CN102475701B - Application of pyrone compound - Google Patents
Application of pyrone compound Download PDFInfo
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- CN102475701B CN102475701B CN201010565368.4A CN201010565368A CN102475701B CN 102475701 B CN102475701 B CN 102475701B CN 201010565368 A CN201010565368 A CN 201010565368A CN 102475701 B CN102475701 B CN 102475701B
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- pyrone
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Abstract
The present invention discloses application of an alpha-pyrone compound, wherein the compound is 5-ethyl-4-methoxy-6-methyl-2H-pyrone-9-ethyl ester, the structure of the compound is shown in the description, and the compound is used for preparation of anti-tumor drugs.
Description
Technical field
The present invention relates to microbial technology field, be specifically related to a kind of application of alpha-pyrone compound, its 5-ethyl-4-methoxyl group-6-methyl-9-hydroxyl-2H-pyrone-9-ethyl ester.
Background technology
Pyrone compound has the multiple physiologically actives such as parasite killing, antibacterial, antiviral, plant growth regulating and smooth muscle relaxation, it is the important synthetic precursor of medicine, if armillarisin A is a material that contains α-pyrone structure, there is function of gallbladder promoting active component, the sphincter of lax common bile duct end, can significantly promote bile secretion.
Alpha-pyrone compound, its 5-ethyl-4-methoxyl group-6-methyl-9-hydroxyl-2H-pyrone-9-ethyl ester obtains (Sakae Shimizu by Sakae Shimizu by microorganism fermentation and chemosynthesis two-stage process first, Ikuo Sakurai, Yuzuru Yamamoto.Chem.Pharm.Bull 1983,31 (10): 3781-3784), but have no it and have the report of physiologically active.
Summary of the invention
The object of the present invention is to provide a kind of application of alpha-pyrone compound, its.
Alpha-pyrone compound, its of the present invention, is 5-ethyl-4-methoxyl group-6-methyl-9-hydroxyl-2H-pyrone-9-ethyl ester, has following structure:
Applicant of the present invention has obtained first this material from endophyte of plant, and find that this material is all inhibited to lung carcinoma cell, breast cancer cell and pancreatic cancer cell, can be used in the medicine that preparation suppresses tumor, suppress the medicine of pulmonary carcinoma, breast carcinoma or cancer of pancreas in particular for preparation.
Brief description of the drawings
Fig. 1 is mass spectrogram.
Fig. 2 is hydrogen spectrum spectrogram.
Fig. 3 is carbon spectrum spectrogram.
Fig. 4 is hsqc spectrum spectrogram.
Fig. 5 is H-H COSY spectrum spectrogram.
Fig. 6 is HMBC spectrum spectrogram.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention will be further described.Should be understood that following examples are only for the present invention is described but not for limiting the scope of the invention.
The present invention's strain used is from the leaf of Herba Ludwigiae Prostratae plant, to separate the plants endogenetic bacterium that obtains, and this bacterial strain is cultivated after 2 days on 28 DEG C, the flat board of PDA, and aerial hyphae and substrate mycelium are white.After 6 days, aerial hyphae and substrate mycelium are fine and close and become Lycoperdon polymorphum Vitt, and produce spore.Spore color is Lycoperdon polymorphum Vitt, and conidiophore bears from subiculum or Stroma, and branch is not separated yet, intensive one-tenth paliform, and conidium is often embedded in colloid, makes spore become orange etc. while trooping.Aceravlus has bristle, and bristle is born in aceravlus around, and conidium is oval or crescent, straight or micro-curved.Sequence in the 18S rDNA of this bacterial strain and GeneBank data base is carried out to Blast compare of analysis, and result shows that the sequence the highest with its similarity is mainly distributed in Colletotrichum (Colletotrichum sp.).Analyze in conjunction with bibliographical information, determine that this bacterial strain belongs to Colletotrichum (Colletotrichum sp.), this judgement is consistent with the result according to Morphological Identification.Within 30th, be preserved in China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC) in JIUYUE in 2010, preserving number CGMCC No.4180.
The formula (percentage by weight) of slant medium described in following examples, described seed culture medium, described rice medium is as follows:
Slant medium: PDA culture medium.
Seed culture medium: glucose (1.0%), analysis for soybean powder (2.0%), Semen Maydis powder (1.0%), KH
2pO
4(0.1%), all the other are water.
Rice solid fermentation culture medium: rice 800g, pure water 1000ml.
The preparation of embodiment 1, alpha-pyrone compound, its
Bacterial strain CGMCC No.4180 is inoculated into slant medium from lyophilizing pipe and carries out activation culture, in 28 DEG C of constant incubators, cultivate after 5 days, the inclined-plane that covers with mycelia is dug to piece to be inoculated into be equipped with in four 250ml triangular flasks of the seed culture medium of 121 DEG C of autoclaving 30min and to carry out seed culture, wherein, 50ml seed culture medium is housed in each triangular flask, in 28 DEG C, rotating speed is constant temperature culture after 2 days on 220rpm shaking table, after seed culture fluid in four triangular flasks is mixed, be inoculated into and contain 800g rice through 115 DEG C of autoclaving 20min, in the container of 1000ml pure water, in 28 DEG C of static culture 30 days.
