KR20140137644A - Antioxidant Compound Isolated from Serratia sp. and Use Thereof - Google Patents

Abstract

The present invention relates to a compound from a serratia sp. and the use thereof and, more specifically, a compound with an outstanding antioxidant activity from a serratia sp. and the use thereof. The compound, serratinin, from the serratia sp. PAMC 25557 in the present invention has an outstanding performance like removing free radicals compared with that of an existing antioxidant agent and an outstanding stability for heat at the temperatures of large ranges and has an outstanding effect of chelating for Fe^2+ and accordingly replaces an existing synthesis antioxidant as a preventive antioxidant material.

Description

Antioxidative compounds derived from the genus Serratia sp. And its uses {Antioxidant Compound Isolated from Serratia sp. and Use Thereof}

The present invention is based on the genus Serratia The present invention relates to a compound derived from Serratia sp. sp.), and uses thereof.

Life has been improved due to economic development. However, due to increased stress incidence, an aging society, irregular eating habits and dietary pattern changes such as high fat dietary intake, diseases caused by diseases such as cerebrovascular diseases, heart diseases, hypertension and diabetes, As the mortality rate is greatly increased and the diseases of psychosis are increasing, interest in health is increasing day by day.

The most important factor that includes the free radical theory in the aging process is to give electrons generated by normal body metabolism to oxygen molecule (O ₂ ), which is an electron acceptor (e ₂ ), to generate water and use the generated energy. The body constantly needs oxygen to make the energy needed to sustain life. However, if oxygen is produced by such a tetravalent reduction, only water is produced. However, oxygen molecules are not limited by partial reduction (electron relocation at an electron angle) due to the specificity of the electron arrangement in the electron angle Reactive oxygen species, which are referred to as reactive oxygen species, active oxygens, toxic oxygens, or oxygen radicals. This is a by-product of the mitochondrial electron transport system associated with energy production. They are highly reactive and destroy cellular components such as lipids, proteins, polysaccharides and nucleic acids.

Active oxygen is chemically reactive, and the free radical reaction induced by these radicals affects various reactions in the body and causes aging. Organisms are always exposed to the hazards posed by free radicals, and as their age increases, their toxicity can gradually accumulate and cause many diseases. In addition, the oxidative stress, that is, the oxidation-reduction reaction of the body is broken, so that a large amount of oxygen compound having a large reaction force is generated, and these oxygen compounds cause the oxidation promotion reaction and cause many diseases. In addition, tissue damage including changes in physiological characteristics of cells caused by free radicals and free radicals (Asada, K., Nippon Nogeikagaku Kaishi , 62: 1100, 1988), and others (Fridovich et al . , Annu . Rev. Physiol., 48: 693, 1986), liver (Halliwell, B. et al . Free radical in biology and medicine . Clarendon press, 10, 1989), cardiovascular disease, inflammatory disease, cataracts (Yagi, K., Chem Phys, 45:.. 337, 1987) as well as cause a variety of diseases, etc., that are very closely associated with aging (Floyd, RA, The FASEB J., 4: 2587,1990).

The generation of free radicals (free radicals) by oxidative stress in vivo oxidizes unsaturated fatty acids which are constituents of biological membranes, and the increase of lipid peroxidation produced thereby damages various tissues and causes metabolic disturbance, and it is known to be closely associated with the cause of chronic degenerative diseases (Halwell, B., Drugs, 42 :... 569, 1991; Fukuzawa, K. and Takaishi, Y., J. Act Oxyg Free Rad,. 1:55, 1990; Neuzil, J. et al, Biochem J., 293:.. 601, 1993; Sies, H., ed,. Oxidative Stress , 1985; Steinberg, D. et al., N. Engl . J. Med ., 320: 915, 1989).

Therefore, if there is a physiologically active substance that can inhibit oxidative damage in the body due to the formation of free radicals in vivo, it will contribute to lowering the incidence of chronic diseases such as circulatory diseases and cancer. Recently, Studies on the search for physiologically active substances have been actively conducted in various directions.

