The Experts below are selected from a list of 4335 Experts worldwide ranked by ideXlab platform
William H Gerwick - One of the best experts on this subject based on the ideXlab platform.
-
cytotoxic microcolin lipopeptides from the marine cyanobacterium Moorea producens
Journal of Natural Products, 2019Co-Authors: Evgenia Glukhov, Lena Gerwick, Haobing Yu, Yueying Li, Arihiro Iwasaki, Pieter C Dorrestein, Bing Hua Jiao, William H GerwickAbstract:Nine new linear lipopeptides, microcolins E–M (1–9), together with four known related compounds, microcolins A–D (10–13), were isolated from the marine cyanobacterium Moorea producens using bioassay-guided and LC-MS/MS molecular networking approaches. Catalytic hydrogenation of microcolins A–D (10–13) yielded two known compounds, 3,4-dihydromicrocolins A and B (14, 15), and two new derivatives, 3,4-dihydromicrocolins C and D (16, 17), respectively. The structures of these new compounds were determined by a combination of spectroscopic and advanced Marfey’s analysis. Structurally unusual amino acid units, 4-methyl-2-(methylamino)pent-3-enoic (Mpe) acid and 2-amino-4-methylhexanoic acid (N-Me-homoisoleucine), in compounds 1–3 and 8, respectively, are rare residues in naturally occurring peptides. These metabolites showed significant cytotoxic activity against H-460 human lung cancer cells with IC50 values ranging from 6 nM to 5.0 μM. The variations in structure and attendant biological activities provided f...
-
comparative genomics uncovers the prolific and distinctive metabolic potential of the cyanobacterial genus Moorea
Proceedings of the National Academy of Sciences of the United States of America, 2017Co-Authors: Tiago Leao, William H Gerwick, Guilherme P Castelao, Anton Korobeynikov, Emily A Monroe, Sheila Podell, Evgenia Glukhov, Eric E Allen, Lena GerwickAbstract:Abstract Cyanobacteria are major sources of oxygen, nitrogen, and carbon in nature. In addition to the importance of their primary metabolism, some cyanobacteria are prolific producers of unique and bioactive secondary metabolites. Chemical investigations of the cyanobacterial genus Moorea have resulted in the isolation of over 190 compounds in the last two decades. However, preliminary genomic analysis has suggested that genome-guided approaches can enable the discovery of novel compounds from even well-studied Moorea strains, highlighting the importance of obtaining complete genomes. We report a complete genome of a filamentous tropical marine cyanobacterium, Moorea producens PAL, which reveals that about one-fifth of its genome is devoted to production of secondary metabolites, an impressive four times the cyanobacterial average. Moreover, possession of the complete PAL genome has allowed improvement to the assembly of three other Moorea draft genomes. Comparative genomics revealed that they are remarkably similar to one another, despite their differences in geography, morphology, and secondary metabolite profiles. Gene cluster networking highlights that this genus is distinctive among cyanobacteria, not only in the number of secondary metabolite pathways but also in the content of many pathways, which are potentially distinct from all other bacterial gene clusters to date. These findings portend that future genome-guided secondary metabolite discovery and isolation efforts should be highly productive.
-
Moorea producens gen nov sp nov and Moorea bouillonii comb nov tropical marine cyanobacteria rich in bioactive secondary metabolites
International Journal of Systematic and Evolutionary Microbiology, 2012Co-Authors: Niclas Engene, Erin C Rottacker, Jan Kastovský, Tara Byrum, Hyukjae Choi, Mark H Ellisman, Jiři Komarek, William H GerwickAbstract:The filamentous cyanobacterial genus Moorea gen. nov., described here under the provisions of the International Code of Botanical Nomenclature, is a cosmopolitan pan-tropical group abundant in the marine benthos. Members of the genus Moorea are photosynthetic (containing phycocyanin, phycoerythrin, allophycocyanin and chlorophyll a), but non-diazotrophic (lack heterocysts and nitrogenase reductase genes). The cells (discoid and 25–80 µm wide) are arranged in long filaments (<10 cm in length) and often form extensive mats or blooms in shallow water. The cells are surrounded by thick polysaccharide sheaths covered by a rich diversity of heterotrophic micro-organisms. A distinctive character of this genus is its extraordinarily rich production of bioactive secondary metabolites. This is matched by genomes rich in polyketide synthase and non-ribosomal peptide synthetase biosynthetic genes which are dedicated to secondary metabolism. The encoded natural products are sometimes responsible for harmful algae blooms and, due to morphological resemblance to the genus Lyngbya , this group has often been incorrectly cited in the literature. We here describe two species of the genus Moorea: Moorea producens sp. nov. (type species of the genus) with 3LT as the nomenclature type, and Moorea bouillonii comb. nov. with PNG5-198R as the nomenclature type.
