• 제목/요약/키워드: $^{13}C-NMR$ data

검색결과 310건 처리시간 0.027초

제주 자생 물사과 가지 유래 Flavonoid 화합물의 항산화 활성 (Anti-oxidative Activities for the Flavonoids of the Syzygium aqueum Burm.f. Alston Branches from Jeju Island)

  • 염현숙;이남호;현주미
    • 대한화장품학회지
    • /
    • 제44권2호
    • /
    • pp.151-159
    • /
    • 2018
  • 본 연구에서는 물사과 가지 추출물 및 용매 분획물의 항산화 활성과 세포보호효과를 검색하고 유효성분을 분리하여 화학구조를 규명하였다. 물사과 가지 추출물 및 용매 분획물의 DPPH 및 $ABTS^+$ 라디칼 소거 활성을 측정한 결과, 에틸아세테이트 및 부탄올 분획물에서 우수한 라디칼 소거 활성이 있음을 확인하였다. 또한 $H_2O_2$로 유도된 세포 손상에 대한 세포보호효과를 확인한 결과, $20{\mu}g/mL$의 농도에서 추출물 및 에틸아세테이트 분획물에서 보호효과가 나타남을 확인하였다. 항산화 활성이 좋은 에틸아세테이트 분획물에서 유효성분을 찾고자 medium pressure liquid chromatography (MPLC)를 실시하여 2개의 화합물을 분리하였으며 $^1H$$^{13}C$ NMR 데이터 분석 및 문헌 비교를 통하여 화학구조를 동정하였다; pinocembrin (1), desmethoxymatteucinol (2). 분리된 화합물에 대한 DPPH 및 $ABTS^+$ 라디칼 소거 활성을 측정한 결과, 화합물 1, 2 모두 농도의존적으로 우수한 라디칼 소거 활성이 나타났다. $100{\mu}M$의 농도에서 화합물 1, 2는 $H_2O_2$로 유도된 세포손상에 대하여 세포보호효과를 나타냈다. 이러한 연구 결과를 바탕으로 물사과 가지 추출물은 천연 항산화 소재로써 활용 가능할 것이라 사료된다.

섬오갈피나무 줄기 유래 테르펜 화합물의 멜라닌 생성 저해 활성 (Anti-melanogenesis Activities for the Terpenes from the Acantophanax koreanum Stems)

  • 문승리;현주미;조연정;정은영;이남호
    • 대한화장품학회지
    • /
    • 제43권4호
    • /
    • pp.289-295
    • /
    • 2017
  • 본 연구에서는 섬오갈피 줄기 추출물 및 용매 분획물의 미백 활성을 검색하고 유효성분을 분리하여 화학구조를 규명하였다. 섬오갈피 줄기 에탄올 추출물 및 용매 분획물의 멜라닌 생성 억제활성을 측정한 결과, 헥산 및 에틸아세테이트 분획물에서 우수한 멜라닌 생성 억제 효과가 있음을 확인하였다. 비교적 세포독성이 적은 헥산 분획물에서 유효성분을 찾고자 크로마토크래피를 실시하여 3개의 화합물을 분리하였으며 $^1H$$^{13}C$ NMR 데이터 분석 및 문헌 비교를 통하여 화학구조를 동정하였다; kaurenoic acid (1), $16{\alpha}$-hydro-17-isovaleroyloxy-ent-kauran-19-oic acid (2), $16{\alpha}$-hydroxy-17-isovaleroyloxy-ent-kauran-19-oic acid (3). 분리된 화합물에 대한 미백 활성 실험 결과, 화합물 1-3 모두 농도의존적으로 멜라닌 생성을 억제하였다. 또한 세포 내 티로시나제 효소의 활성을 감소시킴을 확인하였으며 이러한 연구 결과를 바탕으로 섬오갈피 줄기 추출물은 기능성 미백 화장품 소재로써 활용 가능할 것이라 사료된다.

