultraviolet lamp, and the colour developing of 5% sulfuric acid Vanillin solution is single bluish voilet spot.At methylene dichloride: Rf=0.53 in methyl alcohol=12:1 system, at chloroform: Rf=0.41 in acetone=1:1 system, at sherwood oil: Rf=0.28 among ethyl acetate=1:2.
Its infrared data: IR(pressing potassium bromide troche, ν cm-1): 3351(is strong, and is wide), 1605,1516(is strong), illustrate and contain hydroxyl and phenyl in the molecule.
Its mass-spectrometric data: molecular ion peak m/z 514.1608 among the HR-EI-MS, quasi-molecular ion peak is m/z 515.1694 [M+H] among the TOF-ESI-MS
+, determine that its molecular formula is C
30H
26O
8(calcd.514.1628);
Its nuclear magnetic data:
13Occur 15 carbon signals altogether in the CNMR spectrum, comprise 10 aromatic carbons, the phenyl ring that prompting exists symmetry to replace, high field region also have two saturated methine carbon δ: 88.6,63.3, DEPT to experimental results show that there is not methylene radical CH except the methoxyl group carbon at δ 55.8 places
2By molecular weight as can be known, this molecular structure of compounds has high symmetry, only occurs the signal of half in the NMR collection of illustrative plates.
1Two groups of phenyl ring proton peak appear in the fragrance zone in the HNMR spectrum, δ 6.85(1H, and d, J=1.8Hz), and δ 6.82(1H, dd, J=1.8,8.2Hz), and δ 6.76(1H, d J=8.1Hz) is an ABX system; δ 6.12 (1H, s), δ 6.11 (1H, m) and δ 6.09 (1H, t J=2.1Hz) are A on another phenyl ring
2System X, corresponding carbon signal appears at δ: 141.1,107.3(x2), and 101.8,158.9(x2), be illustrated as 3,5-dihydroxy phenyl; δ 3.44(1H, dd, J=2.85,6.4Hz) with δ 5.22(1H, dd, J=2.85, appearance 6.4Hz) prompts for the tetrahydrofuran (THF) compounds, corresponding carbon atom signal appears at δ 63.3(CH respectively) and δ 88.6 (CH); δ 3.8(3H, s) explanation has a methoxyl group.In HMBC spectrum, δ 3.44(H-3) with δ 88.6(C-2), δ 141.1(C-1''), δ 133.9(C-1'), δ 107.3(C-2'', 6'') have long-range relevant; δ 5.22(H-2) with δ 63.3(C-3), δ 141.1(C-1''), δ 110.4(C-2'), δ 119.4(C-6'), δ 107.3(C-2'', 6'') have long-range relevant.2 on above data declaration tetrahydrofuran (THF) ring is connected with ABX system phenyl ring, and 3 and 3, the 5-dihydroxy phenyl connects.Comprehensive above data, determine that compound structure is: 2,5-bis (4-methoxy-3-epoxylphenyl)-3,4-bis (3,5-dihydroxyphenyl)-tetrahydrofuran
Spectral data is as follows in detail:
UVλmax(MeOH)：280nm
The IR(pressing potassium bromide troche, ν cm
-1): 3351,2938,2844,2158,1605,1516,1459,1435,1347,
1273,1238,1209,1156,1124,1031,1001,947,921,842,820,775,755,728,694,636,554,521,456。
1H-NMR?(CD
3OD,?500MHz)δ(ppm):?3.8(3H,s),?3.44(1H,dd,J?=?2.85,?6.4?Hz),?5.22(1H,dd,J?=?2.85,?6.4?Hz),6.09(1H,t,J?=?2.1?Hz),6.11?(1H,?m),6.12?(1H,?s),?6.76(1H,d,J?=?8.1?Hz),6.82(1H,dd,?J?=?1.8,?8.2?Hz),6.85(1H,d,J=?1.8?Hz);
13C-NMR(CD
3OD,125MHz)δ(ppm):55.8(OCH
3),63.3(C-3,4),88.6(C-2.5),101.8(C-4''),107.3(C-2'',6''),110.4(C-2'),115.5(C-5'),119.4(C-6'),133.9(C-1'),141.1(C-1''),146.6(C-3'),148.3(C-4'),158.9(C-3'',5'')。
1. experiment material
1.1 bacterial strain: staphylococcus aureus strains separates preservation by basis institute of Guangdong Pharmaceutical University microorganism with the immunization experiment preparation room.
