• Journal of Microbiology and Biotechnology
• /
• 제33권6호
• /
• pp.797-805
• /
• 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 Gastric Cancer
• /
• 제3권3호
• /
• pp.151-157
• /
• 2003

Purpose: In this study, we attempted to ascertain the proton magnetic resonance spectroscopy (${1}^H$ MRS) peak characteristics of human gastric tissue layers and finally to use the metabolic peaks of MRS to distinguish between normal and abnormal gastric specimens. Materials and Methods: Ex-vivo ${1}^H$ MRS examinations of thirty-five gastric specimens were performed to distinguish abnormal gastric tissues invaded by carcinoma cells from normal stomach-wall tissues. High-resolution 400-MHz (9.4-T) ${1}^H$ nuclear magnetic resonance (NMR) spectra of two gastric layers, a proper muscle layer, and a composite mucosasubmucosa layer were compared with those of clinical 64- MHz (1.5-T) MR spectra. Three-dimensional spoiled gradient recalled (SPGR) images were used to determine the size and the position of a voxel for MRS data collection. Results: For normal gastric tissue layers, the metabolite peaks of 400-MHz ${1}^H$ MRS were primarily found to be as follows: lipids at 0.9 ppm and 1.3 ppm; alanine at 1.58 ppm; N-acetyl neuraminic acid (sialic acid) at 2.03 ppm; and glutathione at 2.25 ppm in common. The broad and featureless featureless spectral peaks of the 64-MHz MRS were bunched near 0.9, 1.3, and 2.0, and 2.2 ppm in human specimens without respect to layers. In a specimen (Borrmmann type III) with a tubular adenocarcinoma, the resonance peaks were measured at 1.26, 1.36 and 3.22 ppm. All the peak intensities of the spectrum of the normal gastric tissue were reduced, but for gastric tumor tissue layers, the lactate peak split into 1.26 and 1.39 ppm, and the peak intensity of choline at 3.21 ppm was increased. Conclusion: We found that decreasing lipids, an increasing lactate peak that split into two peaks, 1.26 ppm and 1.36 ppm, and an increasing choline peak at 3.22 ppm were markers of tumor invasion into the gastric tissue layers. This study implies that MR spectroscopy can be a useful diagnostic tool for gastric cancer.

• Journal of Microbiology and Biotechnology
• /
• 제33권8호
• /
• pp.1023-1029
• /
• 2023

Biosurfactants reduce surface and interfacial tension due to their amphiphilic properties and are an eco-friendly alternative for chemical surfactants. In this study, a new yeast strain JAF-11 that produces a biosurfactant was selected using drop collapse method, and the properties of the extracts were investigated. The nucleotide sequences of the strain were compared with closely related strains and identified based on the D1/D2 domain of the large subunit ribosomal DNA (LSU) and internal transcribed spacer (ITS) regions. Neodothiora populina CPC 39399^T, the closest species with strain JAF-11, showed a sequence similarity of 97.75% for LSU and 94.27% for ITS, respectively. The result suggests that the strain JAF-11 represents a distinct species that cannot be assigned to any existing genus or species in the family Dothideaceae. Strain JAF-11 produced a biosurfactant reducing the surface tension of water from 72 mN/m to 34.5 mN/m on the sixth day of culture and the result of measuring the critical micelle concentration (CMC) by extracting the crude biosurfactant was found to be 24 mg/l. The molecular weight 502 of the purified biosurfactant was confirmed by measuring the fast atom bombardment mass spectrum. The chemical structure was analyzed by measuring ¹H nuclear magnetic resonance (NMR), ¹³C NMR, and two-dimensional NMRs of the compound. The molecular formula was C₂₆H₄₆O₉, and it was composed of one octanoyl group and two hexanoyl groups to myo-inositol moiety. The new biosurfactant is the first report of a compound produced by a new yeast strain, JAF-11.

• 한국잡초학회지
• /
• 제15권1호
• /
• pp.85-98
• /
• 1995

말포민 B로부터 신규의 $B_3$, $B_4$ 및 $B_5$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 $B_{1a}$는 $0.25{\mu}m$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.

