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Tareq, Fakir Shahidullah,Shin, Hee Jae American Chemical Society and American Society of 2017 Journal of natural products Vol.80 No.11
<P>LC-MS and NMR spectroscopy guided metabolic profiling and dereplication of a crude extract obtained from the fermentation of a marine-derived bacterium, <I>Bacillus subtilis</I>, followed by chromatographic isolation yielded two new cyclic-lipotetrapeptides, bacilotetrins A (<B>1</B>) and B (<B>2</B>). Based on extensive 1D and 2D NMR and high-resolution ESIMS data analysis, the structures of <B>1</B> and <B>2</B> were elucidated, revealing the unique structures of these lipopeptides consisting of three leucines and a glutamic acid residue cyclized with a lipophilic 3-hydroxy fatty acid. The absolute stereochemistries at selected stereocenters in <B>1</B> and <B>2</B> were assigned by chemical derivatization and comparison to literature data. Compounds <B>1</B> and <B>2</B> exhibited anti-MRSA activity with MIC values of 8 to 32 μg/mL. However, these compounds showed no cytotoxicity when tested against prostate and liver cancer cell lines using the standard SRB assay.</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.7b00356/production/images/medium/np-2017-00356k_0003.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np7b00356'>ACS Electronic Supporting Info</A></P>
Tareq, Fakir Shahidullah,Lee, Min Ah,Lee, Hyi-Seung,Lee, Yeon-Ju,Lee, Jong Seok,Hasan, Choudhury M.,Islam, Md. Tofazzal,Shin, Hee Jae American Chemical Society 2014 Journal of agricultural and food chemistry Vol.62 No.24
<P>Antifungal resistance and toxicity problems of conventional fungicides highlighted the requirement of search for new safe antifungal agents. To comply with the requirement, we discovered four new non-cytotoxic lipopeptides, gageopeptides A–D, <B>1–4,</B> from a marine-derived bacterium <I>Bacillus subtilis</I>. The structures and stereochemistry of gageopeptides were determined by NMR data analysis and chemical means. Gageopeptides exhibited significant antifungal activities against pathogenic fungi <I>Rhizoctonia solani</I>, <I>Botrytis cinerea</I>, and <I>Colletotrichum acutatum</I> with minimum inhibitory concentration (MIC) values of 0.02–0.06 μM. In addition, these lipopeptides showed significant motility inhibition and lytic activities against zoospores of the late blight pathogen <I>Phytophthora capsici</I>. These compounds also showed potent antimicrobial activity against Gram positive and Gram negative bacteria with MIC values of 0.04–0.08 μM. However, gageopeptides A–D did not exhibit any cytotoxicity (GI<SUB>50</SUB> > 25 μM) against cancer cell lines in sulforhodamine B (SRB), 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT), and WST-1 ((4-[3–4-iodophenyl]-2-(4-nitrophenyl)-2<I>H</I>-5-tetrazolio)-1,3-benzene disulfonate)) assays, demonstrating that these compounds could be promising candidates for the development of non-cytotoxic antifungal agents.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jafcau/2014/jafcau.2014.62.issue-24/jf502436r/production/images/medium/jf-2014-02436r_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jf502436r'>ACS Electronic Supporting Info</A></P>
Tareq, Fakir Shahidullah,Kim, Ji Hye,Lee, Min Ah,Lee, Hyi-Seung,Lee, Jong-Seok,Lee, Yeon-Ju,Shin, Hee Jae American Chemical Society 2013 Journal of agricultural and food chemistry Vol.61 No.14
