CN110183415B - One of two color jackfruits diphenyl ethylene derivatives and its purposes in preparation treatment diseases associated with inflammation drug - Google Patents
One of two color jackfruits diphenyl ethylene derivatives and its purposes in preparation treatment diseases associated with inflammation drug Download PDFInfo
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
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Abstract
The present invention relates to a kind of diphenyl ethylene derivatives and it preparation treatment diseases associated with inflammation drug in application.The diphenyl ethylene derivatives are from two color jackfruit of Moraceae jackfruit platymisciumArtocarpus styracifoliusAn isolated noval chemical compound in Pierre is named as (±)-two color polo phenol C, has a structure in which.The compound has strong inhibitory activity, IC to Polymorphonuclear Leukocyte respiratory burst50For 4.24 ± 0.58 uM, treatment diseases associated with inflammation drug can further be prepared, syndrome, systemic toxin are reacted for various oxidative damages caused by clinical treatment neutrophil leucocyte excessive activation, such as rheumatoid arthritis, Compensatory Anti-Inflammatory.
Description
Technical field
The invention belongs to field of medicaments, and in particular to one of two color jackfruits diphenyl ethylene derivatives are treated in preparation
Application in diseases associated with inflammation drug.
Background technique
Neutrophil leucocyte (PMNs) is a kind of candidate stem cell from marrow, in marrow after differentiation and development, into
Enter blood or tissue, serves as the direct effect cell of body nospecific immunity.When the invasion of external pathogen, PMNs is swashed
It is living, a large amount of oxygen are consumed, superoxide anion, hydroxy radical, hydrogen peroxide and the hypochlorous acid isoreactivity oxygen of high activity are generated
(ROS), this phenomenon is known as neutrophil leucocyte " respiratory burst ".The ROS that respiratory burst of PMN generates has two aspects
Physiological function: on the one hand, the pathogenic microorganism of invasion can be efficiently eliminated, maintains body health；On the other hand, ROS can pass through
Lipid peroxidation insult normal surrounding tissue, and the signaling molecule as inflammatory reaction, raise the table of inflammation-related gene
It reaches, amplifies inflammatory effector.Under normal physiological conditions, it is maximally efficient to form body by accuracy controlling for the respiratory burst of PMNs
Pathogen resist mechanism.But under some pathological conditions, PMNs is caused serious by excessive activation, a large amount of ROS of generation
Diseases associated with inflammation.The very classical example that myocardial ischemia-reperfusion injury caused by PMNs respiratory burst is just.When cardiac muscle lacks
When blood, anoxic then lead to blood, logical oxygen again for a period of time, a large amount of PMNs for being gathered in ischemic region are activated rapidly, while activation is deposited
It is reduced Coenzyme II inactive in cell membrane (NADPH) oxidizing ferment, induces PMNs respiratory burst, oxygen demand increases, and is
Under normal circumstances 2-20 times.At this moment on the one hand PMNs swallows tissue and cell fragment, and discharges contained in its cytoplasmic granule
A variety of enzymes are come kill and degrade tissue and cell fragment, antigen antibody complex and other foreign matters, to eliminate pathogen and inflammation
Deng；On the other hand, by being catalyzed O2Consumption generate a large amount of reactive oxygen metabolite, peroxidating occurs with lipid on cell membrane
Reaction generates lipid peroxide, destroys permeability of cell membranes, changes eucaryotic cell structure, eventually leads to cell death, cause tissue
With the damage of organ.For another example in Patients With Rheumatoid Arthritis, neutrophil leucocyte is made by wrongful activation, a large amount of ROS of generation
At the corrosion of articular cartilage tissue.For another example septicopyemia or surgical injury, wound, in burn, the PMNs meeting of excessive activation
Cause tissue damage, runaway inflammatory reaction, including compensatory anti-inflammatory response syndrome (cARS), whole body inflammation are caused when serious
Disease response syndrome (SIRS) etc..Thus, it is found that inhibiting the substance of PMNs respiratory burst for caused by treatment PMNs respiratory burst
Various inflammatory injuries be of great significance.