당근 지상부 추출물 유래 항염 및 항균 활성 성분 (Anti-inflammatory and Anti-bacterial Constituents from the Extracts of Daucus carota var. sativa Aerial Parts)

  • 김정은;조연정;이남호
    • 대한화장품학회지
    • /
    • 제44권4호
    • /
    • pp.427-436
    • /
    • 2018
  • 본 연구에서는 당근 지상부 추출물 및 용매 분획물의 항염, 항균 활성을 확인하고 유효성분을 분리하여 화학구조를 동정하였다. 당근 지상부 에탄올 추출물 및 용매 분획물의 항염 활성을 측정하기 위해 LPS로 자극된 RAW 264.7 세포를 이용하여 NO 생성 억제 활성을 확인하였다. 그 중 에틸아세테이트 분획물이 NO의 생성을 농도 의존적으로 감소시키는 효과가 나타났고, 추가적인 항염 기전 연구를 위해 에틸아세테이트 분획물에 대해 $PGE_2$, 전염증성 사이토카인의 생성량 및 iNOS, COX-2 단백질의 발현량을 측정하였다. 그 결과, 에틸아세테이트 분획물이 $PGE_2$, IL-$1{\beta}$, IL-6의 생성을 감소시키고, iNOS, COX-2 단백질의 발현도 억제 시키는 효과가 있음을 확인하였다. 또한 표피포도상구균과 여드름균을 이용한 활성 실험 결과, 헥산 및 에틸아세테이트 분획물에서 항균 활성이 나타났다. 이와 같은 결과를 바탕으로 에틸아세테이트 분획물에 대해 컬럼 크로마토그래피를 수행하여 3개의 화합물을 분리하였으며, $^1H$$^{13}C$ NMR 데이터 분석과 문헌을 통하여 화학구조를 동정하였다; diosmetin (1), disomin (2), cynaroside (3). 분리된 화합물 1-3에 대해 항염 및 항균 활성을 측정하였으며, 그 결과 화합물 1-3 모두 NO의 생성을 저해시키는 효과가 있음을 확인하였다. 또한 화합물 3은 여드름균에 대해 항균 활성이 우수하였다. 이상의 연구 결과를 바탕으로 당근 지상부 추출물을 이용한 항염 및 항균 효과를 갖는 천연 화장품 소재로의 개발이 가능할 것이라 사료된다.

Agelas속의 미동정 해면으로부터 항말라리아 활성을 갖는 Dibromosceptrin의 분리 (Isolation of Dibromosceptrin with Antimalarial Activity from the Unidentified Sponge, Agelas sp.)

  • 박영범;이종수;임치원
    • 생약학회지
    • /
    • 제35권3호통권138호
    • /
    • pp.189-193
    • /
    • 2004
  • In order to find some lead compounds for the treatment of opportunistic infections of malaria and pathogenic microbes, an undescribed Indonesian sponge Agelas sp. collected at Manado, Indonesian Waters, was suggested containing active compounds. Crude ethanolic extract of the sponge exhibited significant in vitro antimalarial and antimicrobial activity against Plasmodium falciparum (D6 colne) with $IC_{5O}$ values of $8\;{\mu}/ml$ and against pathogenic microbes such as Candida albicans $(150\;{\mu}/ml)$, Cryptococcus neoformans $(<20\;{\mu}/ml)$, Staphylococcus aureus $25\;{\mu}/ml$, methicillin-resistant Staphylococcus aureus $(<20\;{\mu}/ml)$, and Pseudomonas aeruginosa $(<20\;{\mu}/ml)$. Active compound (5.0 mg) was isolated from the ethanolic extracts of the sponge and purified by using silica gel and ODS column, successively. Active compound was elucidated as dibromosceptrin $(C_{22}H_{24}Br_2N_{10}O_2)$ by detailed analysis of FTESI-MS and comparison of $^1H,\;^{13}C$, DEPT and HMQC NMR spectral data with those reported.

Spectroscopic, Thermal and Biological Studies of Zn(II), Cd(II) and Hg(II) Complexes Derived from 3-Aminopyridine and Nitrite Ion