• 한국식품영양과학회지
• /
• 제46권6호
• /
• pp.759-764
• /
• 2017

당뇨합병증에 효과적인 천연물 유래의 신소재를 개발하기 위하여 본 연구를 수행하여 단풍취 70% 에탄올 추출물의 EtOAc 가용부로부터 최종당화산물 생성 억제능($IC_{50}=5.5{\pm}1.1{\mu}g/mL$)을 확인하였다. 활성을 나타내는 성분의 동정을 위하여 $C_{18}$겔 등을 활용한 칼럼크로마토그래피를 수행하여 4종의 dicaffeoylquinic acid 유도체 화합물을 분리하였고, 각 화합물의 화학구조는 NMR 스펙트럼 데이터 해석 및 표품과의 HPLC 직접 비교를 통하여 methyl 3,5-di-O-caffeoyl-epi-quinate(1), 3,5-di-O-caffeoyl-epi-quinic acid(2), 4,5-di-O-caffeoyl-quinic acid(3) 및 methyl 4,5-di-O-caffeoyl-quinate(4)로 동정하였다. 이들 화합물에 대해 최종당화산물 생성 억제능을 평가한 결과 4,5-di-O-caffeoyl-quinic acid(3)가 가장 강한 $0.4{\pm}0.1{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 3,5-di-O-caffeoyl-epi-quinic acid(2)가 $0.6{\pm}0.1{\mu}M$의 $IC_{50}$ 값을 나타내었다. 또한, 이들 물질에 대해 $ABTS^+$ 소거 활성을 평가하여 4,5-di-O-caffeoyl-quinic acid(3)가 가장 강한 라디칼 소거 활성인 $14.6{\pm}0.4{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 구조 이성질체인 3,5-di-O-caffeoyl-epi-quinic acid(2)가 $18.8{\pm}0.4{\mu}M$의 $IC_{50}$ 값을 확인하였다. 단풍취에서 분리한 화합물의 활성은 caffeic acid의 결합방식 및 methyl화 여부에 따른 화합물의 구조에 따라 다름이 시사되었다. 향후 우수한 활성을 나타낸 이들 화합물의 in vivo 실험을 통한 활성기작의 검증이 필요하다고 생각된다. 또한, 추가적인 연구를 통하여 식의약 소재로 활용이 가능한 새로운 천연신소재 발굴을 위한 기초자료제공 및 당뇨합병증에 효과적인 천연 물질의 상업화를 위한 귀중한 자료로 활용할 수 있으리라 판단된다.

• Applied Biological Chemistry
• /
• 제33권3호
• /
• pp.239-246
• /
• 1990

유기 용매에 추출되는 유리형의 홍국 색소를 보다 많이 얻기 위하여 Monascus anka의 균주를 자연 및 자외선 변이균주에서 선발하고 배양 조건을 탐색하였다. 균주 N3를 Lin's medium에서 진탕 배양, Nishikawa's medium에서 정치 배양 및 진탕 배양하여 균체성장과 색소생성에 소요되는 시간, 유기용매에 추출되는 색소의 양을 비교하여 보았다. Lin's medium에서의 액침 배양에서는 수용성 색소가 우세하게 생성되는 반면 Nishikawa's medium에서의 정치 배양에서는 보다 많은 유기용매 가용성의 색소를 얻을 수 있었다. 한편 탄소원으로는 자당외에 에탄올이 가장 효과적이었다. Sterol 합성저해제를 처리하였을 때는 상당한 색소 형성의 증가를 볼 수 있었다. 이차원 TLC로써 아직 보고된 바 없는 색소들이 존재함을 알 수 있었다. 이 균주의 색소중 가장 다량으로 존재하는 황색소의 하나를 분리하였고 분광학적 방법으로 ankaflavin으로 동정하였다.

• Journal of Microbiology and Biotechnology
• /
• 제20권7호
• /
• pp.1061-1068
• /
• 2010

The biological synthesis of nanoparticles has gained considerable attention in view of their excellent biocompatibility and low toxicity. We isolated and purified rhamnolipids from Pseudomonas aeruginosa strain BS-161R, and these purified rhamnolipids were used to synthesize silver nanoparticles. The purified rhamnolipids were further characterized and the structure was elucidated based on one- and two-dimensional $^1H$ and $^{13}C$ NMR, FT-IR, and HR-MS spectral data. Purified rhamnolipids in a pseudoternary system of n-heptane and water system along with n-butanol as a cosurfactant were added to the aqueous solutions of silver nitrate and sodium borohydride to form reverse micelles. When these micelles were mixed, they resulted in the rapid formation of silver nanoparticles. The synthesized nanoparticles were characterized by UV-Visible spectroscopy, transmission electron microscopy, and energy dispersive X-ray spectroscopy (EDS). The nanoparticles formed had a sharp adsorption peak at 410 nm, which is characteristic of surface plasmon resonance of the silver nanoparticles. The nanoparticles were monodispersed, with an average particle size of 15.1 nm (${\sigma}={\pm}5.82$ nm), and spherical in shape. The EDS analysis revealed the presence of elemental silver signal in the synthesized nanoparticles. The formed silver nanoparticles exhibited good antibiotic activity against both Grampositive and Gram-negative pathogens and Candida albicans, suggesting their broad-spectrum antimicrobial activity.

