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Sarcotragins A and B, new sesterterpenoid alkaloids from the sponge Sarcotragus sp.
Shin, Jongheon,Rho, Jung-Rae,Seo, Youngwan,Lee, Hyi-Seung,Cho, Ki Woong,Sim, Chung J. 한국해양대학교 해양과학기술연구소 2001 硏究論文集 Vol.10 No.1
Sarcotragins A (1) and B (2), two terpenoid alkaloids of an unusual structural class, have been isolated from the sponge Sarcotragus sp. collected from Jaeju Island, Korea. The structures of these compounds have been determined as linear trisnorsesterterpenes containing a phenethylamine lactam or the corresponding glycine lactam moiety by combined chemical and spectral methods. ⓒ 2001 Elsevier Science Ltd. All rights reserved.
Inhibition of infection of the rice blast fungus by halisulfate 1, an isocitrate lyase inhibitor
Shin, Dong-Sun,Lee, Tae-Hoon,Lee, Hyi-Seung,Shin, Jongheon,Oh, Ki-Bong Oxford University Press 2007 FEMS microbiology letters Vol.272 No.1
<P>Halisulfate 1, a sesterterpene sulfate and an isocitrate lyase (ICL) inhibitor that is isolated from tropical sponge Hippospongia spp., reduces both appressorium formation and infection of rice plants by the fungus Magnaporthe grisea. Rice plants infected with wild-type M. grisea Guy 11 exhibited significantly lower disease severity after halisulfate 1 treatment than without, and the treatment effect was comparable to the behavior of the Delta icl knockout mutant I-10. The protection observed upon applying halisulfate 1 to rice plants suggests that the ICL inhibitor may be a promising candidate for crop protection, particularly to protect rice plants against M. grisea.</P>
Shin, Yern-Hyerk,Bae, Suhyun,Sim, Jaehoon,Hur, Joonseong,Jo, Shin-Il,Shin, Jongheon,Suh, Young-Ger,Oh, Ki-Bong,Oh, Dong-Chan American Chemical Society and American Society of 2017 Journal of natural products Vol.80 No.11
<P>Nicrophorusamides A and B (<B>1</B> and <B>2</B>) were discovered from a rare actinomycete, <I>Microbacterium</I> sp., which was isolated from the gut of the carrion beetle <I>Nicrophorus concolor</I>. The structures of the nicrophorusamides were established as new chlorinated cyclic hexapeptides bearing uncommon amino acid units mainly based on 1D and 2D NMR spectroscopic analysis. The absolute configurations of the amino acid residues 5-chloro-<SMALL>l</SMALL>-tryptophan, <SMALL>d</SMALL>-<I>threo</I>-β-hydroxyasparagine/<SMALL>d</SMALL>-asparagine, <SMALL>l</SMALL>-ornithine, <SMALL>l</SMALL>-<I>allo</I>-isoleucine, <SMALL>d</SMALL>-leucine, and <SMALL>d</SMALL>-valine were determined using Marfey’s method and chemical derivatization with 2,3,4,6-tetra-<I>O</I>-acetyl-β-<SMALL>d</SMALL>-glucopyranosyl isothiocyanate followed by LC/MS analysis. Nicrophorusamide A (<B>1</B>) showed antibacterial activity against several Gram-positive bacteria.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2017/jnprdf.2017.80.issue-11/acs.jnatprod.7b00506/production/images/medium/np-2017-005068_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np7b00506'>ACS Electronic Supporting Info</A></P>
Shin, Bora,Kim, Byung-Yong,Cho, Eunji,Oh, Ki-Bong,Shin, Jongheon,Goodfellow, Michael,Oh, Dong-Chan American Chemical Society and American Society of 2016 Journal of natural products Vol.79 No.7
<P>A new secondary metabolite, actinomadurol (1), was isolated along with the known compound JBIR-65 (2) from a rare actinomycete, Actinomadura strain KC 191. The structure of 1 was established as a rare member of the bacterial C-19 norditerpenoid class by NMR data and ECD calculations. The absolute configuration of 2, which was previously reported without stereochemical analysis, was determined by using the modified Mosher's method and ECD calculations. Actinomadurol (1) exhibited potent antibacterial activity against pathogenic strains, such as Staphylococcus aureus, Kocuria rhizophila, and Proteus hauseri (MIC = 0.39-0.78 mu g/mL), whereas JBIR-65 (2) showed no antibacterial activity.</P>
Suncheonosides A–D, Benzothioate Glycosides from a Marine-Derived <i>Streptomyces</i> sp.
