• Natural Product Sciences
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• 제26권2호
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• pp.151-157
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• 2020

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B₅ (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B₂ (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.

• 생명과학회지
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• 제23권7호
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• pp.933-940
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• 2013

본 연구는 박하(Mentha arvensis) 식물 유래 향료의 향기성분을 구명하고, 향기성분들이 인간의 뇌파에 어떠한 영향을 미치는지를 이해하고자 수행하였다. 초임계추출기를 이용하여 박하 식물(Mentha arvensis L. f. piperascens)로부터 에센셜오일을 얻었으며, 최적 회수율은 $70^{\circ}C$, 200 bar 조건에서 2.38%이었다. 박하 에센셜오일에 함유되어 있는 향기 화합물을HS-SPME/GC-MS로 분석한 결과, 총 32종의 화합물이 검출되었는데 alcohol 류가 6종(67.11%), hydrocarbon 류가 13종(17.05%), ester 류가 9종(11.50%), ketone 류가 2종(7.16%), oxide가 1종(2.77%) 그리고 aldehyde가 1종(0.56%)이었다. 박하 에센셜오일에 함유된 주된 향기 화합물은 (Z,Z,Z)-9,12,15-octadecatrien-1-ol (50.06%), 2-hydroxy-4-methoxyacetophenone (7.50%)과 3,4-dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one (6.60%) 이었다. 총 20명의 피험자(남녀 각 10명)를 대상으로 박하 에센셜오일 향기 흡입 전과 흡입 중에 뇌파분석을 수행한 결과, 향기를 흡입 중에는, 흡입 전과 비교하여, relative fast alpha power spectrum이 유의성 있게 증가하는 반면(p<0.05), gamma power spectrum과 spectral edge frequency 90% 지표는 유의성 있게 감소하는 결과를 얻었다(p<0.05). 본 연구의 결과들은 박하의 향기성분이 정신적 긴장을 완화시킨다는 것을 시사하여 준다.

• Journal of the Korean Wood Science and Technology
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• 제48권6호
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• pp.888-895
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• 2020

Ulmus genus has excellent various physiological activities, including anti-ulcer, antioxidant, antibacterial, anti-cancer, immunity, and homeostasis maintenance effects, and it is known to have many additional drug effects And one of reasons for these excellentbiological activities is a flavan-3-ol chemical group in Ulmus genus. In this study a new flavan-3-ol compound was identified in Ulmus davidiana var. japonica. A flavan-3-ol,(2R,3S)-7-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5-diol, named as catechin 7-O-beta-D apiofuranoside, was isolated from the stems and barks of Ulmus davidiana var. japonica for. suberosa, which is a species belonging to the genus Ulmus, growing throughout the Korea peninsula. The structure was elucidated by various spectroscopic methods including high-resolution TOF mass spectrometry, ¹H-NMR and ¹³C-NMR spectrometry and comparison with chemical structures of defined compounds.

• 약학회지
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• 제52권6호
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• pp.514-519
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• 2008

We developed a convenient synthetic route to 3-alkylated 2-phenyl-4-quinolone derivatives (4a-h and 5a-c), which were expected to retain antitumor activity. A series of 2,3-dihydro-2-hydroxy-2-phenyl-4-quinolones (3a-h) was synthesized through dehydration, dealcoholation and hydration using acid-catalyzed one-pot reaction from anilines and ethyl benzoylacetates. 3-Methyl (or 3,3-dimethyl)-2-phenyl-4-quinolone derivatives 4 and 5 were synthesized from 3a-h through the methylation using methyl iodide. Formation of quinolone nucleus was undertaken with p-toluenesulfonic acid (p-TSA) at $90{\sim}110^{\circ}C$ in toluene for 3${\sim}$7.5 hr over the Dean-Stark apparatus. The key intermediates in these preparations are ${\beta}$-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.

• Archives of Pharmacal Research
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• 제15권3호
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• pp.224-228
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• 1992

Arylhydrazones of diethylacetondicarboxylate 3 was treated with formaldehyde to give 1 aryl-4, 5, 6-trihydropyridaine derivatives 4a-f Cyclization of compound 4a-f by hydroxylamine afforded [3, 4d] 1, 3, 4, 5-tetrahydropyridazine derivatives 5a-f. Also cyclization of compound 4c with semicarbazide gave 1-amidopyrazolo-5-one-1-aryl-3-carboxypyridazine 6. On the other hand compounds 3 reacted with ethylorthoformate to give diethyl-1, 4-dihydro-1-arylpyridazine-4one-2.5 dicarboxylate 7, which on treatment with hydrazine. Semicarbazide and thiosemicarbazide gave pyridazine, amido and thioamido derivatives. The spectral and antimicrobial data of these compounds 1-8 were studied.

