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Ansalactams B–D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway
Le, Tu Cam,Yang, Inho,Yoon, Yeo Joon,Nam, Sang-Jip,Fenical, William American Chemical Society 2016 Organic letters Vol.18 No.9
<P>Further chemical investigation of a marine-derived bacterium of the genus Streptomyces has led to the isolation of ansalactams B-D (1-3) along with the previously reported metabolite ansalactam A (4). Ansalactams B-D are significantly modified ansamycins, representing three new carbon skeletons and further illustrating the biosynthetic plasticity of the ansalactam class. Unlike ansalactam A, ansalactams B and D are penta- and hexacyclic metabolites, while ansalactam C illustrates an open polyene chain with a terminal carboxylic acid.</P>
( Hyun Woo Lee ),( Hansol Choi ),( Sang-jip Nam ),( William Fenical ),( Hoon Kim ) 한국미생물 · 생명공학회 2017 Journal of microbiology and biotechnology Vol.27 No.4
Two piloquinone derivatives isolated from Streptomyces sp. CNQ-027 were tested for the inhibitory activities of two isoforms of monoamine oxidase (MAO), which catalyzes monoamine neurotransmitters. The piloquinone 4,7-dihydroxy-3-methyl-2-(4-methyl-1- oxopentyl)-6H-dibenzo[b,d]pyran-6-one (1) was found to be a highly potent inhibitor of human MAO-B, with an IC<sub>50 </sub>value of 1.21 μM; in addition, it was found to be highly effective against MAO-A, with an IC<sub>50 </sub> value of 6.47 μM. Compound 1 was selective, but not extremely so, for MAO-B compared with MAO-A, with a selectivity index value of 5.35. Compound 1,8- dihydroxy-2-methyl-3-(4-methyl-1-oxopentyl)-9,10-phenanthrenedione (2) was moderately effective for the inhibition of MAO-B (IC<sub>50 </sub> = 14.50 μM) but not for MAO-A (IC<sub>50 </sub> > 80 μM). There was no time-dependency in inhibition of MAO-A or -B by compound 1, and the MAO-A and -B activities were almost completely recovered in the dilution experiments with an excess amount of compound 1. Compound 1 showed competitive inhibition for MAO-A and -B, with Ki values of 0.573 and 0.248 μM, respectively. These results suggest that piloquinones from a microbial source could be potent reversible MAO inhibitors and may be useful lead compounds for developing MAO enzyme inhibitors to treat related disorders, such as depression, Parkinson`s disease, and Alzheimer`s disease.
Meyer, Sven W.,Mordhorst, Thorsten F.,Lee, Choonghwan,Jensen, Paul R.,Fenical, William,Kö,ck, Matthias Royal Society of Chemistry 2010 Organic & biomolecular chemistry Vol.8 No.9
<P>A novel lumazine peptide, penilumamide (1), was isolated from the fermentation broth of a marine-derived fungal strain, identified as <I>Penicillium</I> sp. (strain CNL-338) and the structure of the new metabolite was determined by analysis of ESI-TOF MS data combined with 1D and 2D NMR experiments.</P> <P>Graphic Abstract</P><P>Penilumamide was isolated from the fungal strain <I>Penicillium</I> sp. and its structure was determined by analysis of ESI-TOF MS data combined with 1D and 2D NMR experiments. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=b910629d'> </P>
Lodopyridones B and C from a marine sediment-derived bacterium <i>Saccharomonospora</i> sp.
Le, Tu Cam,Yim, Chae-Yoon,Park, Songhee,Katila, Nikita,Yang, Inho,Song, Myoung Chong,Yoon, Yeo Joon,Choi, Dong-Young,Choi, Hyukjae,Nam, Sang-Jip,Fenical, William Elsevier 2017 Bioorganic & medicinal chemistry letters Vol.27 No.14
<P><B>Abstract</B></P> <P>HPLC-UV guided isolation of the culture broth of a marine bacterium <I>Saccharomonospora</I> sp. CNQ-490 has led to the isolation of two new natural products, lodopyridones B and C (<B>1</B> and <B>2</B>) along with the previously reported lodopyridone A (<B>3</B>). Their chemical structures were established from the interpretation of 2D NMR spectroscopic data and the comparison of NMR data with the lodopyridone A (<B>3</B>). Lodopyridones B and C (<B>1</B> and <B>2</B>) possess the thiazole, and chloroquinoline groups which are characteristic features of these molecules. Lodopyridones A–C show weak inhibitory activities on the β-site amyloid precursor protein cleaving enzyme 1 (BACE1).</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>