-
Moorea producens gen. nov., sp. nov. and Moorea bouillonii comb. nov., tropical marine cyanobacteria rich in bioactive secondary metabolites.
International Journal of Systematic and Evolutionary Microbiology, 2012Co-Authors: Niclas Engene, Erin C Rottacker, Jan Kastovský, Tara Byrum, Hyukjae Choi, Mark H Ellisman, Jiři Komarek, William H GerwickAbstract:The filamentous cyanobacterial genus Moorea gen. nov., described here under the provisions of the International Code of Botanical Nomenclature, is a cosmopolitan pan-tropical group abundant in the marine benthos. Members of the genus Moorea are photosynthetic (containing phycocyanin, phycoerythrin, allophycocyanin and chlorophyll a), but non-diazotrophic (lack heterocysts and nitrogenase reductase genes). The cells (discoid and 25–80 µm wide) are arranged in long filaments (
Hiroshi Nagai - One of the best experts on this subject based on the ideXlab platform.
-
neo aplysiatoxin a isolated from okinawan cyanobacterium Moorea producens
Molecules, 2020Co-Authors: Mioko Kawaguchi, Yueyun Xiao, Hajime Uchida, Masayuki Satake, Botao Zhang, Masayuki Fukuoka, Hiroshi NagaiAbstract:A new aplysiatoxin derivative, neo-aplysiatoxin A (1), along with seven known compounds, neo-debromoaplysiatoxin A (2), dolastatin 3 (3), lyngbic acid (4), malyngamide M (5), hermitamide A (6), (−)-loliolide (7), and (+)-epiloliolide (8), was isolated from the Okinawan cyanobacterium Moorea producens. Their structures were elucidated on the basis of spectroscopic data, including high-resolution mass spectrometry and nuclear magnetic resonance. The compounds were evaluated for cytotoxic and diatom growth inhibition activities.
-
new aplysiatoxin derivatives from the okinawan cyanobacterium Moorea producens
Tetrahedron, 2019Co-Authors: Hiroshi Nagai, Minami Watanabe, Shingo Sato, Mioko Kawaguchi, Yueyun Xiao, Kazutaka Hayashi, Ryuichi Watanabe, Hajime Uchida, Masayuki SatakeAbstract:Abstract The marine cyanobacterium Moorea producens is a rich source of diverse compounds that possess a variety of biological activities. In the present study, eight new aplysiatoxin derivatives, namely 6, 8–13, and 15, along with aplysiatoxin (1), debromoaplysiatoxin (2), 3-methoxyaplysiatoxin (3), anhydroaplysiatoxin (4), anhydrodebromoaplysiatoxin (5), oscillatoxin B2 (7), and 30-methyloscillatoxin D (14) were isolated and identified from the Okinawan M. producens. In cytotoxicity and diatom growth inhibition tests, the fifteen compounds tested (1–15) showed moderate or no activity at a concentration of 10 μg/mL.
-
a new malyngamide from the marine cyanobacterium Moorea producens
Natural Product Research, 2018Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Wei Zhou, Toshiyuki Suzuki, Bryan Sakamoto, Raymie Othman, Hiroshi NagaiAbstract:AbstractA new malyngamide (1) was isolated along with seven known compounds (2–8) from the marine cyanobacterium Moorea producens collected in Hawaii. Compound 1 represented the first reported malyngamide with a hydroxy moiety at C-7 of the characteristic fatty acid portion of the compound. Compound 1 showed cytotoxicity against L1210 cell line at an IC50 value of 2.9 mM and lethal toxicity against the shrimp Palaemon paucidens at a LD100 value of 33.3 mg/kg. The bioactivity of compound 1 was approximately 10–100 times weaker than those of isomalyngamides A and B (3, 4). These results indicated that the methoxy group at C-7 of the fatty acid section confers a degree of bioactivity in malyngamides.
