CN101671379B - 5-alpha reductase inhibitor-smartweed diffractive ring lignan glucoside A and preparation method thereof - Google Patents
5-alpha reductase inhibitor-smartweed diffractive ring lignan glucoside A and preparation method thereof Download PDFInfo
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- CN101671379B CN101671379B CN2009100127073A CN200910012707A CN101671379B CN 101671379 B CN101671379 B CN 101671379B CN 2009100127073 A CN2009100127073 A CN 2009100127073A CN 200910012707 A CN200910012707 A CN 200910012707A CN 101671379 B CN101671379 B CN 101671379B
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Abstract
The invention relates to an extraction and preparation method of bioactive components of a traditional Chinese medicine, in particular to 5-alpha reductase inhibitor-smartweed diffractive ring lignan glucoside A and a preparation method thereof. In the invention, a triangle-leaf smartweed is separated to obtain smartweed diffractive ring lignan glucoside A on the basis of previous research, the component has a structure different from a lignans component and is a novel diffractive ring lignans component, and a molecular structural formula of the novel diffractive ring lignans component is as above; and the preparation method of the 5-alpha reductase inhibitor-smartweed diffractive ring lignan glucoside A takes the triangle-leaf smartweed as a raw material. The 5-alpha reductase inhibitor-smartweed diffractive ring lignan glucoside A is discovered to have higher activity on the research of inhibiting 5-alpha reductase action and is a potential prostatic hyperplasia resistant medical component.
Description
Technical field
The present invention relates to Chinese traditional medicine biology extraction of active ingredients preparation method, be specifically related to a kind of 5-alpha reductase inhibitor-nettle diffractive cyclolignan anthocyanin A and preparation method thereof.
Background technology
Contain a large amount of lignan components in the Urtica plant; 13 Lignanoids compounds have therefrom been identified: (+)-Xin olivil; (-)-Secoisolariciresinol; isolariciresinol; pine vinegar alcohol; 3; 4-two vanillyl tetrahydrochysenes are barked and are muttered; new olivil-4-O-β-D-glucoside; 9-ethanoyl-Xin olivil; 9-ethanoyl-Xin olivil-4-O-β-D-glucoside; 9; 9 '-diacetyl-Xin olivil; 9,9 '-diacetyl-Xin olive is pulled resene-4-O-β-D-glucoside; (-)-Secoisolariciresinol-9-O-β-D-glucoside; (-)-Secoisolariciresinol-4-O-β-D-glucoside; new olivil-9-O-β-D-glucoside.Its structure type mainly contains new olivil and glycoside and open loop lariciresinol, lariciresinol and glycoside thereof, and wherein new olivil and glycoside structure thereof are as follows:
The new new olivil of olivil-4-O-β-D-glucoside
New olivil-9-O-β-D-glucoside 9-ethanoyl-Xin olivil
9,9`-diacetyl-Xin olivil, 9-ethanoyl-Xin olivil-4-O-β-D-glucoside
9,9`-diacetyl one new olive is pulled resene-4-O-β-D-glucoside olivil
Open loop lariciresinol, lariciresinol and glycoside structure thereof are as follows:
(-)-Secoisolariciresinol (-)-Secoisolariciresinol-9-O-β-D-glucoside
()-Secoisolariciresinol-4-O-β-D-glucoside 5-methoxyl group Secoisolariciresinol
Isolariciresinol
There are some researches show and from the stinging nettle root, be separated to (+)-Xin olivil, (-)-Secoisolariciresinol, dehydrogenation two lubanols, isolariciresinol, rosin spirit and 3,4-two vanillyl tetrahydrofuran (THF)s, and checked the external affinity interaction with SBHG of above several materials, the result is except that rosin spirit, all the other compounds all have avidity, wherein 3, the affinity interaction of 4-two vanillyl tetrahydrofuran (THF)s is the strongest, and inhibiting rate was 95% when concentration was 250 μ g/ml.Lignanoids is one of activeconstituents of treatment BPH in the prompting stinging nettle root.
Seminar of the present invention had once carried out the bioactivity screening of anti-prostatic hyperplasia to the different extracts of 8 kinds of Urtica roots of plants of home-made, the result shows that 20% and 95% ethanol extraction that Yunnan subtracts Root of Narrowleaf Nettle can suppress the pathological tissues of hyperplasia of prostate rat significantly.