Examples of synthetic antioxidants include butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), propyl gallate (PG), and the like. Examples of the antioxidative substances in natural products include phenolic compounds, flavone derivatives, tocopherols, ascorbic acid, amino acids, peptides, , TBHQ (t-butylhydroquinone), and the like.

Phenolic compounds are one of the secondary metabolites widely distributed in the vegetable field. They have various structures and molecular weights. They have a phenolic hydroxyl group and thus have a property of binding to macromolecules such as proteins. It also has an active function.

In addition, the antioxidant capacity of antioxidants varies depending on the type of plant containing the antioxidant and the extraction method. Most of the fruits and vegetables contain vitamin C, vitamin E, beta-carotene, flavonoids, flavones, flavonones, anthocyanin, catechin, It contains polyphenol compounds with antioxidant properties, such as isocatechin, which are antioxidant in living organisms, foods and drinks.

BHT and BHA, which are phenolic synthetic antioxidants, have been widely used because of their excellent effect and economy (Kitahara, K. et al ., Chem . Pharm . Bull ., 40: 2208,1992; Hatano, T., Natural Medicines , 49: 357,1995; Masaki, H. et al ., Biol . Pharm . Bull, 18:. 162, 1995 ), to raise the risk of cancer and poor thermal stability, and (Branen, natural materials, such as AL, JAOCS, 52:59, 1975) , Toko phenol safety is one alone oxide chain It has the disadvantage that the reaction inhibiting ability is low and the price is high. On the other hand, the use of synthetic antioxidants is becoming increasingly limited. Therefore, there is a desperate need for the development of new natural antioxidants which are excellent in efficacy and more safe. Recently, natural antioxidants, Many studies have been actively conducted to develop antioxidants.

In recent years, studies on antioxidants derived from microorganisms having excellent antioxidative effects have been actively conducted, and antioxidative effects have been reported in cultures derived from fungi and bacteria. On the other hand, as a result of searching for antioxidant microorganisms which inhibit oxidation of fish oil for the purpose of feeding fish oil, Aspergillus sojae, Aspergillus oryzae and Saccharomyces cerevisiae ) Have been reported to produce superior lipid oxidation inhibitors in fungi and yeast. In addition, lactic acid bacteria Streptococcus thermophilus and Lactobacillus It has also been reported that bulgaricus cell culture fluids have antioxidant effects.

To date, studies using Serratia sp. Have shown that the new strain Serratia sp. (KCTC 18086P) and the ammonia nitrogen removal method using it (KR 10-2001-0021625), the serratia producing sera peptidase (KR 10-2003-0001803), a strain of the genus Ceratio (KFCC 10970) producing a red natural pigment, a method of preparing a red pigment using the same (KR 10-1997-00368839), a novel microorganism of the genus Serratia, (KR 10-2006-0014586), and Serratia genus Gsm01 (KR 10-2001-0035046), which have a plant virus disease control effect, have been reported, but the production of pigment (pigment) Serratia that is much involved in sp. There is little research on antioxidant production and antioxidant effects of

Therefore, in the present invention, examples efforts to develop a natural antioxidant, Serratia sp. A novel substance having excellent antioxidative activity was isolated from PAMC 25557, and it was confirmed that the separated substance had high heat stability and excellent ferros chelating effect, which is a role of preventive antioxidant, and thus completed the present invention.

It is an object of the present invention to provide a method for producing Serratia sp.) antioxidant activity, and uses thereof.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1) or a salt thereof.

[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.

The present invention also relates to the use of the Serratia spp. sp.) KCTC 12384BP.

The present invention also provides a process for the production of (a) Serratia spp. sp.) microorganism to produce a compound of formula (1); And (b) recovering the compound of formula (I) in a culture medium of the microorganism.

[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.

The present invention also relates to a method for producing Serratia spp. Containing the compound represented by the formula (1) or (2) sp.) microorganism.

The present invention also provides an antioxidative composition comprising the compound represented by the general formula (1) or (2) or a salt thereof as an active ingredient.