-
Five new indole derivatives from the cyanobacterium Moorea producens
Phytochemistry Letters, 2017Co-Authors: Weina Jiang, Mioko Kawaguchi, Ryuichi Watanabe, Hajime Uchida, Masayuki Fukuoka, Toshiyuki Suzuki, Yingyue Bu, Hiroki Osada, Hiroshi NagaiAbstract:Abstract Chemical analysis of the hydrophilic fraction from marine cyanobacterium Moorea producens extracts led to the isolation of five new indole derivatives (1-5). So far, 2-formyl-4,5,6,7-tetrahydroindole has been reported only for 6 from the nature, consequently compounds 1-5 were the second representatives of this class. Cytotoxicity, diatom growth inhibition, and antibacterial activity tests for compounds 1-5 showed no bioactivity at the concentration tested.
-
two new lyngbyatoxin derivatives from the cyanobacterium Moorea producens
Marine Drugs, 2014Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Kazuhiro Irie, Toshiyuki Suzuki, Bryan Sakamoto, Michiya Kamio, Yusuke Hanaki, Hiroshi NagaiAbstract:The toxin-producing cyanobacterium, Moorea producens, is a known causative organism of food poisoning and seaweed dermatitis (also known as “swimmer’s itch”). Two new toxic compounds were isolated and structurally elucidated from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies, as well as optical rotations and CD spectra indicated two new lyngbyatoxin derivatives, 2-oxo-3(R)-hydroxy-lyngbyatoxin A (1) and 2-oxo-3(R)-hydroxy-13-N-desmethyl-lyngbyatoxin A (2). The cytotoxicity and lethal activities of 1 and 2 were approximately 10- to 150-times less potent than lyngbyatoxin A. Additionally, the binding activities of 1 and 2 possessed 10,000-times lower affinity for the protein kinase Cδ (PKCδ)-C1B peptide when compared to lyngbyatoxin A. These findings suggest that these new lyngbyatoxin derivatives may mediate their acute toxicities through a non-PKC activation pathway.
Hajime Uchida - One of the best experts on this subject based on the ideXlab platform.
-
neo aplysiatoxin a isolated from okinawan cyanobacterium Moorea producens
Molecules, 2020Co-Authors: Mioko Kawaguchi, Yueyun Xiao, Hajime Uchida, Masayuki Satake, Botao Zhang, Masayuki Fukuoka, Hiroshi NagaiAbstract:A new aplysiatoxin derivative, neo-aplysiatoxin A (1), along with seven known compounds, neo-debromoaplysiatoxin A (2), dolastatin 3 (3), lyngbic acid (4), malyngamide M (5), hermitamide A (6), (−)-loliolide (7), and (+)-epiloliolide (8), was isolated from the Okinawan cyanobacterium Moorea producens. Their structures were elucidated on the basis of spectroscopic data, including high-resolution mass spectrometry and nuclear magnetic resonance. The compounds were evaluated for cytotoxic and diatom growth inhibition activities.
-
new aplysiatoxin derivatives from the okinawan cyanobacterium Moorea producens
Tetrahedron, 2019Co-Authors: Hiroshi Nagai, Minami Watanabe, Shingo Sato, Mioko Kawaguchi, Yueyun Xiao, Kazutaka Hayashi, Ryuichi Watanabe, Hajime Uchida, Masayuki SatakeAbstract:Abstract The marine cyanobacterium Moorea producens is a rich source of diverse compounds that possess a variety of biological activities. In the present study, eight new aplysiatoxin derivatives, namely 6, 8–13, and 15, along with aplysiatoxin (1), debromoaplysiatoxin (2), 3-methoxyaplysiatoxin (3), anhydroaplysiatoxin (4), anhydrodebromoaplysiatoxin (5), oscillatoxin B2 (7), and 30-methyloscillatoxin D (14) were isolated and identified from the Okinawan M. producens. In cytotoxicity and diatom growth inhibition tests, the fifteen compounds tested (1–15) showed moderate or no activity at a concentration of 10 μg/mL.
-
a new malyngamide from the marine cyanobacterium Moorea producens
Natural Product Research, 2018Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Wei Zhou, Toshiyuki Suzuki, Bryan Sakamoto, Raymie Othman, Hiroshi NagaiAbstract:AbstractA new malyngamide (1) was isolated along with seven known compounds (2–8) from the marine cyanobacterium Moorea producens collected in Hawaii. Compound 1 represented the first reported malyngamide with a hydroxy moiety at C-7 of the characteristic fatty acid portion of the compound. Compound 1 showed cytotoxicity against L1210 cell line at an IC50 value of 2.9 mM and lethal toxicity against the shrimp Palaemon paucidens at a LD100 value of 33.3 mg/kg. The bioactivity of compound 1 was approximately 10–100 times weaker than those of isomalyngamides A and B (3, 4). These results indicated that the methoxy group at C-7 of the fatty acid section confers a degree of bioactivity in malyngamides.