Compound shown in the formula I that 1.2 reagent: embodiment 1 obtains; Dimethyl sulfoxide (DMSO) (Guangzhou Chemical Reagent Factory); Coptis medicinal material (pharmaceutcal corporation, Ltd is write in Guangzhou);
1.3 substratum: nutrient agar medium bacterium dehydrated medium, nutrient broth bacterium dehydrated medium (Huankai Microbes Tech Co., Ltd., Guangdong);
2. method
2.1 the preparation of sample
Precision takes by weighing that compound powder 2mg adds the sterilized 1%DMSO of 500 μ L and makes its dissolving as in the sterilized EP pipe shown in the formula I of embodiment 1 preparation, and concentration is 4mg/mL.4 ℃ of preservations are standby.
2.2 rhizoma extracting liquid preparation
Pulverize the coptis, take by weighing 1g medicinal powder, to tool plug Erlenmeyer flask, adding distil water 25mL, ultrasonic 20min filters, and filter residue adds the ultrasonic 10min of distilled water of 20mL again, merges 2 times filtrate, and is settled to 100mL.Making concentration is the positive control drug that contains crude drug 0.01g/mL.121 ℃ of autoclaving 20min.4 ℃ of preservations are standby.
2.3 the preparation of experimental bacteria liquid
On the aseptic technique platform, in the sterilization test tube, add 5mL nutrient broth nutrient solution, add streptococcus aureus strain liquid 0.1mL, in 37 ℃ of constant temperature culture 12h.It is 3 * 10 that bacterium is diluted
7Individual mL
-1Standby bacterium liquid.
2.4 the mensuration of external fungistatic effect
Adopt punch method to be improved.On the aseptic technique platform with about nutrient agar fusion and constant temperature to 58 ℃, pour aseptic plate into, every plate impouring 10 mL.Fully the cooling back is stand-by.
Add nutrient agar and 0.1mL bacterium liquid about 5mL fusion and constant temperature to 58 ℃ in sterile test tube, rubbing fast makes abundant mixing, pours into while hot in the nutrient agar medium culture dish that has prepared, and it is evenly spread out.After waiting to solidify, evenly and vertically make a call to 3 holes with 6mm glass sterilization punch tool in plate, choose agar, pipette 25 μ L test liquids with quantitative pipettor respectively and 1%DMSO does negative control, each sample is parallel to be done 3 times.In 37 ℃ of thermostat containers, cultivate 24h, measure the diameter of two vertical direction of each inhibition zone respectively with vernier callipers, the edge of antibacterial ring be invisible to the naked eye bacterium obviously growth be limited.Get its mean value after having measured and carry out statistical study, calculate mean value and the standard deviation of 3 hole antibacterial circle diameters.The criterion of external antibacterial qualitative results: antibacterial circle diameter is insensitive (-) less than 7mm, and 7～12 mm are low responsive (+), and 12～18 mm are medium sensitivity (++), and 18 mm are above to be extremely sensitive (+++).
3. result
The visible significantly inhibition zone of coptis positive controls (containing crude drug 0.01g/mL), the about 16mm of diameter, its bacteriostatic action is medium sensitivity.As seen the periphery of compound shown in the formula I has inhibition zone, the about 7.0mm of diameter, and its bacteriostatic action is low responsive.
The experiment of embodiment 3 tumor promotions
1. experiment material
Compound shown in the formula I of 1.1 medicine: embodiment 1 preparation
1.2 cell: osteosarcoma cell line MG-63, breast carcinoma cell strain SKBR-3
1.3 reagent: PRMI1640, foetal calf serum, pancreatin, DMSO, MTT, penicillin, Streptomycin sulphate (Sigma company); 96 orifice plates (Coring company)
2. method
Osteosarcoma MG-63 cell and mammary cancer SKBR-3 cell separately be incubated at contain 10% foetal calf serum, 1 * 10
5In the PRMI1640 nutrient solution of U/L penicillin, Streptomycin sulphate, 37 ℃, 5%CO
2Cultivate in the incubator.The cell of taking the logarithm vegetative period, the trysinization with 0.25%, piping and druming becomes uniform single cell suspension, and counting cells is diluted to 5 * 10 with substratum
4Cell/mL is inoculated in 96 orifice plates, every hole 200 μ L, 37 ℃, 5%CO
2Cultivate 24 h in the incubator.The experimental group dosage is 3.13 μ M, 6.25 μ M, 12.5 μ M, 25 μ M, 50 μ M, 100 μ M, 200 μ M, and the blank group adds the equivalent substratum, and negative control group adds the substratum that equivalent contains 1 ‰ DMSO, every group of 3 holes.After hatching 24 h continuously, discard substratum, clean 2 times with PBS, every hole adds 180 μ L and does not contain blood serum medium and 20 μ L MTT (5 mg/mL).37 ℃, 5%CO
2After incubator is cultivated 4 h, inhale and abandon supernatant, every hole adds the abundant dissolved cell precipitation of l50 μ L DMSO, and vibration 10min measures absorbance (OD value) with microplate reader at 490 nm places in l h.
