CN107417697B - A kind of phloroglucin derivative and its application in preparation antibacterials - Google Patents
A kind of phloroglucin derivative and its application in preparation antibacterials Download PDFInfo
- Publication number
- CN107417697B CN107417697B CN201610347417.4A CN201610347417A CN107417697B CN 107417697 B CN107417697 B CN 107417697B CN 201610347417 A CN201610347417 A CN 201610347417A CN 107417697 B CN107417697 B CN 107417697B
- Authority
- CN
- China
- Prior art keywords
- myrtucyclitone
- staphylococcus aureus
- phloroglucin
- derivative
- phloroglucin derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of phloroglucin derivative and its applications in preparation antibacterials, and the phloroglucin derivative is (±) Myrtucyclitone C and (±) Myrtucyclitone D, and structure is shown in formula I.Ring polyketone-phloroglucin-ring polyketone the tripolymer that (±) Myrtucyclitone C and (±) Myrtucyclitone D are made of 38 carbon atoms, and one of ring polyketone segment is reset, and is the chemical entities with novel skeleton structure；Such compound all has significant antibacterial activity to staphylococcus aureus, methicillin-resistant staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus under low concentration, very low to eukaryocyte toxicity.
Description
Technical field
The invention belongs to natural drug and chemical medicine field, in particular to a kind of phloroglucin derivative and its preparing
Application in 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 is often used as preservative and disinfectant etc..Myrtle essential oil or its extract have stronger antibacterial activity.
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 are needed to be studied and are excavated.
Summary of the invention
The primary purpose of the present invention is that providing a kind of phloroglucin derivative of structure novel.
Another object of the present invention is to provide application of the above-mentioned phloroglucin derivative in preparation antibacterials.
The purpose of the invention is achieved by the following technical solution:
A kind of phloroglucin derivative is (±) Myrtucyclitone C and (±) Myrtucyclitone D, structure
Shown in formula I；(±) Myrtucyclitone C is enantiomter, and configuration is respectively 1S, 9S, 10S, 17S and 1R, 9R,
10R,17R；(±) Myrtucyclitone D is enantiomter, and configuration is respectively 1S, 9S, 10S, 17R and 1R, 9R, 10R,
17S；
The separating and extracting process of above-mentioned phloroglucin derivative is the following steps are included: by myrtle (Myrtus communis
Linn.) branches and leaves crush, and are extracted with 95% (w/w) ethanol percolation, use petroleum ether extraction after extract concentration, then pass through silicagel column
Chromatography, Sephadex LH-20, octadecyl silane (ODS) column chromatography and preparative HPLC isolate and purify, and obtain above-mentioned
Phloroglucin derivative.
Above-mentioned phloroglucin derivative can be used for preparing antibacterials；
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 antibacterials further include pharmaceutically acceptable auxiliary material.
The present invention has the following advantages and effects with respect to the prior art:
(1) present invention finds the phloroglucin derivatives of structure novel a kind of in myrtle, (±) preferably wherein
Myrtucyclitone C and (±) Myrtucyclitone D.The ring polyketone-that this kind of compound is made of 38 carbon atoms
Phloroglucin-ring polyketone tripolymer, and one of ring polyketone segment is reset, and is that the chemistry with novel skeleton structure is real
Body.
(2) present invention discover that (±) Myrtucyclitone C and (±) Myrtucyclitone D low concentration (2~
4 μ g/mL) under i.e. to staphylococcus aureus, methicillin-resistant staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus
All have significant antibacterial activity.
(3) (±) Myrtucyclitone C of the invention and (±) Myrtucyclitone D to eukaryocyte toxicity very
It is low.
Detailed description of the invention
Fig. 1 is phloroglucin derivative (±) Myrtucyclitone C1H NMR spectra.
Fig. 2 is phloroglucin derivative (±) Myrtucyclitone C13C NMR spectra.
Fig. 3 is the hsqc spectrum figure of phloroglucin derivative (±) Myrtucyclitone C.