-
Five new indole derivatives from the cyanobacterium Moorea producens
Phytochemistry Letters, 2017Co-Authors: Weina Jiang, Mioko Kawaguchi, Ryuichi Watanabe, Hajime Uchida, Masayuki Fukuoka, Toshiyuki Suzuki, Yingyue Bu, Hiroki Osada, Hiroshi NagaiAbstract:Abstract Chemical analysis of the hydrophilic fraction from marine cyanobacterium Moorea producens extracts led to the isolation of five new indole derivatives (1-5). So far, 2-formyl-4,5,6,7-tetrahydroindole has been reported only for 6 from the nature, consequently compounds 1-5 were the second representatives of this class. Cytotoxicity, diatom growth inhibition, and antibacterial activity tests for compounds 1-5 showed no bioactivity at the concentration tested.
-
two new lyngbyatoxin derivatives from the cyanobacterium Moorea producens
Marine Drugs, 2014Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Kazuhiro Irie, Toshiyuki Suzuki, Bryan Sakamoto, Michiya Kamio, Yusuke Hanaki, Hiroshi NagaiAbstract:The toxin-producing cyanobacterium, Moorea producens, is a known causative organism of food poisoning and seaweed dermatitis (also known as “swimmer’s itch”). Two new toxic compounds were isolated and structurally elucidated from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies, as well as optical rotations and CD spectra indicated two new lyngbyatoxin derivatives, 2-oxo-3(R)-hydroxy-lyngbyatoxin A (1) and 2-oxo-3(R)-hydroxy-13-N-desmethyl-lyngbyatoxin A (2). The cytotoxicity and lethal activities of 1 and 2 were approximately 10- to 150-times less potent than lyngbyatoxin A. Additionally, the binding activities of 1 and 2 possessed 10,000-times lower affinity for the protein kinase Cδ (PKCδ)-C1B peptide when compared to lyngbyatoxin A. These findings suggest that these new lyngbyatoxin derivatives may mediate their acute toxicities through a non-PKC activation pathway.
Masayuki Satake - One of the best experts on this subject based on the ideXlab platform.
-
neo aplysiatoxin a isolated from okinawan cyanobacterium Moorea producens
Molecules, 2020Co-Authors: Mioko Kawaguchi, Yueyun Xiao, Hajime Uchida, Masayuki Satake, Botao Zhang, Masayuki Fukuoka, Hiroshi NagaiAbstract:A new aplysiatoxin derivative, neo-aplysiatoxin A (1), along with seven known compounds, neo-debromoaplysiatoxin A (2), dolastatin 3 (3), lyngbic acid (4), malyngamide M (5), hermitamide A (6), (−)-loliolide (7), and (+)-epiloliolide (8), was isolated from the Okinawan cyanobacterium Moorea producens. Their structures were elucidated on the basis of spectroscopic data, including high-resolution mass spectrometry and nuclear magnetic resonance. The compounds were evaluated for cytotoxic and diatom growth inhibition activities.
-
new aplysiatoxin derivatives from the okinawan cyanobacterium Moorea producens
Tetrahedron, 2019Co-Authors: Hiroshi Nagai, Minami Watanabe, Shingo Sato, Mioko Kawaguchi, Yueyun Xiao, Kazutaka Hayashi, Ryuichi Watanabe, Hajime Uchida, Masayuki SatakeAbstract:Abstract The marine cyanobacterium Moorea producens is a rich source of diverse compounds that possess a variety of biological activities. In the present study, eight new aplysiatoxin derivatives, namely 6, 8–13, and 15, along with aplysiatoxin (1), debromoaplysiatoxin (2), 3-methoxyaplysiatoxin (3), anhydroaplysiatoxin (4), anhydrodebromoaplysiatoxin (5), oscillatoxin B2 (7), and 30-methyloscillatoxin D (14) were isolated and identified from the Okinawan M. producens. In cytotoxicity and diatom growth inhibition tests, the fifteen compounds tested (1–15) showed moderate or no activity at a concentration of 10 μg/mL.
Ryuichi Watanabe - One of the best experts on this subject based on the ideXlab platform.
