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Jang, Jun-Pil,Hwang, Gwi Ja,Kwon, Min Cheol,Ryoo, In-Ja,Jang, Mina,Takahashi, Shunji,Ko, Sung-Kyun,Osada, Hiroyuki,Jang, Jae-Hyuk,Ahn, Jong Seog American Chemical Society and American Society of 2018 Journal of natural products Vol.81 No.4
<P>Two new cyclic peptides, pentaminomycins A (<B>1</B>) and B (<B>2</B>), were isolated from cultures of <I>Streptomyces</I> sp. RK88-1441. Based on the interpretation of the NMR, UV, IR, and MS data, the planar structures of <B>1</B> and <B>2</B> were elucidated as cyclic pentapeptides with a modified amino acid residue, <I>N</I><SUP>5</SUP>-hydroxyarginine (N5-OH-Arg). The absolute configurations of the constituent amino acid residues were determined by the advanced Marfey’s method. Localization of <SMALL>L</SMALL>- and <SMALL>D</SMALL>-amino acids in the sequence was ascertained by chiral analysis of the fragment peptide obtained from a partial hydrolysate; amino acids were identified by LC-MS. Pentaminomycin A (<B>1</B>) reduced α-MSH-stimulated melanin synthesis by suppressing the expression of melanogenic enzymes including tyrosinase, tyrosinase-related protein-1 (TRP-1), and tyrosinase-related protein-2 (TRP-2).</P> [FIG OMISSION]</BR>
Ahn, Jang-Hyuk,Kwak, Byung-Man,Park, Jung-Min,Kim, Na-Kyeoung,Kim, Jin-Man Korean Society for Food Science of Animal Resource 2014 한국축산식품학회지 Vol.34 No.6
A rapid and simple analytical method for L-carnitine was developed for infant and toddler formulas by liquid chromatography tandem mass spectrometry (LC-MS/MS). A 0.3 g of infant formula and toddler formula sample was mixed in a 50 mL conical tube with 9 mL water and 1 mL 0.1 M hydrochloric acid (HCl) to chemical extraction. Then, chloroform was used for removing a lipid fraction. After centrifuged, L-carnitine was separated and quantified using LC-MS/MS with electrospray ionization (ESI) mode. The precursor ion for L-carnitine was m/z 162, and product ions were m/z 103 (quantitative) and m/z 85 (qualitative), respectively. The results for spiked recovery test were in the range of 93.18-95.64% and the result for certified reference material (SRM 1849a) was within the range of the certificated values. This method could be implemented in many laboratories that require time and labor saving.
Jang-Hyuk Ahn,Young-Su Jeong,Tae Geol Lee,김영필,김학성 한국바이오칩학회 2012 BioChip Journal Vol.6 No.1
A rapid and reliable analysis of toxins is prerequisite for food control and human healthcare. Here we demonstrate a simple and multiplexed assay of aflatoxins using time-of-flight secondary ion mass spectrometry (TOF-SIMS). By simply adsorbing either a single analyte or mixed ones onto a gold substrate, the corresponding secondary molecular ions([M+H]+) were clearly observed in a single mass spectrum. As a result of concentration-dependent peak intensity, quantitative and multiplexed analysis of different aflatoxin analogs from corns was accomplished with immunoaffinity column and TOF-SIMS analysis, which showed a good correlation with HPLC data. The detection sensitivity was estimated to be as low as 10 ng mL-1. This approach presented here will find a wide application to detection of low-levels of toxins in a rapid and multiplexed way.
Fusarisetin A, an Acinar Morphogenesis Inhibitor from a Soil Fungus, Fusarium sp. FN080326
Jang, Jae-Hyuk,Asami, Yukihiro,Jang, Jun-Pil,Kim, Sun-Ok,Moon, Dong Oh,Shin, Kee-Sun,Hashizume, Daisuke,Muroi, Makoto,Saito, Tamio,Oh, Hyuncheol,Kim, Bo Yeon,Osada, Hiroyuki,Ahn, Jong Seog American Chemical Society 2011 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.133 No.18
<P>An acinar morphogenesis inhibitor named fusarisetin A (<B>1</B>) that possesses both an unprecedented carbon skeleton and a new pentacyclic ring system has been identified from an in-house fractionated fungal library using a three-dimensional matrigel-induced acinar morphogenesis assay system. The structure of <B>1</B> was determined in detail by NMR and circular dichroism spectroscopy, X-ray analysis, and chemical reaction experiments.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2011/jacsat.2011.133.issue-18/ja1110688/production/images/medium/ja-2010-110688_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja1110688'>ACS Electronic Supporting Info</A></P>
Jang, Jun-Pil,Hwang, Gwi Ja,Jang, Mina,Takahashi, Shunji,Ko, Sung-Kyun,Osada, Hiroyuki,Jang, Jae-Hyuk,Ahn, Jong Seog American Chemical Society and American Society of 2018 Journal of natural products Vol.81 No.9
