CN106967085A - A kind of phloroglucinol derivatives noval chemical compound and its application in antibacterials are prepared - Google Patents

A kind of phloroglucinol derivatives noval chemical compound and its application in antibacterials are prepared Download PDF

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CN106967085A
CN106967085A CN201610029289.9A CN201610029289A CN106967085A CN 106967085 A CN106967085 A CN 106967085A CN 201610029289 A CN201610029289 A CN 201610029289A CN 106967085 A CN106967085 A CN 106967085A
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myrtucyclitone
antibacterials
phloroglucinol derivatives
chemical compound
staphylococcus aureus
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CN106967085B (en
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王磊
叶文才
刘超
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Jinan University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07B2200/07—Optical isomers
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    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Abstract

The present invention discloses a kind of phloroglucinol derivatives noval chemical compound and its application in antibacterials are prepared.Compound structure is shown in formula I, including two pairs of enantiomters, (+) Myrtucyclitone A, (-) Myrtucyclitone A, (+) Myrtucyclitone B and (-) Myrtucyclitone B are named as.Above-claimed cpd structure is novel, with notable antibacterial activity, the activity of especially methicillin-resistant staphylococcus aureus resistance and vancomycin intermediary resistant Staphylococcus aureus is better than ampicillin and cefotaxime, and it is very low to normal cytotoxicity, they have good prospect in medicine for indication, can apply to prepare antibacterials.