-
new aplysiatoxin derivatives from the okinawan cyanobacterium Moorea producens
Tetrahedron, 2019Co-Authors: Hiroshi Nagai, Minami Watanabe, Shingo Sato, Mioko Kawaguchi, Yueyun Xiao, Kazutaka Hayashi, Ryuichi Watanabe, Hajime Uchida, Masayuki SatakeAbstract:Abstract The marine cyanobacterium Moorea producens is a rich source of diverse compounds that possess a variety of biological activities. In the present study, eight new aplysiatoxin derivatives, namely 6, 8–13, and 15, along with aplysiatoxin (1), debromoaplysiatoxin (2), 3-methoxyaplysiatoxin (3), anhydroaplysiatoxin (4), anhydrodebromoaplysiatoxin (5), oscillatoxin B2 (7), and 30-methyloscillatoxin D (14) were isolated and identified from the Okinawan M. producens. In cytotoxicity and diatom growth inhibition tests, the fifteen compounds tested (1–15) showed moderate or no activity at a concentration of 10 μg/mL.
-
a new malyngamide from the marine cyanobacterium Moorea producens
Natural Product Research, 2018Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Wei Zhou, Toshiyuki Suzuki, Bryan Sakamoto, Raymie Othman, Hiroshi NagaiAbstract:AbstractA new malyngamide (1) was isolated along with seven known compounds (2–8) from the marine cyanobacterium Moorea producens collected in Hawaii. Compound 1 represented the first reported malyngamide with a hydroxy moiety at C-7 of the characteristic fatty acid portion of the compound. Compound 1 showed cytotoxicity against L1210 cell line at an IC50 value of 2.9 mM and lethal toxicity against the shrimp Palaemon paucidens at a LD100 value of 33.3 mg/kg. The bioactivity of compound 1 was approximately 10–100 times weaker than those of isomalyngamides A and B (3, 4). These results indicated that the methoxy group at C-7 of the fatty acid section confers a degree of bioactivity in malyngamides.
-
Five new indole derivatives from the cyanobacterium Moorea producens
Phytochemistry Letters, 2017Co-Authors: Weina Jiang, Mioko Kawaguchi, Ryuichi Watanabe, Hajime Uchida, Masayuki Fukuoka, Toshiyuki Suzuki, Yingyue Bu, Hiroki Osada, Hiroshi NagaiAbstract:Abstract Chemical analysis of the hydrophilic fraction from marine cyanobacterium Moorea producens extracts led to the isolation of five new indole derivatives (1-5). So far, 2-formyl-4,5,6,7-tetrahydroindole has been reported only for 6 from the nature, consequently compounds 1-5 were the second representatives of this class. Cytotoxicity, diatom growth inhibition, and antibacterial activity tests for compounds 1-5 showed no bioactivity at the concentration tested.
-
two new lyngbyatoxin derivatives from the cyanobacterium Moorea producens
Marine Drugs, 2014Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Kazuhiro Irie, Toshiyuki Suzuki, Bryan Sakamoto, Michiya Kamio, Yusuke Hanaki, Hiroshi NagaiAbstract:The toxin-producing cyanobacterium, Moorea producens, is a known causative organism of food poisoning and seaweed dermatitis (also known as “swimmer’s itch”). Two new toxic compounds were isolated and structurally elucidated from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies, as well as optical rotations and CD spectra indicated two new lyngbyatoxin derivatives, 2-oxo-3(R)-hydroxy-lyngbyatoxin A (1) and 2-oxo-3(R)-hydroxy-13-N-desmethyl-lyngbyatoxin A (2). The cytotoxicity and lethal activities of 1 and 2 were approximately 10- to 150-times less potent than lyngbyatoxin A. Additionally, the binding activities of 1 and 2 possessed 10,000-times lower affinity for the protein kinase Cδ (PKCδ)-C1B peptide when compared to lyngbyatoxin A. These findings suggest that these new lyngbyatoxin derivatives may mediate their acute toxicities through a non-PKC activation pathway.
-
a new lyngbyatoxin from the hawaiian cyanobacterium Moorea producens
Marine Drugs, 2014Co-Authors: Weina Jiang, Ryuichi Watanabe, Hajime Uchida, Wei Zhou, Masayuki Kikumori, Kazuhiro Irie, Toshiyuki Suzuki, Bryan Sakamoto, Michiya Kamio, Hiroshi NagaiAbstract:Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of “swimmer’s itch” with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicated that the compound was a new lyngbyatoxin A derivative, 12-epi-lyngbyatoxin A (1). While 12-epi-lyngbyatoxin A showed comparable toxicities with lyngbyatoxin A in cytotoxicity and crustacean lethality tests, it showed more than 100 times lower affinity for protein kinase Cδ (PKCδ) using the PKCδ-C1B peptide when compared to lyngbyatoxin A.
