• 대한화학회지
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• 제54권4호
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• pp.429-436
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• 2010

Guanine (1)으로부터 생물활성이 있는 halogenopurines계 화합물을 합성하였다. Guanine을 acetic anhydride와 반응시켜서 2,9-diacetylguanine (2-1)을 합성하여 얻어진 화합물을 $POCl_3$와 반응시켜서 화합물 3a를 합성하고, 다음 단계에서 2-amino-6-halogenopurines (3b-d)를 합성하였다. 2-Halogenopurines (2-2a-d, 4-2a-d, 5a-d)을 2-amino-6-substituted purines (1, 3a, 4-1)로부터 효율적으로 합성한 후에, 새로운 화합물인 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c 및 5d를 합성하였다. 합성한 화합물의 구조를 원소분석, $^1H$ NMR, mass spectral data로 확인하였으며, 합성한 화합물에 대한 항균 활성을 시험하였다.

• Journal of Applied Biological Chemistry
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• 제58권3호
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• pp.233-236
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• 2015

황목련 꽃으로부터 3개의 alkyl glycoside 화합물을 분리, 동정하였다. 황목련 꽃을 80% MeOH에 추출하여 이를 EtOAc, n-BuOH, 그리고 $H_2O$ 층으로 계통분획을 실시하였다. 이중 EtOAc 분획에 대하여 silica gel과 ODS column chromatography를 반복 실시하여 3종의 화합물을 분리, 정제하였다. Nuclear magnetic resonance, infrared spectroscopy 및 mass spectrometry의 spectroscopic data를 해석하여 이 화합물들을 2-methylbutan-1-ol-${\beta}$-$\small{D}$-galactopyranoside (1), 2-methylbutan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (2), 2-methylpropan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (3)로 각각 동정하였다. 동정된 화합물 모두 황목련 꽃에서는 이번 연구에서 처음으로 분리, 동정되었다.

• Natural Product Sciences
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• 제29권2호
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• pp.113-119
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• 2023

Descurainia sophia seeds methanol extract showed significant anti-influenza activity and we tried to isolate anti-influenza compounds from the D. sophia extract. D. sophia seeds were extracted with 80% methanol and fractionated with n-hexane, ethyl acetate, CHCl₃ and n-butanol. The anti-influenza activity of each fraction was assessed using sulforhodamine B (SRB) method in A549 cells, human-derived lung cancer cells. The ethyl acetate and CHCl₃ fractions showed the most potent anti-influenza activity. Seven compounds were isolated from CHCl₃ fraction and identified 1-decanol (1), 2-(3,4-dihydroxy-2-methylenebutoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (2), daucosterol (3), isorhamnetin (4), quercetin (5), sinapic acid (6), and helveticoside (7) by spectroscopic data such as UV, IR, ¹H-NMR, ¹³C-NMR and mass spectroscopy. Anti-influenza activities of isolated compounds were evaluated using SRB method in A549 cells. Compounds 3, 4 and 7 had significant anti-influenza activity in a dose-dependent manner.

• 약학회지
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• 제37권4호
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• pp.325-330
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• 1993

Four flavonoide glycosides and (-)-Epicatechin were isolated from the aqueous extracts of dried whole part of Lysimachia clethroides Duby(Primulaceae). They were 3-0-Methyl-quercetin-7-0-[$\alpha$-L- rhamnopyranosyl (1-2) glucopyranoside], Quercetin-3-0-$\beta$-D-glucopyranoside, Kaempferol-3-0-$\beta$-D-glucopyranoside, Kaempferol-3-0-[$\alpha$-L-rhamnopyranosyl (1-6)-$\beta$-D-glucopyranoside] and (-)-Epicatechin. 3-0-[$\alpha$-L-rhamnopyranosyl (1-6)-$\beta$-D-glucopyranoside]and (-)-Epicatechin. 3-0-Methyl-quercetin-7-0-[$\alpha$-L-rhamnopyranosyl (1-2)-$\beta$-D-glucopyranoside] and (-)-Epicatechin were first isolated from this plant. Their structures were elucidated by spectral analysis [$^{1}$H-, $^{13}C-$ NMR, $^{1}$H-$^{1}$H-COSY, DEPT-analysis, HMQC(Heteronuclear multiple quantum coherence), FAB-MS].

• 한국자기공명학회논문지
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• 제25권2호
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• pp.12-16
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• 2021

Daphnia magna is used as target organism for environmental metabolomics. The metabolome of D. magna was studied with NMR spectroscopy. Most studies used the extract of D. magna, but the reproducibility cannot be obtained using extracted sample. In this study, lyophilized D. magna samples were analyzed with two different ¹H NMR techniques, HR-MAS on intact tissues and solution NMR on extracted tissues. Samples were measured three times using 600 MHz NMR spectrometer. Metabolite extraction required more than twice as many D. magna, but the metabolite intensity was lower in solution NMR. In the spectra of HR-MAS NMR, the lipid signal was observed, but they did not interfere with metabolite profiling. We also confirmed the effect of swelling time on signal intensities of metabolites in HR-MAS NMR, and the results suggest that appropriate swelling should be used in lyophilized D. magna to improve the accuracy of metabolite profiles.

