• 제목/요약/키워드: $^1H-NMR$

검색결과 2,516건 처리시간 0.027초

인삼 지용성성분인 유전독성억제효과와 작용기전 (Antigenotoxicity of Ginseng Petroleum Ether Extract and its Action Mechanism)

  • 허문영
    • 한국식품위생안전성학회지
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    • 제13권3호
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    • pp.243-251
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    • 1998
  • 백삼(Pampx ginseng C.A. Meyer, 4년근)을 가루로 한 다음 petroleum ether로 24시간 추출 후 감압 농축시켜 인삼 석유에텔추출물(GPE)로 하였다. 이때 GPE의 수율은 평균 2.24%였다. 또한 GPE를 petroleum ether 소량에 녹이고 petroleum ether:ether 용매계열로 silicagel column chromatography에 의한 partition을 실시하여 P1, P2, P3 , P4, P5의 5개의 분획을 얻었다. 본 실험에서는 소핵생성 물질인 N-methyl-N-nitrosourea(MNU) 및 benzo(a) pyrene[B(a)P]를 이용하여 소핵생성억제실험을 하였따. 상기의 5가지 분획 중에서 MNU에 대해서는 GPE, P1, P2에서 억제효과가 나타났다. 한편, B(a)P에 대해서는 GPE, P1, P2, P3 , P4, P5 모두에게 억제효과를 나타내었다. 그러나 여러 가지 활성을 보인 분획 중에서 여러 가지 양성대조물질들에 대해서 가장 두드러져 보이는 것은 P2였다. P2는 MNU, B(a)P 모두에 대해서 GPE와 유사한 억제경향을 보이면서 억제활성은 크게 나타난T다. EK라서 P2가 GPE가 보이는 소핵생성억제효과에 깊은 관련이 있는 물질로 판단되었다. 이와 같은 유전독성억제효과의 작용기전을 알기 위하여 B(a)P의 대사에 미치는 영향을 연구한 결과 GPE와 P2는 S-9 mix에 의해 유도된 B(a)P 대사를 억제시켰으며, DNA-B(a)P binding도 감소시켰다. 한편, MNU에 의한 DNA binding 과 O6-methyl guanine 및 7-methyl guanine 생성에 있어서도 억제적인 경향을 나타내었다. 따라서 GPE와 P2는 B(a)P와 같은 2차 발암 물질과 MNU와 같은 알킬화제에 의한 유전독성을 활성대사억제 및 methylation 억제 , DNA binding 억제 등의 기전으로 감소시키고 있는 것으로 판단되었다. 한편, 소핵생성억제 효과에서 가장 활성이 좋았던 P2를 NMR과 GC/MS결과, aliphatic ketone류의 혼합물로서 주성분은 분질량 330과 386의 두 개 물질이 함유되어 있는 혼합물이었으며 향후 계속적으로 분리 동정이 필요한 물질이다.

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Dammarane-type triterpene oligoglycosides from the leaves and stems of Panax notoginseng and their antiinflammatory activities

  • Li, Juan;Wang, Ru-Feng;Zhou, Yue;Hu, Hai-Jun;Yang, Ying-Bo;Yang, Li;Wang, Zheng-Tao
    • Journal of Ginseng Research
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    • 제43권3호
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    • pp.377-384
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    • 2019
  • Background: Inflammation is widespread in the clinical pathology and closely associated to the progress of many diseases. Triterpenoid saponins as a key group of active ingredients in Panax notoginseng (Burk.) F.H. Chen were demonstrated to show antiinflammatory effects. However, the chemical structures of saponins in the leaves and stems of Panax notoginseng (PNLS) are still not fully clear. Herein, the isolation, purification and further evaluation of the antiinflammatory activity of dammarane-type triterpenoid saponins from PNLS were conducted. Methods: Silica gel and reversed-phase C8 column chromatography were used. Furthermore, preparative HPLC was used as a final purification technique to obtain minor saponins with high purities. MS, NMR experiments, and chemical methods were used in the structural identifications. The antiinflammatory activities of the isolated saponins were assessed by measuring the nitric oxide production in RAW 264.7 cells stimulated by lipopolysaccharides. Real-time reverse transcription polymerase chain reaction was used to measure the gene expressions of inflammation-related gene. Results: Eight new minor dammarane-type triterpene oligoglycosides, namely notoginsenosides LK1-LK8 (1-8) were obtained from PNLS, along with seven known ones. Among the isolated saponins, gypenoside IX significantly suppressed the nitric oxide production and inflammatory cytokines including tumor necrosis $factor-{\alpha}$, interleukin 10, interferon-inducible protein 10 and $interleukin-1{\beta}$. Conclusion: The eight saponins may enrich and expand the chemical library of saponins in Panax genus. Moreover, it is reported for the first time that gypenoside IX showed moderate antiinflammatory activity.

