Bingchamides A and B, two novel cyclic pentapeptides from the Streptomyces bingchenggensis: fermentation, isolation, structure elucidation and biological properties

Xiang, Wensheng; Wang, Jidong; Wang, Xiangjing; Zhang, Ji

doi:10.1038/ja.2009.60

Cited by 25 publications

(26 citation statements)

References 21 publications

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“…It can efficiently produce the commercialized anthelmintic macrolide compounds milbemycins A3 and A4 together with 10 novel milbemycin analogs (10)(11)(12)(13)(14). Another insecticidal antibiotic, the polyether ionophore nanchangmycin, can also be produced by S. bingchenggensis (8).…”

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confidence: 99%

Genome Sequence of the Milbemycin-Producing Bacterium Streptomyces bingchenggensis

et al. 2010

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Streptomyces bingchenggensis is a soil-dwelling bacterium producing the commercially important anthelmintic macrolide milbemycins. Besides milbemycins, the insecticidal polyether antibiotic nanchangmycin and some other antibiotics have also been isolated from this strain. Here we report the complete genome sequence of S. bingchenggensis. The availability of the genome sequence of S. bingchenggensis should enable us to understand the biosynthesis of these structurally intricate antibiotics better and facilitate rational improvement of this strain to increase their titers.

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Genome Sequence of the Milbemycin-Producing Bacterium Streptomyces bingchenggensis

et al. 2010

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“…The first description corresponds to rhizonin A, a peptide described as produced by the zygomycete fungus Rhizopus microsporus [4,5], and later confirmed to be encoded by the symbiotic endobacterium Burkholderia endofungorum [6]. The second report of 3-(3-furyl)-alanine was associated with the cytotoxic bingchamides from Streptomyces bingchenggensis [7], reinforcing the hypothesis of a possible bacterial biosynthetic origin of this rare amino acid. The sponge-derived fungus S. bicolor 293K04 also produces the unprecedented bioactive polyketide-like phthalimidine and phthalide derivatives, marilines (Figure 1), marilones, maristachones, cyclomarinone and marilactone.…”

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confidence: 86%

Time-Dependent Production of the Bioactive Peptides Endolides A and B and the Polyketide Mariline A from the Sponge-Derived Fungus Stachylidium bicolor 293K04

et al. 2017

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Previous investigations of the sponge-derived fungus Stachylidium bicolor (S. bicolor)293K04 led to the isolation of the biosynthetically unusual polyketides marilines A-C and the bioactive tetrapeptides endolides A-B, identified as potential neuropathic drug leads. Furthermore, prior extended solid cultivation of S. bicolor 293K04 for 60 days resulted in a significant increase of polyketide yield, and the isolation of seven new polyketides. Due to the interest in endolide activity, unusual biosynthetic diversity, and the late stage polyketide production, we studied the cultivation conditions for determining the production time distribution and yields of these secondary metabolites. Results indicated a first production phase of secondary metabolite dominated by peptides, after 21-23 days. Polyketide mariline A1/A2 only started at day 35 of growth, an unusually late period for secondary metabolite expression. This unusual bimodal sequential expression of different families of secondary metabolites suggests value in exploring extended cultivation times to identify novel bioactive fungal compounds.

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“…1,4,5 Although these compounds showed potent acaricidal and nematocidal activities (data not shown), the bioactivities were weaker than those of the commercial acaricide and nematocide milbemycins A 3 / A 4 . However, the discovery of compounds 1, 2 and 3 in the mutant S. bingchenggensis X-4 may shed new insight into the biosynthesis of milbemycin.…”

Section: ) Secomilbemycins E (2) and F (3) (Coupling Constants In Pamentioning

confidence: 94%

“…[1][2][3][4][5] Milbemycins belong to a 16-membered macrolide antibiotic with an outstanding activity against various kinds of mites. 6 During a screening program for high production of A 3 and A 4 , a mutant S. bingchenggensis X-4 was obtained by UV treated, N-methyl-N¢-nitroso-N-nitroso-guanidine mutation and genetic manipulative techniques.…”