Description

A kind of phloroglucinol derivatives noval chemical compound and its application in antibacterials are prepared
Technical field
The invention belongs to natural drug and chemical medicine field, more particularly to a kind of phloroglucinol derivatives noval chemical compound And its application in antibacterials are prepared.
Background technology
Bacterium infection is common disease and frequently-occurring disease.At present, drug-fast bacteria infection clinically is on the rise, bacterium Resistance shows the trend developed to multidrug resistance, methicillin-resistant staphylococcus aureus (MRSA), resistance to Ampicillin streptococcus pneumonia (PRSP) and multidrug resistance tubercle bacillus (MDR-TB) etc. are rapid Spread.Drug-fast bacteria infection is increasing and the death rate is stepped up, and illustrates that traditional antibacterials can not expire The need for sufficient modern clinical treatment.Therefore, research and development novel antibacterial medicine has important clinical practice valency Value.
Myrtle (Myrtus communis Linn.) is Myrtaceae (Myrtaceae) Myrtle, Originate 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. had found there is antibacterial activity from myrtle first Acyl phloroglucinol class compound Myrtucommulones A-B (Antimicrobial Agents and Chemotherapy,1974,6:539-542).In recent years, there are the phloroglucinol derivatives in document report myrtle Composition Myrtucommulones C-E have good antibacterial and hypoglycemic activity (European Journal of Organic Chemistry,2006,10:2371-2377).It can be seen that, phloroglucinol derivatives compound is probably fragrant peach The main active of wood.However, the research of myrtle phloroglucinol derivatives chemical composition at present is not goed deep into still, Only report less than 20 compounds.Therefore, its Antibacterial Constituents needs deep excavation.
The content of the invention
The primary and foremost purpose of the present invention is to overcome the shortcoming and deficiency of prior art novel there is provided a kind of structure Phloroglucinol derivatives noval chemical compound.
Another object of the present invention is to provide the application of described phloroglucinol derivatives noval chemical compound.
The purpose of the present invention is achieved through the following technical solutions：A kind of phloroglucinol derivatives noval chemical compound, is named as (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B, structure is 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 configuration For 1S, 9S, 10S, 17R, 1'S, 6'R；(-) Myrtucyclitone B's is configured as 1R, 9R, 10R, 17S, 1'R, 6'S。
Described phloroglucinol derivatives noval chemical compound is extracts isolated from myrtle branches and leaves, and specific steps are such as Under：Myrtle branches and leaves are crushed, extracted with 95% (w/w) ethanol percolation, silica gel is passed through after extract concentration Column chromatography, Sephadex LH-20, octadecyl silane (ODS) column chromatography and preparation HPLC point From purifying, (±) Myrtucyclitones A-B are obtained, is further split using chirality HPLC and obtains optically pure Enantiomter.
Application of the described phloroglucinol derivatives noval chemical compound in antibacterials are prepared.
Described antibacterials include effective dose as active component (+) Myrtucyclitone A or (+) Myrtucyclitone B or (-) Myrtucyclitone A or (-) Myrtucyclitone B and it can pharmaceutically connect The carrier received.
Described bacterium bag is included in staphylococcus aureus, methicillin-resistant staphylococcus aureus, vancomycin Jie's resistant Staphylococcus aureus, MRSE, enterococcus faecalis, VREF, EHEC and Pseudomonas aeruginosa.
The present invention has the following advantages and effect relative to prior art：
(1) present invention finds the novel phloroglucinol derivatives compound of a class formation in myrtle, it is named as (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B, this kind of compound is by 38 carbon atoms Ring polyketone-phloroglucin-ring polyketone the tripolymer of composition, and one of ring polyketone fragment resets, and is tool There are the chemical entities of novel skeleton structure.
(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 under (2~4 μ g/mL) Intermediary's drug-resistant staphylococcus aureus are respectively provided with significant antibacterial activity, its activity be better than positive drug ampicillin and cephalo he Pyridine.
(3) (+) Myrtucyclitones A-B of the invention and (-) Myrtucyclitones A-B are to eukaryotic poison Property is very low.
Brief description of the drawings
Fig. 1 is phloroglucinol derivatives compound (±) Myrtucyclitone A1H NMR spectras.
Fig. 2 is phloroglucinol derivatives compound (±) Myrtucyclitone A13C NMR spectras.
Fig. 3 is phloroglucinol derivatives compound (±) Myrtucyclitone A hsqc spectrum figure.
Fig. 4 is phloroglucinol derivatives compound (±) Myrtucyclitone A HMBC spectrograms.
Fig. 5 is phloroglucinol derivatives compound (+) Myrtucyclitone A CD spectrograms.
Fig. 6 is phloroglucinol derivatives compound (-) Myrtucyclitone A CD spectrograms.
Fig. 7 is phloroglucinol derivatives compound (±) Myrtucyclitone B1H NMR spectras.
Fig. 8 is phloroglucinol derivatives compound (±) Myrtucyclitone B13C NMR spectras.