Shin, Bora,Ahn, Seyeon,Noh, Minsoo,Shin, Jongheon,Oh, Dong-Chan American Chemical Society and American Society of 2015 Journal of natural products Vol.78 No.6
<P>A marine-derived Streptomyces strain, SSC21, was isolated from the sediment of Suncheon Bay, Republic of Korea. Chemical analysis of the bacterial strain resulted in the isolation of four new metabolites, suncheonosides A-D (1-4, respectively), each bearing a,sulfur atom. The planar structures of the suncheonosides were identified as hexasubstituted benzothioate glycosides by combined spectroscopic analyses. Analysis of the configuration of the sugar moieties based on ROESY nuclear magnetic resonance correlations, one-bond H-1-C-13 coupling constant analysis, and chemical derivatizations indicated that the suncheonosides incorporate only L-rhamnose. Suncheonosides A, 13, and ID promoted adiponectin production in a concentration-dependent manner during adipogenesis in human mesenthymal stein cells, suggesting antidiabetic potential.</P>
Shin, Yern-Hyerk,Beom, Ji Yoon,Chung, Beomkoo,Shin, Yoonho,Byun, Woong Sub,Moon, Kyuho,Bae, Munhyung,Lee, Sang Kook,Oh, Ki-Bong,Shin, Jongheon,Yoon, Yeo Joon,Oh, Dong-Chan American Chemical Society 2019 ORGANIC LETTERS Vol.21 No.6
<P>Bombyxamycins A and B (<B>1</B> and <B>2</B>) were discovered from a silkworm gut <I>Streptomyces</I> bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of <B>2</B>, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.</P> [FIG OMISSION]</BR>
Reaction of Thianthrene Cation Radical Perchlorate with Cumene Hydroperoxides
신종헌,김경태,Jongheon Shin,Kyongtae Kim Korean Chemical Society 1983 대한화학회지 Vol.27 No.2
아세토니트릴용액중의 티안트렌 양이온 라디칼 과염소산 염(1)은 Cumene hydroperoxide(4), p-chlorocumene hydroperoxide(2), p-nitrocumene hydroperoxide(3)와 상온에서 반응한다. 이 반응의 공통 생성물로서 티안트렌을 얻었으며 4로 부터 5-(4'-hydroxyphenyl) thianthrenium perchlorate (5), 2로부터 5-(5'-chloro-2'-hydroxyphenyl) thianthrenium perchlorate (7)와 5-acetonylthianthrenium perchlorate (6), 그리고 3으로부터 6만을 얻었다. 이 반응의 양관계는 1의 2몰이 티안트렌 1몰과 티안트렌이움 염(또는 염들) 1몰을 생성한다. 1에 대한 친핵성 활성도는 페놀 > > p-클로로페놀 ${\sim}$아세톤 > > p-니트로페놀 순서임이 밝혀졌다. Hydroperoxide의 산촉매 불균일 분해반응외에도 소량의 균일분해 반응생성물이 3과 4로부터 생성됨을 알았다. Reaction of thianthrene cation radical perchlorate (1) with cumene (4), p-chlorocumene (2), and p-nitrocumene (3) hydroperoxides in acetonitrile at room temperature afforded, inter alia, thianthrene as a common product and 5-(4'-hydroxyphenyl) thianthrenium perchlorate (5) for 4, 5-(5'-chloro-2'-hydroxyphenyl) thianthrenium perchlorate (7) and 5-acetonylthianthrenium perchlorate (6) for 2 and 6 for 3, respectively. Stoichiometry of these reactions showed that 2 moles of 1 gave rise to 1mole of thianthrene and 1 mole of thianthrenium salt (or salts). Nucleophilic reactivity to 1 was found to be in the order of phenol > > p-chlorophenol ${\sim}$ acetone > > p-nitrophenol. Apart from acid-catalyzed heterolytic decomposition of hydroperoxides, small amount of homolytic decomposition products were found from 3 and 4.
Pentacyclic Antibiotics from a Tidal Mud Flat-Derived Actinomycete
Moon, Kyuho,Chung, Beomkoo,Shin, Yoonho,Rheingold, Arnold L.,Moore, Curtis E.,Park, Sung Jean,Park, Sunghyouk,Lee, Sang Kook,Oh, Ki-Bong,Shin, Jongheon,Oh, Dong-Chan American Chemical Society and American Society of 2015 Journal of natural products Vol.78 No.3
<P>The combination of investigating a unique source of chemically prolific bacterium with an LC/MS-based bacterial strain selection approach resulted in the discovery of two new secondary metabolites, buanmycin (<B>1</B>) and buanquinone (<B>2</B>), from the culture of a marine <I>Streptomyces</I> strain, which was isolated from a tidal mudflat in Buan, Republic of Korea. The carbon backbone of buanmycin (<B>1</B>), comprising 20 quaternary carbons out of 30 total carbons, was determined via <SUP>13</SUP>C–<SUP>13</SUP>C COSY NMR analysis after labeling <B>1</B> with <SUP>13</SUP>C by culturing the bacterium with <SUP>13</SUP>C-glucose. The complete structure of <B>1</B> was confidently elucidated, primarily based on 1D and 2D NMR spectroscopic and X-ray crystallographic analysis, as that of a new pentacyclic xanthone. The absolute configuration of the α-methyl serine unit in <B>1</B> was established by applying the advanced Marfey’s method. The structure of buanquinone (<B>2</B>) was determined to be a new pentacyclic quinone based on NMR and MS spectroscopic data. Buanmycin exhibited potent cytotoxicity against colorectal carcinoma cells (HCT-116) and gastric carcinoma cells (SNU-638) with submicromolar IC<SUB>50</SUB> values and strongly inhibited the pathogenic Gram-negative bacterium <I>Salmonella enterica</I> (MIC = 0.7 μM). In particular, buanmycin demonstrated inhibition of sortase A, which is a promising target for antibiotic discovery.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2015/jnprdf.2015.78.issue-3/np500736b/production/images/medium/np-2014-00736b_0004.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np500736b'>ACS Electronic Supporting Info</A></P>