CN110183312B - A kind of isopentene group talan and its purposes in preparation treatment diseases associated with inflammation drug - Google Patents
A kind of isopentene group talan and its purposes in preparation treatment diseases associated with inflammation drug Download PDFInfo
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- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
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- C07—ORGANIC CHEMISTRY
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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Abstract
The present invention relates to a kind of isopentene group talan and it preparation treatment diseases associated with inflammation drug in application.The isopentene group talan is from two color jackfruit of Moraceae jackfruit platymisciumArtocarpus styracifoliusAn isolated noval chemical compound in Pierre is named as (±)-two color polo phenol A, has a structure in which.The compound has strong inhibitory activity, IC to Polymorphonuclear Leukocyte respiratory burst50It is 2.62 ± 0.35 μM, 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 isopentene group diphenylethylene compounds
Application in preparation treatment diseases associated with inflammation drug.
Background technique
Neutrophil leucocyte (PMNs) is the first line of defence that human body resists external pathogen invasion.When PMNs identify by
It is fast through the activation for causing cell receptor-mediated on film after the complex that the small peptide of body secretion or bacterium and Serum Antibody are formed
Speed generates a large amount of superoxide anion (O2 •-)。O2 •-One is had occurred under the catalysis of superoxide dismutase and myeloperoxidase
Serial free chain reaction produces various active oxygens (ROS), including hydroxy radical (HO), hydrogen peroxide (H2O2)
And hypochlorous acid (HOCl).These ROS can efficiently eliminate the pathogenic microorganism of invasion, and this phenomenon is known as respiratory burst.
Under normal physiological conditions, the respiratory burst of PMNs is formd the maximally efficient pathogen of body and is resisted mechanism by accuracy controlling.
However, ROS can also cause to damage while killing invasion bacterium to normal surrounding tissue, obstruction microcirculation, damage blood are caused
Endothelial cell and extravascular tissue cell, release and promotion release inflammatory mediator, become " saboteur ".Such as rheumatoid arthritis
In patient, for neutrophil leucocyte by wrongful activation, a large amount of ROS of generation cause the corrosion of articular cartilage tissue.For another example septicopyemia
Mass formed by blood stasis or surgical injury, wound, burn, in ischemical reperfusion injury, the PMNs of excessive activation can cause tissue damage, sternly
Lead to runaway inflammatory reaction, including compensatory anti-inflammatory response syndrome (cARS), systemic inflammatory response syndrome when weight
(SIRS) etc..Thus, it is found that inhibiting the substance of PMNs respiratory burst for various oxidisability caused by treatment PMNs respiratory burst
Damage is 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 isopentene group talan extracted in two color jackfruit roots, tool
Have it is following shown in chemical structure:
。
The compound is to have no noval chemical compound reported in the literature, is a racemic modification, is named as (±)-two color polo
Phenol A.
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.Flow point H4O3M3L2 (0.3 g) is by preparation HPLC column chromatography (column specification: 2*25
Cm), 50% acetonitrile elute, obtain-two color polo phenol A of compound (±) of the present invention (40.3 mg,t R 45
min)。
By screening active ingredients it is experimentally confirmed that-two color wave of isopentene group diphenylethylene compounds (±) of the present invention
Sieve phenol A has significant inhibiting effect, half suppression to the Polymorphonuclear Leukocyte outburst that Buddhist wave acetate (PMA) stimulates
Concentration (IC processed50) reach 2.62 ± 0.35μM, activity are better than positive control Vc (IC50 = 24.51±1.64 μM)。
- two color polo phenol A of isopentene group diphenylethylene compounds (±) of the present invention, which can be further prepared into, to be controlled
Treat the drug of PMNs respiratory burst caused inflammation out of control.
Detailed description of the invention
Fig. 1 is the chemical structural formula of (±)-two color polo phenol A.
Fig. 2 be-two color polo phenol A of noval chemical compound (±) of the present invention nuclear magnetic resonance spectroscopy (1H NMR)。
Fig. 3 be-two color polo phenol A 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 A of noval chemical compound (±) of the present invention is composed.