Fig. 9 is phloroglucinol derivatives compound (±) Myrtucyclitone B hsqc spectrum figure.
Figure 10 is phloroglucinol derivatives compound (±) Myrtucyclitone B HMBC spectrograms.
Figure 11 is phloroglucinol derivatives compound (+) Myrtucyclitone B CD spectrograms.
Figure 12 is phloroglucinol derivatives compound (-) Myrtucyclitone B CD spectrograms.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention Not limited to this.
The extraction separation of the compound of embodiment 1 and Structural Identification
(1) dry myrtle branches and leaves 8kg is weighed, pulverizer is ground into coarse powder, with 95% (w/w) ethanol Seepage pressure effects 4 times, each 25L merges percolate and is concentrated under reduced pressure into no alcohol taste, obtained total medicinal extract is about 1.2kg.Medicinal extract add water suspension after use petroleum ether extraction, obtain petroleum ether extraction position 389g.
(2) the petroleum ether extraction position that is prepared to step (1) carries out silica gel column chromatography, with petroleum ether- Ethyl acetate is eluant, eluent, is 100 according to petroleum ether and ethyl acetate volume ratio:0、100:1、100:3、100:5、 100:7、100:10、100:30、100:50、100:100 and 0:100 gradient is eluted, through thin Layer chromatography (TLC) is analyzed and merges similar stream part, obtains 10 main flows part Fr.1~Fr.10.Wherein stream part Fr.5 (petrol ether/ethyl acetates 100:7 elution fractions, 70g) silica gel column chromatography is continued on through, according to petroleum ether It is 100 with ethyl acetate volume ratio:0、100:1、100:3、100:5、100:7、100:10、100:30、100:50、 100:100 gradient is eluted, and obtains 9 Arius part Fr.5A~Fr.5I.
(3) Arius part Fr.5B (petrol ether/ethyl acetates 100 1. to being obtained in step (2):1 elution portion Point, 12.8g), Sephadex LH-20 chromatographic columns are splined on after concentration, with chloroform-methanol (CHCl3-MeOH) By volume 1:1 mixed solvent being mixed to get is mobile phase, and flow velocity is that 0.5mL/min is eluted, and is received Collect eluent (elution volume 50-1000mL), analyzed through TLC and merge similar stream part, obtain 4 streams Part Fr.5B-1~Fr.5B-4。
2. the stream part Fr.5B-3 (elution volume 300-500mL) (0.8g) that step (3) is 1. obtained is entered The anti-phase ODS column chromatographies of row, with methanol-water (MeOH-H2O it is) eluant, eluent, according to methanol and water volume ratio For 60:40、70:30、80:20、90:10、100:0 gradient is eluted, and collects methanol-water volume Than for 80:20 elution stream part.
3. dissolved after eluent concentration step (3) 2. obtained with methanol, then use Reverse phase preparative HPLC Isolate and purify, using volume ratio as 90:10 methanol-water is eluant, eluent, and flow velocity is that 3mL/min is eluted, Retention time 14.4min and 18.4min chromatographic peak are collected, (±) Myrtucyclitone A (46.8mg) are obtained (±) Myrtucyclitone B (27.6mg).
4. step (3) is 3. obtained the chiral HPLC columns of (±) Myrtucyclitone A (Phenomenex, Lux Cellulose-1) isolate and purify, using volume ratio as 65:35 acetonitrile-water is eluant, eluent, and flow velocity is 1 ML/min is eluted, and is collected retention time 14.8min and 15.5min chromatographic peak, is obtained (+) Myrtucyclitone A (19.8mg) and (-) Myrtucyclitone A (19.4mg).
5. step (3) is 3. obtained the chiral HPLC columns of (±) Myrtucyclitone B (Phenomenex, Lux Cellulose-1) isolate and purify, using volume ratio as 60:40 acetonitrile-water is eluant, eluent, and flow velocity is 1 ML/min is eluted, and is collected retention time 21.9min and 22.9min chromatographic peak, is obtained (+) Myrtucyclitone B (11.9mg) and (-) Myrtucyclitone B (12.6mg).
(4) 1. (±) Myrtucyclitone A Structural Identification
Faint yellow flat crystal；Vanillic aldehyde-strong sulfuric acid response (TLC) displaing amaranth；UV(CHCl3)λmax(log ε)242(3.43),294(5.39)nm；IR(KBr)νmax3477,2958,1703,1623,1462,1385, 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 maps are shown in Fig. 1~4.According to above physicochemical data and NMR data, mirror Fixed (±) Myrtucyclitone A structure is as shown in formula I.Wherein (+) Myrtucyclitone A： CD collection of illustrative plates is shown in Fig. 5；(-)Myrtucyclitone A： CD collection of illustrative plates is shown in Fig. 6.
2. (±) Myrtucyclitone B Structural Identification
Faint yellow flat crystal；Vanillic aldehyde-strong sulfuric acid response (TLC) displaing amaranth；UV(CHCl3)λmax(log ε)242(2.39),294(4.70)nm；IR(KBr)νmax3418,2931,1698,1616,1461,1387, 1250,1160,1135,1092,923,863,757cm-1；HR-ESI-MS m/z 653.3687[M+H]+(meter Calculation 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 maps are shown in Fig. 7-10.According to above physicochemical data and NMR data, identification (±) Myrtucyclitone B structure is as shown in formula I, wherein (+) Myrtucyclitone B：CD collection of illustrative plates is shown in Figure 11；(-)Myrtucyclitone B： CD collection of illustrative plates is shown in Figure 12.
Table 1. (±) Myrtucyclitone A's1H (500MHz) and13C (125MHz) NMR data
Note：(solvent is CDCl3, δ units are ppm, and J units are Hz)
Table 2. (±) Myrtucyclitone B's1H (500MHz) and13C (125MHz) NMR data
Note：(solvent is CDCl3, δ units are ppm, and J units are Hz)
Embodiment 2 (+) Myrtucyclitones A-B and suppressions of (-) Myrtucyclitones A-B to various bacteria Make and use