Phytochemical analysis of Panax species: a review

  • Yang, Yuangui;Ju, Zhengcai;Yang, Yingbo;Zhang, Yanhai;Yang, Li;Wang, Zhengtao
    • Journal of Ginseng Research
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    • 제45권1호
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    • pp.1-21
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    • 2021
  • Panax species have gained numerous attentions because of their various biological effects on cardiovascular, kidney, reproductive diseases known for a long time. Recently, advanced analytical methods including thin layer chromatography, high-performance thin layer chromatography, gas chromatography, high-performance liquid chromatography, ultra-high performance liquid chromatography with tandem ultraviolet, diode array detector, evaporative light scattering detector, and mass detector, two-dimensional high-performance liquid chromatography, high speed counter-current chromatography, high speed centrifugal partition chromatography, micellar electrokinetic chromatography, high-performance anion-exchange chromatography, ambient ionization mass spectrometry, molecularly imprinted polymer, enzyme immunoassay, 1H-NMR, and infrared spectroscopy have been used to identify and evaluate chemical constituents in Panax species. Moreover, Soxhlet extraction, heat reflux extraction, ultrasonic extraction, solid phase extraction, microwave-assisted extraction, pressurized liquid extraction, enzyme-assisted extraction, acceleration solvent extraction, matrix solid phase dispersion extraction, and pulsed electric field are discussed. In this review, a total of 219 articles published from 1980 to 2018 are investigated. Panax species including P. notoginseng, P. quinquefolius, sand P. ginseng in the raw and processed forms from different parts, geographical origins, and growing times are studied. Furthermore, the potential biomarkers are screened through the previous articles. It is expected that the review can provide a fundamental for further studies.

지방산 기반 에스토라이드 합성 및 윤활특성 (Synthesis and Lubricant Properties of Estolides based on Fatty Acid)

  • 손정매;유승현;이상준;신지훈;정근우;양영도;김영운
    • Tribology and Lubricants
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    • 제30권5호
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    • pp.256-264
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    • 2014
  • Enhancing the value of fine chemicals based on biomass resources is an important objective for addressing environmental and other concerns such as demand for renewable or green products, as well as from the political perspective to reduce dependence on fossil feedstock associated with the use of petroleum-based products. Based on these considerations, we studied the synthesis of estolide using waste plant-based oil materials and their application as lubricants and pour point depressants. Five estolides were prepared by varying molar ratio of palmitic acid (PA) to oleic acid (OA) using a reaction time of 48 h. The estolides were characterized by size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR). The isolated yields were in the range of 57-78 % and purity was 93-97%, showing iodine values of 18.2-37.8, total acid numbers (TANs) of 75.6-94.2 mg KOH/g and estolide numbers (ENs) of 1.2-1.8. Increasing the ratio of OA to PA in the synthesis decreased the kinematic viscosity and clouding point of the estolides. Four ball wear test of the estolides as a base oil demonstrated that the wear scar diameter (WSD) of the estolides was significantly lower (0.320-0.495 mm) than the WSD of general base oils such as 150N and Yubase (0.735 and 0.810 mm, respectively), indicating better wear resistance of the estolides. However, the lubricant property was found to be independent of the amount of OA in the estolides. These new materials are prospective candidates for application as a lubricant base oil.

