• 대한화학회지
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• 제11권3호
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• pp.111-116
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• 1967

韓國 山野에 野生하는 참조팝나무 Spiraea Koreana Nakai(Spiraeceae)엽으로 부터 m.p. 182~$184^{\circ}C$의 苦味를 갖인 Alkaloid를 無色 柱狀의 結晶으로 얻었다.(收得率 0.13%). 이 物質은 光學的으로 活性이며(比旋光度$[{\alpha}]d^{19}+3.4^{\circ}$ in $CHCl_3$), Mass Spectrometry에 依해 決定한 分子式은 $C_{23}H_{33}NO_3$이다. 文獻未記載의 것임으로 Spirajine이라 命名하였다. Spiraea Koreane N. 葉 中에는 이 外에도 다른 2種의 알칼로이드가 微量으로 含有되어 있음을 Thin Layer Chromatography로 確認하였으나 結晶으로는 못 얻었다. Spirajine의 部分化學構造에 對해 化學反應, UV, IR, NMR, MS, ORD 等으로 分析檢討함과 아울러 Mass Spectrogram의 Cracking Pattern으로부터의 Fragmentation Analysis의 結果, 分子 中 Cyclohexane 및 Cyclopentane 고리들을 갖으며 그 中 하나는 ${\alpha},{\beta}$ 不飽和 Cyclohexenone고리이고 그 外에 methyl基, 카보닐基, 水酸基, N-Methyl基 等 여러 作用基의 存在를 決定하였다.

• Natural Product Sciences
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• 제26권3호
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• pp.230-235
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• 2020

A pregnane steroid, 3α-hydroxy-pregn-7-ene-6,20-dione (1), was isolated from a Hydractinia-associated Cladosporium sphaerospermum SW67 by repetitive column chromatographic separation and high-performance liquid chromatography (HPLC) purification. The planar structure of 1 was elucidated from the analysis of the spectroscopic data (1D and 2D NMR spectra) and LC-MS data. The absolute configuration of 1 was determined by interpretation of ROESY spectrum of 1, together with the comparison of reported spectroscopic values in previous studies. To the best of our knowledge, this is the first report of the identification of the pregnane scaffold from C. sphaerospermum, a natural source. Compound 1 was evaluated for its effects on lipid metabolism and adipogenesis during adipocyte maturation and showed that compound 1 substantially inhibited lipid accumulation compared to the control. Consistently, the expression of the adipocyte marker gene (Adipsin) was reduced upon incubation with 1. Further, we evaluated the effects of 1 on lipid metabolism by measuring the transcription of lipolytic and lipogenic genes. The expression of the lipolytic gene ATGL was significantly elevated upon exposure to 1 during adipogenesis, whereas the expression of lipogenic genes FASN and SREBP1 was significantly reduced upon treatment with 1. Thus, our findings provide experimental evidence that the steroid derived from Hydractinia-associated C. sphaerospermum SW67 is a potential therapeutic agent for obesity.

• Journal of Applied Biological Chemistry
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• 제61권1호
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• pp.39-46
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• 2018

Column chromatographic separation of the MeOH extract from the roots of Dicentra spectabilis yielded fourteen compounds, menisdaurin (1), menisdaurilide (2), trans-N-p-coumaroyltyramine (3), trans-N-p-feruloyltyramine (4), 4-O-feruloylquinicacid (5), chlorogenic acid (6), 3-O-feruloylquinicacid (7), ferulic acid (8), protopine (9), Kaempferol 3,7-di-O-${\beta}-{\text\tiny{D}}$-glucopyranoside (10), kaempferol 3-O-${\beta}-{\text\tiny{D}}$-glucopyranosyl-7-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranoside (11), ${\alpha}-rhamnoisorobin$ (12), astragalin (13), and nicotiflorin (14). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 1, 3-8, and 10-14 isolated from this plant were reported for the first time. The isolated compounds (1-14) were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide-stimulated RAW 264.7 cells. Compound 3, 4 and 12 significantly inhibited NO production. Moreover, Compound 3 suppressed pro-inflammatory cytokines ($TNF-{\alpha}$, $IL-1{\beta}$ and IL-6) in a dose- dependent manner. These data suggest that compound 3 possess anti-inflammatory activity and might be useful natural materials for development of anti-inflammatory agent.

• 대한핵의학회지
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• 제24권2호
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• pp.215-221
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• 1990

HM-PAO was synthesized by two step reaction. d, 1-HM-PAO was separated from the racemic product by fractional recrystalization in ethylacetate, and the chemical structure and purity was confirmed by proton NMR spectroscopy. The synthesized 0, 1-HM-PAO was labeled with $^{99m}Tc$ and studied the biodistribution in mice. From the results we could find that liver uptake of synthesized $^{99m}Tc$ d, 1-HM-PAO was higher than that of Amersham kit, but no conspicuous difference was found in brain and other tissues (blood, lung, stomach, intestine, muscle, spleen and kidney).