<P>Marine bacteria are a potential source of structurally diversified bioactive secondary metabolites that are not found in terrestrial sources. In our continuous effort to search for new antimicrobial agents from marine-derived bacteria, we isolated bacterial strain 109GGC020 from a marine sediment sample collected from Gageocho, Republic of Korea. The strain was identified as <I>Bacillus subtilis</I> based on a 16s rRNA sequence analysis. After a 7-day fermentation of the <I>B. subtilis</I> strain under optimum growth conditions three new and four known secondary metabolites were discovered using chromatographic procedures, and their biological activities were evaluated against both bacteria and crop-devastating fungi. The discovered metabolites were confirmed by extensive 2D NMR and high-resolution ESI-MS data analyses to have the structures of new macrolactin derivatives gageomacrolactins <B>1</B>–<B>3</B> and known macrolactins A (<B>4</B>), B (<B>5</B>), F (<B>6</B>), and W (<B>7</B>). The stereoconfigurations of <B>1</B>–<B>3</B> were assigned based on coupling constant values, chemical derivatization studies, and a literature review. The coupling constants were very crucial to determine the relative geometries of olefins in <B>1</B>–<B>3</B> because of overlap of the <SUP>1</SUP>H NMR signals. The NMR data of these compounds were recorded in different solvents to overcome this problem and obtain accurate coupling constant values. The new macrolactin derivatives <B>1</B>–<B>3</B> displayed good antibiotic properties against both Gram-positive (<I>S. aureus</I>,<I> B. subtilis</I>, and <I>B. cereus</I>) and Gram-negative (<I>E. coli</I>,<I> S. typhi</I>, and <I>P. aeruginosa</I>) bacteria with minimum inhibitory concentration (MIC) values of 0.02–0.05 μM. Additionally, the antifungal activities of <B>1</B>–<B>7</B> were evaluated against pathogenic fungi and found to inhibit mycelial growth of <I>A. niger</I>,<I> B. cinerea</I>,<I> C. acutatum</I>,<I> C. albicans</I>, and <I>R. solani</I> with MIC values of 0.04–0.3 μM, demonstrating that these compounds were good fungicides.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jafcau/2013/jafcau.2013.61.issue-14/jf4009229/production/images/medium/jf-2013-009229_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jf4009229'>ACS Electronic Supporting Info</A></P>
Tareq, Fakir Shahidullah,Lee, Min Ah,Lee, Hyi-Seung,Lee, Yeon-Ju,Lee, Jong Seok,Hasan, Choudhury M.,Islam, Md. Tofazzal,Shin, Hee Jae American Chemical Society 2014 ORGANIC LETTERS Vol.16 No.3
<P>Gageotetrins A–C (<B>1</B>–<B>3</B>), a unique class of linear lipopeptides, consisting of di- and tetrapeptides and a new fatty acid were isolated from a Marine <I>Bacillus subtilis</I>. The structures of <B>1</B>–<B>3</B> were assigned by spectroscopic data and their absolute stereochemistries were ascertained by chemical derivatization. Compounds <B>1</B>–<B>3</B> displayed good antimicrobial activities with MIC values of 0.01–0.06 μM. However, these compounds failed to register any cytotoxicity (GI<SUB>50</SUB> > 30 μg/ml) against human cancer cell lines.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2014/orlef7.2014.16.issue-3/ol403657r/production/images/medium/ol-2013-03657r_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol403657r'>ACS Electronic Supporting Info</A></P>
Mondol, M. A.Mojid,Tareq, Fakir Shahidullah,Kim, Ji Hye,Lee, Min ah,Lee, Hyi-Seung,Lee, Yeon-Ju,Lee, Jong Seok,Shin, Hee Jae American ChemicalSociety and AmericanSociety of Ph 2011 Journal of natural products Vol.74 No.12
<P>Bioassay-guided isolation of bioactive metabolites fromthe ethylacetate extract of a marine <I>Bacillus</I> sp. fermentationbroth has led to the discovery of three new 24-membered macrolactones,macrolactins <B>1</B>–<B>3</B>, which contain anoxetane, an epoxide, and a tetrahydropyran ring, respectively. Theconfigurations of <B>1</B>–<B>3</B> were assignedby a combination of coupling constants, ROESY data analysis, and applicationof the modified Mosher’s method. Compounds <B>1</B>–<B>3</B> showed <I>in vitro</I> antimicrobial activity.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2011/jnprdf.2011.74.issue-12/np200487k/production/images/medium/np-2011-00487k_0006.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np200487k'>ACS Electronic Supporting Info</A></P>