순비기 나무(Vitex rotundifolia) 추출.분획물 및 화합물의 인체 암세포 증식억제 효과 (Antiproliferative Effect of Extracts, Fractions and Compound from Vitex rotundifolia on Human Cancer Cells)

  • 김유아;이정임;김해진;공창숙;남택정;서영완
    • Journal of Applied Biological Chemistry
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    • 제52권4호
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    • pp.180-186
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    • 2009
  • 본 연구에서는 염생식물의 한 종인 순비기나무의 추출 분획물 및 화합을 이용하여 항발암성 및 생체방어 물질로서의 유용성을 검토하고자 4종의 인체 암세포(HT1080, AGS, MCF-7 및 HT-29)에 대한 증식억제 효과를 검토하였다. 추출물에 대한 암세포 증식억제능 측정 결과, 10, 50 및 $100\;{\mu}g/mL$의 시료 처리 농도에서 농도 의존적으로 암세포의 생존율이 감소하는 경향을 확인하였으며, 모든 세포주에 대하여 methanol 추출물 보다 methylene chloride 추출물이 뛰어난 효과를 나타냄을 알 수 있었다. 따라서, 물질의 극성도에 따른 암세포 증식억제능을 확인하고자 추출물을 순차적으로 용매 분획하여 $H_2O$, n-BuOH, 85% aq. MeOH 및 n-hexane의 네 가지 분획층을 얻었으며, 추출물과 동일한 조건하에서 암세포 증식억제 효과를 재검토하였다. 그 결과, 비교적 극성이 덜한 85% aq. MeOH 분획층에서 우수한 암세포 증식억제능이 확인되었다. $100\;{\mu}g/mL$의 농도에서 85% aq. MeOH 분획층의 시료를 처리한 결과 HT1080, AGS, MCF-7 및 HT-29 세포는 각각 93.8, 91.6, 90.9% 그리고 82.7%의 강력한 억제 효과를 나타내었으며, 낮은 농도의 시료($10\;{\mu}g/mL$)를 처리한 결과에서도 HT1080과 AGS 세포에서 주목할 만한 억제효과를 보여 주었다. 생리활성 결과를 바탕으로 85% aq. MeOH 분획층의 분리를 통해 1종의 화합물을 분리할 수 있었으며, artemetin으로 알려진 화합물로 확인되었다. 분리된 화합물의 암세포 증식억제 효과를 확인해 본 결과 HT1080 세포에 선택적으로 효과를 보임을 확인하였으며, 그 효과는 항암제인 doxorubicin에 상응하는 결과였다. 따라서 본 연구를 통해 염생식물 순비기나무의 각종 인체 암세포에 대한 높은 증식억제 효과와 함께 암예방을 위한 기능성 소재로서의 개발 가능성이 확인되었다. 추후 순비기나무의 85% aq. MeOH 분획층 및 분리된 화합물에 대한 집중적인 연구를 통해 새로운 생리활성물질의 개발이 기대되어진다.

Brief Introduction of Research Progresses in Control and Biocontrol of Clubroot Disease in China