Fig. 4 is the HMBC spectrogram of phloroglucin derivative (±) Myrtucyclitone C.
Fig. 5 is the X-ray diffraction structure chart of phloroglucin derivative (±) Myrtucyclitone C.
Fig. 6 is phloroglucin derivative (±) Myrtucyclitone D1H NMR spectra.
Fig. 7 is phloroglucin derivative (±) Myrtucyclitone D13C NMR spectra.
Fig. 8 is the hsqc spectrum figure of phloroglucin derivative (±) Myrtucyclitone D.
Fig. 9 is the HMBC spectrogram of phloroglucin derivative (±) Myrtucyclitone D.
Figure 10 is the X-ray diffraction structure chart of phloroglucin derivative (±) Myrtucyclitone D.
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.
Embodiment 1
The separation and Extraction and Structural Identification of phloroglucin derivative, comprising the following steps:
(1) dry myrtle (Myrtus communis Linn.) branches and leaves 8kg is weighed, pulverizer is ground into coarse powder, uses
95% (w/w) ethanol percolation extracts 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 uses petroleum ether extraction after adding water to be suspended, and obtains petroleum ether extraction position 389g.
(2) petroleum ether extraction position carries out silica gel column chromatography, using petroleum ether-ethyl acetate as eluant, eluent, according to petroleum ether
It is 100:0,100:1,100:3,100:5,100:7,100:10,100:30,100:50,100:100 with ethyl acetate volume ratio
It is eluted with the gradient of 0:100, analyzed through thin-layer chromatography (TLC) and merges similar fraction, obtain 10 mainstream parts
Fr.1~Fr.10.Wherein fraction Fr.5 (petrol ether/ethyl acetate 100:7 elution fraction, 70g) continues on through silica gel column chromatography, presses
Be 100:0,100:1 according to petroleum ether and ethyl acetate volume ratio, 100:3,100:5,100:7,100:10,100:30,100:50,
The gradient of 100:100 is eluted, and 9 Arius part Fr.5A~Fr.5I are obtained.
(3) 1. Arius part Fr.5C (petrol ether/ethyl acetate 100:3 elution fraction, 15.1g) is splined on after concentration
Sephadex LH-20 chromatographic column, with chloroform-methanol (CHCl3- MeOH) 1:1 is mixed to get by volume mixed solvent is stream
Dynamic phase, flow velocity are that 0.5mL/min is eluted, and collect eluent (elution volume 100-1500mL), analyze through TLC and merge phase
Like fraction, 4 fraction Fr.5C-1~Fr.5C-4 are obtained.
2. fraction Fr.5C-2 (elution volume 300-500mL) (0.9g) is carried out reverse phase ODS column chromatography, with methanol-water
(MeOH-H2It O) is eluant, eluent, according to the elution ladder that methanol and water volume ratio are 60:40,70:30,80:20,90:10,100:0
Degree 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 88:12 methanol-water as eluant, eluent, flow velocity be 3mL/min eluted, collect retention time 21.4min
With the chromatographic peak of 25.3min, (±) Myrtucyclitone C (35.6mg) and (±) Myrtucyclitone D are obtained
(38.3mg)。
(4) the 1. Structural Identification of (±) Myrtucyclitone C
Colourless bulk crystals；Vanillic aldehyde-strong sulfuric acid response (TLC) displaing amaranth；M.p.226~228 DEG C；UV(CHCl3)
λmax(logε)243(2.44),290(2.91)nm；IR(KBr)νmax 3384,2973,2929,2876,1703,1619,1599,
1462,1386,1248,1139,1033,844,752cm-1；HR-ESI-MS m/z653.3685[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-magnetism is total
Vibration map is shown in Fig. 1~4.X-ray diffraction structure is shown in Fig. 5.
According to the above physicochemical data, NMR data and X ray diffracting data, the knot of (±) Myrtucyclitone C is identified
Structure is shown in formula I, and configuration is respectively 1S, 9S, 10S, 17S and 1R, 9R, 10R, 17R.
