• 제목/요약/키워드: 1D and 2D NMR

검색결과 920건 처리시간 0.027초

식물생장조절물질 말포민 B동족체의 화학구조 및 생리활성 (Chemical Structures and Physiological Activities of Plant Growth Substance, Malformin B's)

  • 김건우
    • 한국잡초학회지
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    • 제15권1호
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    • pp.85-98
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    • 1995
  • 말포민 B로부터 신규의 $B_3$, $B_4$$B_5$를 포함한 6종의 B동족체들이 단리 구조결정되었다. 본 연구에 의해 말포민 B동족체의 화학구조는, $B_{1a}$(1)가 cyclo-D-Cys-D-Cys-L-Val-D-Leu-L-allo-Ile, $B_{1b}$(2)가 cyclo-D-Cys-D-Cys-L-Val-D-Leu-L-Leu, $B_2$(3)가 cyclo-D-Cys-D-Cys-L-V al-D-Val-L-Leu, $B_3$(4)가 cyclo-D-Cys-D-Cys-L-Val-D-Ile-L-Leu, $B_4$(5)가 cyclo-D-Cys-D-Cys-L-Val-D-Ile-L-Ile, $B_5$(6)가 cyclo-D-Cys-D-Cys-L-Val-D-Val-L-Ile으로서 확정되었다. B's, $B_{1b}$ C 이들 중, 말포민 $B_{1b}$(2)의 화학구조는 말포민 $A_3$ 및 말포민 C와 동일한 것으로 판명되었다. 단리된 말포민 B동족체에 대해서 옥수수 근부굴곡활성과 녹두 상배축산장활성을 지표로 하여 생물검정을 실시한 결과, 모든 B동족체가 활성을 나타내었다. 옥수수 근부굴곡활성의 검정으로부터, 분자량 529의 동족체가 분자량 515의 동족체보다 높은 활성을 보여주었으며, 이는 HPLC상의 retention time에서 확인된 바와 같이, 전체 말포민분자의 극성 이 옥수수 근부굴곡활성에 대해서 영향을 마친다는 사실을 시사한다. 또한, 말포민의 구조를 유지시켜주는 -S-S-가교구조와 제4-제5 아미노산 잔기에 측쇄구조가 상이한 leucine과 isoleucine의 조합이 말포민 수용부위와의 결합에 있어서 최적의 형상을 취할 수 있다는 점에서 말포민류의 활성 발현에 중요한 구조적 요소들일 것으로 추정되어진다. 말포민 $B_{1a}$$0.25{\mu}m$에서 90%의 옥수수 근부굴곡활성을 나타내었다. 그러나, 녹두 상배축산장활성의 경우 분자량에 따른 활성의 차이는 인정되지 않았으며, 말포민 $B_5$의 처리시 $0.1{\mu}m$에서 대조구에 비해 1.54%의 신장촉진을 보여주었다.

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Molybdenum(VI), -(V), and -(IV) Oxo Complexes with S-methyl 3-(2-hydroxypheny)methylenedithiocarbazate and Its Derivatives

  • Hee-Jung Kim;Bon-Kweon Koo
    • Bulletin of the Korean Chemical Society
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    • 제15권9호
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    • pp.766-771
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    • 1994
  • A number of molybdenum(VI), -(V), and -(IV) oxo complexes with S-methyl 3-(2-hydroxyphenyl)methylenedithiocarbazate and its derivatives as the ONS-donor metal-binding substrate are synthesized. The Mo(VI)-dioxo complexes are cis-dioxo Mo$O_2$L(D), where D is solvent molecules such as MeOH, DMF, Py(pyridine), DMSO, and ${\gamma}$-Pic(${\gamma}$-picoline). The Mo(V)-oxo complexes are of the type (PyH)[MoO(NCS$)_2$L] with an octahedral geometry. The Mo(IV)-oxo complexes, MoOL are derived from corresponding Mo(VI)-dioxo complexes by oxo abstraction with PP$h_3$. The complexes are characterized by IR, $^1$H-NMR, UV-Vis spectroscopy and cyclic voltammetry. On the basis of ligand displacement reaction, the qualitative order of D binding for Mo$O_2$L(D) complexes is also discussed.

Synthesis and Guest Binding Properties of Cyclophanes Containing Two Benzo[b]furan Rings

  • Park, Kwang-Hee;Kim, Sun-Hyuk;Park, Joon-Woo
    • Bulletin of the Korean Chemical Society
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    • 제25권11호
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    • pp.1635-1640
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    • 2004
  • The cyclophanes 1a-d containing two benzo[b]furan rings connected by various bridges have been prepared and their binding behaviors with N-benzylphenethylammonium cation 2 were examined by NMR titration method. The successive alkylation reactions of 4-hydroxyl groups and then 2-hydroxyl groups of 2,4-dihydroxybenzophenonse gave macrocycles 5a-c. Photoirradiation of the macrocycles 5a-c with 350 nm mercury lamp followed by dehydration afforded the cyclophanes 1a-c. Hydrolysis of two ester groups pendant on a bridge of 1b produced the carboxyl group-containing cyclophane 1d. The cyclophane 1a having a p-xylene bridge showed 1 : 1 binding with 2 with the binding constant of $36{\pm}6M^{-1}$ in 3 : 1 $CDCl_3$/methanol-$d_4$ solvent, while 1b and 1c which have neutral flexible bridges exhibited no appreciable binding with 2. The disodium salt of 1d showed much higher binding affinity for 2 forming 1 : 1 and 1 : 2 complexes.