Summary of the invention
The objective of the invention is on the basis of early-stage Study, in order further to study the reactive site and the mechanism of action of extract anti-prostatic hyperplasia, choose that a key enzyme-5 is an action target spot in the prostata tissue, adopt the method for enzyme linked immunological (Enzyme-linked immunospecific assay ELISA), set up and suppress the 5 external model, from the rat prostate tissue, extract 5, formed a kind of micro-reaction system jointly with substrate testosterone and hydrogen donor NADPH, utilize microplate reader to detect the content of Standone (DHT), judge with the content of DHT whether the nettle extract has the activity that suppresses 5.
The present invention separates from Herba Urticae triangularis and has obtained nettle diffractive cyclolignan anthocyanin A, the structure of this composition is different from above-mentioned lignan component, be a kind of new driffractive ring lignan component, discovering to have strong activity to suppressing the 5 effect, is a kind of potential anti-prostatic hyperplasia pharmaceutical cpd.
Technical scheme of the present invention is: a kind of 5-alpha reductase inhibitor-nettle diffractive cyclolignan anthocyanin A, and its molecular structural formula is as follows:
The preparation method of above-mentioned 5-alpha reductase inhibitor-nettle diffractive cyclolignan anthocyanin A is to be raw material with the Herba Urticae triangularis, and preparation process is as follows:
(1) with Herba Urticae triangularis dryly after the pulverization process of lower section, be 95% industrial alcohol refluxing extraction with mass concentration, filter the back concentrating under reduced pressure;
(2) with the water suspendible of alcohol extract with 50-90 ℃, with sherwood oil, ethyl acetate, water-saturated n-butanol extraction, each extracts three times successively;
(3) n-butyl alcohol extract separates through macroporous resin D101, and the employing mass concentration is 30% ethanol elution, collects elutriant;
(4) ethanol eluate silica gel column chromatogram separating purification, the employing volume ratio is a chloroform: methyl alcohol=30: 1,10: 1,5: 1,3: 1,1: 1 gradient elution, collect elutriant;
(5) elutriant of step (4) is through the reversed-phase silica gel column chromatography separation and purification, and the employing volume ratio is a methyl alcohol: the eluant solution of water=3: 7, every 15-30ml is gathered into 1 part, collects 15-20 part elutriant, merges to obtain nettle diffractive cyclolignan anthocyanin A after concentrating.
Adopt nucleus magnetic resonance spectroscopic techniques such as (NMR) to measure its structure, the spectral data of nettle diffractive cyclolignan anthocyanin A sees Table 1.
Table 1. nettle diffractive cyclolignan anthocyanin A's
1H NMR profit
13C NMR
Nettle diffractive cyclolignan anthocyanin A can be used to prepare the anti-prostatic hyperplasia medicine, the nettle diffractive cyclolignan anthocyanin A of effective dose is mixed and makes the medicine of appropriate dosage forms with pharmaceutical carrier.
The invention has the beneficial effects as follows: raw material is the natural plant root, and safety is easy to get, and method is simple to operation, does not introduce toxic substance, and is with low cost, has very important significance on the anti-prostatic hyperplasia drug development research.
Embodiment
The present invention is further illustrated with specific embodiment below, but do not influence protection scope of the present invention.
Embodiment 1
The Herba Urticae triangularis medicinal material is gathered from the A Bazhou of Sichuan Province.
Preparation nettle driffractive ring wood fat glycosides A method steps is as follows from Herba Urticae triangularis:
(1) with Herba Urticae triangularis dryly after the pulverization process of lower section, be 95% industrial alcohol refluxing extraction with mass concentration, solid-liquid ratio (kg/l)=1: 8, extract 90 ℃ of temperature, extraction time 3h, extraction time 3 times, united extraction liquid, being evaporated to after the filtration does not have the alcohol flavor;
(2) be 60 ℃ water suspendible with alcohol extract 200g with the 2L temperature, with sherwood oil, ethyl acetate, the water-saturated n-butanol extraction of 2L, each extracts 3 times successively.
(3) n-butyl alcohol extract 30g separates through D101 macroporous resin (1kg), and the employing mass concentration is 30% ethanol elution, collects elutriant 10L;
(4) ethanol eluate is concentrated into dried 5g, and with silica gel column chromatography (silica gel 150g) separation and purification, the employing volume ratio is a chloroform: methyl alcohol=30: 1,10: 1,5: 1,3: 1,1: 1 gradient elution, collect each ratio elutriant 1L;
(5) elutriant of step (4) is concentrated into dried 1g, then through reversed-phase silica gel column chromatography (reverse phase silica gel 30g) separation and purification, adopt volume ratio methyl alcohol: the eluant solution of water=3: 7, every 25ml is gathered into 1 part, merge 15-20 part elutriant, obtain nettle diffractive cyclolignan anthocyanin Al20mg after concentrating.