  • He, Yueqiu;Wu, Yixin;He, Pengfei;Li, Xinyu
    • 한국균학회소식:학술대회논문집
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    • 한국균학회 2015년도 춘계학술대회 및 임시총회
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    • pp.45-46
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    • 2015
  • Clubroot disease of crucifers has occurred since 1957. It has spread to the whole China, especially in the southwest and nourtheast where it causes 30-80% loss in some fields. The disease has being expanded in the recent years as seeds are imported and the floating seedling system practices. For its effective control, the Ministry of Agriculture of China set up a program in 2010 and a research team led by Dr. Yueqiu HE, Yunnan Agricultural University. The team includes 20 main reseachers of 11 universities and 5 institutions. After 5 years, the team has made a lot of progresses in disease occurrence regulation, resources collection, resistance identification and breeding, biological agent exploration, formulation, chemicals evaluation, and control strategy. About 1200 collections of local and commercial crucifers were identified in the field and by artificiall inoculation in the laboratories, 10 resistant cultivars were breeded including 7 Chinese cabbages and 3 cabbages. More than 800 antagostic strains were isolated including bacteria, stretomyces and fungi. Around 100 chemicals were evaluated in the field and greenhouse based on its control effect, among them, 6 showed high control effect, especially fluazinam and cyazofamid could control about 80% the disease. However, fluzinam has negative effect on soil microbes. Clubroot disease could not be controlled by bioagents and chemicals once when the pathogen Plasmodiophora brassicae infected its hosts and set up the parasitic relationship. We found the earlier the pathogent infected its host, the severer the disease was. Therefore, early control was the most effective. For Chinese cabbage, all controlling measures should be taken in the early 30 days because the new infection could not cause severe symptom after 30 days of seeding. For example, a biocontrol agent, Bacillus subtilis Strain XF-1 could control the disease 70%-85% averagely when it mixed with seedling substrate and was drenching 3 times after transplanting, i.e. immediately, 7 days, 14 days. XF-1 has been deeply researched in control mechanisms, its genome, and development and application of biocontrol formulate. It could produce antagonistic protein, enzyme, antibiotics and IAA, which promoted rhizogenesis and growth. Its The genome was sequenced by Illumina/Solexa Genome Analyzer to assembled into 20 scaffolds then the gaps between scaffolds were filled by long fragment PCR amplification to obtain complet genmone with 4,061,186 bp in size. The whole genome was found to have 43.8% GC, 108 tandem repeats with an average of 2.65 copies and 84 transposons. The CDSs were predicted as 3,853 in which 112 CDSs were predicted to secondary metabolite biosynthesis, transport and catabolism. Among those, five NRPS/PKS giant gene clusters being responsible for the biosynthesis of polyketide (pksABCDEFHJLMNRS in size 72.9 kb), surfactin(srfABCD, 26.148 kb, bacilysin(bacABCDE 5.903 kb), bacillibactin(dhbABCEF, 11.774 kb) and fengycin(ppsABCDE, 37.799 kb) have high homolgous to fuction confirmed biosynthesis gene in other strain. Moreover, there are many of key regulatory genes for secondary metabolites from XF-1, such as comABPQKX Z, degQ, sfp, yczE, degU, ycxABCD and ywfG. were also predicted. Therefore, XF-1 has potential of biosynthesis for secondary metabolites surfactin, fengycin, bacillibactin, bacilysin and Bacillaene. Thirty two compounds were detected from cell extracts of XF-1 by MALDI-TOF-MS, including one Macrolactin (m/z 441.06), two fusaricidin (m/z 850.493 and 968.515), one circulocin (m/z 852.509), nine surfactin (m/z 1044.656~1102.652), five iturin (m/z 1096.631~1150.57) and forty fengycin (m/z 1449.79~1543.805). The top three compositions types (contening 56.67% of total extract) are surfactin, iturin and fengycin, in which the most abundant is the surfactin type composition 30.37% of total extract and in second place is the fengycin with 23.28% content with rich diversity of chemical structure, and the smallest one is the iturin with 3.02% content. Moreover, the same main compositions were detected in Bacillus sp.355 which is also a good effects biocontol bacterial for controlling the clubroot of crucifer. Wherefore those compounds surfactin, iturin and fengycin maybe the main active compositions of XF-1 against P. brassicae. Twenty one fengycin type compounds were evaluate by LC-ESI-MS/MS with antifungal activities, including fengycin A $C_{16{\sim}C19}$, fengycin B $C_{14{\sim}C17}$, fengycin C $C_{15{\sim}C18}$, fengycin D $C_{15{\sim}C18}$ and fengycin S $C_{15{\sim}C18}$. Furthermore, one novel compound was identified as Dehydroxyfengycin $C_{17}$ according its MS, 1D and 2D NMR spectral data, which molecular weight is 1488.8480 Da and formula $C_{75}H_{116}N_{12}O_{19}$. The fengycin type compounds (FTCPs $250{\mu}g/mL$) were used to treat the resting spores of P. brassicae ($10^7/mL$) by detecting leakage of the cytoplasm components and cell destruction. After 12 h treatment, the absorbencies at 260 nm (A260) and at 280 nm (A280) increased gradually to approaching the maximum of absorbance, accompanying the collapse of P. brassicae resting spores, and nearly no complete cells were observed at 24 h treatment. The results suggested that the cells could be lyzed by the FTCPs of XF-1, and the diversity of FTCPs was mainly attributed to a mechanism of clubroot disease biocontrol. In the five selected medium MOLP, PSA, LB, Landy and LD, the most suitable for growth of strain medium is MOLP, and the least for strains longevity is the Landy sucrose medium. However, the lipopeptide highest yield is in Landy sucrose medium. The lipopeptides in five medium were analyzed with HPLC, and the results showed that lipopeptides component were same, while their contents from B. subtilis XF-1 fermented in five medium were different. We found that it is the lipopeptides content but ingredients of XF-1 could be impacted by medium and lacking of nutrition seems promoting lipopeptides secretion from XF-1. The volatile components with inhibition fungal Cylindrocarpon spp. activity which were collect in sealed vesel were detected with metheds of HS-SPME-GC-MS in eight biocontrol Bacillus species and four positive mutant strains of XF-1 mutagenized with chemical mutagens, respectively. They have same main volatile components including pyrazine, aldehydes, oxazolidinone and sulfide which are composed of 91.62% in XF-1, in which, the most abundant is the pyrazine type composition with 47.03%, and in second place is the aldehydes with 23.84%, and the third place is oxazolidinone with 15.68%, and the smallest ones is the sulfide with 5.07%.

