Aldose Reductase Inhibitory Alkaloids from Corydalis ternata

서원세,정상훈,심상희 한국생약학회 2016 Natural Product Sciences Vol.22 No.2

A methanolic extract of Corydalis ternata having aldose reductase inhibitory activity was examined as a possible aldose reductase (ALR2) inhibitor, a key enzyme involved in diabetic complications. Seven alkaloids, tetrahydrocoptisine (1), corydaline (2), tetrahydropalmatine (3), isocorybulbine (4), corybulbine (5), dehydrocorydaline (6), and N-methyltetrahydroberbinium (7) were isolated from CHCl3 fraction of C. ternata methanol extract. Among them, compounds 1, 5, and 7 exhibited 5.04 ± 1.97%, 5.00 ± 1.26%, and 1.80 ± 2.33% inhibitions, respectively at 40 μM. The activities of the single compounds were not comparable to that of the whole extract, suggesting that the whole combination of each single compound was responsible for the activity of the extract as shown in many cases of natural medicines. Even though this is the second report on aldose reductase inhibition activity of C. ternata, recombinant human aldose reductase was employed in this study unlike in the previous report. Furthermore, the aldose reductase inhibitory activities of isocorybulbine, corybulbine, and N-methyltetrahydroberbinium, to the best of our knowledge, were evaluated for the first time in this study. These results suggest a use of the extract of C. ternata for ameliorating diabetic complications.

Chemical Constituents Identified from Fruit Body of Cordyceps bassiana and Their Anti-Inflammatory Activity

서원세,남경숙,양우석,성기호,심상희,조재열 한국응용약물학회 2017 Biomolecules & Therapeutics(구 응용약물학회지) Vol.25 No.2

Cordyceps bassiana is one of Cordyceps species with anti-oxidative, anti-cancer, anti-inflammatory, anti-diabetic, anti-obesity, anti-angiogenic, and anti-nociceptive activities. This mushroom has recently demonstrated to have an ability to reduce 2,4-dinitrofluorobenzene- induced atopic dermatitis symptoms in NC/Nga mice. In this study, we further examined phytochemical properties of this mushroom by column chromatography and HPLC analysis. By chromatographic separation and spectroscopic analysis, 8 compounds, such as 1,9-dimethylguanine (1), adenosine (2), uridine (3), nicotinamide (4), 3-methyluracil (5), 1,7-dimethylxanthine (6), nudifloric acid (7), and mannitol (8) were identified from 6 different fractions and 4 more subfractions. Through evaluation of their anti-inflammatory activities using reporter gene assay and mRNA analysis, compound 1 was found to block luciferase activity induced by NF-kB and AP-1, suppress the mRNA levels of cyclooxygenase (COX)-2 and tumor necrosis factor (TNF)-a. Therefore, our data strongly suggests that compound 1 acts as one of major principles in Cordyceps bassiana with anti-inflammatory and anti-atopic dermatitis activities.

오미자로부터 분리된 화합물의 암세포 증식 억제 효과

서원세(Won-Se Suh),박소연(So Yeon Park),민병선(Byung Sun Min),김세현(Sea Hyun Kim),송정호(Jeong Ho Song),심상희(Sang Hee Shim) 한국식품과학회 2014 한국식품과학회지 Vol.46 No.6