After cultivation finishes, by the rice in container and thalline mechanical activation comminution, soak and extract 3 times by ethyl acetate, under reduced pressure, solvent evaporate to dryness is obtained to brown oil-like extracts.Extract, with after 300 order silica gel mixed samples, is loaded in the decompression post (Φ 7.0*40cm) that contains 300 order silica gel, and the wherein high 2cm of sample, separates the high 5cm of silica gel; Use 1200ml petroleum ether: ethyl acetate (volume ratio is 13: 7) washing, then use 400ml petroleum ether: ethyl acetate (volume ratio is 3: 2) eluting, obtains sample fraction.
By after sample fraction evaporated under reduced pressure, use 2ml dichloromethane: methanol=3: 1 dissolves, be splined on dichloromethane: methanol=3: in the good gel sephadex LH20 post (Φ 2.0*60cm) of 1 balance, with dichloromethane: methanol=3: 1 eluting, substep is collected, every 3ml receives a pipe, and wherein 6～19 pipes are target fraction.
By after concentrated fraction doing, separate and obtain faint yellow grease with half preparative liquid chromatography, condition is: adopt Agilent 1100 chromatographic systems, semi-preparative column is Agilent ZORBAX ODS 5 μ m, 9.4mm*250mm, condition is 35% methanol for 0～40min (65% water) isocratic elution, the retention time t of this compound
rbe about 36.5min.
The qualification of embodiment 2, alpha-pyrone compound, its
Through high-resolution positive ion electrospray spraying Mass Spectrometer Method, collection of illustrative plates as shown in Figure 1, shows that its quasi-molecular ion peak is: m/z 227.0880 (M+H)
+, molecular formula is C
11h
15o
5.Adopt Bruker Avance II-400 type NMR spectrometer with superconducting magnet to measure the hydrogen spectrum (Fig. 2) of sample, carbon spectrum (Fig. 3) and relevant two-dimensional spectrum (HMQC spectrum (Fig. 4), H-H COSY spectrum (Fig. 5), HMBC compose (Fig. 6)), its nuclear magnetic data is in table 1.
Table 1, nuclear magnetic data table (400MHZ, Actone-d
6)
By resolving, determine the ownership of all carbon atoms of this compound and hydrogen atom, the structure that has obtained this compound is as follows:
Known this compound is a kind of alpha-pyrone compound, its, chemistry 5-ethyl-4-methoxyl group-6-methyl-2H-pyrone-9-ethyl ester by name.
Embodiment 3,5-ethyl-4-methoxyl group-6-methyl-2H-pyrone-9-ethyl ester antitumor cytolytic activity
The trophophase tumor cell of taking the logarithm, with RPMI1640 nutritional solution (containing 10% calf serum, 100U/mL penicillin and 100U/mL streptomycin), is made into 5 × 10
4individual/mL single cell suspension, is inoculated in 96 orifice plates by every hole 200 μ L.In 37 DEG C, 5%CO
2incubator is cultivated.Cultivate after 24h, carefully suck culture fluid, add the sample solution 200 μ L of variable concentrations, establish simultaneously blank to group zeroing (without inoculating cell, only adding culture fluid), (inoculating cell, does not add drug treating to negative control group, only add culture fluid), every group establish 8 parallel.In 37 DEG C, 5%CO
2in incubator, cultivate.Cultivate after 72h, every hole adds 20 μ L, and the MTT solution (PBS (pH=7.4) dissolves for 3-(4,5-dimethylthiazole-2)-2,5-diphenyl tetrazole bromine salt, and concentration is 5mg/mL) of 5 μ g/mL, continues to cultivate in incubator.Cultivate after 4h, add 4% isopropyl alcohol-0.01mol/L HCl, 100 μ L dye to living cells and keep spending the night.The full-automatic microplate reader of inferior daily MK-2 is measured OD value under wavelength 570nm.Repeated measure is calculated as follows cell inhibitory rate 3 times: cell inhibitory rate (%)=(1-test group absorption value A/ matched group absorbance value A) × 100%.
Table 2,5-ethyl-4-methoxyl group-6-methyl-2 '-hydroxyl-2H-pyrone-9-ethyl ester anti-tumor activity
5-ethyl-4-methoxyl group-6-methyl-2 '-hydroxyl-2H-anti-lung carcinoma cell of pyrone-9-ethyl ester (A549), breast cancer cell (MDA-MB-231) and pancreatic cancer cell (PANC-1) determination of activity result are as shown in table 2.Result is as shown in Table 2 known, this pyrone compound is inhibited to lung carcinoma cell (A549), breast cancer cell (MDA-MB-231) and pancreatic cancer cell (PANC-1), especially lung carcinoma cell (A549) and breast cancer cell (MDA-MB-231) are had to stronger inhibition activity, can be for the preparation of the medicine that suppresses tumor.
Claims (2)
1. an application for alpha-pyrone compound, its, described alpha-pyrone compound, its has following structure:
It is characterized in that, for the preparation of the medicine that suppresses tumor.
2. application as claimed in claim 1, is characterized in that, described tumor is pulmonary carcinoma, breast carcinoma or cancer of pancreas.
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| CN201010565368.4A CN102475701B (en) | 2010-11-30 | 2010-11-30 | Application of pyrone compound |
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| CN201010565368.4A CN102475701B (en) | 2010-11-30 | 2010-11-30 | Application of pyrone compound |
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| CN102475701B true CN102475701B (en) | 2014-07-23 |
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| CN104211670B (en) * | 2013-05-30 | 2015-11-18 | 福州大学 | A kind of alkyl pyrone compound and its production and use |
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