Fig. 5 is the nuclear magnetic resonance of-two color polo phenol A 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 A of noval chemical compound (±) of the present invention.
The nuclear magnetic resonance HMBC that Fig. 7 is-two color polo phenol A of noval chemical compound (±) of the present invention is composed.
The nuclear magnetic resonance NOESY that Fig. 8 is-two color polo phenol A of noval chemical compound (±) of the present invention is composed.
Fig. 9 be-two color polo phenol A of noval chemical compound (±) of the present invention main HMBC (H → C) and1H-1H COSY
(H → H) is related.
Specific embodiment
The present invention can be further well understood in the specific embodiment being given by the following.
Embodiment 1
The preparation of-two color polo phenol A of isopentene group talan (±) in two color jackfruits:
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 H4O3M3L2 (0.3 g) is by preparation HPLC column chromatography (column specification: 2*25
Cm), 50% acetonitrile elute, obtain-two color polo phenol A of compound (±) of the present invention (40.3 mg,t R 45
min)。
Embodiment 2
The Structural Identification of-two color polo phenol A of isopentene group talan (±) in two color jackfruits:
(±)-two color polo phenol A, a kind of Yellow amorphous powder (acetone).HR-ESI-MS provides quasi-molecular ion peakm/z 379.1906 ([M-H]-, calculated value: 379.1915), determine its molecular formula be C24H28O4.Its ultraviolet spectra is shown
Non-conjugated aromatic ring characteristic absorption (λ max211 and 285 nm), prompting (±)-two color polo phenol A may be two diphenyl hydrogens
Ethene derivatives.(±)-two color polo phenol A's1H H NMR spectroscopy (600 MHz, acetone-d 6) show following proton letter
Number: the aromatic protons of a pair of of meta position couplingδ H 6.23 (1 H, d, J=2.3 Hz, H-2) and 6.07 (1 H, d,J
= 2.3 Hz, H-4);Two aromatic protons occurred with single peak formδ H6.98 (1 H, s, H-7) and 6.37 (1
H, s, H-10);One 1,1- dimethallyl fundamental mode isoprene substituent groupδ H 6.24 (1 H, dd, J = 17.5,
10.6 Hz, H-23), 4.97 (1 H, dd, J = 17.5, 1.6 Hz, H α -24), 4.93 (1 H, dd, J =
10.6, 1.6 Hz, H β - 24) and 1.42 (6 H, s, H3- 21,22) (table 1).Other 11 proton signals can recognize are as follows:
One end alkeneδ H 4.75 (1 H, d, J = 2.3 Hz, H a - 18) and 4.56 (1 H, m, H b -18)；Two methyleneδ H 2.77 (1 H, dd, J = 16.5, 5.5 Hz, H α -5), 2.74 (1 H, dd, J = 16.5, 11.8 Hz,
H β -5), 2.84 (1 H, dd, J = 16.2, 5.3 Hz, H α - 14) and 2.56 (1 H, dd,J = 16.2, 11.8
Hz, H β -14)；Two methinesδ H 3.28 (1 H, td, J = 11.8,5.5 Hz, H-6) and 2.87 (1 H, td,J = 11.8, 5.3 Hz, H-13)；One unimodal methylδ H 1.58 (3 H, s, H3- 19) (table 1).Analyze (±)-two
Color polo phenol A's1H-1This 11 protons can be spliced two structure pieces interconnected by H COSY, HSQC and HMBC spectrum
Section-CH2–CH–CH–CH2And-CH-C (Me)=CH2.Below to the further analysis of HSQC and HMBC data, make we determined that
The chemical structure of (±)-two color polo phenol A.H3-21/22 (δ H1.42) and H-23 (δ H6.24) with C-8 (δ C125.4)
With HMBC long-range related (Fig. 9), this shows that 1.1- dimethyl-allyl is connected on C-8.The HMBC relevant peaks of some keys
It confirmed such structure fragment, that is, one end of C ring is condensed by C-15/C-16 and A ring in (±)-two color polo phenol A, separately
One end be connected to B ring C-17:H-5 (δ H2.77) with C-4 (δ C106.8)、C-15 (δ C115.1)、C-16 (δ C139.6)
With C-17 (δ C122.1) related；H-6 (δ H3.28) with C-5 (δ C39.4)、C-7 (δ C127.8)、C-11 (δ C154.2)、
C-13 (δ C47.8) have to C-17 related；H-13 (δ H2.87) related to C-15 and C-17；H α /H β -14 (δ H2.84/