• Archives of Pharmacal Research
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• 제26권1호
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• pp.1-8
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• 2003

In this study, a series of new $N^2$ substituted 1,2-dihydro-3H-indazol-3-ones (3a-d) as well as their condensed pyrazolo, pyridazino derivatives such as pyridazino[1,2-a]indazole-6,9,11-triones (4a-h) and 3,9-dioxo-3H,9H-pyrazolo[1,2-a]indazole (7) were synthesized. The antiinflammatory activity of some synthesized compounds was determined by carrageenan-induced rat paw edema technique using diclofenac as reference drug. The pharmacological data showed that most of the tested compounds exhibited a significant long lasting antiinflammatory activity, which in the case of compound 3b was superior to that of diclofenac.

• Archives of Pharmacal Research
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• 제16권2호
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• pp.164-167
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• 1993

Arylhydrazones of diethyl acetonedicarboxylate 3 was treated with fomaldehyde to 1-aryl-1, 4, 5, 6-tetrahyeheypyridazine derivatives 4a-f Cyclization of compound 4a-f by hydroxy-lamine afforded [3, 4-d] 1, 4, 5, 6-tetrahydropyridazine derivative 5a-f. Also, cyclization of compound 4c with semicarbazide gave pyrazolote [4, 3-c] pyridazine 6. On the other hand compound 3 reacted with ethylothofomate to give diethyl-1, 4-dihydro-1-arypyridazine-4-one-3, 5 dicaboxylate 7, which on treatment with hydrazine, semicarbazide and thiosemicarbazide gave pyridazine, amido and thioamido derivatives. The spectrl and antimicrobial data of these compounds 1-8 were studied.

• 대한화학회지
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• 제33권2호
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• pp.238-246
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• 1989

옥사티올란 고리에 대해서 술폭시드기와 2-메틸기가 동일 평면상에 놓인 1,3-옥사티올란술폭시드 4는 sigmatropic 전위를 통하여 고리확대 생성물로 전환한다. 이 생성물의 구조는 디히드로-1,4-옥사티인 6 또는 이것의 구조 이성체인 exo형 화합물 7의 가능성이 있다. 본 연구에서는 물리적 및 화학적 방법에 의하여 두 alternative 구조 중 올바른 구조를 밝혔다. 즉 수소핵자기 공명스펙트럼, 자외선 흡수스펙트럼, 그리고 질량분석 스펙트럼으로부터 실제로 얻어진 화합물은 디히드로옥시티인 6이었다. 또한 중수소 치환반응으로부터 환팽창 반응에서 처음 exo형 화합물 7이 생성되나 tautomerization에 의해서 결국 디히드로-1,4-옥사티인 6으로 전환함을 알았다.

• Natural Product Sciences
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• 제16권1호
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• pp.10-14
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• 2010

Phytochemical examination of the barks of Pinus densiflora Siebold et Zuccarini has led to the isolation of one phenylpropanoid, one lignan, one flavonoid, one flavan 3-ol and two procyanidins : 4-O-$\beta$-D-glucopyranosyl-p-coumaric acid (1), 2,3-dihydro-2-(4-methoxy)-7-hydroxy-3-hydroxymethyl-5-(3-hydroxy propyl)-benzofuran 3-O-$\alpha$-D-glucopyranoside (2), taxifolin 3'-O-$\beta$-D-glucopyranoside (3), (+)-catechin (4), procyanidin B1 (5) and epicatechin-($4{\beta}$-8)-catechin-($4{\alpha}$-8)-catechin (6). Among them, Compound 4, 5 and 6 showed potent anti-oxidative activities and these anti-oxidative activities were significantly different compared with ascorbic acid as positive control.

• Bulletin of the Korean Chemical Society
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• 제26권6호
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• pp.959-965
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• 2005

Investigation of structure-activity relationships of novel quinazolines has identified 7,8-dihydro-[1,4]dioxino-[2,3-g]quinazolines as a potent inhibitor of EGFR. These compounds have a benzodioxane framwork, which was prepared by regioselective O-alkylation of ethyl 3,4-dihydroxy benzoate by epoxide ring opening. Compounds 3f and 3k were more potent than ZD-1839 in EGF enzyme and EGFR autophosporylation inhibition assays.