  • Dhaveethu, Karuthakannan;Ramachandramoorthy, Thiagarajan;Thirunavukkarasu, Kandasamy
    • 대한화학회지
    • /
    • 제57권6호
    • /
    • pp.712-720
    • /
    • 2013
  • Microwave assisted syntheses of Zn(II), Cd(II) and Hg(II) complexes with 3-aminopyridine (3AP) and nitrite ($NO_2{^-}$) ions have been reported. The metal complexes were characterized by elemental analyses, molar conductance, IR, Far-IR, electronic, NMR ($^1H$, $^{13}C$), thermal and electron impact mass spectral studies. The spectroscopic studies reveal the composition, the nature of nitrite ligand in the complexes, electronic transitions, chemical environments of C and H atoms thermal degradation of the complexes. On the basis of characterization data, distorted tetrahedral geometry is suggested for Zn(II), Cd(II) and Hg(II) complexes. The organic ligand (3AP) and their metal complexes were screened against gram negative pathogenic bacteria and fungi in vitro. The results are compared with our previous report J. Korean Chem. Soc. 2013, 57, 341 on 4-aminopyridine and nitrite ion complexes of the same metal ions.

Chemical Constituents of Impatiens balsamina Stems and Their Biological Activities

  • Kim, Dong Hyun;Lee, Tae Hyun;Subedi, Lalita;Kim, Sun Yeou;Lee, Kang Ro
    • Natural Product Sciences
    • /
    • 제25권2호
    • /
    • pp.130-135
    • /
    • 2019
  • The purification of the MeOH extract from Impatiens basamina by repeated column chromatography led to the isolation of one new tetrahydronaphthalene (1), together with eleven known compounds (2 - 12). The structure of the new compound (1) was determined by spectral data analysis ($^1H$ and $^{13}C$-NMR, $^1H-^1H$ COSY, HSQC, HMBC, NOESY, and HR-ESI-MS). Isolated compounds (1 - 12) were evaluated for their inhibitory effects on NO production in LPS-activated murine microglial BV-2 cells and their effects on NGF secretion from C6 glioma cells. Compounds 3, 7, and 10 reduced NO levels in LPS-activated murine microglial cells with $IC_{50}$ values of 26.89, 25.59, and $44.21{\mu}M$, respectively. Compounds 1, 5, and 9 upregulated NGF secretion to $153.09{\pm}4.66$, $156.88{\pm}8.86$, and $157.34{\pm}3.30%$, respectively.

An NMR Study on Internal Rotation of $CH_3$ Group in 1,1,1-Trichloroethane

  • Hyung Namgoong;Kim, Joa-Jin;Lee, Jo-Woong
    • 한국자기공명학회논문지
    • /
    • 제4권1호
    • /
    • pp.29-40
    • /
    • 2000
  • Coupled carbon-13 relaxation study of 1,1,1-trichloroethane dissolved in DMSO has been performed to gain some crucial insight into the dynamics of methyl group in this compound. For this purpose the relaxation behaviors of several observable magnetization modes for CH3 spin system generated by various perturbing pulse sequences have been carefully investigated and various dipolar spectral densities were estimated by nonlinear numerical fittings of the observed data with the relaxation curves, which were then employed to determine the three principal values for the diffusion tensor for end-over-end molecular rotation as well as internal rotational parameters of methyl group. In this process we could uniquely determine two correlation times $\tau$int(1) and $\tau$int(2) which give valuable information on internal rotor dynamics and thus obtained data were interpreted on the basis of various proposed models for internal rotation. compound undergoes three-fold jumps at 25$^{\circ}$. The fact that the ratio $\tau$int(1) / $\tau$int(2) is close to 1.0 may be interpreted as indicating that methyl group in this C.

  • PDF

생강나무(Lindera obtusiloba Blume) 목부로부터 Flavonoid 및 Lignan 화합물의 분리 (Isolation of Flavonoids and Lignans from the Stem Wood of Lindera obtusiloba Blume)

  • 서경화;백미영;이대영;조진경;강희철;안은미;백남인;이윤형
    • Journal of Applied Biological Chemistry
    • /
    • 제54권3호
    • /
    • pp.178-183
    • /
    • 2011
  • 생강나무 목부를 80% methanol로 추출, 농축하였으며, 얻어진 추출물을 ethyl acetate (EtOAc), butanol (n-BuOH) 및 $H_2O$로 분배, 추출하였다. 이 중 EtOAc 분획과 n-BuOH 분획에 대하여 silica gel, octadecyl silica gel (ODS) 및 Sephadex LH-20 column chromatography를 반복 수행하여 2종의 lignan과 3종의 flavonoid 화합물을 분리하였다. 분리한 화합물의 구조는 NMR, MS 및 IR 등의 스펙트럼 데이터를 해석하여 asarinin (1), (+)-catechin (2), (-)-epicatechin (3), hyperin (4) 및 nudiposide (5)로 구조 동정하였다. Asarinin (1)과 nudiposide (5)는 생강나무에서 이번에 처음으로 분리되었다.