오미자 추출물의 n-hexane 분획으로부터 open column chromatography, 분취용 HPLC 등 여러 가지 크로마토그라피를 이용하여 총 15종의 화합물을 분리하였다. 분리된 화합물들은 각각의 기기분석 데이터를 문헌치와 비교하여, 각각 wuweizisu C (1), gomisin N (2), deoxyschisandrin (3), gomisin A (4), schisandrin (5), chamigrenal (6), schisanlactone D (7), methylgomisin O (8), angeloylgomisin O (9), (?)-gomisin L₂ (10), schisandronic acid (11), (?)-gomisin L₁ (12), (+)-gomisin K₃ (13), gomisin J (14), tigloylgomisin H (15)으로 동정하였다. 이들 중 methylgomisin O (8)는 이 식물에서 처음으로 분리되었다. 분리된 화합물들은 HL-60 (human leukemia), HeLa (human cervical carcinoma) 및 MCF-7 (breast cancer cells) 세포주에 대하여 세포독성 실험을 실시하였다. 그 결과 화합물 7, 8 및 9는 HL-60 세포주에 대하여 각각 7.37, 6.60 및 8.00 μM의 IC<SUB>50</SUB>로 비교적 강한 세포독성 효과를 나타냈다. 화합물 6은 MCF-7 에 대하여 IC<SUB>50</SUB> 30.50 μM로 적정한 세포독성을 나타냈다. 그리고 화합물 8은 HeLa cells에 대하여 IC<SUB>50</SUB> 1.46 μM로 비교적 강한 세포 독성으로 나타냈다. We isolated twelve lignans and three terpenoids were isolated from the n-hexane fraction of Schisandra chinensis extract. Using spectroscopic data and comparison with available literature, the following compounds were identified: (1) wuweizisu C, (2) gomisin N, (3) deoxyschisandrin, (4) gomisin A, (5) schisandrin, (6) chamigrenal, (7) schisanlactone D, (8) methylgomisin O, (9) angeloylgomisin O, (10) (?)-gomisin L₂, (11) schisandronic acid, (12) (?)-gomisin L₁, (13) (+)-gomisin K<SUB>3</SUB>, (14) gomisin J, and (15) tigloylgomisin H. Notably, this was the first finding that compound (8) was isolated from this plant. Each compound was evaluated for its in vitro cytotoxic activities toward HL-60 (human leukemia), HeLa (human cervical carcinoma), and MCF-7 (breast cancer) cell lines. Compounds (7), (8), and (9) exhibited strong cytotoxic effects on HL-60 (IC<SUB>50</SUB> 7.37, 6.60, and 8.00 μM, respectively), whereas compound (6) exhibited weak cytotoxicity towards MCF-7 (IC<SUB>50</SUB> 30.50 μM). In addition, compound (8) showed the strongest activity towards HeLa cells (IC<SUB>50</SUB> 1.46 μM).

부채마의 스테로이드 사포닌 및 생리활성

박경진,서원세,차준민,박종일,우경완,김선여,이강노 한국생약학회 2017 생약학회지 Vol.48 No.4

As part of the search for bioactive constituents of Korean medicinal plants, twelve steroids (1-12) were isolated from the rhizomes of Dioscorea nipponica. The isolated compounds were identified as diosgenin (3β, 25R)-spirost-5-en-3-ol (1), 25(R)-dracaenoside E (2), dioscin (3), gracillin (4), prosapogenin B (5), 25(R)-dracaenoside G (6), diosgenin 3-O-β-D-glucopyranosyl(1→3)-β-D-glucopyranoside (7), ophipogonin C′ (8), 7-oxodioscin (9), protodioscin (10), hypoglaucin F (11), and protoneogracillin (12). Their structures were characterized by spectroscopic data and identified by comparing these data with those in the literatures. All the isolates (1-12) were evaluated for their neuroprotective effects through induction of nerve growth factor in C6 glioma cells and effects on nitric oxide (NO) production in murine microglia cell line BV-2. Compounds 7 and 12 were found to induce upregulation of NGF secretion without causing significant cell toxicity and compound 4 exhibited potent anti-neuroinflammatory activity.

HPLC에 의한 오미자 리그난 성분의 정량분석

구동칠,서원세,백소윤,심상희 한국생약학회 2011 생약학회지 Vol.42 No.3

A reversed phase HPLC method was established for quantitative determination of lignans including schizandrin (1),gomisin A (2), deoxyschizandrin (3), gomisin N (4), and wuweizisu C (5) from Schizandra chinensis using a binary gradient of acetonitrile and water as a mobile phase with UV detection at 254nm. In result, contents of schizandrin (1), gomisin A (2),deoxyschizandrin (3), gomisin N (4), and wuweizisu C (5) in Schizandra chinensis from Moonkyung were 8.41 ± 0.30,3.01 ± 0.13, 1.06 ± 0.05, 7.69 ± 0.30, and 1.68 ± 0.06 mg/g, respectively.