Separation identification structure novel, the significant natural products of activity are always the main way of new drug discovery from natural drug
One of diameter.Two color jackfruits (Artocarpus styracifoliusPierre a kind of) the arbor tree belonged to for Moraceae jackfruit
Kind.According to records, two color jackfruits have multiple pharmaceutical usage, such as treatment psoriasis, diabetes and hemiplegia etc. civil.Modernization
It learns and pharmacological research shows that the root of two color jackfruits is rich in a large amount of isopentene group phenolic constituent, these ingredients have extensive
Pharmacological activity.This seminar finds in the screening active ingredients of early period, the chloroform extraction portion of two color jackfruit roots, 95% ethanol extract
Position is demonstrated by stronger inhibitory activity to rat PMN s respiratory burst.Therefore, the present invention has carried out the active site deep
Research.
Summary of the invention
The object of the present invention is to provide having to inhibit the active substance of PMNs respiratory burst, breathed for clinically with PMNs quick-fried
The treatment for sending out related inflammation provides drug.More particularly to a kind of diphenyl ethylene derivatives extracted in two color jackfruit roots, have
Chemical structure as follows:
。
The compound is to have no noval chemical compound reported in the literature, is a racemic modification, is named as (±)-two color polo phenol
C。
The further object of the present invention is to provide above compound and is preparing anti-inflammatory (with PMNs respiratory burst related inflammation)
New application in drug.
Compound of the present invention is prepared by following methods:
Two color jackfruit roots, 13.9 Kg is taken, is leaked and is extracted with 95% ethyl alcohol, 1.3 Kg of medicinal extract is concentrated under reduced pressure to obtain in extracting solution.Leaching
Cream is suspended with 1 L water, successively uses petroleum ether, chloroform, ethyl acetate and extracting n-butyl alcohol (volume ratio 2:1), and be concentrated into respectively
It is dry.Chloroform is taken to extract 118.9 g of position medicinal extract, HP-20 macroporous absorbent resin is mixed sample (weight ratio 1:1), upper HP-20 type macropore
Adsorption resin column (column specification: 10*45 cm) obtains 6 flow point Frs. H1- with alcohol-water (0 ~ 95%) gradient elution
H6.50% ethanol elution fraction Fr. H4 (44.8 g) passes through ODS column chromatography (column specification: 4*22 cm), MeOH-H2O (body
Product is than 6:4,7:3,8:2,9:1,10:0) gradient elution, obtain 15 flow point Frs. H4O1-H4O15.Flow point Fr.
H4O3 (4.6 g) is through MCI CHP-20P resin column chromatography (column specification: 4*45 cm), MeOH-H2O (volume ratio 6:4,
7:3,8:2,9:1,10:0) gradient elution, obtain 5 flow point Frs. H4O3M1-H4O3M5.Flow point Fr. H4O3M3
(1.8 g) further across Sephadex LH-20 gel column chromatography (column specification: 2*200 cm), methanol elutes to obtain 6 streams
Divide Frs. H4O3M3L1-H4O3M3L6.From flow point Fr. H4O3M3L1 (0.2 g) by preparation HPLC column chromatography (column rule
Lattice: 2*25 cm), 50% acetonitrile elution, obtain-two color polo phenol C of compound (±) of the present invention (3.0 mg,t R
40 min)。
By screening active ingredients it is experimentally confirmed that-two color polo phenol C of diphenyl ethylene derivatives of the present invention (±) is to Buddhist
The Polymorphonuclear Leukocyte outburst of wave acetate (PMA) stimulation has significant inhibiting effect, half-inhibitory concentration
(IC50) reaching 4.24 ± 0.58 uM, activity is better than positive control Vc (IC50 = 24.51±1.64 uM)。
- two color polo phenol C of diphenyl ethylene derivatives (±) of the present invention can be further prepared into treatment PMNs breathing
Break out the drug of caused inflammation out of control.
Detailed description of the invention
Fig. 1 is the chemical structural formula of (±)-two color polo phenol C.
Fig. 2 be-two color polo phenol C of noval chemical compound (±) of the present invention nuclear magnetic resonance spectroscopy (1H NMR)。
Fig. 3 be-two color polo phenol C of noval chemical compound (±) of the present invention carbon-13 nmr spectra (13C NMR)。
The nuclear magnetic resonance DEPT 135 that Fig. 4 is-two color polo phenol C of noval chemical compound (±) of the present invention is composed.
Fig. 5 is the nuclear magnetic resonance of-two color polo phenol C of noval chemical compound (±) of the present invention1H-1H COSY spectrum.