The present invention also relates to the use of the Serratia spp. sp.) microorganism as an active ingredient.

Serratinin, a compound derived from Serratia sp. PAMC 25557 according to the present invention, is superior to conventional antioxidants in terms of free radical scavenging activity, excellent thermal stability at a wide range of temperatures, and Fe ^{2 +} , Which can replace conventional synthetic antioxidants as prophylactic antioxidants.

FIG. 1 shows a DPPH activity graph of serratinin according to the present invention.

In the present invention, a novel antioxidant represented by the following formula 1 having no antimicrobial activity and toxic effects and excellent free radical scavenging activity can be obtained from Serratia sp. PAMC 25557 (KCTC 12384BP), which was named serratinin .

[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.

In the present invention, specific rotation of serratinin was measured using a polarimeter, and it was confirmed that [] _D ²⁰ +3 ( c 0.02, EtOH).

In the present invention, the infrared spectrum (IR spectrum) of serratinin is 3570, 3410 (OH, NH), 2987 (CH), 1730 (C = O), 1590-1610 cm < ^-1 > (CO), and UV absorption of aromatic energy occurs at 233 and 277 nm.

Accordingly, in one aspect, the present invention relates to a compound represented by the following formula (1).

[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.

The compounds according to the present invention are useful for the treatment and / sp.), wherein the Serratia spp. ( Serratia spp. sp.) was serratia sp. PAMC 25557. < / RTI >

In another aspect, the present invention relates to the use of the Serratia spp. sp.) KCTC 12384BP.

In the present invention, high-resolution electrospray ionization mass spectroscopy (HRESIMS) of serratinin shows a molecular ion (M + Na) ⁺ at m / z 303.0740 and a molecular formula is C ₁₆ H ₁₂ N ₂ O ₃ .

The compound of the present invention is a compound of formula I wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are all hydrogen, or a salt thereof, and a specific example of the compound according to the present invention may be represented by the general formula (2).

(2)

In one embodiment of the present invention, protons and carbon can be identified by NMR (nuclear magnetic resonance) data of serratinin and include eight aromatic protons, one hydroxyl and two amides (amide) protons, and the structure was confirmed by analyzing the data obtained by 2D NMR spectroscopy.

Hydrogen correlation spectroscopy data analysis of ¹ H, ¹ HCOSY and splitting patterns of aromatic protons showed that two di-substituted benzene rings with two substitution atoms in one molecule , And two carbonyl carbons (C = O) were confirmed to be resonant at 176.7 ppm and 173.9 ppm, and twelve olefinic carbons were confirmed. This result means that there are two benzene rings in the structure of serratinin.

In addition, three exchangeable singlet protons were identified at 6.50 ppm (OH), 10.12 ppm (NH) and 10.27 ppm (NH), and twelve double bond equivalents double bond equivalents, considering that two carbonyl carbon and two benzene rings are substituted in this structure, two fused tetracyclic heterocycles are bonded to one benzene ring ring and one heterocycle are combined.

The residual structural features of the present invention and the two aromatic ring connections were analyzed by HMBC (Heteronuclear Multiple Bond Correlation) data, and in particular, the HMBC correlation of the three exchangeable protons was determined using the dihydrodibenzonaphthyridinedione skeleton ), And considering the chemical shift to C-12a, the HMBC correlation of C-11, C-12a and C-4a with NH-12 is shown as Allowing the bonding of coarse C-12a and C-11 to the nitrogen atom.

(Key HMBC correlations)

In addition, the signal for the proton of the hydroxyl group on C-4b shows the HMBC correlation for C-4a, C-4b, C-5 and C-10. Based on this correlation, the quaternary carbon C-4b is linked to C-4a, C-5, and C-10, followed by C-4b, C-5, C-6a, And 6-NH in the NH group between C-5 and C-6a. Finally, the HMBC correlations of C-10, C-10a, and C-11 and H-10b lead to the creation of a planar structure of serratinin.

