A novel antibiotic, sohbumycin. Taxonomy, fermentation, isolation and physico-chemical and biological characteristics.

Umezawa, Iwao; Tronquet, Claude; Funayama, Shinji; Okada, Kenji; Komiyama, Kanki

doi:10.7164/antibiotics.38.967

Cited by 12 publications

(18 citation statements)

References 11 publications

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“…As our 2D NMR data were also in agreement with the published structure of piperazimycin A (1a) [17], we state that the previously unidentified antibiotic sohbumycin is identical with piperazimycin A (1a), a cyclodepsipeptide containing the rare acids S-methylserine, g-hydroxypiperazic acid, g-chloropiperazic acid, 2-amino-8-methyl-4,6-nonadienoic acid and hydroxyacetic acid.…”

Section: Cid-ms/ms Analysis Of Piperazimycins a And Bsupporting

confidence: 89%

“…Two further highly cytotoxic antibiotics were identified as chlorinecontaining peptides by their formulas C 31 H 47 N 8 O 10 Cl and C 31 H 47 N 8 O 9 Cl (by HRESI-MS) and the positive chlorine/tolidine reaction for amide bonds. According to their NMR data, they were found to be identical with the previously reported but incompletely defined sohbumycin [17] and the recently published antibiotics piperazimycin A (1a) and B (1b) [18]. As part of our ongoing investigation of the MS/MS fragmentation of cyclopeptides and cyclodepsipeptides [19], we report here their massspectrometric fragmentation pattern.…”

Section: Cid-ms/ms Analysis Of Piperazimycins a And Bsupporting

confidence: 75%

“…Sohbumycin was reported as a potent cytotoxic agent against multiple tumor cell lines in the nanomolar range [17]. Recently, also the piperazimycins A and B (1a/1b) were found to be highly potent cytotoxins [18].…”

Section: Biological Activitymentioning

confidence: 99%

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Electrospray Ionization Mass Spectra of Piperazimycins A and B and γ-Butyrolactones from a Marine-derived Streptomyces sp.†

Shaaban

Facey

et al. 2008

J Antibiot

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Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (1a, 1b). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4-olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three g -butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed 1D and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.Keywords g -butyrolactones, piperazimycins, marinederived Streptomyces sp. The extract from the marine-derived Streptomyces sp. Act8015 exhibited in vitro antitumor activities against a number of cancer cells at very low concentrations. TLC of the crude extract displayed several UV absorbing zones, which turned yellowish-brown and/or reddish-brown with anisaldehyde/sulfuric acid. Further zones without UV absorption appeared as violet-blue and/or greenish-blue spots with the same reagent. IntroductionA large-scale shaker culture was performed on M 2 ϩ medium [15] for 5 days at 28°C. Chromatography of the ethyl acetate extract afforded 12 compounds, the peptides

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Section: Cid-ms/ms Analysis Of Piperazimycins a And Bsupporting

confidence: 89%

Section: Cid-ms/ms Analysis Of Piperazimycins a And Bsupporting

confidence: 75%

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Electrospray Ionization Mass Spectra of Piperazimycins A and B and γ-Butyrolactones from a Marine-derived Streptomyces sp.†

Shaaban

Facey

et al. 2008

J Antibiot

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show abstract

“…At the time when this compound was isolated, a substructure search in all databases delivered no hits, indicating the novelty of 254. However, it was found that a compound of undetermined structure named sohbumycin [366] had the same mass; the published 1 H NMR diagram was very similar to that of 254.…”

Section: Act8015 (20 L Shaker) Mycelium Filtratementioning

confidence: 98%

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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“…The antibiotic showed no inhibitory activity against Gram-negative bacteria, yeast and fungi at the concentration of 500//g/ml. This paper deals with the isolation and structure elucidation of octacyclomycin (1). Physico-chemical properties of octacyclomycin (1) Na salt are listed on observed.…”

Section: Isolation and Structure Of A New Polyether Antibiotic Octacmentioning

confidence: 99%

Isolation and Structure of a New Polyether Antibiotic, Octacyclomycin

et al. 1992

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A novel antibiotic, sohbumycin. Taxonomy, fermentation, isolation and physico-chemical and biological characteristics.

Cited by 12 publications

References 11 publications

Electrospray Ionization Mass Spectra of Piperazimycins A and B and γ-Butyrolactones from a Marine-derived Streptomyces sp.†

Electrospray Ionization Mass Spectra of Piperazimycins A and B and γ-Butyrolactones from a Marine-derived Streptomyces sp.†

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Isolation and Structure of a New Polyether Antibiotic, Octacyclomycin

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