Fig. 6 is the nuclear magnetic resonance hsqc spectrum of-two color polo phenol C of noval chemical compound (±) of the present invention.
The nuclear magnetic resonance HMBC that Fig. 7 is-two color polo phenol C of noval chemical compound (±) of the present invention is composed.
Fig. 8 is that the main HMBC (H → C) of-two color polo phenol C of noval chemical compound (±) of the present invention is related to COSY.
Specific embodiment
The present invention can be further well understood in the specific embodiment being given by the following.
The preparation of-two color polo phenol C of diphenyl ethylene derivatives (±) in 1 two color jackfruit of embodiment
Two color jackfruit roots, 13.9 Kg is taken, is leaked and is extracted with 95% ethyl alcohol, 1.3 Kg of medicinal extract is concentrated under reduced pressure to obtain in extracting solution.Leaching
Cream is suspended with 1 L water, successively uses petroleum ether, chloroform, ethyl acetate and extracting n-butyl alcohol (volume ratio 2:1), and be concentrated into respectively
It is dry.Chloroform is taken to extract 118.9 g of position medicinal extract, HP-20 macroporous absorbent resin is mixed sample (weight ratio 1:1), upper HP-20 type macropore
Adsorption resin column (column specification: 10*45 cm) obtains 6 flow point Frs. H1- with alcohol-water (0 ~ 95%) gradient elution
H6.50% ethanol elution fraction Fr. H4 (44.8 g) passes through ODS column chromatography (column specification: 4*22 cm), MeOH-H2O (body
Product is than 6:4,7:3,8:2,9:1,10:0) gradient elution, obtain 15 flow point Frs. H4O1-H4O15.Flow point Fr.
H4O3 (4.6 g) is through MCI CHP-20P resin column chromatography (column specification: 4*45 cm), MeOH-H2O (volume ratio 6:4,
7:3,8:2,9:1,10:0) gradient elution, obtain 5 flow point Frs. H4O3M1-H4O3M5.Flow point Fr. H4O3M3
(1.8 g) further across Sephadex LH-20 gel column chromatography (column specification: 2*200 cm), methanol elutes to obtain 6 streams
Divide Frs. H4O3M3L1-H4O3M3L6.Flow point H4O3M3L1 (0.2 g) is by preparation HPLC column chromatography (column specification: 2*25
Cm), 50% acetonitrile elute, obtain-two color polo phenol C of compound (±) of the present invention (3.0 mg,t R 40
min)。
The Structural Identification of-two color polo phenol C of diphenyl ethylene derivatives (±) in 2 two color jackfruit of embodiment
(±)-two color polo phenol C, a kind of Yellow amorphous powder (methanol).HR-ESI-MS provides quasi-molecular ion peakm/z 379.1907 ([M-H]-, calculated value: 379.1915), determine its molecular formula be C24H28O4.(±)-two color polo phenol C
's1H H NMR spectroscopy (600 MHz, methanol-d 4) show following proton signal: a set of fragrance ABX spin coupling system matter
Sonδ H 7.16 (1 H, d, J = 8.5 Hz, H-7), 6.31 (1 H, dd, J=8.5,2.5 Hz, H-8) and
6.16 (1 H, d, J= 2.5 Hz, H-10);The aromatic of a pair of of meta position couplingδ H 6.24 (1 H, d, J =
2.3 Hz, H-4) and 6.19 (1 H, d,J= 2.3 Hz, H-2);A set of 1,1- dimethallyl fundamental mode isoprene
Substituent group protonδ H 5.84 (1 H, dd, J = 17.9, 10.4 Hz, H-23), 4.95 (1 H, dd, J = 17.9,
1.3 Hz, H α -24), 4.94 (1 H, dd, J = 10.4, 1.3 Hz, H β -24), 1.14 (3H, s, H3- 21) and
0.99 (3H, s, H3-22).In addition, through analyzing (±)-two color polo phenol C's1H-1H COSY, HSQC and HMBC spectrum, can
Following 11 protons are spliced into two structure fragment-CH-CH-CH-CH interconnected2And-CH-C (Me2) O-:δ H
3.19 (1 H, d, J = 4.0 Hz, H α -5), 2.85 (1 H, dd, J = 12.0, 4.0 Hz, H-6), 1.20
(1 H, td, J = 12.0, 2.8 Hz, H-13), 2.91 (1 H, dd, J = 14.3, 2.8 Hz, H α -14),
2.01 (1 H, t, J = 13.1 Hz, H β -14), 1.40 (3 H, s, H3- 18) and 1.31 (3 H, s, H3-19)
(table 1).(±)-two color polo phenol C's1H H NMR spectroscopy and known compound hypargystilbene B are closely similar, main