• Journal of Microbiology and Biotechnology
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• 제33권6호
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• pp.797-805
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• 2023

Species belonging to the Vernonia (Asteraceae), the largest genus in the tribe Vernonieae (consisting of about 1,000 species), are widely used in food and medicine. These plants are rich sources of bioactive sesquiterpene lactones and steroid saponins, likely including many as yet undiscovered chemical components. A phytochemical investigation resulted in the separation of three new stigmastane-type steroidal saponins (1 - 3), designated as vernogratiosides A-C, from whole plants of V. gratiosa. Their structures were elucidated based on infrared spectroscopy (IR), one-dimensional (1D) and two-dimensional nuclear magnetic resonance (2D NMR), high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and electronic circular dichroism analyses (ECD), as well as chemical reactivity. Molecular docking analysis of representative saponins with α-glucosidase inhibitory activity was performed. Additionally, the intended substances were tested for their ability to inhibit α-glucosidase activity in a laboratory setting. The results suggested that stigmastane-type steroidal saponins from V. gratiosa are promising candidate antidiabetic agents.

• Journal of Microbiology and Biotechnology
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• 제33권12호
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• pp.1606-1614
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• 2023

Biochemical gut metabolism of dietary bioactive compounds is of great significance in elucidating health-related issues at the molecular level. In this study, a human gut bacterium cleaving C-C glycosidic bond was screened from puerarin conversion to daidzein, and a new, gram-positive C-glycoside-deglycosylating strain, Dorea sp. MRG-IFC3, was isolated from human fecal sample under anaerobic conditions. Though MRG-IFC3 biotransformed isoflavone C-glycoside, it could not metabolize other C-glycosides, such as vitexin, bergenin, and aloin. As evident from the production of the corresponding aglycons from various 7-O-glucosides, MRG-IFC3 strain also showed 7-O-glycoside cleavage activity; however, flavone 3-O-glucoside icariside II was not metabolized. In addition, for mechanism study, C-glycosyl bond cleavage of puerarin by MRG-IFC3 strain was performed in D₂O GAM medium. The complete deuterium enrichment on C-8 position of daidzein was confirmed by ¹H NMR spectroscopy, and the result clearly proved for the first time that daidzein is produced from puerarin. Two possible reaction intermediates, the quinoids and 8-dehydrodaidzein anion, were proposed for the production of daidzein-8d. These results will provide the basis for the mechanism study of stable C-glycosidic bond cleavage at the molecular level.

• Natural Product Sciences
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• 제15권4호
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• pp.203-207
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• 2009

A homoisoflavanone, 7,4'-dihydroxyhomoisoflavanone (1) and a flavanone, (2S)-7,4'-dihydroxy-5-methoxyflavanone (2), were isolated from the rhizomes of Anemarrhena asphodeloides, together with 4,4'-dihydroxychalcon (3), 2'-O-methylphlorethin (4), 1,3-bis-di-p-hydroxyphenyl-4-penten-1-one (5), and 2,4'-dihydroxy-4-methoxybenzophenone (6) on the basis of spectroscopic and physicochemical analyses including 1Dand 2D- NMR techniques as well as by comparison of their data with the published values. Compounds 1 - 4 were isolated for the first time from this plant source. Among isolates, compound 2 exhibited moderate inhibitory effect on the differentiation of pre-adipocyte 3T3-L1 cells.

• Bulletin of the Korean Chemical Society
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• 제32권8호
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• pp.2643-2647
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• 2011

Efficient ditopic receptor, uranyl(II) N,N'-(ethylenedioxy)benzenebis(salicylideneimine) (3) for beryllium ion has been obtained upon functionalization of 1,2-ethylenedioxybenzene (1) with a uranyl-salphen (salphen = N,N'-phenylenebis(salicylideneimine)) unit. Binding affinities of the receptor, 3 in AN-DMSO (v/v 95:5) solution have been measured for alkali and alkaline earth metal ions by conductometry comparing 1. The results showed that both monotopic 1 and ditopic receptor 3 were selective for $Be^{2+}$ ions over other cations, while especially 3 that can complex both with cations (coordinated to basic oxygen of ethylenedioxybenzene) and anions (coordinated to the Lewis acidic uranyl center) results in an increase of the stability constants by a factor of $10^{2.42}$ with respect to 1. Furthermore, the $Be^{2+}$-3 interactions are demonstrated by $^1H$ NMR experiments in highly polar solvent medium, DMSO-$d_6$. Higher selectivities were also observed for $Be^{2+}$ when the ditopic receptor, 3 was incorporated into PVC membranes and tested as ion selective electrodes at neutral pH.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1998년도 Proceedings of UNESCO-internetwork Cooperative Regional Seminar and Workshop on Bioassay Guided Isolation of Bioactive Substances from Natural Products and Microbial Products
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• pp.89-94
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• 1998

