CN106967085B - A kind of phloroglucinol derivatives compound and its application in preparation antibacterials - Google Patents
A kind of phloroglucinol derivatives compound and its application in preparation antibacterials Download PDFInfo
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Abstract
The present invention discloses a kind of phloroglucinol derivatives noval chemical compound and its application in preparation antibacterials.Compound structure is shown in formula I, including two pairs of enantiomters, it is named as (+) Myrtucyclitone A, (-) Myrtucyclitone A, (+) Myrtucyclitone B and (-) Myrtucyclitone B.Above compound structure novel, with significant antibacterial activity, the especially activity of methicillin-resistant staphylococcus aureus resistance and vancomycin intermediary resistant Staphylococcus aureus is better than ampicillin and cefotaxime, and it is very low to normal cell toxicity, indicate that they have good prospect in medicine, can be applied to preparation antibacterials.
Description
Technical field
The invention belongs to natural drug and chemical medicine field, in particular to a kind of phloroglucinol derivatives compound and its making
Application in standby antibacterials.
Background technique
Bacterium infection is common disease and frequently-occurring disease.Currently, drug-fast bacteria infection clinically is on the rise, bacterial resistance is presented
The trend developed out to multidrug resistance, methicillin-resistant staphylococcus aureus (MRSA), resistance to ampicillin streptococcus pneumonia
(PRSP) and the sprawling rapidly such as multidrug resistance tubercle bacillus (MDR-TB).Drug-fast bacteria infection is increasing and the death rate
It is stepped up, illustrates that traditional antibacterials are no longer satisfied the needs of modern clinical treatment.Therefore, novel antibacterial is researched and developed
Drug has important clinical value.
Myrtle (Myrtus communis Linn.) is Myrtaceae (Myrtaceae) Myrtle, is originated in
Mediterranean Region, be often used as preservative and disinfectant etc. (Journal of Ethnopharmacology, 1984,11:275-
281).Myrtle essential oil or its extract have stronger antibacterial activity (Phytochemistry, 2006,67:1249-
1255).1974, Rotstein A etc. was found to have the acyl phloroglucinol class compound of antibacterial activity from myrtle for the first time
Myrtucommulones A-B(Antimicrobial Agents and Chemotherapy,1974,6:539-542).Closely
Nian Lai, have phloroglucin constituents Myrtucommulones C-E in document report myrtle have good antibacterial and
Hypoglycemic activity (European Journal of Organic Chemistry, 2006,10:2371-2377).As it can be seen that isophthalic
Three phenolic compounds may be the main active of myrtle.However, current myrtle phloroglucinol derivatives chemical component is ground
Study carefully and do not go deep into still, only reports less than 20 compounds.Therefore, Antibacterial Constituents need to be goed deep into excavation.
Summary of the invention
The primary purpose of the present invention is that the shortcomings that overcoming the prior art and deficiency, provide a kind of isophthalic three of structure novel
Phenolic compound.
Another object of the present invention is to provide the applications of the phloroglucinol derivatives compound.
The purpose of the invention is achieved by the following technical solution: a kind of phloroglucinol derivatives compound is named as (+)
Myrtucyclitones A-B and (-) Myrtucyclitones A-B, structure are shown in formula I:
In Formulas I, (+) Myrtucyclitone A's is configured as 1S, 9S, 10S, 17S, 1'R, 6'S；(-)
Myrtucyclitone A's is configured as 1R, 9R, 10R, 17R, 1'S, 6'R；(+) Myrtucyclitone B's is configured as 1S,
9S,10S,17R,1'S,6'R；(-) Myrtucyclitone B's is configured as 1R, 9R, 10R, 17S, 1'R, 6'S.
The phloroglucinol derivatives compound is isolated to extract from myrtle branches and leaves, the specific steps are as follows: will be fragrant
Mahogany branches and leaves crush, and are extracted with 95% (w/w) ethanol percolation, pass through silica gel column chromatography, Sephadex LH- after extract concentration
20, octadecyl silane (ODS) column chromatography and preparative HPLC isolate and purify, and obtain (±) Myrtucyclitones A-
B further splits to obtain optically pure enantiomter using chirality HPLC.