구척으로부터 신경재생 효능 성분 분리 (Isolation of the Efficacy Constituent for Neuronal Regeneration from Cibotium barometz)

  • 김상태;한용남;손연경;장형석;김수장;신준식
    • 약학회지
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    • 제46권6호
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    • pp.398-404
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    • 2002
  • A phytochemical study on the root of Cibotium barometz J. Smith led to the isolation of onitin (I), daucosterol (II) and a new compound (III). Compound III was characterized as 2-Ο-(9Z,12Z-octadecadienoyl)-3-Ο-[$\alpha$-D-galactopyranosyl-(1"-6")-Ο-$\beta$-D-galactopyranosyl] glycerol, named shinbarometin by $^1$H-, $^{13}$ C-NMR and LC/MS data. Compound III exerted an induced neuronal regeneration on nogo-A induced neuroblastoma cells.

Flavonoids from Thyrsanthera suborbicularis and Their NO Inhibitory Activity

  • Song, Hyuk-Hwan;Khiev, Piseth;Chai, Hee-Sung;Lee, Hyeong-Kyu;Oh, Sei-Ryang;Choi, Young Hee;Chin, Young-Won
    • Natural Product Sciences
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    • 제18권4호
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    • pp.273-278
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    • 2012
  • Further phytochemical investigation on the whole plant of Thyrsanthera suborbicularis, collected in Cambodia, led to kaempferol (1), vitexin (2), apigenin-7-O-neohesperidoside (3), chrysoeriol-7-O-${\beta}$-D-glucopyranoside (4), isorhamnetin 3-O-rutinoside (5), kaempferol-3-O-[${\alpha}$-L-rhamnopyranosyl-(13)-${\alpha}$-L-rhamnopyranosyl-(16)-${\beta}$-D-galactopyranoside (6), kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl(12)-O-[${\alpha}$-L-rhamnopyranosyl (16)]-${\beta}$-D-glucopyranoside (7), kaempferol-3-O-[6"-O-(E)-p-coumaroyl]-${\beta}$-D-glucopyranoside (8), kaempferol-3-O-[6"-O-(E)-p-coumaroyl]-${\beta}$-D-galactopyranoside (9), and amentoflavone (10). All the structures were confirmed by the interpretation of NMR (1D and 2D) and MS data, and comparison with the published values. Of the isolated compounds 1 - 10, compounds 8 and 10 displayed the inhibitory activity against NO production in LPS-induced Raw 264.7 cells with $IC_{50}$ values, 3.56 and $15.73{\mu}M$, respectively.

퉁퉁마디에서 항산화 물질의 분리 및 동정 (Isolation and Identification of Antioxidant Flavonoids from Salicornia herbacea L.)

  • 김관수;박시형
    • Applied Biological Chemistry
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    • 제47권1호
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    • pp.120-123
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    • 2004
  • 퉁퉁마디(Salicornia herbacea L.) MeOH 추출물로부터 2종의 화합물을 분리하고 DPPH 라디칼 소거 반응을 이용하여 항산화 활성을 측정하였다. UV-Vis 흡수 스펙트럼과 MS와 NMR스펙트럼으로부터 물질 1과 2는 quercetin $3-O-{\beta}-D-glucopyranoside$와 isorhamnetin $3-O-{\beta}-D-glucopyranoside$로 동정하였다. 분리된 화합물 1과 2의 DPPH 라디칼 소거 활성을 측정한 결과 1은 quercetin, rutin과 비슷한 활성을 나타내었으며, B-ring의 hydroxyl 그룹이 methoxyl 그룹으로 치환된 화합물 2는 이보다 약한 활성을 나타내었다. 화합물 1과 2는 퉁퉁마디에서는 처음으로 분리되어 보고되는 화합물이다.