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전통 발효 청국장으로부터 분리한 Bacillus 균주들의 특성 및 기능 분석 (Characteristics and functional analysis of Bacillus strains from the fermented soybean products, Cheonggukjang)

  • 문지영;권순우;홍승범;석순자;김정선;김수진
    • 미생물학회지
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    • 제51권3호
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    • pp.300-307
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    • 2015
  • 좋은 청국장을 발효하는 균주를 선발하기 위하여 청국장 시료로부터 8개의 균주를 선발하였다. 이들 중 7균주는 Bacillus subtilis subsp. subtilis와 99.9% 이상의 가장 높은 16S rRNA 유사도를 보였고, 한 균주는 B. licheniformis와 높은 유사도를 보였다. 선발 균주의 효소 생성을 분석한 결과 모든 균주에서 amylase, cellulase, protease 그리고 lipase 활성을 보였고, 6균주에서 혈전용해능을 보였다. 또한 전통방법으로 제조한 청국장에서 분리한 균주들의 안전성을 확보하고자 분리균주와 계통학적으로 가까운 Bacillus cereus의 독소유전자 7종의 유무를 확인한 결과 모든 선발균주에서 독소유전자 7종을 가지고 있지 않았다. 선발 균주 중 8균주에서 histamine과 tyramine의 생성이 없거나 최소한의 생성을 보였고, HPLC를 이용한 바이오제닉 아민 분해능 분석 결과 대부분의 균주가 tyramine 분해능을 보였다. 선발된 균주로 발효한 청국장의 발효능, 관능, 휘발성염기질소 생성을 확인 하여 7균주가 좋은 품질의 청국장을 만드는 것으로 확인되었고, 이들 선발된 균주로 만든 청국장의 metabolic profile을 분석하였다.

약물 및 유전자 전달체로 응용하기 위한 Poly(L-Lysine)이 결합된 O-Carboxymethyl Chitosan PEG의 제조와 특성 (Preparation and Characterization of O-Carboxymethyl Chitosan Ion-complexed Poly(L-Lysine) for Drug and Gene Delivery System)

  • 남정표;김영민;박진수;이응재;최창용;장미경;나재운
    • 공업화학
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    • 제21권6호
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    • pp.643-647
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    • 2010
  • 키토산의 응용성을 높이기 위해 제조된 O-carboxymethyl water soluble chitosan (OCMCh)의 구조에 인체 내 순환시간을 증가시키기 위하여 PEG를 도입하였으며, 약물 및 유전자 전달체로 응용하기 위하여 PEG가 결합된 OCMCh-PEG를 Poly(L-Lysine) (PLL)과 이온복합체를 형성함으로써 OCMCh-PEG-PLL를 제조하였다. 제조된 OCMCh-PEG-PLL의 물리화학적특성은 적외선 분광광도계와 핵자기공명장치를 이용하여 분석하였으며, 성공적으로 PLL이 결합되었음을 확인하였다. 또한 동적광산란장치와 투과전자현미경을 통하여 PLL의 양을 고정하였을 때, PEG의 양이 증가함에 따라 입자의 크기가 감소하는 것을 볼 수 있었으며, 구형의 입자형태를 가지는 것을 확인할 수 있었다. 이상의 결과는 OCMCh-PEG-PLL이 약물 및 유전자 전달체 등과 같은 생체재료로의 응용 가능성을 가지는 것을 볼 수 있다.