Application of the phloroglucinol derivatives compound in preparation antibacterials.
The antibacterials include a effective amount of as (+) Myrtucyclitone A of active constituent or (+)
Myrtucyclitone B or (-) Myrtucyclitone A or (-) Myrtucyclitone B and pharmaceutically acceptable
Carrier.
The bacterium bag includes staphylococcus aureus, methicillin-resistant staphylococcus aureus, vancomycin intermediary drug resistance
Staphylococcus aureus, staphylococcus epidermis, enterococcus faecalis, enterococcus faecium, escherichia coli and pseudomonas aeruginosa.
The present invention has the following advantages and effects with respect to the prior art:
(1) present invention finds the phloroglucinol derivatives compound of structure novel a kind of in myrtle, it is named as (+)
Myrtucyclitones A-B and (-) Myrtucyclitones A-B, the ring that this kind of compound is made of 38 carbon atoms
Polyketone-phloroglucin-ring polyketone tripolymer, and one of ring polyketone segment is reset, and is to have novel skeleton structure
Chemical entities.
(2) present invention discover that (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B are in low concentration
I.e. to staphylococcus aureus, methicillin-resistant staphylococcus aureus and vancomycin intermediary drug resistance gold under (2~4 μ g/mL)
Portugal bacterium all has significant antibacterial activity, and activity is better than positive drug ampicillin and cefotaxime.
(3) (+) Myrtucyclitones A-B of the invention and (-) Myrtucyclitones A-B is to eukaryocyte poison
Property is very low.
Detailed description of the invention
Fig. 1 is phloroglucinol derivatives compound (±) Myrtucyclitone A1H NMR spectra.
Fig. 2 is phloroglucinol derivatives compound (±) Myrtucyclitone A13C NMR spectra.
Fig. 3 is the hsqc spectrum figure of phloroglucinol derivatives compound (±) Myrtucyclitone A.
Fig. 4 is the HMBC spectrogram of phloroglucinol derivatives compound (±) Myrtucyclitone A.
Fig. 5 is the CD spectrogram of phloroglucinol derivatives compound (+) Myrtucyclitone A.
Fig. 6 is the CD spectrogram of phloroglucinol derivatives compound (-) Myrtucyclitone A.
Fig. 7 is phloroglucinol derivatives compound (±) Myrtucyclitone B1H NMR spectra.
Fig. 8 is phloroglucinol derivatives compound (±) Myrtucyclitone B13C NMR spectra.
Fig. 9 is the hsqc spectrum figure of phloroglucinol derivatives compound (±) Myrtucyclitone B.
Figure 10 is the HMBC spectrogram of phloroglucinol derivatives compound (±) Myrtucyclitone B.
Figure 11 is the CD spectrogram of phloroglucinol derivatives compound (+) Myrtucyclitone B.
Figure 12 is the CD spectrogram of phloroglucinol derivatives compound (-) Myrtucyclitone B.
Specific embodiment
Present invention will now be described in further detail with reference to the embodiments and the accompanying drawings, but embodiments of the present invention are unlimited
In this.
The extraction separation of 1 compound of embodiment and Structural Identification
(1) dry myrtle branches and leaves 8kg is weighed, pulverizer is ground into coarse powder, it is extracted 4 times with 95% (w/w) ethanol percolation,
Each 25L merges percolate and is concentrated under reduced pressure into no alcohol taste, obtained total medicinal extract about 1.2kg.Medicinal extract uses petroleum after adding water to be suspended
Ether extraction, obtains petroleum ether extraction position 389g.
(2) silica gel column chromatography is carried out to the petroleum ether extraction position that step (1) is prepared, with petroleum ether-ethyl acetate
For eluant, eluent, according to petroleum ether and ethyl acetate volume ratio be 100:0,100:1,100:3,100:5,100:7,100:10,
The gradient of 100:30,100:50,100:100 and 0:100 are eluted, and are analyzed and are merged similar through thin-layer chromatography (TLC)
Fraction obtains 10 mainstream part Fr.1~Fr.10.Wherein fraction Fr.5 (petrol ether/ethyl acetate 100:7 elution fraction, 70g)
Continue on through silica gel column chromatography, according to petroleum ether and ethyl acetate volume ratio be 100:0,100:1,100:3,100:5,100:7,
The gradient of 100:10,100:30,100:50,100:100 are eluted, and 9 Arius part Fr.5A~Fr.5I are obtained.