• 한국환경과학회:학술대회논문집
• /
• 한국환경과학회 2006년도 추계 학술발표회 발표논문집
• /
• pp.285-289
• /
• 2006

In screening of algicidal bacteria, we isolated a marine bacterium which had potent algicidal effects on harmful algal bloom (HAB) species. This organism was identified as a strain very close to Bacillus subtilisby 16S rRNA gene sequencing. This bacterium, Bacillus sp. SY-1, produces very active algicidal compounds against the harmful dinoflagellate Cochlodinium polykrikoides. We isolated three algicidal compounds (MS 1056, 1070, 1084) and identified them by amino acid analyses, fast atom bombardment mass spectrometry (FAB-MS), infrared spectroscopy (IR), $^1H$, $^{13}C$, and extensive two-dimensional nuclear magnetic resonance (2D NMR) techniques including $^1H-^{15}N$ HMBC analysis. One of them, MS 1056, contains a b-amino acid residue with an alkyl side chain of $C_{15}$. MS 1056, 1070, and 1084 showed algicidal activities against C. polykrikoides with an $LC_{50}$ (6 hrs) of 2.3, 0.8, $0.6\;{\mu}g/ml$, respectively. These compounds also showed significant algicidal activities against other harmful dinoflagellates and raphidophytes. In contrast, MS 1084 showed no significant growth inhibition against various organisms coexisting with HAB species in natural environments, including bacteria, eukaryotic microalgae, and cyanobacteria, although it inhibited growth of some fungi and yeasts. These observations imply that algicidal bacterium Bacillus sp. SY-1 and its algicidal compounds could play an important role in regulating the onset and development of HABs in the natural environments.

• Archives of Pharmacal Research
• /
• 제29권1호
• /
• pp.50-58
• /
• 2006

Translationally controlled tumor protein (TCTP), also known as histamine releasing factor (HRF), is found abundantly in different eukaryotic cell types. The sequence homology of TCTP between different species is very high, belonging to the MSS4/DSS4 superfamily of proteins. TCTP is involved in both cell growth and human late allergy reaction, as well as having a calcium binding property; however, its primary biological functions remain to be clearly elucidated. In regard to many possible functions, the TCTP of Plasmodium falciparum (Pf) is known to bind with an antimalarial agent, artemisinin, which is activated by heme. It is assumed that the endoperoxide-bridge of artemisinin is opened up by heme to form a free radical, which then eventually alkylates, probably to the Cys14 of PfTCTP. Study of the docking of artemisinin with heme, and subsequently with PfTCTP, was carried out to verify the above hypothesis on the basis of structural interactions. The three dimensional (3D) structure of PfTCTP was built by homology modeling, using the NMR structure of the TCTP of Schizosaccharomyces pombe as a template. The quality of the model was examined based on its secondary structure and biological function, as well as with the use of structure evaluating programs. The interactions between artemisinin, heme and PfTCTP were then studied using the docking program, FlexiDock. The center of the peroxide bond of artemisinin and the Fe of heme were docked within a short distance of $2.6{\AA}$, implying the strong possibility of an interaction between the two molecules, as proposed. When the activated form of artemisinin was docked on the PfTCTP, the C4-radical of the drug faced towards the sulfur of Cys14 within a distance of $2.48{\AA}$, again suggesting the possibility of alkylation having occurred. These results confirm the proposed mechanism of the antimalarial effect of artemisinin, which will provide a reliable method for establishing the mechanism of its biological activity using a molecular modeling study.

• Mycobiology
• /
• 제49권6호
• /
• pp.604-606
• /
• 2021

In our ongoing search for new secondary metabolites from fungal strains, one novel compound (1) and nine known compounds (2-10) were isolated from the EtOAc-soluble layer of the culture broth of Panus rudis. The culture broth of P. rudis was extracted in acetone and fractionated by solvent partition; column chromatography using silica gel, Sephadex LH-20, and Sephadex G-10; MPLC; and HPLC. The structures of isolated compounds were elucidated by one- and two-dimensional NMR and LC-ESI-mass measurements. One new compound, panepoxydiol (1), and nine known compounds, (E)-3-(3-hydroxy-3-methylbut-1-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol (2), isopanepoxydone (3), neopanepoxydone (4), panepoxydone (5), panepophenanthrin (6), 4-hydroxy-2,2-dimethyl-6-methoxychromane (7), 6-hydroxy-2,2-dimethyl-3-chromen (8), 2,2-dimethyl-6-methoxychroman-4-one (9), 3,4-dihydroxy-2,2-dimethyl-6-methoxychromane (10), were isolated from the culture broth of P. rudis. This is the first report of isolation of a new compound panepoxydiol (1) and nine other chemical constituents (2-5, 7-10) from the culture broth of P. rudis.