Synthesis and Micellar Characterization of CBABC Type PLGA-PEO-PPO-PEO-PLGA Pentablock Copolymers

  • Seong, Haseob;Cho, Eun-Bum;Oh, Joongseok;Chang, Taihyun
    • Bulletin of the Korean Chemical Society
    • /
    • 제35권8호
    • /
    • pp.2342-2348
    • /
    • 2014
  • Poly(lactic-co-glycolic acid) (PLGA) were grafted to both ends of Pluronic$^{(R)}$ F68 ($(EO)_{75}(PO)_{30}(EO)_{75}$) triblock copolymer to produce poly{(lactic acid)$_m$-co-(glycolic acid)$_n$}-b-poly(ethylene oxide)$_{75}$-b-poly(propylene oxide)$_{30}$-b-poly(ethylene oxide)$_{75}$-b-poly{(lactic acid)$_m$-co-(glycolic acid)$_n$} (PLGA-F68-PLGA) pentablock copolymers. Molecular weights of PLGA blocks were controlled and five kinds of pentablock copolymers with different PLGA block lengths were synthesized using in-situ ring-opening polymerization of D,L-lactide and glycolide with tin(II) 2-ethylhexanoate ($Sn(Oct)_2$) catalyst. PLGA-F68-PLGA pentablock copolymers were characterized by $^1H$- and $^{13}C$-NMR, GPC, and TGA. The numbers (2m, 2n) of repeating units for lactic acid and glycolic acid inside PLGA segments were obtained as (48, 17), (90, 23), (125, 40), (180, 59), and (246, 64), with $^1H$-NMR measurement. From NMR data, the resultant molecular weights were determined in the range of 12,700-29,700, which were similar to those obtained from GPC. Polydispersity index was increased in the range of 1.32-1.91 as the content of PLGA blocks increased. TG and DTG thermograms showed discrete degradation traces for PLGA and F68 blocks, which indicate the weight fractions of PLGA blocks in pentablock copolymers can be calculated by TG profile and it is possible to remove PLGA block selectively. Hydrodynamic radius and radius of gyration of pentablock copolymer micelle were obtained in the range of 46-68 nm and 31-49 nm, respectively, in very dilute (i.e. 0.005 wt %) aqueous solution of THF:$H_2O$ = 10:90 by volume at $25^{\circ}C$.

Chemical Constituents from the Leaf and Twig of Acer okamotoanum Nakai and their Cytotoxicity

  • Jin, Wen-Yi;Min, Byung-Sun;Youn, Ui-Jung;Hung, Tran-Manh;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • 한국약용작물학회지
    • /
    • 제14권2호
    • /
    • pp.77-81
    • /
    • 2006
  • As a result of cytotoxic compounds against cancer cell lines from natural sources, senven compounds were isolated from the leaf and twig of Acer okamotoanum Nakai. The compounds (1-7) were identified as ethyl gallate (1), methyl gallate (2), gallic acid (3), trans $resveratrol-3-O-{\beta}-D-glucopyranoside$ (4), acertannin (5), nikoenoside (6), and fraxin (7) by physicochemical and spectroscopic data (including mp, UV, IR, MS, $^1H-NMR,\;^{13}C-NMR$, DEPT, and HMBC) in comparison with those of published papers. All the compounds were tested for their cytotoxic activity against L1210, HL-60, K562, and B16F10 cancer cell lines in vitro by MTT assay method. Compounds 1-3 and 5 showed cytotoxic activity against all tested cell lines with $IC_{50}$ values ranged from 12.5 to $72.2\;{\mu}M$. Of the compounds, methyl gallate (2) exhibited the most potent cytotoxic activity against L1210, HL-60, K562, and B16F10 tumor cells with $IC_{50}$ values of 12.5, 48.3, 22.8, and $22.8\;{\mu}M$, respectively. Other compounds did not show any cytotoxic activity against four cancer cell lines.