Table 1. (±) Myrtucyclitone C's1H (500MHz) and13C (125MHz) NMR data
*OH；Solvent is CDCl3, δ unit is ppm, and J unit is Hz
The Structural Identification of (2. ±) Myrtucyclitone D
Colourless bulk crystals；Vanillic aldehyde-strong sulfuric acid response (TLC) displaing amaranth；M.p.234~235 DEG C；UV(CHCl3)
λmax(logε)243(2.56),290(3.26)nm；IR(KBr)νmax 3277,2978,1720,1600,1462,1386,1253,
1070,841cm-1；HR-ESI-MS m/z 653.3686[M+H]+(calcd for 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. 6~9.X is penetrated
Line diffraction structure is shown in Figure 10.
According to the above physicochemical data, NMR data and X ray diffracting data, the knot of (±) Myrtucyclitone C is identified
Structure is shown in formula I, and configuration is respectively 1S, 9S, 10S, 17R and 1R, 9R, 10R, 17S.
Table 2. (±) Myrtucyclitone D's1H (500MHz) and13C (125MHz) NMR data
*OH；Solvent is CDCl3, δ unit is ppm, and J unit is Hz
Embodiment 2
Inhibiting effect of (±) Myrtucyclitone C and (±) Myrtucyclitone D to various bacteria
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, the above bacterial strain are purchased from middle traditional Chinese medical science
Institute of Medicinal Biological Technique, subject institute.
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.
Inhibiting effect of table 3. (±) the Myrtucyclitone C and (±) Myrtucyclitone D to various bacteria
The results show that compound (±) Myrtucyclitone C and (±) Myrtucyclitone D are to golden yellow grape
Coccus, methicillin-resistant staphylococcus aureus and vancomycin intermediary drug-resistant staphylococcus aureus all have significant antibacterial activity, MIC
Value is 2 μ g/mL；There is stronger antibacterial activity to staphylococcus epidermis, enterococcus faecalis, enterococcus faecium, MIC value is 8 μ g/mL；It is right
Escherichia coli and pseudomonas aeruginosa have certain antibacterial activity, and MIC value is 64~128 μ g/mL.
Especially above compound is to staphylococcus aureus, Methicillin-resistant Staphylococcus aureus and vancomycin intermediary drug resistance gold
For the antibacterial activity of Portugal bacterium better than clinical commonly used drugs such as ampicillin, cefotaximes, this has the drug for researching and developing antimicrobial agent
It is significant.
(±) Myrtucyclitone C of the invention and (±) Myrtucyclitone D as molecular structure completely not
The new chemical entities of existing antibacterials are same as, there is good activity for drug-fast bacteria, it is most likely that as new chemical entities
Development is novel antibacterial drug.
Embodiment 3
(±) Myrtucyclitone C and influence of (±) Myrtucyclitone D to normal cell
Test method: human embryonic kidney cells HEK 293 (being purchased from Shanghai Cell Bank of the Chinese Academy of Sciences) Yu Hanyou 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.
Cytotoxicity of table 4. (±) the Myrtucyclitone C and (±) Myrtucyclitone D to HEK 293
Test result is shown: even if under the high concentration of 200 μ g/ml, the compound of the present invention (±)
Myrtucyclitone C and (±) Myrtucyclitone D only show very human normal cell line embryonic kidney cell HEK 293
Low cytotoxicity, inhibitory rate of cell growth are 10.65% and 11.91%.
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 phloroglucin derivative, it is characterised in that: be (±) Myrtucyclitone C and (±)
Myrtucyclitone D, structure are shown in formula I；(±) Myrtucyclitone C is enantiomter, and configuration is respectively 1S,
9S, 10S, 17S and 1R, 9R, 10R, 17R；(±) Myrtucyclitone D is enantiomter, and configuration is respectively 1S, 9S,
10S, 17R and 1R, 9R, 10R, 17S；
2. application of the phloroglucin derivative described in claim 1 in preparation antibacterials, it is characterised in that: the bacterium
Including staphylococcus aureus, staphylococcus epidermis, enterococcus faecalis, enterococcus faecium, escherichia coli and pseudomonas aeruginosa.