Serratinin confirmed that the proton was located on the same plane of the ring system in the NOE (Nuclear overhauser effect) correlation of OH-4b and H-10b. Therefore, the ring junction at C-4b and C-10b means cis .

In another aspect, the present invention relates to a method for producing (a) Serratia sp.) microorganism to produce a compound of formula (1); And (b) recovering the compound of formula (I) in a culture medium of the microorganism.

[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 6 to 20 carbon atoms Or alkenyl.

In the present invention, (i) serratia sp.) microorganism in a first solvent using column chromatography; (ii) the serratia species obtained in step (a) ( Serratia sp.) concentrating the eluate of the microorganism and extracting it with a second solvent; And (iii) purifying the extract obtained in step (b) using chromatography to obtain a compound of formula (1).

In the present invention, the Serratia < RTI ID = 0.0 > sp.) Microorganisms are Serratia sp. PAMC 25557. < / RTI >

In the present invention, the first solvent may be water, methanol or ethanol, and the second solvent may be n-hexane, ethyl acetate (EtOAc) or butanol (BuOH) Is characterized by performing silica gel column chromatography or Sephadex column chromatography (Sephadex LH-20) followed by preparative thin layer chromatography (preparative TLC) .

Examples of the solvent for extracting serratinin which can be used in the present invention include alcohols or alcohol aqueous solutions such as methanol, aqueous methanol solution, ethanol, aqueous ethanol solution, isopropanol and isopropanol, ethyl acetate, dichloromethane, trichloromethane, Of C3 to C7 saturated hydrocarbons can be used, and when they are made into preparations, it is preferable to extract them with an ethanol or ethanol aqueous solution for convenience in quality control of the preparation by the residual solvent.

A compound of Formula _{1 R 1, R 2, R} 3 in the present _{invention, R 4, R 5, R} 6, R 7, R 9 And R < ₁₀ > are both hydrogen.

To prepare the extract for use in the present invention, it is possible to immerse serratinin in one or more suitable solvents such as ethanol, methanol and acetone; To separate the liquid from the solid residue; The liquid can be concentrated. The extract thus obtained can be further processed. For example, impurities can be removed or the proportion of the component can be changed by chromatography.

In order to confirm the free radical scavenging ability in the present invention, test samples of various concentrations (0-32 占 퐂 / ml) were irradiated with ultraviolet light (UV) using DPPH (1-diphenyl-2-picryl- hydazil) Absorbance was measured at 517 nm using a spectrophotometer (UV-Visible spectrophotometer (SCINCO)). As a result, serratinin showed free radical scavenging ability for prokaryotes and eukaryotes without toxicity.

In another aspect, the present invention relates to a method for producing Serratia spp., Which contains a compound represented by formula (1) or (2) sp.) microorganisms.

In the present invention, Serratia < RTI ID = 0.0 > sp.) microorganism is KCTC 12384BP.

In another aspect, the present invention relates to a composition for antioxidation comprising a compound represented by the general formula (1) or (2) or a salt thereof as an active ingredient.

In another aspect, the present invention relates to the use of the Serratia spp. sp.) microorganism as an effective ingredient.

Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for describing the present invention in more detail and that the scope of the present invention is not limited by these embodiments in accordance with the gist of the present invention

Example  One : Serratia sp . PAMC  25557 fermentation, extraction and Serratinin  refine

The strains used in this example were extracted from Antarctic waters near Antarctic Sejong Scientific Base on King George Island (61 ° 50'-62 ° 15'S and 57 ° 30-59 ° 01'W) in Antarctica. The bacterial strain was deposited in the culture collection of the Polar Research Institute (KOPRI) under the name of PAMC 25557 and deposited in the Korea Biotechnology Research Institute (KCTC 12384BP) on March 13, 2015, and the 16S rDNA sequence (SEQ ID NO: 1) Data were analyzed and identified. As a result, the strain of this strain has been identified as Serratia of the Enterobacteraceae family of Enterobacteriaceae .