(3) 1. to Arius part Fr.5B obtained in step (2) (petrol ether/ethyl acetate 100:1 elution fraction,
12.8g), Sephadex LH-20 chromatographic column is splined on after concentration, with chloroform-methanol (CHCl3- MeOH) by volume 1:1 it is mixed
Closing obtained mixed solvent is mobile phase, and flow velocity is that 0.5mL/min is eluted, and collects eluent (elution volume 50-
1000mL), similar fraction is analyzed and merged through TLC, obtains 4 fraction Fr.5B-1~Fr.5B-4.
2. the fraction Fr.5B-3 (elution volume 300-500mL) (0.8g) that step (3) is 1. obtained carries out reverse phase ODS column
Chromatography, with methanol-water (MeOH-H2O) be eluant, eluent, according to methanol and water volume ratio be 60:40,70:30,80:20,90:10,
The gradient of 100:0 is eluted, and the elution fraction that methanol-water volume ratio is 80:20 is collected.
3. being dissolved after the eluent that step (3) 2. obtains is concentrated with methanol, then separated with Reverse phase preparative HPLC pure
Change, using volume ratio for 90:10 methanol-water as eluant, eluent, flow velocity be 3mL/min eluted, collect retention time 14.4min
With the chromatographic peak of 18.4min, (±) Myrtucyclitone A (46.8mg) and (±) Myrtucyclitone B are obtained
(27.6mg)。
4. (±) Myrtucyclitone A chiral HPLC column (Phenomenex, Lux that step (3) is 3. obtained
Cellulose-1) isolate and purify, using volume ratio for 65:35 acetonitrile-water as eluant, eluent, flow velocity be 1mL/min eluted,
The chromatographic peak for collecting retention time 14.8min and 15.5min, obtains (+) Myrtucyclitone A (19.8mg) and (-)
Myrtucyclitone A(19.4mg)。
5. (±) Myrtucyclitone B chiral HPLC column (Phenomenex, Lux that step (3) is 3. obtained
Cellulose-1) isolate and purify, using volume ratio for 60:40 acetonitrile-water as eluant, eluent, flow velocity be 1mL/min eluted,
The chromatographic peak for collecting retention time 21.9min and 22.9min, obtains (+) Myrtucyclitone B (11.9mg) and (-)
Myrtucyclitone B(12.6mg)。
(4) the 1. Structural Identification of (±) Myrtucyclitone A
Faint yellow flat crystal；Vanillic aldehyde-strong sulfuric acid response (TLC) displaing amaranth；UV(CHCl3)λmax(logε)242
(3.43),294(5.39)nm；IR(KBr)νmax 3477,2958,1703,1623,1462,1385,1256,1117,1033,
860cm-1；HR-ESI-MS m/z 653.3689[M+H]+(calculated value C38H53O9,653.3684).Hydrogen spectrum (1H NMR) and carbon spectrum
(13C NMR) data are shown in Table 1.1H NMR,13C NMR, HSQC and HMBC nuclear magnetic resonance map is shown in Fig. 1~4.According to the above physical and chemical number
According to and NMR data, identify (±) Myrtucyclitone A structure as shown in formula I.Wherein (+) Myrtucyclitone A:+37.8(c1.12,CHCl3), CD map is shown in Fig. 5；(-) Myrtucyclitone A:-35.6(c 1.23,
CHCl3), CD map is shown in Fig. 6.
The Structural Identification of (2. ±) Myrtucyclitone B
Faint yellow flat crystal；Vanillic aldehyde-strong sulfuric acid response (TLC) displaing amaranth；UV(CHCl3)λmax(logε)242
(2.39),294(4.70)nm；IR(KBr)νmax 3418,2931,1698,1616,1461,1387,1250,1160,1135,
1092,923,863,757cm-1；HR-ESI-MS m/z 653.3687[M+H]+(calculated value C38H53O9,653.3684).Hydrogen spectrum
(1H NMR) and carbon spectrum (13C NMR) data are shown in Table 2.1H NMR,13C NMR, HSQC and HMBC nuclear magnetic resonance map is shown in Fig. 7-10.