동충하초의 Diketopiperazine 성분 (Diketopiperazines from Cordyceps militaris)

  • 김선범;황방연;이미경
    • 생약학회지
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    • 제44권4호
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    • pp.336-343
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    • 2013
  • In a continuation of investigation on Cordyceps militaris, thirteen compounds were isolated from the $CH_2Cl_2$ and n-BuOH-soluble fraction of C. militaris. They were identified as twelve diketopiperazines such as cyclo($\small{L}$-Gly-$\small{L}$-Pro) (1), cyclo($\small{L}$-Ala-$\small{L}$-Pro) (2), cyclo($\small{L}$-Ser-$\small{L}$-Pro) (3), cyclo($\small{L}$-Val-$\small{L}$-Pro) (4), cyclo($\small{L}$-Thr-$\small{L}$-Pro) (5), cyclo($\small{L}$-Pro-$\small{L}$-Pro) (6), cyclo($\small{L}$-Thr-$\small{L}$-Leu) (7), cyclo($\small{L}$-Tyr-$\small{L}$-Ala) (8), cyclo($\small{L}$-Phe-$\small{L}$-Ser) (9), cyclo($\small{L}$-Phe-$\small{L}$-Pro) (10), cyclo($\small{L}$-Tyr-$\small{L}$-Pro) (11) and brevianamide F (13), and an amino acid, tryptophan (12). Their structures were identified on the basis of chemical evidences and spectroscopic analysis including 1D-NMR ($^1H$, $^{13}C$), 2D-NMR (HSQC, HMBC) and MS spectral data. Among the isolated compounds, compounds 1, 2, 6-11 are first reported from C. militaris.

Neuroprotective Effects of N-Acetyldopamine Dimers from Cicadidae Periostracum

  • Thapa, Punam;Katila, Nikita;Choi, Hyukjae;Han, Ah-Reum;Choi, Dong-Young;Nam, Joo-Won
    • Natural Product Sciences
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    • 제27권3호
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    • pp.161-168
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    • 2021
  • The chemical investigation of the 90% EtOH extract from Cicadidae Periostracum led to the isolation and identification of seven known N-acetyldopamine dimers (1-7). These compounds were identified by comparing mass spectrometry data and NMR spectroscopic data with those previously reported. In this study, complete interpretation of 1D and 2D NMR data of 1 and 2 were reported for the first time. In addition, compounds 3 and 4 were isolated from this material for the first time. All isolates were obtained as racemic mixtures, as confirmed by chiral HPLC. Furthermore, we evaluated the neuroprotective activities of compounds 1-7 and found that compounds 1, 5, and 6 significantly attenuated rotenone-induced death of SH-SY5Y neuroblastoma cells at a concentration of 100 μM. Parallel to this result, compounds 3 and 6 displayed antioxidant effects in the cytoplasm, as determined by CM-H2DCFDA fluorescence intensity, while compounds 1 and 5 showed antioxidant effects in the mitochondria, as assessed by MitoSox fluorescence intensity. Overall, these results suggest that some of these compounds protect neuroblastoma cells by ameliorating the release of reactive oxygen species. Further studies are warranted to elucidate the underlying mechanisms by which these compounds exhibit antioxidant and neuroprotective actions.

Spinoside, New Coumaroyl Flavone Glycoside from Amaranthus spinosus

  • Azhar-ul-Haq,;Malik, Abdul;Khan, Anwar-ul-Haq Sher Bahadar;Shah, Muhammad Raza;Muhammad, Pir
    • Archives of Pharmacal Research
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    • 제27권12호
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    • pp.1216-1219
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    • 2004
  • Spinoside, new coumaroyl flavone glycoside was isolated from the n-butanol fraction of the mathanolic extract of the whole plant of Amaranthus spinosus and assigned the structure 7-pcoumaroyl apigenin 4-O-${\beta}$ -D-glucopyranoside (1) on the basis of spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition ${\alpha}$ - xylofuranosyl uracil (2), ${\beta}$ -D-ribofuranosyl adenine (3) and ${\beta}$ -sitosterol glucoside (4) have also been isolated for the first time from this species.

Purification and NMR Studies of RNA Polymerase II C-Terminal Domain Phosphatase 1 Containing Ubiquitin Like Domain

  • Ko, Sung-Geon;Lee, Young-Min;Yoon, Jong-Bok;Lee, Weon-Tae
    • Bulletin of the Korean Chemical Society
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    • 제30권5호
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    • pp.1039-1042
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    • 2009
  • RNA polymerase II C-terminal domain phosphatase 1 containing ubiquitin like domain (UBLCP1) has been identified as a regulatory molecule of RNA polymerase II. UBLCP1 consists of ubiquitin like domain (UBL) and phosphatase domain homologous with UDP and CTD phosphatase. UBLCP1 was cloned into the E.coli expression vectors, pET32a and pGEX 4T-1 with TEV protease cleavage site and purified using both affinity and gel-filtration chromatography. Domains of UBLCP1 protein were successfully purified as 7 mg/500 mL (UBLCP1, 36.78 KDa), 32 mg/500 mL (UBL, 9 KDa) and 8 mg/500 mL (phosphatase domain, 25 KDa) yielded in LB medium, respectively. Isotope-labeled samples including triple-labeled ($^2H/^{15}N/^{13}C$) UBLCP1 were also prepared for hetero-nuclear NMR experiments. $^{15}N-^{1}H$ 2D-HSQC spectra of UBLCP1 suggest that both UBL and phosphatase domain are properly folded and structurally independent each other. These data will promise us further structural investigation of UBLCP1 by NMR spectroscopy and/or X-ray crystallography.