<P>A chemical investigation of a culture extract from a soil-derived <I>Streptomyces</I> sp. RK88-1441 led to the isolation and characterization of two new glycosylated anthraquinones, aturanosides A (<B>1</B>) and B (<B>2</B>), and a new anthraquinone derivative, aturanocin (<B>3</B>). The structures of these compounds were elucidated by detailed NMR and MS spectroscopic analyses. The absolute configurations of the sugar units, based on the magnitudes of the coupling constants, ROESY correlations, and chemical derivatization, from <B>1</B> and <B>2</B> are 6-<I>O</I>-[<I>N</I>-acetyl-α-<SMALL>D</SMALL>-glucosamino-(1→2)-α-<SMALL>L</SMALL>-rhamnoside] and 6-<I>O</I>-α-<SMALL>L</SMALL>-rhamnoside, respectively. Compounds <B>1</B> and <B>2</B> showed no cytotoxicity against human umbilical vein endothelial cells (HUVECs), but significantly suppressed vascular endothelial growth factor (VEGF)-induced tube formation and invasion of HUVECs. The down-regulation of both the phosphorylation of VEGF receptor 2 and the expression of vascular endothelial cadherin at the protein level were also observed.</P> [FIG OMISSION]</BR>
Anti-Angiogenesis Effects Induced by Octaminomycins A and B against HUVECs
( Jun-pil Jang ),( Jang Mi Han ),( Hye Jin Jung ),( Hiroyuki Osada ),( Jae-hyuk Jang ),( Jong Seog Ahn ) 한국미생물생명공학회(구 한국산업미생물학회) 2018 Journal of microbiology and biotechnology Vol.28 No.8
In the course of studies to discover natural products with anti-angiogenic properties, two cyclic octapeptides, octaminomycins A (1) and B (2), were isolated from the cultures of Streptomyces sp. RK85-270. Octaminomycins suppressed the vascular endothelial growth factor (VEGF)-induced proliferation, adhesion, tube formation, migration, and invasion of HUVECs. Anti-angiogenic activity was futher confirmed in vivo by the chicken chorioallantoic membrane assay. We also identified that 1 and 2 inhibited the phosphorylation of VEGF receptor 2, AKT, and ERK1/2 and the expression and activities of MMP-2 and MMP-9. These results suggest that 1 and 2 may serve as potential scaffolds for the development of therapeutic agents to angiogenesis-dependent diseases.
RK-270D and E, Oxindole Derivatives from Streptomyces sp. with Anti-Angiogenic Activity
( Jun-pil Jang ),( Mina Jang ),( Toshihiko Nogawa ),( Shunji Takahashi ),( Hiroyuki Osada ),( Jong Seog Ahn ),( Sung-kyun Ko ),( Jae-hyuk Jang ) 한국미생물 · 생명공학회 2022 Journal of microbiology and biotechnology Vol.32 No.3
A chemical investigation of a culture extract from Streptomyces sp. RK85-270 led to the isolation and characterization of two new oxindoles, RK-270D (1) and E (2). The structures of 1 and 2 were determined by analyzing spectroscopic and spectrometric data from 1D and 2D NMR and High-resolution electrospray ionization mass spectrometry (HRESIMS) experiments. Compound 1 exhibited anti-angiogenic activities against human umbilical vein endothelial cells (HUVECs) without cytotoxicity. Results of Western blot analysis revealed that 1 inhibits VEGF-induced angiogenesis in the HUVECs via VEGFR2/ p38 MAPK-mediated pathway.
Jang, Jung Eun,Ko, Myoung Seok,Yun, Ji-Young,Kim, Mi-Ok,Kim, Jin Hee,Park, Hye Sun,Kim, Ah-Ram,Kim, Hyuk-Joong,Kim, Bum Joong,Ahn, Young Eun,Oh, Jin Sun,Lee, Woo Je,Harris, Robert A.,Koh, Eun Hee,Lee, American Diabetes Association 2016 Diabetes Vol. No.
<P>Fibrosis of adipose tissue induces ectopic fat accumulation and insulin resistance by inhibiting adipose tissue expandability. Mechanisms responsible for the induction of adipose tissue fibrosis may provide therapeutic targets but are poorly understood. In this study, high-fat diet (HFD)-fed wild-type (WT) and iNOS(-/-) mice were used to examine the relationship between nitric oxide (NO) produced by macrophages and adipose tissue fibrosis. In contrast to WT mice, iNOS(-/-) mice fed an HFD were protected from infiltration of proinflammatory macrophages and adipose tissue fibrosis. Hypoxia-inducible factor 1 alpha (HIF-1 alpha) protein level was increased in adipose tissue of HFD-fed WT mice, but not iNOS(-/-) mice. In contrast, the expression of mitochondrial biogenesis factors was decreased in HFD-fed WT mice, but not iNOS(-)/(-) mice. In studies with cultured cells, macrophage-derived NO decreased the expression of mitochondrial biogenesis factors, and increased HIF-1 alpha protein level, DNA damage, and phosphorylated p53 in preadipocytes. By activating p53 signaling, NO suppressed peroxisome proliferator-activated receptor gamma coactivator is expression, which induced mitochondrial dysfunction and inhibited preadipocyte differentiation in adipocytes. The effects of NO were blocked by rosiglitazone. The findings suggest that NO produced by macrophages induces mitochondrial dysfunction in preadipocytes by activating p53 signaling, which in turn increases HIF-1 alpha protein level and promotes a profibrogenic response in preadipocytes that results in adipose tissue fibrosis.</P>