According to the above physicochemical data and NMR data, the structure of (±) Myrtucyclitone B is identified as shown in formula I, wherein (+)
MyrtucyclitoneB:+33.9(c 0.81,CHCl3), CD map is shown in Figure 11；(-) Myrtucyclitone B:
-32.1(c 0.83,CHCl3), CD map is shown in Figure 12.
Table 1. (±) Myrtucyclitone A's1H (500MHz) and13C (125MHz) NMR data
Note: (solvent CDCl3, δ unit is ppm, and J unit is Hz)
Table 2. (±) Myrtucyclitone B's1H (500MHz) and13C (125MHz) NMR data
Note: (solvent CDCl3, δ unit is ppm, and J unit is Hz)
Embodiment 2 (+) Myrtucyclitones A-B and inhibition of (-) Myrtucyclitones A-B to various bacteria
Effect
Staphylococcus aureus S.aureus ATCC29213, methicillin-resistant staphylococcus aureus S.aureus
ATCC33591 (MRSA), vancomycin intermediary resistant Staphylococcus aureus S.aureus Mu50 (VISA), epidermis grape ball
Bacterium S.epidermidis ATCC12228, enterococcus faecalis E.faecalis ATCC29212, enterococcus faecium E.faecium 13-
01, escherichia coli E.coli ATCC25922, pseudomonas aeruginosa Ps.Aeruginosa, are all from the Chinese Academy of Medical Sciences
Institute of Medicinal Biological Technique.
Using the micro doubling dilution of meat soup, the minimal inhibitory concentration (MIC) of Compound ira vitro bacteriostasis is measured, specifically
Operating method is as follows:
(1) Bacteria Culture: with Mueller-Hinton (MH) broth bouillon culture experiment bacterium, when it grows 8-12h extremely
About 0.5 Mcfarland concentration (1 × 108It is spare when CFU).
(2) in ethanol by test sample dissolution, 1000 μ g/mL are diluted to culture solution.Continuing to be diluted with culture solution makes
Sample concentration range is from 256 μ g/mL to 0.25 μ g/mL.In addition, preparing certain density ampicillin and cefotaxime conduct
Positive control.
(3) medical fluid and 100 μ L bacterium solutions of 100 μ L various concentrations is added in every hole on 96 orifice plates, makes final bacterial concentration 5
×104CFU adds bacterium solution as negative control (each 100 μ of TSB culture medium, bacterium solution using trypticase soy broth (TSB)
L), the TSB broth bouillon blank control (200 μ L of TSB culture medium) of bacterium solution is not added, 96 pore plate by sealing are placed on 37 DEG C of perseverances
In warm incubator, it is incubated for 20h.
(4) precondition is grown to obviously with bacterium in negative control hole, observed by the naked eye, with bacterium in dosing metapore
It is the MIC (μ g/mL) of the drug without the drug minimum concentration obviously grown, experiment is parallel in triplicate.It the results are shown in Table 3.
The results show that compound (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B are to golden yellow
It is living that staphylococcus, methicillin-resistant staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus all have significant antibacterial
Property, MIC value is 2~4 μ g/mL；There is stronger antibacterial activity, MIC value 4 to staphylococcus epidermis, enterococcus faecalis, enterococcus faecium
~16 μ g/mL；There is certain antibacterial activity to Escherichia coli and pseudomonas aeruginosa, MIC value is 64~128 μ g/mL.Especially
It is that above compound is living to the antibacterial of staphylococcus aureus, Methicillin-resistant Staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus
Property better than the clinical commonly used drugs such as ampicillin, cefotaxime, this is of great significance for researching and developing the drug of antimicrobial agent.This
(+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B of invention are totally different from as molecular structure
There are the new chemical entities of antibacterials, there is good activity for drug-fast bacteria, it is most likely that is as new chemical entities development
Novel antibacterial drug.