Difference has been (±)-two color polo phenol C more than a low field area aromatic protons signalδ H 6.31, and high field region exists originally
The signal of H-5 is belonged in hypargystilbene Bδ H 2.47 disappear in the hydrogen spectrum of (±)-two color polo phenol C.This is strong
Strong prompt 1,1- dimethyl-allyl replaces generation in C-5 rather than C-8.This speculates the support for obtaining HMBC data: H3-
21 (δ H And H 1.14)3-22 (δ H 0.99) with C-5 (δ C 51.6) there are HMBC correlations；H-23 (δ H And C-5 5.84)
There is HMBC related (Fig. 8).In addition, we further determined that the oxidation of A ring and B ring replaces class by analysis HMBC data
Type.Coupling constant between H-6 and H-13J 6.13 For 12.0 Hz, this shows that C-6 and C-13 has anti relative configuration.Herein
On the basis of, hydrogen, carbon signal (table 1) in the one-dimensional NMR spectrum of our full ownerships (±)-two color polo phenol C.After tested, (±)-
The optical activity of two color polo phenol C is 0, and circular dichroism spectra, which also shows it, does not have Cotton effect (Cotton effect), this prompt
(±)-two color polo phenol C is a racemic modification.We further use chiral column [Phenomenex Lux Cellulose-2
column (5 μ250 × 4.6 mm of M, i.d.)] HPLC analysis has been carried out to (±)-two color polo phenol C, the results showed that,
It is mobile phase (3:1, v/v) in acetonitrile-water, under conditions of 1.2 mL/min of flow velocity, (±)-two color polo phenol C shows peak
Area ratio is two chromatographic peaks of 1:1.This further demonstrates that (±)-two color polo phenol C is one by equivalent enantiomter
The racemic modification of composition.Therefore, we finally determine that the chemical structure of (±)-two color polo phenol C is [6aS(R),12R(S),
12aS(R)] -6,6- dimethyl -12- (1,1- dimethyl-allyl) -6a, 7,12,12a- tetrahydro -6HNaphtho- [2,3-c] chromogen
Alkene -3,8,10- triol.Its structural formula is as shown in Figure 1.
The nuclear magnetic resonance spectroscopy and carbon modal data of-two color polo phenol C of table 1 (±)
- two color polo phenol C of embodiment 3 (±) tests the Cytotoxic evaluation of rat PMN s
Using the separation of following experimental procedure, purification of rat PMNs.Take (Jiangxi University of Traditional Chinese Medicine's experiment of cleaning grade SD rat
Animal center, animal certificate number: JZDW2011304), eye socket takes 9 mL of blood, and vertical instillation is anticoagulant with 1 mL, 1% heparin sodium
In good glass centrifuge tube.It is mixed with the glucan T-500 normal saline solution that the ratio of 5:1 is added 4.5%, 4 °C stand about 1
Hour.Supernatant is taken, is added in the centrifuge tube for being pre-loaded with lymphocyte separation medium in the ratio of 3:1,800 rev/min (275g) centrifugation 15 minutes, centrifuge tube is taken out, three layers are divided in pipe, upper layer is faint yellow serum, and white misty area in middle part is monocyte
And lymphocyte, that lower layer is deposited to tube bottom is PMNs.Supernatant is abandoned, the special separating liquid rinsing of 2 mL is added once, after oscillation
In 2500 rev/min (531g) centrifugation 5 minutes.Supernatant is abandoned, in each centrifuge tube plus 2 mL distilled waters, piping and druming are vibrated
After 20 seconds (being swollen red blood cell), 2 mL of NaCl solution of addition 1.8% is mixed immediately, and 2500 rev/min (531g) from
The heart 5 minutes, supernatant is abandoned, repeats this operation, until achroacyte remains.Again with HBSS-FCS buffer rinsing 1-2 times, use every time
2 mL of HBSS-FCS solution, at 2500 rev/min (531g) centrifugation 3 minutes, discard supernatant liquid.PMNs is separated to obtain, again
2 mL of HBSS-FCS buffer is added, mixes, trypan blue staining surveys vigor (vigor > 95% of PMNs in 3 h), 4 °C of preservations
It is spare as cell mother's suspension.