3. application of the phloroglucin derivative according to claim 2 in preparation antibacterials, it is characterised in that: described
Staphylococcus aureus include methicillin-resistant staphylococcus aureus and vancomycin intermediary resistant Staphylococcus aureus.
4. application of the phloroglucin derivative according to claim 2 in preparation antibacterials, it is characterised in that: described
Antibacterials include pharmaceutically acceptable auxiliary material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610347417.4A CN107417697B (en) | 2016-05-23 | 2016-05-23 | A kind of phloroglucin derivative and its application in preparation antibacterials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610347417.4A CN107417697B (en) | 2016-05-23 | 2016-05-23 | A kind of phloroglucin derivative and its application in preparation antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107417697A CN107417697A (en) | 2017-12-01 |
| CN107417697B true CN107417697B (en) | 2019-07-19 |
Family
ID=60422535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610347417.4A Active CN107417697B (en) | 2016-05-23 | 2016-05-23 | A kind of phloroglucin derivative and its application in preparation antibacterials |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107417697B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109054014B (en) * | 2018-07-24 | 2020-06-26 | 上海中医药大学 | Polyphenol polymer and application thereof |
| CN113480510A (en) * | 2020-09-12 | 2021-10-08 | 中国科学院华南植物园 | Rapid preparation and application of phloroglucinol derivatives in myrtle fruits |
| CN116585293B (en) * | 2023-05-16 | 2024-06-25 | 山东大学 | Use of phenolic compound-induced iron death in cell growth and tumor treatment |
| CN117683002B (en) * | 2024-02-01 | 2024-04-19 | 暨南大学 | Phloroglucinol derivative and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103638012A (en) * | 2013-12-04 | 2014-03-19 | 常州科立信医疗器械有限公司 | Application of Myrtucommuacetalone in medicine for treatment of myocardial ischemia |
| CN103655550A (en) * | 2013-12-05 | 2014-03-26 | 常州科立信医疗器械有限公司 | Application of Myrtucommuacetalone in preparation of drugs for treatment of hemorrhagic fever with renal syndrome |
| CN103655549A (en) * | 2013-12-05 | 2014-03-26 | 常州科立信医疗器械有限公司 | Application of Myrtucommuacetalone in preparation of drugs for treatment or prevention of acute heart failure |
| CN103705500A (en) * | 2013-12-04 | 2014-04-09 | 常州科立信医疗器械有限公司 | Applications of Myrtucommuacetalone in medicines treating renal insufficiency |
| CN103705504A (en) * | 2013-12-05 | 2014-04-09 | 常州科立信医疗器械有限公司 | Applications of Myrtucommuacetalone in medicines treating ischemic cerebral damage |
-
2016
- 2016-05-23 CN CN201610347417.4A patent/CN107417697B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103638012A (en) * | 2013-12-04 | 2014-03-19 | 常州科立信医疗器械有限公司 | Application of Myrtucommuacetalone in medicine for treatment of myocardial ischemia |
| CN103705500A (en) * | 2013-12-04 | 2014-04-09 | 常州科立信医疗器械有限公司 | Applications of Myrtucommuacetalone in medicines treating renal insufficiency |
| CN103655550A (en) * | 2013-12-05 | 2014-03-26 | 常州科立信医疗器械有限公司 | Application of Myrtucommuacetalone in preparation of drugs for treatment of hemorrhagic fever with renal syndrome |
| CN103655549A (en) * | 2013-12-05 | 2014-03-26 | 常州科立信医疗器械有限公司 | Application of Myrtucommuacetalone in preparation of drugs for treatment or prevention of acute heart failure |
| CN103705504A (en) * | 2013-12-05 | 2014-04-09 | 常州科立信医疗器械有限公司 | Applications of Myrtucommuacetalone in medicines treating ischemic cerebral damage |
Non-Patent Citations (2)
| Title |
|---|