Serratia sp. PAMC 25557 was cultured for 8 days in M2 medium (10 g / L maltose, 4 g / L yeast extract, 4 g / l glucose, pH 7.8) at 27 ° C. After the culture was filtered with a celite filter, the water-soluble fraction was extracted with an XAD-16 column, and the absorbed organic extract was eluted with methanol (MeOH). The methanol extract was concentrated under vacuum at 40 ° C and re-extracted with ethyl acetate. In addition, it was purified by silica gel column chromatography, Sephadex LH-20 and preparative TLC.

The isolated light yellow solid was named serratinin.

Example  2 : Serratinin  Analysis and confirmation of chemical structure

Optical rotation was measured using a polarimeter (Autopol III, Rudolph, USA). As a result, it was confirmed that [a] _D ²⁰ + 3 ( c 0.02, EtOH).

Infrared spectra were recorded on a FT-IR Nicolet 6700 (Thermo, USA) and were found to be 3570, 3410 (OH, NH), 2987 (CH), 1730 (C = O), 1590-1610 Ar) and 1135 cm ^-1 (CO), and the UV spectrum shows the absorption of aromatic energy at 233 and 277 nm.

ESIMS data were measured using Mariner ESI-MS (Perseptive Biosystem, USA). As a result, HRESIMS of serratinin showed molecular ion (M + Na) ⁺ at m / z 303.0740, formula was found to be C ₁₆ H ₁₂ N ₂ O ₃ .

NMR spectra 1D and 2D were recorded in DMSO-d ₆ using a JEOL JNM ECP-400 spectrometer (400 MHz for ¹ H and 100 MHz for ¹³ C). As a result, eight aromatic protons, one hydroxyl and two amide protons were identified.

The HMQC and HMBC of serratinin were optimized at ¹ J _CH = 140 Hz and ⁿ J _CH = 8 Hz, respectively, and the HMBC correlation of the three exchangeable protons was optimized for dihydrodibenzonaphthyridinedione skeleton ) Were identified.

Flash column chromatography was performed using silica gel (particle size 60-100 μm) and size exclusion chromatography was performed using Sephadex LH-20 (Sigma) Respectively. NMR of serratinin The data are shown in Table 1.

NMR of serratinin data δc C-type [delta] H (mult.J, Hz) HMBC (1H-C) COZY One 123.44 CH 6.20 (d, 7.4 Hz) 2,12a 6.66, 7.13 2 120.79 CH 6.66 (t, 7.5 Hz) 1,3,4,4a ^△, 12a 6.20, 6.75, 7.13 3 129.36 CH 7.13, (t, J 7.7 Hz) 1,2,4,4a, 12a ^? 6.66, 6.75 4 109.38 CH 6.75 (d, 7.7 Hz) 1 ^△, 2,3,4a, 12a 6.66, 7.13 4a 128.11 Cq - - - 4b 75.40 Cq - - - 5 173.91 C = O - - - 6 NH 10.12 (s) 5, 4b, 6a, 10a, 10b ^? 6a 143.12 Cq - - - 7 126.18 CH 7.46, (d, 7.5 Hz) 6a, 9 6.99 8 120.87 CH 6.99 (t, 7.5 Hz) 6a, 7, 9, 10, 10a ^? 7.25, 7.46, 6.75 9 128.20 CH 7.25, (t, J 7.7 Hz) 6a ^△, 7,8,10,10a 6.76, 6.99 10 108.83 CH 6.76 (d, 7.7 Hz) 6a, 8, 10a 7.25, 6.99 10a 125.61 Cq - - - 10b 51.23 CH 4.0 (s) 4a, 4b, 6a, 10, 10a, 11 11 176.74 C = O - - - 12 NH 10.27, (s) 4a, 4b ^△, 11,12a, 12a 142.51 Cq - - - 13 OH 6.50 (s) 4a, 4b, 5, 10b

^{* NMR data were recorded in DMSO-} d 6, 1 HNMR was recorded in 300MHz, 13 C NMR were recorded in 125 MHz, △ 4-bond HMBC correlation

