Antimycins A10∼A16, Seven New Antimycin Antibiotics Produced by Streptomyces spp. SPA-10191 and SPA-8893

Hosotani, Nobuo; Kumagai, Kazuo; Nakagawa, Hiroyuki; Shimatani, Takuro; Saji, Ikutaro

doi:10.1038/ja.2005.61

Cited by 48 publications

(42 citation statements)

References 9 publications

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“…Antimycin-type compounds are a class of depsipeptides sharing a nine-membered bis -lactone ring with a conserved substitution of 3-formamidosalicylic acid, which exhibited a wide range of bioactivities including antifungal, insecticidal, antiviral, anticancer, and anti-inflammatory (Hosotani et al, 2005; Shiomi et al, 2005; Raveh et al, 2013; Liu J. et al, 2016). Antimycins are generated from a hybrid NRPS (non-ribosomal peptide synthetase)–PKS (polyketide synthase) assembly line in various Streptomyces species with the 3-formamidosalicylate substitution as a starter unit.…”

Section: Discussionmentioning

confidence: 99%

Discovery of Antimycin-Type Depsipeptides from a wbl Gene Mutant Strain of Deepsea-Derived Streptomyces somaliensis SCSIO ZH66 and Their Effects on Pro-inflammatory Cytokine Production

Huang

Hou

et al. 2017

Front. Microbiol.

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Deepsea microbes are a rich source of novel bioactive compounds, which have developed unique genetic systems as well as biosynthetic pathways compared with those of terrestrial microbes in order to survive in extreme living environment. However, a large variety of deepsea-microbial secondary metabolic pathways remain “cryptic” under the normal laboratory conditions. Manipulation of global regulators is one of the effective approaches for triggering the production of cryptic secondary metabolites. In this study, by combination of various chromatographic purification process, we obtained somalimycin (1), a new antimycin-type depsipeptide, with an unusual substitution of 3-aminosalicylate instead of conserved 3-formamidosalicylate moiety, along with two known (2 and 3) analogs from the ΔwblAso mutant strain of deepsea-derived Streptomyces somaliensis SCSIO ZH66. The structures of 1–3 were elucidated on the basis of extensive spectroscopic analyses including LC-MS and NMR. In the evaluation of potent anti-inflammatory activity, compound 2 exhibited strong inhibitory activity on the IL-5 production in ovalbumin-stimulated splenocytes with IC50 value of 0.57 μM, while 1 and 3 displayed mild effect (>10 μM), which might be attributed to their different side-chain substitutions. Moreover, compounds 1–3 showed very weak cytotoxicity against human umbilical vein endothelial cells with LD50 values of 62.6, 34.6, and 192.9 μM, respectively, which were far over their IL-5 inhibitory activity. These results indicated that these compounds have good potential for further use in anti-inflammatory drug development.

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Section: Discussionmentioning

confidence: 99%

Discovery of Antimycin-Type Depsipeptides from a wbl Gene Mutant Strain of Deepsea-Derived Streptomyces somaliensis SCSIO ZH66 and Their Effects on Pro-inflammatory Cytokine Production

Huang

Hou

et al. 2017

Front. Microbiol.

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“…The extract was dried with Na 2 SO 4 , and then concentrated under reduced pressure to obtain syrup (20 g). It was then chromatographed on a column of silica gel (120 g, 100-200 mesh, Qingdao Ocean Chemical Group, Qingdao City, China, i.d.…”

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confidence: 99%

“…7 Owing to the free hydroxyl group at C-8, kitamycins A and B, as well as urauchimycins A and B, showed weak antifungal activities only. 7 Hosotani et al 4 have reported that there are inverse relationships between the antifungal activity and the length of the 7-alkyl and 8-O-acyl side chains of antimycins. Using four strains of plant pathogenic fungi: Colletotrichum lindemuthianum, Botrytis cinerea, Alternaria solani and M. grisea as test strains, 1 and positive control, blasticidin S (Invitrogen, Carlsbad, CA, USA) were tested in serials dilution assay on a paper (6 mm i.d.)…”