Cytotoxicity of pertinent literature measurement (±)-two color polo phenol C of reference standard trypanblue exclusion method to PMNs.It takes
50 μL PMNs cell mother's suspension, being diluted to cell concentration with the HBSS liquid of 2% calf serum is 2 × 106A/mL.Take 1 mL
PMNs cell diluent and 10μL DMSO or (±)-two color polo phenol C (dissolved with DMSO, final concentration range from 1 to
1000 μM it) mixes, is incubated for 30 minutes under 37 °C.112 are added in every part of sampleμThe trypan blue dye liquor of L 0.4%, high power are micro-
Under mirror, sample is calculated to the cytotoxic effect of PMNs by counting the case where 100 cells absorb trypan blue.As a result table
Bright, (±)-two color polo phenol C just starts to show the toxicity to PMNs in 150 uM or more.
Measurement of-two color polo phenol C of embodiment 4 (±) to rat PMN s respiratory burst inhibiting rate
Rat PMN s cell mother's suspension is prepared using step same as Example 3.Take 50μL PMNs cell mother's suspension,
Being diluted to cell concentration with the HBSS liquid of 2% calf serum is 2 × 106A/mL.4 °C save backup.PMNs is by exogenous
Respiratory burst occurs after stimulant-Fo Bo acetate (phorbol) (PMA) activation, it is free to generate a large amount of active oxygen
Base, free radical by luminous agent luminol capture generate chemiluminescence (Chemiluminesence, CL), PMN-CL intensity with
The cell quantity of PMNs and the respiratory burst of PMNs and phagocytic function are positively correlated.BPCL-K superweak luminescence measuring instrument (Chinese section
Beijing biophysics research institute, institute, mating BPCL Appl.7.2 data processing stations) parameter setting are as follows: shine pond temperature
37 °C, 800 V of voltage value, 1800 s of longest detection time, 5 s of counting time period.Instrument is preheated into half an hour using preceding, and
Walk baseline.After baseline is steady, takes 1 ml PMNs cell diluent in glow cup, 200 are added theretoμL luminol work
Make liquid, is placed in superweak luminescence measuring instrument and is incubated for 10 min (parameter setting: luminous 37 °C of pond temperature, 800 V of voltage, longest
Detection time 1800 s), records spontaneous photoreduction process (5 s of counting time period).Then 10 are addedμL sample solution is (with 10μL DMSO is blank control) continue to measure 5 min, 8ugml is added-1PMA stimulant 10μL continues to measure 15 min,
Record measurement result.PMN-CL intensity is indicated with the numeration peak height that shines.PMN-CL inhibiting rate is calculated by formula (1).
PMN-CL inhibiting rate (%)=×100% (1)
Using PMN-CL inhibiting rate as ordinate, sample concentration is abscissa, establishes amount effect relation curve, passes through amount effect curve
Concentration (the i.e. IC for calculating sample when the inhibiting rate that shines is 50% can be sought50Value).With vitamin C (Vc) it is used as positive control.Knot
Fruit shows that (±)-two color polo phenol C has significant inhibiting effect, IC to the rat PMN s outburst that PMA is stimulated50It is 4.24
± 0.58 uM is better than positive control Vc (IC50 = 24.51±1.64 uM)。
Claims (3)
1. a kind of-two color polo phenol C of diphenyl ethylene derivatives (±), it is characterised in that the compound has change as shown below
Learn structure:
。
2.-two color polo phenol C of a kind of diphenyl ethylene derivatives (±) according to claim 1 and its can physiologically receive
Salt preparation treatment diseases associated with inflammation drug in application.
3.-two color polo phenol C of a kind of diphenyl ethylene derivatives (±) as described in claim 2 and its can physiologically receive
Salt preparation treatment diseases associated with inflammation drug in application, it is characterised in that diseases associated with inflammation refer to rheumatoid arthritis,
Compensatory Anti-Inflammatory reacts syndrome, systemic toxin.
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