열방성 블록 코폴리에스테르와 poly(ethylene 2,6-naphthalate)의 복합재료 연구(I) (On the Composites of poly(ethylene 2,6-naphthalate) with a Thermotropic Block Copolyester(I))

  • 최재곤
    • 공업화학
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    • 제8권3호
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    • pp.454-462
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    • 1997
  • 새로운 poly(tetramethylene 2,6-(naphthaloyldioxy)dibenzoates)(TLCP) 블록과 poly (butylene 2,6-naphthalate)(PBN) 블록으로 구성된 열방성 블록공중합체(TLCP-b-PBN)를 용액중합에 의하여 합성하였고, in-situ 복합재료를 제조하기 위해서 poly(ethylene 2,6-naphthalate) (PEN)과 용응블렌드하였다. TLCP domain은 용융상태에서 네마틱 상을 보여 주었다. 블록공중합체는 DSC 열곡선에서 PBN과 TLCP domain에 해당되는 두 개의 뚜렷한 용응전이점을 보여 주었다. 블렌드내의 PEN의 유리전이온도 ($T_g$)는 TLCP-b-PBN의 함량에 따라 감소하였으며, TLCP-b-PBN은 매트릭스 고분자에 대한 기핵제로 작용하였다. 편광현미경 관찰결과 20% TLCP-b-PBN 블렌드 경우 PEN의 용융점이상 온도에서 잘 배향된 TLCP fibril을 볼 수 있었다. 압출된 블렌드를 액체질소내에서 절단하여 전자현미경을 이용하여 모폴로지를 관찰한 결과 TLCP domain은 $0.15{\mu}m$에서 $0.2{\mu}m$ 크기로 균일하게 분포되어 있음을 확인하였다. 매트릭스 곡분자와 TLCP와의 계면접착력은 비교적 좋았으며, 매트릭스 고분자내의 TLCP domain은 중앙에서는 구형의 모양을, 표면에서는 가늘게 배향된 섬유 모양을 보였다.

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인삼(Panax ginseng) 열매로부터 분리한 ginsenoside의 동정 및 암세포독성 효과 (Ginsenosides from the fruits of Panax ginseng and their cytotoxic effects on human cancer cell lines)

  • 곽정은;이영근;황보전;김형근;오선민;이대영;백남인
    • Journal of Applied Biological Chemistry
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    • 제61권4호
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    • pp.371-377
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    • 2018
  • 인삼(Panax. ginseng) 열매를 80% MeOH 수용액으로 3회 반복 추출한 뒤, 감압 농축한 추출물을 EtOAc, n-BuOH과 $H_2O$ 층으로 계통 분획을 실시하였다. EtOAc분획에 대하여 $SiO_2$ 및 ODS column chromatography를 반복실시하여 5종의 ginsenoside 화합물을 분리 및 정제하였다. NMR, IR, FAB/MS 데이터를 해석하여, 각각 ginsenoside F1 (1), ginsenoside F2 (2), ginsenpside F3 (3), ginsenoside Ia (4) 및 notoginsenoside Fe (5)로 구조 동정 하였다. 화합물 2-5는 인삼열매에서는 이번에 처음 분리 보고되었다. 분리한 5종의 화합물을 인체 암세포주(HCT-116, SK-OV-3, HeLa, HepG2, SK-MEL-5)에 처리하여 세포독성을 측정하였다. 이 중 화합물 2, 4, 및 5가 인체 암세포주에 대해 세포독성을 저해시키는 것을 알 수 있었다. 화합물 2는 SK-MEL-5, HepG2, HeLa세포에서 $IC_{50}$값이 82.8, 86.8, $78.3{\mu}M$로 확인되었다. 화합물 4는 HCT-116, SK-MEL-5, SK-OV-3, HepG2, HeLa 세포에서 $IC_{50}$ 값이 24.5, 25.4, 26.3, 22.0, $24.9{\mu}M$로 확인되었다. 화합물 5는 SK-MEL-5 세포에서 $IC_{50}$ 값이 $81.7{\mu}M$로 확인되었다. 인삼 열매에서 분리한 화합물2, 4, 및 5가 암세포주에 대해 강한 세포독성을 나타내는 것을 확인하였으며, 이 화합물들은 공통적으로 3번 수산기에 glucopyranose를 가지고 있음을 확인하였다.