Staphylococcus aureus S.aureus ATCC29213, methicillin-resistant staphylococcus aureus S. Aureus ATCC33591 (MRSA), vancomycin intermediary resistant Staphylococcus aureus S.aureus Mu50 (VISA), MRSE S.epidermidis ATCC12228, enterococcus faecalis E.faecalis ATCC29212, VREF E.faecium 13-01, EHEC E.coli ATCC25922, verdigris Pseudomonad Ps.Aeruginosa, is all from Inst. of Medicinal Biological Technology, Chinese Academy of Medical Sciences.
Using the micro doubling dilution of meat soup, the minimal inhibitory concentration of Compound ira vitro bacteriostasis is determined (MIC), concrete operation method is as follows：
(1) Bacteria Culture：With Mueller-Hinton (MH) broth bouillon culture experiment bacterium, when its life Long 8-12h to about 0.5 Mcfarland concentration (1 × 108It is standby when CFU).
(2) by test sample dissolving in ethanol, 1000 μ g/mL are diluted to nutrient solution.Continuation is cultivated Liquid dilution makes sample concentration scope from 256 μ g/mL to 0.25 μ g/mL.In addition, preparing certain density ammonia Benzyl XiLin and cefotaxime are used as positive control.
(3) decoction and 100 μ L bacterium solutions of 100 μ L various concentrations are added per hole on 96 orifice plates, is made most Whole bacterial concentration is 5 × 104CFU is right using trypticase soy broth (TSB) plus bacterium solution as feminine gender According to (each 100 μ L of TSB culture mediums, bacterium solution), to be not added with the TSB broth bouillon blank controls of bacterium solution (the μ L of TSB culture mediums 200), will be placed in 37 DEG C of constant incubators after 96 pore plate by sealing, be incubated 20h.
(4) precondition is substantially grown to bacterium in negative control hole, observed by the naked eye, after dosing Bacterium tests parallel repetition without the MIC (μ g/mL) that the medicine least concentration substantially grown is the medicine in hole Three times.It the results are shown in Table 3.
As a result show, compound (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B are to golden yellow Staphylococcus, methicillin-resistant staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus are respectively provided with significantly Antibacterial activity, MIC value be 2~4 μ g/mL；To MRSE, enterococcus faecalis, VREF tool There is stronger antibacterial activity, MIC value is 4~16 μ g/mL；Have one to Escherichia coli and pseudomonas aeruginosa Fixed antibacterial activity, MIC value is 64~128 μ g/mL.Especially above-claimed cpd is to Staphylococcus aureus The antibacterial activity of bacterium, Methicillin-resistant Staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus better than ampicillin, The clinical commonly used drugs such as cefotaxime, this is significant for the medicine for researching and developing antimicrobial agent.The present invention (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B be totally different from as molecular structure There is the new chemical entities of antibacterials, there is good activity for drug-fast bacteria, it is most likely that be used as new chemistry Entity develops into novel antibacterial medicine.
Inhibitory action of table 3. (+) the Myrtucyclitones A-B and (-) Myrtucyclitones A-B to various bacteria
Shadows of embodiment 3 (+) the Myrtucyclitones A-B and (-) Myrtucyclitones A-B to normal cell Ring
Test method：Human embryonic kidney cells HEK 293 (be purchased from Chinese Academy of Sciences's Shanghai cell bank) is in containing 10% (v/v) hyclone and dual anti-(penicillin and each 100U/ml of streptomysin) DMEM medium cultures are extremely Logarithmic phase, is washed with PBS, 0.25% (w/v) Trypsin Induced, is then trained with fresh DMEM Base suspension cell is supported, adjustment cell density is 1 × 106Individual/ml, spreads 96 orifice plates, per the μ l of hole 200, treats thin After born of the same parents are adherent, plus various concentrations sample, in 37 DEG C, 5%CO2Under the conditions of co-culture 24 hours, culture After end, 20 μ l 5mg/ml MTT solution are added per hole, continues to cultivate 4h, is suctioned out with liquid-transfering gun in hole Liquid, 100 μ l DMSO is added per hole, at room temperature jog 10 minutes, with ELIASA in 570nm wavelength The absorbance OD values in the place each hole of detection.Inhibitory rate of cell growth is calculated by following equation, experiment is repeated extremely It is few more than 3 times.Inhibitory rate of cell growth calculation formula：Inhibiting rate (%)=(1- dosing group OD values)/right According to group OD value × 100%.It the results are shown in Table 4.
Result of the test is shown：Under 200 μ g/ml high concentration, compound of the invention (+) Myrtucyclitones A-B and (-) Myrtucyclitones A-B are to human normal cell line embryonic kidney cell HEK 293 only show very low CDCC, and inhibitory rate of cell growth is 9.25-12.01%.
Cytotoxicities of table 4. (+) the Myrtucyclitones A-B and (-) Myrtucyclitones A-B to HEK 293
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-mentioned implementation of the invention The change made under the limitation of example, other any Spirit Essences and principle without departing from the present invention, modify, replace Generation, combination, simplification, should be equivalent substitute mode, are included within protection scope of the present invention.