Marine sponges are recognized as a plentiful source of diverse biologically active secondary metabolites. Recently, we have initiated a research to discover antitumor constituents from the marine sponges collected from Korean Waters. Marine sponges collected from the South Sea of Korea were screened for several biological activities including such as brine shrimp lethality and cytotoxicity. Significant brine shrimp lethality was detected in the crude extract of a two-sponge association of Poecillastra sp. and Jaspis sp. A cross-section of this sample showed two layers of morphologically distinct sponges. The thin and dirty yellow outer layer was identified as Poecillastra sp. (Pachastrellidae), the surface of which was very rough. The light-grey inner layer was identified as Jaspis sp. (Jaspidae), the surface of which was smooth. This two-sponge association appears to be consistent as these sponges were always found in associated form regardless of collection site or collection period. Investigation of the bioactive constituents monitored by brine shrimp lethality assay led to the isolation of pectenotoxin II (PTX2) and psammaplin A as causative compounds for the brine shrimp lethality. $^1$H- and $\^$13/C-nmr signals of PTX2 was fully assigned utilizing TOCSY, HETCOR, Long-range HETCOR, and Homonuclear J-resolved 2D experiments. PTX2 displayed very potent and selective cytotoxicities in the 60 cell line panel antitumor assay at the NCI. PTX2 has progressed to acute toxicity determination and in vivo antitumor assay at the NCI (Table 1). However, significant in vitro antitumor activity of PTX2 can not be affirmed in the in vivo assay.

• 한국식품영양학회:학술대회논문집
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• 한국식품영양학회 1997년도 창립 10주년기념 학술심포지움 행사집
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• pp.15-17
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• 1997

암 발생의 원인 중 80% 이상이 식사습관과 환경오염에 있는 것으로 인정되고 있다. 음식물, 담배, 술, 대기오염, 스트레스, 자외선이 그 대표적인 원인물질로 꼽을 수 있으며 그 중에서도 매일 섭취하는 음식물이 가장 중요한 발암요인으로 지적되고 있다. 대장암과 유방암의 발생에 대한 Wynder 등의 역학조사에서도 식사습관이 암 발생에 중요함을 시사 하고 있다. 동물성 단백질과 지방의 다량 섭취가 대장암과 유방암의 발생을 증가 시키고 섬유질이 풍부한 곡류와 야채의 섭취는 대장암 발생을 억제한다는 상관관계가 밝혀졌다. 그러나 우리가 늘 섭취하는 음식물 자체는 대장암과 유방암을 유발하는 기능이 거의 없다. 섭취된 음식물이 암을 일으키려면 장내 부패 미생물의 분해작용에 의하여 발암물질로 변환되는 과정이 필요하다. 그 발암물질들이 장관으로 흡수 자극함으로써 암을 유발할 수 있다. 반대로 일부장내 미생물들은 장내 발암물질들을 무독화 하거나 숙주의 면역기능을 증강 시킴으로써 암 발생을 억제할 수도 있다는 사실을 간과해서는 안 될 것이다. Mitsuoka는 장내 미생물이 암을 유발하는 중요한 요인이라고 강조하였다. Veer 등은 유산균 발효유를 많이 섭취하면 유방암 발생이 억제됨을, 국제암연구위원회는 섬유질을 많이 섭취하고 있는 핀란드 쿠피오의 거주자들에게는 덴마크의 코펜하겐에 거주하는 사람들에 비하여 대장암 발생율이 1/4에 불과하고 분변내 유산간균수는 100배 높은 사실을 역학조사에서 밝혔다. 이 외에 유산균과 발효유제품의 항암효과에 대한 실험결과들이 많이 발표되었다. 여기에서는 유산균의 항암효과에 대한 지금까지의 관련 자료들을 요약, 정리하여 고찰하고자 한다.높은 당 함량을 나타냈으며, T-AS는 70.3%의 당과 7.8%의 단백질로 구성 되었다. GLG 대부분의 분획들은 60~93%의 glucose로 구성된 다당류 이었으며, 주로 $\beta$-glucose로 구성된 다당류 이었다. 아미노산은 Asp 및 Glu의 산성 아미노산과 Ala, Leu 등의 함량이 높게 나타났으며, 비알칼리 추출물에서 Ser과 Thr의 함량이 높게 나타났다. 다당류 T-AS는 평균 분자량이 2,000 kD와 12kD에서 주 peak를 나타냈으며, 수용성 분획의 평균 분자량은 12kD이고 비수용성 분획은 36~2,000 kD의 평균 분자량 분포를 갖는 것으로 나타났다. IR과 NMR 분석 결과 890 cm-1에서 흡수 peak를 나타내어 $\beta$-(1,3)0glucan과 $\beta$-(1,6)-glucan의 구조를 갖는 다당류로 확인 되었다. T-AS 분획은 C:H:O:N의 함량비가 38.9:5.7:49.6:1.84%이며, 이 물질의 융점은 163 $^{\circ}C$로 연한 갈색을 나타낸다. 분리된 GLG의 항암활성 기전 규명을 위해, in vivo 항암실험, 항보체 활성능, 항체 생성능, serum protein 분비능, 대식세포의 탐식능과 활성능 및 세포간 물질 분비 등의 상관관계를 조사하였다. 다당류 GLG 분획물들 가운데 항보체의 활성이 높았던 분획은 sarcome 180에 대한 항암 활성이 높게 나타났다. 다당류 T-AS의 보체 활성화 기작은 classical과 alternative complement pathway의 양 경로를 통해 활성화 되었다.