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Antimicrobial compounds from marine actinomycetes
Cong Wang,Yuanyu Lu,Shugeng Cao 대한약학회 2020 Archives of Pharmacal Research Vol.43 No.7
Marine actinomycetes were the main origin ofmarine natural products in the past 40 years. This review wasto present the sources, structures and antimicrobial activitiesof 313 new natural products from marine actinomycetesreported from 1976 to 2019.
Lee, Seoung Rak,Beemelmanns, Christine,Tsuma, Leah M. M.,Clardy, Jon,Cao, Shugeng,Kim, Ki Hyun NATURAL PRODUCT COMMUNICATIONS 2016 Natural product communications Vol.11 No.4
<P>Bacterially-produced small molecules demonstrate a wide range of structural and functional diversity. A new diketopiperazine, cyclo(D-trans-Hyp-L-Leu) (1), and five other known diketopiperazines (2-6), were isolated and purified from the fermented broth of a Kenyan bacterium Bacillus licheniformis LB 8C(T). The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including 2D NMR and HR-MS, and the absolute configuration was determined by a combination of NOESY analysis and Marfey's method. The known compounds were identified as cyclo(D-cis-Hyp-L-Leu) (2), cyclo(D-cis-Hyp-L-Phe) (3), cyclo(D-Pro-L-Tyr) (4), cyclo-(D-Trp-L-Leu) (5), and cyclo(L-Tyr-Gly) (6) by comparison of their spectroscopic and physical data with reported values. Compounds 1-6 were tested for antifungal and antimicrobial properties.</P>
Macrotermycins A–D, Glycosylated Macrolactams from a Termite-Associated <i>Amycolatopsis</i> sp. M39
Beemelmanns, Christine,Ramadhar, Timothy R.,Kim, Ki Hyun,Klassen, Jonathan L.,Cao, Shugeng,Wyche, Thomas P.,Hou, Yanpeng,Poulsen, Michael,Bugni, Tim S.,Currie, Cameron R.,Clardy, Jon American Chemical Society 2017 ORGANIC LETTERS Vol.19 No.5
<P>Bioassay-guided metabolomic analyses led to the characterization of four new 20-membered glycosylated polyketide macrolactams, macrotermycins A-D, from a termite-associated actinomycete, Amycolatopsis sp. M39. M39's sequenced genome revealed the macrotermycin's putative biosynthetic gene cluster. Macrotermycins A and C had antibacterial activity against human-pathogenic Staphylococcus aureus and, of greater ecological relevance, they also had selective antifungal activity against a fungal parasite of the termite fungal garden.</P>
Wyche, Thomas P.,Ruzzini, Antonio C.,Beemelmanns, Christine,Kim, Ki Hyun,Klassen, Jonathan L.,Cao, Shugeng,Poulsen, Michael,Bugni, Tim S.,Currie, Cameron R.,Clardy, Jon American Chemical Society 2017 ORGANIC LETTERS Vol.19 No.7
<P>Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity.</P>
Iridoid Glycosides from <i>Barleria lupulina</i>
Kim, Ki Hyun,Park, Yong Joo,Chung, Kyu Hyuck,Yip, M. L. Richard,Clardy, Jon,Senger, Donald,Cao, Shugeng American Chemical Society and American Society of 2015 Journal of natural products Vol.78 No.2
<P>Phytochemical investigation of an extract of the aerial part of <I>Barleria lupulina</I> resulted in the identification of four new iridoid glycosides (<B>1</B>–<B>4</B>), together with 14 known analogues (<B>5</B>–<B>18</B>). The structures of <B>1</B>–<B>4</B> were determined through 1D and 2D NMR spectroscopic data analysis, HRMS, and acid hydrolysis. This is the first report of iridoid glycosides with a formate group. The free-radical scavenging activity of compounds <B>9</B>, <B>12</B>, and <B>15</B>–<B>17</B> was assessed using the DPPH assay. Compounds <B>16</B> and <B>17</B> scavenged DPPH radicals weakly with IC<SUB>50</SUB> values of 97.5 and 78.6 μg/mL, respectively.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2015/jnprdf.2015.78.issue-2/np500791a/production/images/medium/np-2014-00791a_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np500791a'>ACS Electronic Supporting Info</A></P>
Jae Sik Yu,Se Yun Jeong,Chunshun Li,Taehoon Oh,Mincheol Kwon,Jong Seog Ahn,Sung-Kyun Ko,Yoon-Joo Ko,Shugeng Cao,Ki Hyun Kim 대한약학회 2022 Archives of Pharmacal Research Vol.45 No.2
Phenalenone derivatives sourced from fungi arepolyketides that have attracted signifi cant interest becauseof their diverse chemical structures and potential bioactivities. As part of our ongoing quest to discover novel naturalproducts with biological properties from diverse naturalresources, three unreported phenalenone derivatives ( 1–3 ),named ent -12-methoxyisoherqueinone ( 1 ), (−)-scleroamide( 2 ), and (+)-scleroamide ( 3 ), together with four known phenalenonederivatives, ent -atrovenetinone ( 4 ), isoherqueinone( 5 ), herqueinone ( 6 ), and ent -peniciherquinone ( 7 ) wereisolated from the Hawaiian soil fungus Penicillium herqueiFT729, collected on the Big Island, Hawaii. Compounds 2 and 3 were enantiomers, which were separated using achiral-phase HPLC column, which provided optically purecompounds 2 and 3 . The structures of the novel compoundswere established by extensive spectroscopic analyses,including 1D and 2D NMR and high-resolution ESIMS. Their absolute confi gurations were determined using quantumchemical electronic circular dichroism (ECD) calculations. The inhibitory activity of the isolated compounds( 1–7 ) against indoleamine 2,3-dioxygenase 1 (IDO1) wasassessed. Compounds 1, 5–7 inhibited IDO1, with IC 50values of 32.59, 36.86, 19.05, and 24.18 μM, respectively. These fi ndings demonstrated that the phenalenone derivatives1 and 5–7, as IDO1 inhibitors, are promising anticancerimmunotherapeutic agents.