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New milbemycins from mutant Streptomyces bingchenggensis X-4

et al. 2011

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Streptomyces bingchenggensis produced milbemycins, including a 1 (A 3 ), a 3 (A 4 ), b 13 , b 14 , a 28 , a 29 , a 30 and ST 906, four secomilbemycins A, B, C and D, and two cyclic pentapeptides. [1][2][3][4][5] Milbemycins belong to a 16-membered macrolide antibiotic with an outstanding activity against various kinds of mites. 6 During a screening program for high production of A 3 and A 4 , a mutant S. bingchenggensis X-4 was obtained by UV treated, N-methyl-N¢-nitroso-N-nitroso-guanidine mutation and genetic manipulative techniques. Significant differences of phenotype, such as the morphology of aerial mycelia, and the metabolite HPLC profiles were observed between the wild-type S. bingchenggensis and its mutant strain X-4. In the course of investigating the metabolites of this mutant strain, three new interesting compounds milbemycin b 15 (1), seco-milbemycins E (2) and F (3) were isolated from the fermentation broth of S. bingchenggensis X-4. The structure of compound 1 was similar with milbemycin D, which is a highly selective and potent nematocide and insecticide. 7 So the bioactivity of compound 1 should be further investigated. Compared with the seco-milbemycins isolated previously, 2,3 the hydroxy groups at C-5 were absent in compounds 2 and 3. Furthermore, all the milbemycins 3,8 and avermectins 9,10 obtained from microorganisms contain the hydroxyl at C-5, and the 5-dehydroxyl derivatives of milbemycins and avermectins can only be obtained using the synthetic methods. 11 So seco-milbemycins E and F may have an important role in understanding and perfecting the proposed biosynthesis pathways of milbemycins.The producing strain S. bingchenggensis X-4 was maintained on an 1/2YM slant agar consisting of sucrose 0.4%, skim milk 0.1%, yeast extract (OXOID Basingstoke, Hampshire, UK) 0.2%, malt extract (BD Biosciences, San Jose, CA, USA) 0.5%, agar (BD Biosciences) 2.0% at 28 1C for 12 days. 12 A seed 15-l fermentor (FUS-15 L (A), Shanghai Guoqiang Bioengineering Equipment, Shanghai, China) containing 10 l of seed medium (sucrose 1.0%, polypepton 0.2%, K 2 HPO 4 0.05%, skim milk 0.05%) 12 was inoculated with 0.5 l of broth cultured in flask with seed medium. The flask with seed medium (2-6Â10 7 spores per ml) was cultured for 30 h at 28 1C on a rotary shake at 250 r.p.m.After incubation for 32 h, the seed broth (3 l) in the 15-l fermentor was transferred into the production 50-l fermentor (FUS-50 L (A), Shanghai Guoqiang Bioengineering Equipment) containing 30-l production medium (16.0% sucrose, 2.0% soybean powder, 0.5% yeast extract, 0.5% meat extract, 0.05% K 2 HPO 4 , 0.05% MgSO 4 7H 2 O, 0.005% FeSO 4 7H 2 O and 0.3% CaCO 3 ). 12 The culture temperature was 28 1C and the initial pH was 7.40 sterilized by sparging with steam at 121 1C for 30 min. The dissolved oxygen was maintained above 35% by adjusting the agitation speed. The initial aeration and agitation rate in the 15-l reactor was 1 vvm and 180 r.p.m., whereas those in the 50 l were 0.8 vvm and 150 r.p.m., respectively. In the process of fermenta...

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Bingchamides A and B, two novel cyclic pentapeptides from the Streptomyces bingchenggensis: fermentation, isolation, structure elucidation and biological properties

Cited by 25 publications

References 21 publications

Genome Sequence of the Milbemycin-Producing Bacterium Streptomyces bingchenggensis

Genome Sequence of the Milbemycin-Producing Bacterium Streptomyces bingchenggensis

Time-Dependent Production of the Bioactive Peptides Endolides A and B and the Polyketide Mariline A from the Sponge-Derived Fungus Stachylidium bicolor 293K04

New milbemycins from mutant Streptomyces bingchenggensis X-4

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