Embodiment 2
5-alpha-reductase restraining effect experimental procedure is as follows:
(1) preparation of 5-alpha-reductase:
3 of male SD rats, body weight 200 ± 10g, Dalian Medical Univ's Experimental Animal Center provides, and the water execution of spending the night is can't help in fasting, and the prostata tissue that takes out veutro rapidly shreds on the ice platform, with homogenate (the sucrose 0.73molL of precooling
-1, calcium chloride 1.91mmolL
-1) homogenate in glass homogenizer, under 4 ℃,, get supernatant liquor again with the centrifugal 30min of 16000rpm low-temperature and high-speed with the centrifugal 20min of 10000rpm low-temperature and high-speed, promptly get the 5 extract.Adopt the lowry method to measure protein content, carry the content that total protein content in the thing is represented the 5 extract, extract is put into little centrifuge tube preserve down at-70 ℃ with enzyme, standby.
(2) 5 suppresses determination of activity:
Operation divides two portions to finish, the nettle driffractive ring wood fat glycosides A sample, positive control drug, NADPH and the enzyme tissue juice that promptly 1. 37 ℃ of constant temperature damping fluids of reacted constituent, testosterone, embodiment 1 are prepared add in 96 orifice plates successively, make it traceization, differential responses hole and contrast orifice plate are set.Temperature of reaction is 37 ℃ (relative saturation humidity), and the reaction times is 60min;
2. adopt EL ISA standard measure to measure product D HT, reflect the power of enzymic activity with the growing amount size of product.When the content of DHT is lower than in the enzyme reaction pipe DHT content in the given the test agent pipe, then be considered as having the activity that suppresses 5.Detection method and calculating are carried out with reference to testosterone test kit (purchasing the company in Adlitteram Diagnostic Laboratories) operation instruction.All experimental ports are two multiple hole operations.On the reaction system basis of determining, coenzyme NADP 11 concentration is 1mmolL
-1, testosterone concentration is 0.5 μ molL
-1,, the total amount of whole reaction system is decided to be 200 μ l in conjunction with the characteristics of testosterone test kit microdetermination.
The original concentration of each component is respectively in the enzyme reaction system: buffered soln (PBS 20mmolL-1, sucrose 0.2molL
-1, EDTA Na
21mmolL
-1, pH6.8); NADPH concentration (20mmolL
-1); Thick enzyme concn (4.3mgml
-1); Testosterone concentration (20 μ molL
-1); Finasteride (1.3mmolL
-1).Measurement result sees Table 2.
Table 2 nettle diffractive cyclolignan anthocyanin A suppresses the 5 effect
The A of nettle driffractive ring lignanoid can significantly suppress the generation of DHT as can be seen from the above table, and is suitable with the positive drug finasteride.
Claims (2)
1. 5-alpha reductase inhibitor-nettle diffractive cyclolignan anthocyanin A is characterized in that its molecular structural formula is as follows:
2. the preparation method of the described a kind of 5-alpha reductase inhibitor of claim 1-nettle diffractive cyclolignan anthocyanin A is characterized in that this method is to be raw material with the Herba Urticae triangularis, and step is as follows:
(1) with Herba Urticae triangularis dryly after the pulverization process of lower section, be 95% industrial alcohol refluxing extraction with mass concentration, filter the back concentrating under reduced pressure;
(2) with the water suspendible of alcohol extract with 50-90 ℃, with sherwood oil, ethyl acetate, water-saturated n-butanol extraction, each extracts three times successively;
(3) n-butyl alcohol extract separates through macroporous resin D101, and the employing mass concentration is 30% ethanol elution, collects elutriant;
(4) ethanol eluate silica gel column chromatogram separating purification, the employing volume ratio is a chloroform: methyl alcohol=30: 1,10: 1,5: 1,3: 1,1: 1 gradient elution, collect elutriant;
(5) elutriant of step (4) is through the reversed-phase silica gel column chromatography separation and purification, and the employing volume ratio is a methyl alcohol: the eluant solution of water=3: 7, every 15-30ml is gathered into 1 part, collects 15-20 part elutriant, merges to obtain nettle diffractive cyclolignan anthocyanin A after concentrating.
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| CN1850979A (en) * | 2006-03-07 | 2006-10-25 | 谭兴起 | Chinese starjasmine stem lignin aglycone total extract and its extracting process |
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