• Natural Product Sciences
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• 제12권1호
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• pp.62-66
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• 2006

A steroidal saponin, $3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)-[{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}3)]-{\beta}-D-glucopyranosylpennogenin$ ;(1, spiroconazole A) was isolated from the tubers of Dioscorea bulbifera L. var sativa and $^1H-and\;^{13}C-NMR$ assignment was completed using HMBC correlation. In addition, four phenolic substances, 2,7-dihydroxy-4-methoxyphenanthrene (2), quercetin (3), $quercetin-3-O-{\beta}-D-glucopyranoside$ (4), and $quercetin-3-O-{\beta}-D-galactopyranoside$ (5) were also isolated.

• Journal of the Korean Wood Science and Technology
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• 제30권1호
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• pp.56-62
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• 2002

분버들 수피를 아세톤-물(7:3)로 추출한 후 농축하고 헥산, 클로로포름, 에틸아세테이트 및 수용성으로 분획하여 동결건조하였다. 각 추출물은 메탄올 수용액 및 에탄올-헥산 혼합액을 사용하여 Sephadex LH-20 칼럼크로마토그래피로 화합물을 분리한 후 TBA 및 6% 초산에 전개하는 셀룰로오스 박층크로마토그래피로 단리물질을 확인하였다. 단리물질의 화학적 구조는 ¹H-NMR, ¹³C-NMR 및 질량 분석으로 결정하였으며, 단일의 화합물로 정제된 물질은 flavonoid와 그 배당체 화합물인 (+)-catechin, naringenin, salipurposide, aromadendrin, isosalipurposide, aromadendrin-7-O-𝛽-D-glucopvranoside 및 taxifolin-7-O-𝛽-D-glucopy- ranoside였다.

• Archives of Pharmacal Research
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• 제19권2호
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• pp.153-159
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• 1996

A new streptothricin family antibiotic producing Streptomyces spp. SNUS 8810-111 was isolated from a soil sample. Study of its morphological and physiological characters indicated that the antibiotic producing organism was a Streptomyces spp. Taxonomical studies suggested that the organism might belong to the genus streptomyces gougeroti. The organism produced antibiotics most in calcium carbonate-tryptic soy broth. The active principles were recovered from the broth with a cation exchange resin and eluted from the resin with HCI. Cellulose column chromatography gave two active principles.$^1H-^1H$ Homo-COSY study on the first compound revealed four structural components. Total hydrolysis of the antibiotic with HCI allowed isolation of $\beta-lysine$. From these data the antibiotic was found to be streptothricin D. The other compound showed one additional signal in the .$^1H$NMR and the $^{13}C$ NMR spectra. The signal was from a methyl group attached to a nitrogen atom. Comparison of the NMR signals with those of streptothricin D suggested that the compound was N-methyl-streptothricin D which was a new compound in the family of streptothricin antibiotics.

• Journal of Microbiology and Biotechnology
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• 제16권10호
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• pp.1591-1596
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• 2006

Acaricidal effects of materials derived from Caesalpinia sappan heartwoods against Dermatophagoides farinae and D. pteronyssinus were assessed and compared with those evidenced by commercial benzyl benzoate and DEET. The observed responses varied according to dosage and mite species. The $LD_{50}$ values of the methanol extracts derived from C. sappan heartwoods were 6.13 and $5.44{\mu}g/cm^3$ against D. farinae and D. pteronyssinus, respectively. Furthermore, the ethyl acetate fraction derived from the methanol extract was approximately 8.71 more toxic than DEET against D. farinae, and 4.73 times more toxic against D. pteronyssinus. The biologically active constituent from the ethyl acetate fraction of C. sappan heartwood extract was purified via silica gel chromatography and high-performance liquid chromatography. The structure of the acaricidal component was analyzed by $GC-MS,\;^1H-NMR,\;^{13}C-NMR,\;^1H-^{13}C\;COSY-NMR$, and DEPT-NMR spectroscopy, and identified as juglone (5-hydroxy-l,4-naphthoquinone). Based on the $LD_{50}$ values of juglone and its derivatives, the most toxic compound against D. farinae was juglone ($0.076{\mu}g/cm^3$), followed by benzyl benzoate ($9.143{\mu}g/cm^3$) and 2methyl-l,4-naphthoquinone ($40.0{\mu}g/cm^3$). These results indicate that the acaricidal activity of C. sappan heartwoods is likely to be the result of the effects of juglone. Additionally, juglone treatment was shown to effect a change in the color of the cuticles of house dust mites, from colorless-transparent to dark brownish-black. Accordingly, as a naturally occurring acaricidal agent, C. sappan heartwood-derived juglone should prove to be quite 'useful as a potential control agent, lead compound, and house dust mite indicator.

• 한국식품영양과학회지
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• 제26권2호
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• pp.242-247
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• 1997

엉겅퀴 지상부 중 심혈관계에 대한 영향과 활성성분을 구명하기 위하여 S.D.계 흰쥐의 적출한 성장과 혈관에 대한 작용과 혈압을 측정하였고 그 유효성분을 분리하였다. 엉겅퀴 지상부의 MeOH 추출엑스를 계통분획법에 의하여 분획하여 심장과 혈관에 작용하는 BuOH층을 분리, 정제한 후 UV, IR, $^{1}H-NMR$, $^{13}C-NMR$ 등의 분석방법으로 동정한 결과 flavonoid 배당체인 hispidulin $7-0-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}2)-{\beta}-D-glucopyranoside$로 밝혀졌으며 흰쥐의 심박수 증가 및 심근과 흉부대동맥을 수축시켰고 혈압을 상승시키는 효과가 있었다.