Experimental Example  One: Serratinin  Antimicrobial activity

Paper disk diffusion for the antimicrobial test was performed using Gram positive Staphylococcus aureus , gram negative Escherichia coli And the pathogenic yeast Candida albicans . 100 의 of serratinin was placed on paper disks of 8 mm in diameter and a disc on which serratinin was placed was placed on the surface of agar plates to sterilize the microorganisms with a cotton swab To induce the diffusion of serratinin on agar plates at 4 ° C for 12 hours. In addition, bacterial plates were incubated at 37 ° C and fungous plates were incubated at 25 ° C for 24 hours. The zone of inhibition was measured after incubation. As a result, serratinin was detected in S. aureus , E. coli And C. albicans .

Experimental Example  2: Serratinin DPPH 감  analysis

0.25 ml of DPPH solution (0.1 mM of DPPH in methanol) was mixed with 0.75 ml of various concentrations (0-32 / / ml) of test samples to obtain DPPH (1-diphenyl-2-picryl-hydazyl) Radical scavenging ability analysis was performed. The mixture was incubated at room temperature for 3 hours and the absorbance was measured at 517 nm using an ultraviolet-visible spectrophotometer (SCINCO). The reaction mixture, which contained no test sample or was mixed with commercially available butylated hydroxyanisole (BHA), was repeated three times using negative and positive controls respectively. The data were averaged to calculate the standard deviation. As a result, an IC ₅₀ of 16.7 / / ml in terms of DPPH free radical scavenging activity (Fig. 1).

Experimental Example  3: Brine Shrimp Mortality rate  Test( Brine shrimp lethality test )

To evaluate the toxicity of the various test samples, a slight modification of the Brine Shrimp Mortality Test (BST) was carried out (Meyer et al., S Afr Med ., 62 (26): 975-8, 1982). The eggs of Artemia salina hatch at 25 ° C in seawater. The hatched active larvae were attracted to the direction of light. The active larvae (about 100) were selected and treated with test samples at various concentrations (0-100 [mu] g / ml). After 24 hours of treatment of the test sample, live larvae were observed and their effects were confirmed. The larval mortality represents the toxicity of the test sample. Berberine chloride, a standard anticancer drug, was used as a positive controls control, and a brine shrimp larvae placed only in seawater was used as a negative control.

As a result, serratinin has antioxidant activity against prokaryotes and eukaryotes without toxicity.

While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will appreciate that such specific embodiments are merely preferred embodiments and that the scope of the present invention is not limited thereby. something to do. It is therefore intended that the scope of the invention be defined by the claims appended hereto and their equivalents.