2.56) and C-1 (δ C156.4)、C-6 (δ C37.1) (Fig. 9) related to C-16.And segment-CH-C (Me)=CH2It is connected to C
On the C-13 of ring, it can also be confirmed by following HMBC correlation: H a /H b -18 (δ H4.75/4.56) and C-12 (δ C149.6), C-
13 and C-19 (δ C18.8) related；H-13 and C-12, C-18 (δ C111.6) (Fig. 9) related to C-19.Above data, really
It accepts the planar structure of (±)-two color polo phenol A.Pass through the coupling constant between H-6 and H-13J 6.13 =11.8 Hz, can be with
Judge the relative configuration between C-6 and C-13 to be trans-, this can be composed by NOESY in H-6 and H a /H b - 18 and H3- 19 NOE
Correlation is further confirmed.On the basis of these data, the one-dimensional NMR spectrum of our full ownerships (±)-two color polo phenol A
In hydrogen, carbon signal (table 1).After tested, the optical activity of (±)-two color polo phenol A is 0, and circular dichroism spectra, which also shows it, not to be had
Cotton effect (Cotton effect), this prompt (±)-two color polo phenol A is a racemic modification.We further use hand
Property column [Phenomenex Lux Cellulose-2 column (5μ250 × 4.6 mm of M, i.d.)] to (±)-two
Color polo phenol A has carried out HPLC analysis, the results showed that, it is mobile phase (3:1, v/v), 1.2 mL/min of flow velocity in acetonitrile-water
Under conditions of, (±)-two color polo phenol A shows that peak area ratio is two chromatographic peaks of 1:1.This further demonstrates that (±)-
Two color polo phenol A are a racemic modification being made of equivalent enantiomter.Therefore, we finally determine (±)-two color wave
The structure of sieve phenol A is [6S(R),7S(R)] -6- [2,4- dihydroxy -5- (1,1- dimethyl-allyl) phenyl] -7- (propyl- 1- alkene -
2- yl) -5,6,7,8- naphthane -1,3- glycol, structural formula is as shown in Figure 1.
The nuclear magnetic resonance spectroscopy and carbon modal data of-two color polo phenol A of table 1 (±)
Embodiment 3
(±)-two color polo phenol A 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 A of reference standard trypanblue exclusion method to PMNs.
Take 50μL PMNs cell mother's suspension, being diluted to cell concentration with the HBSS liquid of 2% calf serum is 2 × 106A/mL.Take 1
The PMNs cell diluent of mL and 10μL DMSO or (±)-two color polo phenol A (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 A is 150μM or more just starts to show the toxicity to PMNs.
Measurement of-two color polo phenol A 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 solvent control) continue to measure 5 min, it is added 8μg·ml-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).
(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 A has significant inhibiting effect, IC to the rat PMN s outburst that PMA is stimulated50It is 2.62
±0.35 μM is better than positive control Vc (IC50 = 24.51±1.64 μM)。
Claims (3)
1. a kind of-two color polo phenol A of isopentene group diphenylethylene compounds (±), it is characterised in that the compound have with
Chemical structure shown in lower:
。
2.-two color polo phenol A of a kind of isopentene group diphenylethylene compounds (±) according to claim 1 and its physiology
Application of the upper acceptable salt in preparation treatment diseases associated with inflammation drug.
3.-two color polo phenol A of a kind of isopentene group diphenylethylene compounds (±) as described in claim 2 and its physiology
Application of the upper acceptable salt in preparation treatment diseases associated with inflammation drug, it is characterised in that diseases associated with inflammation refers to rheumatoid
Property arthritis, Compensatory Anti-Inflammatory react syndrome, systemic toxin.
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