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Antimycin A18 produced by an endophytic Streptomyces albidoflavus isolated from a mangrove plant

et al. 2010

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Mangroves have unique intertidal ecosystems of the tropics, which possess prolific biodiversity of actinomycetes. 1 Recent discoveries 2,3 of new species of microorganisms from the ecosystems encouraged us to explore the bioactive secondary metabolites from endophytic actinomycetes isolated from mangrove plants. As a result, the cultured broth of the strain I07A-01824, an endophytic Streptomyces albidoflavus, isolated from the leaf of Bruguiera gymnorrhiza collected at Shankou, Guangxi Province, People's Republic of China, was found to show moderate inhibiting activity against Magnaporth grisea. By bioassayguided fractionation, antimycin A 18 (1) was purified by chromatographies. By analyzing the spectroscopic data (including 1D and 2D NMR), its chemical structure was identified to be the first naturally occurring antimycin with an acetoxy group at C-8 (Figure 1).The strain I07A-01824 identified as Streptomyces was isolated from the leaf of B. gymnorrhiza collected at Shankou, Guangxi Province, People's Republic of China. A stock culture of the strain I07A-01824 was maintained on yeast and malt extract with glucose (YMG) agar slant consisting of 0.4% yeast extract (Beijing Aoboxing Biotechnology, Beijing, China), 1% malt extract (Beijing Aoboxing Biotechnology), 0.4% glucose and 1.2% agar (pH 7.2). The stock culture was inoculated into 250 ml Erlenmeyer flasks containing 50 ml of seed medium consisting of 0.5% glucose, 0.5% yeast extract, 0.5% peptone, 0.5% beef extract (Beijing Aoboxing Biotechnology), 0.4% corn steep liquor (North China Pharmaceutical Corporation, Shijiazhuang City, China), 2% soluble starch, 1% soybean meal (Beijing Comwin Pharm-Culture, Beijing, China), 0.4% CaCO 3 and 0.002% CoCl 2 (pH 7.2). The flask culture was incubated on a rotary shaker (180 r.p.m.) at 28 1C for 36 h. The seed culture (50 ml) was transferred into each of 40 5-l Erlenmeyer flasks containing 1 l of the same seed medium. The fermentation was carried out at 28 1C for 72 h on a rotary shaker (180 r.p.m.).The fermentation broth (40 l) was filtered and the filtrate was extracted with EtOAc (40 l). The extract was dried with Na 2

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“…Most of the 1 H and 13 C signals from basic skeleton of dilactone ring and benzyl ring of two components in both samples 3 and 5 had completely overlapped on the spectra. Two different acyl groups could be analyzed due to their discrete 1 H and 13 C signals, as seen in Hosotani et al 18 Sample 4 was a single compound antimycin A 2a on the basis of its 1 H and 13 C NMR characteristics. A paper disc method with C. albican was used to guide the fractionation and purification of bioactive molecules.…”

Section: Resultsmentioning

confidence: 99%

Antimycins A19 and A20, two new antimycins produced by marine actinomycete Streptomyces antibioticus H74-18

Quan

Wang

et al. 2011

J Antibiot

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Two new antimycin antibiotics, that is antimycins A 19 (1) and A 20 (2), were isolated from a cultured broth of marine actinomycete Streptomyces antibioticus H74-18 together with antimycins A 1a (3a) and A 1b (3b), A 2a (4), A 3a (5a) and A 3b (5b). Their structures were determined by spectroscopic methods in combination with X-ray diffraction. Antimycin A 19 possessed a chiral acyl chain and an alkyl branch. The absolute configuration of chiral acyl chain in 1 was determined by X-ray diffraction analysis. Antimycin A 20 (2) has the shortest and simplest acetoxy acyl chain in the antimycins family. All the antimycins (1-5) showed potential antifungal activities against Candida albicans with MIC of about 5-10 lg ml -1 .

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Antimycins A10∼A16, Seven New Antimycin Antibiotics Produced by Streptomyces spp. SPA-10191 and SPA-8893

Cited by 48 publications

References 9 publications

Discovery of Antimycin-Type Depsipeptides from a wbl Gene Mutant Strain of Deepsea-Derived Streptomyces somaliensis SCSIO ZH66 and Their Effects on Pro-inflammatory Cytokine Production

Discovery of Antimycin-Type Depsipeptides from a wbl Gene Mutant Strain of Deepsea-Derived Streptomyces somaliensis SCSIO ZH66 and Their Effects on Pro-inflammatory Cytokine Production

Antimycin A18 produced by an endophytic Streptomyces albidoflavus isolated from a mangrove plant

Antimycins A19 and A20, two new antimycins produced by marine actinomycete Streptomyces antibioticus H74-18

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