Korea Biotechnology Research Institute KCTC12384BP 20130315

<110> Korea Polar Research Institute (KOPRI) <120> Antioxidant Compound Isolated from Serratia sp. and Use Thereof <130> P13-B34 <160> 1 <170> Kopatentin 2.0 <210> 1 <211> 1409 <212> DNA <213> Enterobacteraceae family, Serratia <400> 1 tgcaagtcga gcggtagcac aggagagctt gctctctggg tgacgagcgg cggacgggtg 60 agtaatgtct gggaaactgc ctgatggagg gggataacta ctggaaacgg tagctaatac 120 cgcatgacct cgcaagagca aagtggggga ccttcgggcc tcacgccatc ggatgtgccc 180 agatgggatt agctagtagg tggggtaatg gctcacctag gcgacgatcc ctagctggtc 240 tgagaggatg accagccaca ctggaactga gacacggtcc agactcctac gggaggcagc 300 agtggggaat attgcacaat gggcgcaagc ctgatgcagc catgccgcgt gtgtgaagaa 360 ggccttaggg ttgtaaagca ctttcagcga ggaggaaggg ttcagtgtta atagcactga 420 acattgacgt tactcgcaga agaagcaccg gctaactccg tgccagcagc cgcggtaata 480 cggagggtgc aagcgttaat cggaattact gggcgtaaag cgcacgcagg cggtttgtta 540 agtcagatgt gaaatccccg agcttaactt gggaactgca tttgaaactg gcaagctaga 600 gtcttgtaga ggggggtaga attccaggtg tagcggtgaa atgcgtagag atctggagga 660 ataccggtgg cgaaggcggc cccctggaca aagactgacg ctcaggtgcg aaagcgtggg 720 gagcaaacag gattagatac cctggtagtc cacgctgtaa acgatgtcga cttggaggtt 780 gtgcccttga ggcgtggctt ccggagctaa cgcgttaagt cgaccgcctg gggagtacgg 840 ccgcaaggtt aaaactcaaa tgaattgacg ggggcccgca caagcggtgg agcatgtggt 900 ttaattcgat gcaacgcgaa gaaccttacc tactcttgac atccagagaa ttcgctagag 960 atagcttagt gccttcggga actctgagac aggtgctgca tggctgtcgt cagctcgtgt 1020 tgtgaaatgt tgggttaagt cccgcaacga gcgcaaccct tatcctttgt tgccagcaag 1080 taatggtggg aactcaaagg agactgccgg tgataaaccg gaggaaggtg gggatgacgt 1140 caagtcatca tggcccttac gagtagggct acacacgtgc tacaatggca tatacaaaga 1200 gaagcaaact cgcgagagca agcggacctc ataaagtatg tcgtagtccg gattggagtc 1260 tgcaactcga ctccatgaag tcggaatcgc tagtaatcgt agatcagaat gctacggtga 1320 atacgttccc gggccttgta cacaccgccc gtcacaccat gggagtgggt tgcaaaagaa 1380 gtaggtagct taaccttcgg gagggcgct 1409

Claims (15)

A compound represented by the following formula (1) or a salt thereof:
[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.
A compound according to claim 1, wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And And R &lt; ₁₀ &gt; are both hydrogen.
(2)

The method of claim 1, wherein the Serratia sp. sp.). &lt; / RTI &gt;
4. The method according to claim 3, wherein the Serratia sp. sp.) was serratia sp. PAMC 25557. &lt; / RTI &gt;
Genus Serratia sp.) KCTC 12384BP.
(a) Genus Serratia sp.) microorganism to produce a compound of formula (1); And (b) recovering the compound of formula (I) in a culture medium of said microorganism.
[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.
7. The method of claim 6, wherein step (b) comprises the steps of:
(i) the genus Serratia sp.) microorganism in a first solvent using column chromatography;
(ii) the serratia species obtained in step (a) ( Serratia sp.) concentrating the eluate of the microorganism and extracting it with a second solvent; And
(iii) purifying the extract obtained in step (b) by chromatography, and then obtaining a compound represented by the following formula (1).
[Chemical Formula 1]

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R ₁₀ are each independently H, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an allyl group having 2 to 20 carbon atoms, an arylalkyl group or an acyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms Or alkenyl.
8. The method according to claim 6 or 7, wherein the Serratia sp. Microorganism is Serratia sp. PAMC 25557. &lt; / RTI &gt;
The process according to claim 6 or 7, wherein the first solvent is water, methanol or ethanol and the second solvent is n-hexane, ethyl acetate (EtOAc) or butanol (BuOH) .
The method according to claim 6 or 7, wherein step (iii) is performed by performing silica gel column chromatography or Sephadex column chromatography (Sephadex LH-20) thin layer chromatography, preparative TLC).
The method of claim 6 or 7, wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₉ And R &lt; ₁₀ &gt; are both hydrogen.
A method for producing Serratia spp. Containing the compound of claim 1 or 2 or a salt thereof sp.) Cultures of microorganisms.
13. The method of claim 12, wherein the Serratia &lt; RTI ID = 0.0 &gt; sp.) microorganism is KCTC 12384BP.
An antioxidative composition comprising the compound of claim 1 or 2 or a salt thereof as an active ingredient.
Serratia species of Serratia &lt; RTI ID = 0.0 &gt; ( Serratia &lt; sp.) microorganism as an active ingredient.

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