Two new phenylpropane glycosides from Allium tuberosum Rottler

한상현,서원세,박경진,김기현,이강노 대한약학회 2015 Archives of Pharmacal Research Vol.38 No.7

A phytochemical investigation of Allium tuberosum Rottler afforded two new phenylpropane glycosides, named tuberonoid A (1) and B (2), along with four known flavonoids, kaempferol 3-O-b-sophoroside (3), 3-Ob-D-(2-O-feruloyl)-glucosyl-7,40-di-O-b-D-glucosylkaempferol (4), 3-O-b-sophorosyl-7-O-b-D-(2-O-feruloyl)glucosyl kaempferol (5), kaempferol 3,40-di-O-b-D-glucoside (6). The identification and structural elucidation of the new compoundswerecarriedoutbasedonspectraldataanalyses (1H and13C NMR,1H–1H COSY, HMQC) and HR-MS.

Two New Diterpenoids from Thuja orientalis and Their Cytotoxicity

김충섭,서원세,최상운,김기현,이강노 대한화학회 2014 Bulletin of the Korean Chemical Society Vol.35 No.9

히어리나무의 페놀성 화합물 및 세포독성활성

권오길,이강노,김충섭,서원세,박경진,차준민,최상운,권학철 한국생약학회 2016 생약학회지 Vol.47 No.1

Phytochemical investigation of the twigs of Corylopsis coreana afforded 10 phenolic compounds, bergenin (1), 6′-O-galloylbergenin (2), 3′-O-galloylbergenin (3), (-)-catechin (4), (-)-epicatechin (5), (-)-epicatechin-3-O-galloyl ester (6), 4-methoxy-3,-5-dihydroxybenzoic acid (7), gallic acid (8), 2,4,6-trimethoxyphenol-1-O-b-D-glucopyranoside (9), and 2,4,6-trimethoxyphenol-1-O-b-D-(6-O-galloyl)-glucopyranoside (10). Their structures were characterized by spectroscopic data and identified by comparing these data with those in the literatures. The compounds 3, 9 and 10 were isolated for the first time from this source. All the isolates (1-10) were tested for their cytotoxic activity against A549, SK-OV-3, SK-MEL-2, and HCT15 cell lines in vitro using the SRB bioassay. The compounds 5, 7 and 8 exhibited selective cytotoxic activity against SK-MEL-2 cell line.

배롱나무의 항산화 활성 성분

우경완,이강노,심미옥,박종일,김민석,서원세,조현우,권학철,박종철 한국생약학회 2016 생약학회지 Vol.47 No.3

Phytochemical investigation of the 80% MeOH extract from the stems of Lagerstroemia indica resulted in the isolation of eighteen compounds; four norsesquiterpenes, fourteen phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be tachioside (1), isotachioside (2), 2,4,6-trimethoxyphenyl b-D-glucopyranoside (3), gallic acid 4-methyl ether (4), protocatechuic acid (5), gallic acid (6), vanillic acid (7), vanillin (8), 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6''-galloyl)-b-D-glucopyranoside (9), 2,4,6-trimethoxyphenol-1-O-b-D-(6'-O-galloyl)-glucopyranoside (10), 4-hydroxy-3-methoxyphenyl-1-O-(6'-O-galloyl)-b-D-glucopyranoside (11), vomifoliol (12), vomifoliol 9-O-b-D-glucopyranoside (13), 6R,​9R-​3-​oxo-​α-​ionol-​9-​O-​b-​D-​glucopyranoside (14), dihydrophaseic acid 4'-O-b-D-glucopyranoside (15), b-hydroxypropiovanillone 3-O-b-D-glucopyranoside (16), myrciaphenone A (17), and coumaric acid (18). Compounds 1-5 and 7-18 were isolated for the first time from this plant. Compounds 1-18 were investigated for their antioxidant properties using DPPH and ABTS radical scavenging capacity assay, Fe2+ chelating, and FRAP assay. It was found that 4, 6, and 11 possessed the highest antioxidant capacities.