| Cytotoxic Phloroglucinols from the Leaves of Myrtus communis;Filippo Cottiglia et al.;《J.Nat.Prod.》;20120125;第75卷;第225-229页 * |
| New Inhibitors of ROS Generation and T-Cell Proliferation from Myrtus communis;M. Iqbal Choudhary et al.;《Org.Lett.》;20130403;第15卷(第8期);第1862-1865页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107417697A (en) | 2017-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kołodziej et al. | Antibacterial and antimutagenic activity of extracts aboveground parts of three Solidago species: Solidago virgaurea L., Solidago canadensis L. and Solidago gigantea Ait | |
| CN107417697B (en) | A kind of phloroglucin derivative and its application in preparation antibacterials | |
| Jing et al. | Dynamic high pressure microfluidization-assisted extraction and bioactivities of Cyperus esculentus (C. esculentus L.) leaves flavonoids | |
| Negi et al. | In vitro antimicrobial activity of Acacia catechu and its phytochemical analysis | |
| Lai et al. | Blechnum orientale Linn-a fern with potential as antioxidant, anticancer and antibacterial agent | |
| Hearst et al. | Antibacterial activity of elder (Sambucus nigra L.) flower or berry against hospital pathogens | |
| Doughari et al. | Antioxidant, antimicrobial and antiverotoxic potentials of extracts of Curtisia dentata | |
| Xing et al. | Simulated gastrointestinal tract metabolism and pharmacological activities of water extract of Scutellaria baicalensis roots | |
| US20100292318A1 (en) | Antibacterial composition comprising salvia extracts | |
| Goulas et al. | Evaluation of the phytochemical content, antioxidant activity and antimicrobial properties of mountain tea (Sideritis syriaca) decoction | |
| Cao et al. | Emodin is identified as the active component of ether extracts from Rhizoma Polygoni Cuspidati, for anti-MRSA activity | |
| CN106749107B (en) | Terpenoid in Roots of Euphorbia soongarica and its preparation method and application | |
| Yousefbeyk et al. | Bioactive terpenoids and flavonoids from Daucus littoralis Smith subsp. hyrcanicus Rech. f, an endemic species of Iran | |
| CN106986852B (en) | Myrtucommulone R and its application in preparation antibacterials | |
| CN106967085B (en) | A kind of phloroglucinol derivatives compound and its application in preparation antibacterials | |
| Chan et al. | Quick identification of kuraridin, a noncytotoxic anti-MRSA (methicillin-resistant Staphylococcus aureus) agent from Sophora flavescens using high-speed counter-current chromatography | |
| Mahlangeni et al. | Biogenic synthesis, antioxidant and antimicrobial activity of silver and manganese dioxide nanoparticles using Cussonia zuluensis Strey | |
| Murugan et al. | Glycosmis pentaphylla (Rutaceae): a natural candidate for the isolation of potential bioactive arborine and skimmianine compounds for controlling multidrug-resistant Staphylococcus aureus | |
| Al Bimani et al. | A new antimicrobial compound from the leaves of Dodonaea viscosa for infectious diseases | |
| Jeziorek et al. | Bioactive rinderol and cynoglosol isolated from Cynoglossum columnae Ten. in vitro root culture | |
| Leal et al. | Ceanothane and lupane type triterpenes from Zizyphus joazeiro–an anti-staphylococcal evaluation | |
| CN108610258A (en) | One new phenolic acid compound and preparation method thereof and medical usage | |
| CN100491364C (en) | Sesquiterplactone in dandelion and its use of resisting Gram's positive bacteria | |
| CN106800546B (en) | A kind of miscellaneous terpene compound and its application in preparation antibacterials | |
| CN101024636A (en) | Eremophilane containing chlorine atom in Heizituowu and its anti-biotic and cell-toxin activity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |