CN105497004B - The purposes of xanthone dimer class compound IUE-1799a - Google Patents
The purposes of xanthone dimer class compound IUE-1799a Download PDFInfo
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Abstract
The invention discloses the purposes of xanthone dimer class compound IUE-1799a.The specially purposes of antibacterial, than as can inhibiting the growth of methicillin-resistant staphylococcus aureus, to various kinds of cell system without obvious cytotoxicity.It can be used for preparing antibacterials.
Description
Technical field
The present invention relates to antifungal field more particularly to the antibacterials of xanthone dimer class compound IUE-1799a
Purposes.
Background technique
Botanical medicine is quite remote in the application of human history.With the development of human civilization and science and technology, change
Learn the edge that botanical medicine was once once squeezed into market application by drug.Nowadays, people measure, accept or reject chemicals quick-acting and
When pain brought by serious toxic side effect, botanical medicine another drug scholar and patient gone to the theory of its back to nature
In front.Peculiar antibacterials are found from plant, and there is wide development and application space.
Staphylococcus aureus is the stronger bacterium of clinically common toxicity, since the penicillin forties in last century comes out
Afterwards, the infectious diseases as caused by staphylococcus aureus receives control largely.But it is extensive with penicillin
It uses, some staphylococcus aureuses can generate penicillase, hydrolyze beta-lactam nucleus, show as the drug resistance to penicillin
Property.Although scientist has investigated a kind of semisynthetic penicillin of new energy penicillin resistant enzyme, i.e. methicillin
(methicillin), nineteen fifty-nine be applied to it is clinical after once efficiently controlled Beta-lactamase From Staphylococcus Aureuss producing enzyme strain
Infection, but the Jevons of Britain just had found methicillin-resistant staphylococcus aureus (MRSA) in 1961 for the first time, MRSA from
It almost extends over the entire globe, becomes in institute and one of the important pathogen of Nosocomial Infections it was found that infecting so far.
Methicillin-resistant staphylococcus aureus (MRSA) is a kind of superbacteria, it can cause running sore and poison on the person
Blister, or even gradually make the musculature necrosis of people.The fearful place of this germ does not simultaneously lie in its lethality to people, but it
To normal sterile drug --- the resistivity of antibiotic.For this germ, people are available almost without medicine.2010, Britain
Media are produced: South Asia finds novel super germ NDM-1, and drug resistance is extremely strong can global spread.
Summary of the invention
The purpose of the present invention is to provide a kind of xanthones two with methicillin-resistant staphylococcus aureus resistance effect
Aggressiveness class compound IUE-1799a.
To achieve the above object, the present invention provides a kind of xanthone dimer class compound IUE-1799a or its pharmaceutical salts
Purposes in preparation antibacterials.The chemical structural formula of the xanthone dimer class compound IUE-1799a is shown in Fig. 1 institute
Show.
Further, the bacterium is bacterium.
Further, the bacterium is methicillin-resistant staphylococcus aureus.
Further, the purposes refers to the growth that can inhibit methicillin-resistant staphylococcus aureus.
Further, the lowest concentration of antimicrobial is 1.95 μ g/mL.
Further, which is tablet, pill, capsule, granule, solution, suspension or emulsion.
Xanthone dimer class compound IUE-1799a of the invention is the second from the bark of medicinal plant south of the Five Ridges garcinia mangostana
It is isolated in acetoacetic ester extract.Its chemical structure carries out identification knot using nuclear magnetic resonance technique and high resolution mass spectrum technology
Fruit is shown in Table 1, and carries out map with the compound Garciobioxanthone of existing literature report and compare, and confirmation is same
Substance, structure are shown in Fig. 1, and No. CAS is 1466519-37-8;Molecular formula is C37H32O13, molecular weight 684.1843.With reference to text
It offers: Feng, S.; Jiang, Y.; Li, J.; Qiu, S.; Chen, T., A new bixanthone
derivative from the bark of Garcinia oblongifolia. Natural product research
2014,28, 81-5。
1H the and 13CNMR tables of data of 1. IUE-1799a of table
Position | δ H(J = Hz) | δ C |
1-OH | 13.48 s | 163.26 |
2 | 5.86 d (2.11) | 97.16 |
3-OH | 10.61 s | 164.13 |
4 | 6.21 d (2.13) | 92.82 |
4a | 156.02 | |
5-OH | 8.7 s | 131.04 |
6-OH | 9.86 s | 149.72 |
7 | 6.54 s | 112.95 |
8 | 134.86 | |
8a | 111.94 | |
9 | 181.6 | |
9a | 101.47 | |
10a | 145.51 | |
11 | 5.66 d (5.32) | 79.4 |
12 | 2.36 dd (6.51,10.54) | 55.02 |
13 | 34.55 | |
14 | 1.49 s | 48.01 |
2.15 brd (16.52) | ||
15 | 127.76 | |
16 | 4.98 brs | 126.22 |
17 | 5.18 brd (8.14) | 36.53 |
18 | 1.22 s | 22.63 |
19 | 0.98 s | 31.33 |
20 | 1.54 s | 23.39 |
21 | 2.85 s | 55.41 |
1’-OH | 12.81 s | 162.95 |
2’ | 6.07 d (2.13) | 97.51 |
3’-OH | 10.64 s | 164.5 |
4’ | 6.04 d (2.06) | 93.13 |
4’a | 156.21 | |
5’-OH | 8.83 s | 129.99 |
6’-OH | 10.05 s | 149.91 |
7’ | 6.74 s | 113.47 |
8’ | 140.48 | |
8’a | 110.04 | |
9’ | 181.94 | |
9’a | 101.86 | |
10’a | 145.9 |
The compound of the present invention xanthone dimer class compound IUE-1799a can also be prepared by chemical synthesis process
It obtains.
From embodiment as can be seen that xanthone dimer class compound IUE-1799a of the invention can effectively inhibit resistance to
The growth of methicillin staphylococcus aureus, and to various kinds of cell system without obvious cytotoxicity.
Xanthone dimer class compound IUE-1799a of the present invention can with antibacterial, including but not limited to, coccus,
Bacillus and spirillum.It specifically can be, Escherichia coli, streptococcus or staphylococcus etc..
Preservation information
Culture title: staphylococcus aureus Staphylococcus aureus,
Preservation date: on September 20th, 2015,
Depositary institution: China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC),
Deposit number: CGMCC No:1.12409.
Detailed description of the invention
Fig. 1 is the structural formula of the compounds of this invention xanthone dimer class compound IUE-1799a.
Fig. 2 is 2 antibacterial experiment 1 of embodiment) result figure.
Fig. 3 is 2 antibacterial experiment 2 of embodiment) result figure.
Specific embodiment
The embodiment of the present invention is described below in detail, examples of the embodiments are shown in the accompanying drawings, wherein from beginning to end
Same or similar label indicates same or similar element or element with the same or similar functions.Below with reference to attached
The embodiment of figure description is exemplary, it is intended to is used to explain the present invention, and is not considered as limiting the invention.Embodiment
In particular technique or condition person is not specified, described technology or conditions or according to the description of product according to the literature in the art
Book carries out.Reagents or instruments used without specified manufacturer is the conventional products that can be obtained by market purchasing.
Embodiment 1: the preparation and identification of compound xanthone dimer class compound IUE-1799a
The bark part 2kg for taking south of the Five Ridges garcinia mangostana, after drying, with 10L ethyl acetate soaked overnight, in triplicate after, close
And acetic acid ethyl acetate extract, filtering are concentrated under reduced pressure to give total crude extract medicinal extract 210g.Gained medicinal extract and silica gel (100 mesh) mix sample
Mixing, using chloroform-methanol as eluting solvent, is carried out through normal pressure silica gel (200-300 mesh) column chromatogram chromatography from 90:10 to 40:60
Gradient elution, wherein gradient elution, which gets off in thin-layer chromatography, to be 100 with -0.1% aqueous formic acid volume ratio of chloroform-methanol:
The component of 20:2 solution system expansion, presses reversed-phase column (60 μm) after purification in, pure using SephadexLH-20 pillar
Change, eluted with methanol, eluent is a pipe with 10 ml, collects 15 pipes, wherein 6-9 pipe merges picking, and obtains after being concentrated to dryness
To white powder compound IUE-1799a.
Gained is identified using nuclear magnetic resonance technique and high resolution mass spectrum technology, the results are shown in Table 1, and with existing text
The compound Garciobioxanthone for offering report carries out map comparison, and confirmation is same substance, and structure is shown in Fig. 1.It is final true
Fixed its No. CAS is 1466519-37-8;Molecular formula is C37H32O13, molecular weight 684.1843.Bibliography: Feng, S.;
Jiang, Y.; Li, J.; Qiu, S.; Chen, T., A new bixanthone derivative from the
bark of Garcinia oblongifolia. Natural product research 2014,28, 81-5.
Embodiment 2: antibacterial activity test
Using resazurin development process as the active method of detection.The principle of resazurin development process is: the cream in living cells
Acidohydrogenase can convert resazurin (blue) to fluorescent material resorufin (pink red), generate fluorescence signal.Resorufin meeting
Continue to be reduced to non-blooming substance dihydro resorufin (white) by cell, declines fluorescence signal, it is inactive or dead
Cell loss metabolic capability and resazurin cannot be restored, cannot also generate fluorescence signal, so the method energy specific detection
Competent cell.
Bacteriostatic experiment is operated using 96 orifice plates, and color is blue in 96 holes, then representative sample has inhibition to live aimed strain
Property;Color pinkiness or red in 96 holes, then representative sample does not have inhibitory activity to aimed strain.
Aimed strain bacteria suspension preparation: take methicillin resistant Staphylococcus aureus (commercial source: ATCC, deposit number:
43300) and methicillin resistant Staphylococcus aureus (China General Microbiological culture presevation administrative center, deposit number:
CGMCC 1.12409) with 10 volume % it is inoculated in 5mLMHB culture solution (manufacturer: Beijing Baeyer enlightening Bioisystech Co., Ltd, goods
Number: in CM0405), after 180rpm/min shaken cultivation 12 hours, counted with blood counting chamber in 37 DEG C, it is dilute with MHB culture solution
Bacteria suspension concentration is released to 105CFU/mL(clump count/milliliter).
Resazurin solution: the resazurin (commercial source: the limited public affairs of traditional Chinese medicines chemical reagent of 500 μ g/mL is configured with sterile water
Department, article No.: 71035931) solution.
Antibacterial experiment is carried out in 96 microwell plates, and compound is dissolved with DMSO, gradient dilution, while it is right to set compound feminine gender
According to solvent negative control, positive control and blank control, each experimental concentration and all controls are repeated 3 times.Antibacterial experiment and
MIC(minimum inhibitory concentration) measurement bibliography Wibowo, A.; Ahmat, N.; Hamzah, A. S.; Low, A.
L.; Mohamad, S. A.; Khong, H. Y.; Sufian, A. S.; Manshoor, N.; Takayama, H.,
Malaysianol B, an oligostilbenoid derivative from Dryobalanops lanceolata.Fitoterapia 2012,83, 1569-75。
1) experimental group 1(is shown in Fig. 2):
A1-A3: 175.5 μ L of compound solution (250 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin solution
19.5μL;
A4-A6: 175.5 μ L of compound solution (125 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin solution
19.5μL;
A7-A9: 175.5 μ L of compound solution (62.5 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin is molten
19.5 μ L of liquid;
A10-A12: 175.5 μ L of compound solution (31.25 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin
19.5 μ L of solution;
B1-B3: 175.5 μ L of compound solution (15.63 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin
19.5 μ L of solution;
B4-B6: 175.5 μ L of compound solution (7.81 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin is molten
19.5 μ L of liquid;
B7-B9: 175.5 μ L of compound solution (3.91 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin is molten
19.5 μ L of liquid;
B10-B12: 175.5 μ L of compound solution (1.95 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin
19.5 μ L of solution;
C1-C3: 175.5 μ L of compound solution (0.98 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin is molten
19.5 μ L of liquid;
C4-C6: 175.5 μ L of compound solution (0.49 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin is molten
19.5 μ L of liquid;
C7-C9: 175.5 μ L of compound solution (0.24 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin is molten
19.5 μ L of liquid;
C10-C12: 175.5 μ L of compound solution (0.12 μ g/mL) 5 μ L+ bacteria suspension (ATCC 43300)+resazurin
19.5 μ L of solution
5 μ L+ bacteria suspension (ATCC 43300) of compound negative control group G1-G3:DMSO, 175.5 μ L+resazurin is molten
19.5 μ L of liquid;Positive controls G10-G12: 5 μ L+ bacteria suspension (ATCC 43300) 175.5 of chloromycetin solution (50 μ g/mL)
19.5 μ L of μ L+resazurin solution;
5 μ L+ bacteria suspension (ATCC 43300) of solvent negative control group H1-H3:MHB culture solution, 175.5 μ L+resazurin
19.5 μ L of solution;5 μ L+ MHB culture solution of blank control group H10-12:DMSO, 175.5 μ L+19.5 μ L of resazurin solution.
Test result is shown in Fig. 2.Compound negative control G1-G3 is red, solvent negative control H1- as can be seen from Figure 2
H3 is red;Compound positive control G10-G12 is blue, and blank control H10-H12 is blue, illustrates yin and yang attribute test knot
Fruit is correct, does not pollute;A1-A12 is blue, and B1-B12 is blue;C1-C12 is red;Illustrate that when bacteria suspension be 175.5 μ
L, this compound solution concentration drop to 1.95 μ g/mL from 250 μ g/mL, all have the effect of antibacterial, when concentration is reduced to 0.98 μ
When g/mL is even lower, antibacterial effect is just lost.
In summary, compound IUE-1799a is to MRSA(ATCC 43300) minimum inhibitory concentration be 1.95 μ g/mL
(being equivalent to 2.85 μM).
2) experimental group 2(Fig. 3):
A1-A3: 175.5 μ L of compound solution (250 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution;
A4-A6: 175.5 μ L of compound solution (125 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution;
A7-A9: 175.5 μ L of compound solution (62.5 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution;
A10-A12: 175.5 μ L of compound solution (31.25 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+
19.5 μ L of resazurin solution;
B1-B3: 175.5 μ L of compound solution (15.63 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword
Reddish black 19.5 μ L of solution;
B4-B6: 175.5 μ L of compound solution (7.81 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution;
B7-B9: 175.5 μ L of compound solution (3.91 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution;
B10-B12: 175.5 μ L of compound solution (1.95 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword
Reddish black 19.5 μ L of solution;
C1-C3: 175.5 μ L of compound solution (0.98 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution;
C4-C6: 175.5 μ L of compound solution (0.49 μ g/mL) 5 μ L+ bacteria suspension (CGMCC 1.12409)+sword day
Green 19.5 μ L of solution
5 μ L+ bacteria suspension (CGMCC 1.12409) of compound negative control group G1-G3:DMSO, 175.5 μ L+resazurin
19.5 μ L of solution;Positive controls G10-G12: 5 μ L+ bacteria suspension (CGMCC 1.12409) of chloromycetin solution (50 μ g/mL)
175.5 μ L+19.5 μ L of resazurin solution;
5 μ L+ bacteria suspension (CGMCC 1.12409) of solvent negative control group H1-H3:MHB culture solution, 175.5 μ L+sword day
Green 19.5 μ L of solution;5 μ L+ MHB culture solution of blank control group H10-12:DMSO, 175.5 μ L+19.5 μ of resazurin solution
L
Test result is shown in Fig. 3.From figure 3, it can be seen that compound negative control G1-G3 is red, solvent negative control
H1-H3 is red;Compound positive control G10-G12 is blue, and solvent positive control H10-H12 is blue, illustrates yin and yang attribute
Test result is correct, does not pollute;A1-A12 is blue, and B1-B9 is blue;B10-B12 is aubergine;C1-C6 is red;
Illustrating that when bacteria suspension be 175.5 μ L, compound solution concentration drops to 3.91 μ g/mL from 250 μ g/mL, all has antibacterial effect, when
Concentration be 1.95 μ g/mL when, be aubergine, show cannot complete antibacterial, when concentration be 0.98 μ g/mL it is even lower when, then it is complete
Antibacterial effect is lost entirely.
In summary, compound IUE-1799a is to MRSA(CGMCC 1.12409) minimum inhibitory concentration be 3.91 μ g/
ML(is equivalent to 5.72 μM).
Embodiment 3: cellulotoxic experiment
The present embodiment is tested using cell in vitro poison, and IUE- is added in the people or mouse cancer cell by detecting in vitro culture
Survival rate after 1799a measures.
The cell strain of selection has: Non-small cell lung carcinoma H1299, A549, human large cell lung cancer H460, human small cell lung carcinoma
H446, mouse melanoma B16, B16-F10, human breast carcinoma MD-MBA-231, MCF7, MGC803 cell line, human pancreas cancer
PANC-1, human cervical carcinoma HeLa, human osteosarcoma cell U2OS, human liver cancer HepG2, human colon carcinoma HCT116, human laryngeal cancer HEP2.Using
Mtt assay come measure every kind of tumour cell survival rate (or death rate) be 50% when 503nhibiting concentration IC50(the above cell
To be purchased from ATCC).MIC is minimum inhibitory concentration.
Test result is shown in Table 2.
The antibacterial effect and cell toxicant result table of 2 IUE-1799a of table
Test strain and cell | IUE-1799a | |
MIC (μg/mL) | MRSAATCC 43300 | 1.95 |
MRSACGMCC 1.12409 | 3.91 | |
IC50 (μM) | H1299 | >50 |
A549 | >50 | |
H460 | >50 | |
H466 | >50 | |
B16 | >50 | |
B16-F10 | >50 | |
MD-MBA-231 | >50 | |
MCF7 | >50 | |
MGC803 | >50 | |
PANC-1 | >50 | |
HeLa | >50 | |
U2OS | >50 | |
HepG2 | >50 | |
HCT116 | >50 | |
HEP2 | >50 |
From table 2 it can be seen that the anti-MRSA activity of IUE-1799a is significant, while cytotoxicity is low.To people's non-small cell lung
Cancer H1299, A549, human large cell lung cancer H460, human small cell lung carcinoma H446, mouse melanoma B16, B16-F10, human milk gland
Cancer MD-MBA-231, MCF7, MGC803 cell line, human pancreas cancer PANC-1, human cervical carcinoma HeLa, human osteosarcoma cell U2OS, people
The 503nhibiting concentration IC of liver cancer HepG2, human colon carcinoma HCT116, human laryngeal cancer HEP250It is all larger than 50 μM.
Although the embodiments of the present invention has been shown and described above, it is to be understood that above-described embodiment is example
Property, it is not considered as limiting the invention, those skilled in the art are not departing from the principle of the present invention and objective
In the case where can make changes, modifications, alterations, and variations to the above described embodiments within the scope of the invention.
Claims (4)
1. the purposes of xanthone dimer class compound garciobioxanthone or its pharmaceutical salts in preparation antibacterials,
Wherein the bacterium is methicillin-resistant staphylococcus aureus.
2. the purposes of claim 1, which is characterized in that the purposes, which refers to, can inhibit methicillin-resistant staphylococcus aureus
Growth.
3. the purposes of claim 1, which is characterized in that the lowest concentration of antimicrobial is 1.95 μ g/mL.
4. the purposes of claim 1, which is characterized in that the antibacterials be tablet, pill, capsule, granule, solution,
Suspension or emulsion.
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CN103396389A (en) * | 2013-07-18 | 2013-11-20 | 中国科学院南海海洋研究所 | Naphthoquinone sesquiterpenes compound and application thereof in preparation of anti-tumour or antibacterial medicine |
CN104744533A (en) * | 2015-01-30 | 2015-07-01 | 中国科学院南海海洋研究所 | Angucycline compounds and application of angucycline compounds in preparation of anti-tumour or antibacterial medicine |
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CN103396389A (en) * | 2013-07-18 | 2013-11-20 | 中国科学院南海海洋研究所 | Naphthoquinone sesquiterpenes compound and application thereof in preparation of anti-tumour or antibacterial medicine |
CN104744533A (en) * | 2015-01-30 | 2015-07-01 | 中国科学院南海海洋研究所 | Angucycline compounds and application of angucycline compounds in preparation of anti-tumour or antibacterial medicine |
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