Claims (4)

1. a kind of phloroglucinol derivatives noval chemical compound, it is characterised in that：With structure shown in Formulas I, named For (+) 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 configuration For 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 noval chemical compound in antibacterials are prepared described in claim 1.
3. application of the phloroglucinol derivatives noval chemical compound according to claim 2 in antibacterials are prepared, It is characterized in that：Described antibacterials include (+) Myrtucyclitone A as active component of effective dose Or (+) Myrtucyclitone B or (-) Myrtucyclitone A or (-) Myrtucyclitone B and pharmaceutically can be with The carrier of receiving.
4. the answering in antibacterials are prepared of the phloroglucinol derivatives noval chemical compound according to Claims 2 or 3 With, it is characterised in that：Described bacterium be staphylococcus aureus, methicillin-resistant staphylococcus aureus, It is vancomycin intermediary resistant Staphylococcus aureus, MRSE, enterococcus faecalis, VREF, big At least one of the uncommon bacterium of intestines angstrom and pseudomonas aeruginosa.
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Publication number Priority date Publication date Assignee Title
CN107912434A (en) * 2017-12-08 2018-04-17 江汉大学 The application of three phenolic compounds and anti-biotic material
CN110172016A (en) * 2019-06-11 2019-08-27 中国科学院昆明植物研究所 Benzalcohol derivatives and its pharmaceutical composition are applied with it
CN117683002A (en) * 2024-02-01 2024-03-12 暨南大学 Phloroglucinol derivative and preparation method and application thereof

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107912434A (en) * 2017-12-08 2018-04-17 江汉大学 The application of three phenolic compounds and anti-biotic material
CN107912434B (en) * 2017-12-08 2020-08-04 江汉大学 Application of triphenol compounds and antibacterial material
CN110172016A (en) * 2019-06-11 2019-08-27 中国科学院昆明植物研究所 Benzalcohol derivatives and its pharmaceutical composition are applied with it
CN110172016B (en) * 2019-06-11 2021-11-16 中国科学院昆明植物研究所 Benzyl alcohol compound, pharmaceutical composition and application thereof
CN117683002A (en) * 2024-02-01 2024-03-12 暨南大学 Phloroglucinol derivative and preparation method and application thereof
CN117683002B (en) * 2024-02-01 2024-04-19 暨南大学 Phloroglucinol derivative and preparation method and application thereof

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