Table 3. (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B makees the inhibition of various bacteria
With
Embodiment 3 (+) Myrtucyclitones A-B and influence of (-) Myrtucyclitones A-B to normal cell
Test method: human embryonic kidney cells HEK 293 (be purchased from Shanghai Cell Bank of the Chinese Academy of Sciences) is in containing 10% (v/v) tire
The DMEM culture medium culture of cow's serum and dual anti-(penicillin and each 100U/ml of streptomysin) are washed with PBS to logarithmic phase,
The trypsin digestion of 0.25% (w/v), then uses fresh DMEM medium suspension cell, and adjustment cell density is 1 × 106
A/ml spreads 96 orifice plates, and every 200 μ l of hole adds the sample of various concentration after cell is adherent, in 37 DEG C, 5%CO2Under the conditions of altogether
Culture 24 hours, after culture, 20 μ l 5mg/ml MTT solution are added in every hole, are continued to cultivate 4h, are sucked out in hole with liquid-transfering gun
100 μ l DMSO are added in liquid, every hole, and jog 10 minutes, the suction in each hole is detected with microplate reader at 570nm wavelength at room temperature
Luminosity OD value.Inhibitory rate of cell growth is calculated according to the following formula, repeats experiment at least 3 times or more.Inhibitory rate of cell growth calculates
Formula: inhibiting rate (%)=(1- dosing group OD value)/control group OD value × 100%.It the results are shown in Table 4.
Test result is shown: even if under the high concentration of 200 μ g/ml, the compound of the present invention (+)
Myrtucyclitones A-B and (-) Myrtucyclitones A-B are to the only table of human normal cell line embryonic kidney cell HEK 293
Reveal very low cytotoxicity, inhibitory rate of cell growth 9.25-12.01%.
Cytotoxicity of table 4. (+) the Myrtucyclitones A-B and (-) Myrtucyclitones A-B to HEK 293
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (4)
1. a kind of phloroglucinol derivatives compound, it is characterised in that: there is structure shown in Formulas I, be named as (+)
Myrtucyclitones A-B and (-) Myrtucyclitones A-B；
In Formulas I, (+) Myrtucyclitone A's is configured as 1S, 9S, 10S, 17S, 1'R, 6'S；(-)Myrtucyclitone
A's is configured as 1R, 9R, 10R, 17R, 1'S, 6'R；(+) Myrtucyclitone B's is configured as 1S, 9S, 10S, 17R, 1'S,
6'R；(-) Myrtucyclitone B's is configured as 1R, 9R, 10R, 17S, 1'R, 6'S.
2. application of the phloroglucinol derivatives compound described in claim 1 in preparation antibacterials.
3. application of the phloroglucinol derivatives compound according to claim 2 in preparation antibacterials, it is characterised in that: institute
The antibacterials stated include a effective amount of (+) Myrtucyclitone A or (+) Myrtucyclitone as active constituent
B or (-) Myrtucyclitone A or (-) Myrtucyclitone B and pharmaceutically acceptable carrier.
4. application of the phloroglucinol derivatives compound according to claim 2 or 3 in preparation antibacterials, feature exist
In: the bacterium is that staphylococcus aureus, staphylococcus epidermis, enterococcus faecalis, enterococcus faecium, escherichia coli and verdigris are false
At least one of monad.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000016791A1 (en) * | 1998-09-17 | 2000-03-30 | Pierre Fabre Dermo-Cosmetique | Myrtle extract, preparation method and use |
| CN1563014A (en) * | 2004-04-16 | 2005-01-12 | 杭州民生药业集团有限公司 | New compound ramification of garcinia acid |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000016791A1 (en) * | 1998-09-17 | 2000-03-30 | Pierre Fabre Dermo-Cosmetique | Myrtle extract, preparation method and use |
| CN1563014A (en) * | 2004-04-16 | 2005-01-12 | 杭州民生药业集团有限公司 | New compound ramification of garcinia acid |
Non-Patent Citations (2)
| Title |
|---|
| Isolation and Antibacterial Activity of Acylphloroglucinols from Myrtus communis;A. Rotstein等;《Antimicrobial Agents and Chemotherapy》;19741231;第6卷;539-542 * |
| New α-Glucosidase Inhibitors and Antibacterial Compounds from Myrtus communis L.;Farzana Shaheen 等;《Eur. J. Org. Chem.》;20060308;第10卷;2371–2377 * |
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