Streptosporangium oxazolinicum sp. nov., a novel endophytic actinomycete producing new antitrypanosomal antibiotics, spoxazomicins

Inahashi, Yuki; Matsumoto, Atsuko; Omacr, Satoshi; mura,; omacr, Y; Takahashi, ko

doi:10.1038/ja.2011.18

Cited by 42 publications

(18 citation statements)

References 39 publications

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“…Compound 1 was obtained as a white powder by sequential chromatographic techniques (Figure S4). HRESIMS and 1D/2D 1 H and 13 C NMR data (Tables 1 and S3) were consistent with spoxazomicin C, 2,3 an antitrypanosomal alkaloid from Streptosporangium oxazolinicum K07-0460 structurally confirmed by X-ray crystallography (also previously reported with incorrect stereochemistry as nocazoline A). 37 Compound 2 was obtained as a white solid and displayed similar UV and physicochemical properties to 1 .…”

Section: Resultssupporting

confidence: 83%

“…Roughly 0.3% 1 of reported microbial metabolites are classified as phenol-oxazolines or salicylate-containing natural products, where salicylate C7 amino acid or peptide modification is a common feature (e.g., spoxazomicins, 2,3 oxachelin, 4,5 amychelin, 6 madurastatins, 7,8 acinetobactin, 9 asterobactins, 10 carboxymycobactins, 11–13 exochelins, 14 and nocardimicins 15,16 ). While most commonly reported as metal chelators/siderophores, 4,6,10 representative members have also been noted to display cancer cell line cytotoxicity and antimicrobial and antitrypanosomal activities.…”

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confidence: 99%

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Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6

Shaaban¹,

Saunders²,

Zhang³

et al. 2016

J. Nat. Prod.

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The isolation and structure elucidation of six new bacterial metabolites [spoxazomicin D (2), oxachelins B and C (4, 5), and carboxamides 6–8] and 11 previously reported bacterial metabolites (1, 3, 9–12a, and 14–18) from Streptomyces sp. RM-14-6 is reported. Structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry data analysis, along with direct comparison to synthetic standards for 2, 11, and 12a,b. Complete 2D NMR assignments for the known metabolites lenoremycin (9) and lenoremycin sodium salt (10) were also provided for the first time. Comparative analysis also provided the basis for structural revision of several previously reported putative aziridine-containing compounds [exemplified by madurastatins A1, B1, C1 (also known as MBJ-0034), and MBJ-0035] as phenol-dihydrooxazoles. Bioactivity analysis [including antibacterial, antifungal, cancer cell line cytotoxicity, unfolded protein response (UPR) modulation, and EtOH damage neuroprotection] revealed 2 and 5 as potent neuroprotectives and lenoremycin (9) and its sodium salt (10) as potent UPR modulators, highlighting new functions for phenol-oxazolines/salicylates and polyether pharmacophores.

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Section: Resultssupporting

confidence: 83%

mentioning

confidence: 99%

Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6

Shaaban¹,

Saunders²,

Zhang³

et al. 2016

J. Nat. Prod.

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“…The taxonomic study of the spoxazomicin producing strain will be reported in the accompanying paper. 4 …”

Section: Introductionmentioning

confidence: 99%

Spoxazomicins A–C, novel antitrypanosomal alkaloids produced by an endophytic actinomycete, Streptosporangium oxazolinicum K07-0460T

et al. 2011

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Three novel antitrypanosomal alkaloids, named spoxazomicins A-C, were isolated by silica gel column chromatography and HPLC from the culture broth of a new endophytic actinomycete species, Streptosporangium oxazolinicum K07-0460 T . The structures of the spoxazomicins were elucidated by NMR and X-ray crystal analyses and shown to be new types of pyochelin family antibiotic. Spoxazomicin A showed potent and selective antitrypanosomal activity with an IC 50 value of 0.11 lg ml À1 in vitro without cytotoxicity against MRC-5 cells (IC 50 ¼27.8 lg ml À1 ).

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“…The new antitrypanosomal antibiotics, spoxazomicins produced by the new actinomycete Streptosporangium oxazolinicum sp. isolated from the roots of a variety of orchid collected in the subtropical Okinawa prefecture 21 .…”

Section: Antibiotic Compound Produced By Actinomycetesmentioning

confidence: 99%

Update on Bioactive Molecules of Actinomycetes

Jadon¹,

Singh²,

Chaudhary³

2014

Biosci., Biotechnol. Res. Asia

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Marine and terrestrial regions are explored from many years and their bioactive compounds are being exploited. As the use of therapeutic novel compounds increases, researchers from all over the world started exploring oceans for bioactive compounds. Actinomycetes, filamentous bacteria have been extensively studied for their therapeutic compounds. They are found to occur in aquatic environments; freshwater and marine habitats. Mostly the marine actinomycetes have attracted a great attention as they have unique metabolic and physiological capabilities. Aquatic habitats enable them to survive in extremes of pressure, salinity and temperature, with the potential production of novel secondary metabolites not observed in actinomycetes, isolated from terrestrial habitats. Secondary metabolites produced from these actinomycetes viz. amino glycosides (streptomycin and kanamycin), ansamycins (rifampicin), anthracyclines (doxorubicin), blactam (cephalosporines), macrolides (erythromycin and tetracycline) and many others are considered to be bioactive. The biological diversity of actinomycetes is enormous in nature with diverse chemical compounds. These diverse chemical compounds have been responsible for great biological activities such as antimicrobial, antimalarial, antidiabetic, antitumor, antioxidant, insecticidal, antitubercular etc. Hence there is a scope of developing these bioactive metabolites as a potent therapeutic drug or lead compounds. However, the potential of actinomycetes is correctly studied though the exact wealth of these is unexplored.

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Streptosporangium oxazolinicum sp. nov., a novel endophytic actinomycete producing new antitrypanosomal antibiotics, spoxazomicins

Cited by 42 publications

References 39 publications

Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6

Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6

Spoxazomicins A–C, novel antitrypanosomal alkaloids produced by an endophytic actinomycete, Streptosporangium oxazolinicum K07-0460T

Update on Bioactive Molecules of Actinomycetes

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