JBIR-31, a new teleocidin analog, produced by salt-requiring Streptomyces sp. NBRC 105896 isolated from a marine sponge

Izumikawa, Miho; Khan, Shams Tabrez; Komaki, Hisayuki; Takagi, Motoki; Shin‐ya, Kazuo

doi:10.1038/ja.2009.113

Cited by 39 publications

(34 citation statements)

References 28 publications

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“…[2][3][4] We have recently discovered novel compounds, namely the anthracyclines tetracenoquinocin and 5-iminoaranciamycin, 5 a teleocidin JBIR-31, 6 the tetrapeptides JBIR-34 and JBIR-35, 7 the isoprenoids JBIR-46, JBIR-47, JBIR48 8,9 and a new salicylamide JBIR-58. 10 Our intention was to support the idea that new species are capable of producing unique metabolites.…”

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JBIR-65, a new diterpene, isolated from a sponge-derived Actinomadura sp. SpB081030SC-15

et al. 2010

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Marine microorganisms, particularly, marine actinomycetes, are one of the most important resources for new biologically active metabolites, 1 and in fact, many new compounds have been isolated from sponge-derived actinomycetes. [2][3][4] We have recently discovered novel compounds, namely the anthracyclines tetracenoquinocin and 5-iminoaranciamycin, 5 a teleocidin JBIR-31, 6 the tetrapeptides JBIR-34 and JBIR-35, 7 the isoprenoids JBIR-46, JBIR-47, JBIR48 8,9 and a new salicylamide JBIR-58. 10 Our intention was to support the idea that new species are capable of producing unique metabolites. For this purpose, we isolated new species of actinomycetes from marine sponges and then searched for secondary metabolites in the culture of isolated strains. In this study, we isolated a new species (SpB081030SC-15) of Actinomadura from an unidentified marine sponge and purified a new diterpene compound designated as JBIR-65 (1, Figure 1a) from the fermentation broth of Actinomadura sp. SpB081030SC-15. In this study, we report the fermentation procedure to obtain 1 and its subsequent isolation, structure elucidation and, in brief, its biological activities.Actinomadura sp. SpB081030SC-15 was isolated from an unidentified marine sponge collected offshore of Ishigaki Island, Okinawa Prefecture, Japan. To identify the species of the strain SpB081030SC-15, we compared its 16S ribosomal RNA gene sequences (Accession No. AB123566) with those available in the DNA Data Bank of Japan using a basic local alignment search tool. 11 The strain was identified as a new species of the genus Actinomadura because comparison of its 16S ribosomal RNA gene sequence revealed a low sequence similarity of 98% with Actinomadura nitritigenes (AB364595).The strain SpB081030SC-15 was cultivated in 50-ml test tubes each containing 15 ml of a seed medium consisting of starch (Kosokagaku, Tokyo, Japan) 1.0%, polypeptone (Nihon Pharmaceutical, Tokyo, Japan) 1.0%, molasses (Dai-Nippon Meiji Sugar, Tokyo, Japan) 1.0% and meat extract 1.0% (Extract Ehlrich, Wako Pure Chemical Industry, Osaka, Japan), pH 7.2 (adjusted before sterilization). The seed culture in test tubes was agitated on a reciprocal shaker (355 r.p.m.) at 27 1C for 2 days. Aliquots (2.5 ml) of the broth were transferred to 500-ml baffled Erlenmeyer flasks containing 100 ml of a production medium consisting of glycerin 2.0%, molasses 1.0%, casein 0.5% and CaCO 3 0.4%, pH 7.2 (adjusted before sterilization) and cultured on a rotary shaker (180 r.p.m.) at 27 1C for 5 days.The mycelia in the fermentation broth (2 l) was separated by centrifugation and then extracted with 80% acetone. The extract was evaporated in vacuo to remove the acetone, and the aqueous residue was extracted with EtOAc. The organic layer was dried over Na 2 SO 4 and evaporated to dryness. The residue (700 mg) was subjected to normal-phase medium-pressure liquid chromatography (Purif-Pack SI-60, Moritex, Tokyo, Japan) and eluted with a gradient system of n-hexane-EtOAc (0-30% EtOAc) and CHCl 3 -MeOH (0-50% MeOH), successively....

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JBIR-65, a new diterpene, isolated from a sponge-derived Actinomadura sp. SpB081030SC-15

et al. 2010

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“…We isolated 11 new compounds that were cytotoxic to several human MPM cells. 23,[27][28][29][30][31][32] Among these compounds, JBIR-23 possesses a unique structure, consisting of a dodecahydrodibenzo [b,d]furan skeleton (Figure 2a). This compound exerted its cytotoxic effect on MPM cells by promoting tubulin polymerization (Figure 2b) and G 2 /M arrest, which led to the induction of apoptosis via the caspase pathway following phosphorylation of p38 mitogen-activated protein kinase and c-jun N-terminal kinase.…”

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Construction of a natural product library containing secondary metabolites produced by actinomycetes

Takagi

Shin‐ya

2012

J Antibiot

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To construct a natural product library for drug screening, we isolated secondary metabolites from a wide variety of actinomycetes cultured from marine sponges. The results suggested that marine sponges are a promising source of actinomycetes with the potential to produce new metabolites. Furthermore, we evaluated the chemical space occupied by our natural product library (CB library) by multidimensional principal component analysis and compared it with a commercially available compound library (ZINC library), which was randomly selected from the ZINC library (approximately 30 000 000 compounds). The CB library occupied a wider chemical space than the ZINC library. Bioactive compounds in the CB library possessed a wide chemical space that was not covered by ZINC library. These results indicate that the CB library mainly comprises secondary metabolites from actinomycetes, and it has great potential as a source of compounds for drug screening.

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“…[2][3][4] Our group was engaged in the isolation of actinobacteria from marine sponges. We have recently discovered novel compounds, namely the anthracyclines tetracenoquinocin and 5-imino aranciamycin, 5 a teleocidin JBIR-31, 6 the tetrapeptides JBIR-34 and -35, 7 and the isoprenoids JBIR-46-48. 8,9 Our intention was to support the idea that new species are capable of producing unique metabolites.…”

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JBIR-58, a new salicylamide derivative, isolated from a marine sponge-derived Streptomyces sp. SpD081030ME-02

et al. 2010

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JBIR-31, a new teleocidin analog, produced by salt-requiring Streptomyces sp. NBRC 105896 isolated from a marine sponge

Cited by 39 publications

References 28 publications

JBIR-65, a new diterpene, isolated from a sponge-derived Actinomadura sp. SpB081030SC-15

JBIR-65, a new diterpene, isolated from a sponge-derived Actinomadura sp. SpB081030SC-15

Construction of a natural product library containing secondary metabolites produced by actinomycetes

JBIR-58, a new salicylamide derivative, isolated from a marine sponge-derived Streptomyces sp. SpD081030ME-02

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