Cell inhibitory rate (%)=(blank group OD value-experimental group OD value)/blank group OD value * 100%
3. experimental result (seeing the following form)
Compound shown in the formula I is to MG-63 cell and the effect of SKBR-3 cell inhibiting
Above-mentioned experimental result shows: compound all has certain restraining effect to osteosarcoma MG-63 cell and mammary cancer SKBR-3 cell.
Claims (8)
1. norlignan's compounds is characterized in that, described norlignan compounds has structure shown in formula I:
（Ⅰ）。
2. the described compound of claim 1 method of separating from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang is characterized in that, comprises the steps:
S1. Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang is pulverized, added ethanol, refluxing extraction, united extraction liquid is condensed into medicinal extract liquid, and is standby;
S2. the medicinal extract liquid that S1. is obtained adopts sherwood oil, chloroform, ethyl acetate extraction successively, collects acetic acid ethyl acetate extract and concentrated, obtains acetic acid ethyl ester extract;
S3. acetic acid ethyl ester extract is carried out column chromatography, with the mixed solution gradient elution of methylene dichloride and methyl alcohol, the volume ratio of methylene dichloride and methyl alcohol is followed successively by: 80:1,40:1,20:1,10:1,5:1,1:1,0:1; Every 500mL collects a elutriant, and elutriant is known through the tlc inspection, and the thin out gradient of namely changing elutriant of principal spot color merges the 60th ~ 80 part of effluent liquid;
S4. the effluent liquid that S3. is merged separates with the dextrane gel column chromatography that is of a size of 1cm * 150cm, be the mixed solution wash-out of 1:1 with chloroform and methyl alcohol volume ratio, 5mL collects a elutriant, knows colour developing through the tlc inspection, collect the 35th ~ 45 part of effluent liquid, be designated as Fr.4;
S5. S4. gained Fr.4 is carried out column chromatography, carry out wash-out with the mixed solution of chloroform and methyl alcohol, know through the tlc inspection, merge same composition;
S6. S5. gained same composition is carried out the ODS column chromatography, with the methanol-eluted fractions of 30 volume %, elutriant is known through the tlc inspection, merges the colour developing component, concentrates and obtains compound shown in the formula I;
Described thin-layer chromatography inspection is known with 5% sulfuric acid Vanillin solution as developer.
3. according to the described method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating of claim 2, it is characterized in that used ethanol is the aqueous ethanolic solution of 75 % among the S1..
4. according to the described method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating of claim 2, it is characterized in that among the S1., used consumption of ethanol is 10 ~ 20 times of many Sri Lanka Pouzolzia Herbs.
5. according to the described method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating of claim 2, it is characterized in that S5. employing chloroform and methyl alcohol volume ratio are that the mixing solutions of 13:1 carries out wash-out.
6. according to the described method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating of claim 5, it is characterized in that every 50mL collects a elutriant, know through the tlc inspection that this component is collected in the 6th ~ 10 part of colour developing.
7. according to the described method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating of claim 2, it is characterized in that among the S6., every 10mL collects a elutriant, know through the tlc inspection that this component is collected in the 8th ~ 11 part of colour developing.
8. according to the described method of from Pouzolzia zeylanica (L.) Benn. Var. Micro-nhylla (Wedd) W. T. Wang, separating of claim 2, it is characterized in that column chromatography described in S3. and the S5. is silica gel column chromatography.
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| CN105954450A (en) * | 2016-03-23 | 2016-09-21 | 广东药学院 | HPLC fingerprint spectrum of pouzolzia zeylanica var. microphylla medicinal material or general flavonoids of pouzolzia zeylanica var. microphylla and building method and application of HPLC fingerprint spectrum |
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