A novel spiro-heterocycle milbemycin metabolite from a genetically engineered strain of Streptomyces bingchenggensis.

Milbemycin R, a novel spiro-heterocycle milbemycin, was obtained from the metabolites produced by the mutant strain S. bingchenggensis BCJ60B11. Its structure was determined by spectroscopic and spectrometric analyses including 1 D, 2 D NMR, IR, HR-ESI-MS data. The acaricidal and nematicidal activities of milbemycin R against Tetranychus cinnabarinus and Bursaphelenchus xylophilus were tested. Milbemycin R possessed better acaricidal activity than milbemycins A3/A4.

Efficient production of GlcNAc in an aqueous-organic system with a Chitinolyticbacter meiyuanensis SYBC-H1 mutant.

OBJECTIVES: Shellfish waste is a primary source for making N-acetyl-D-glucosamine. Thus, establishing a high-efficiency and low-cost bioconversion method to produce N-acetyl-D-glucosamine directly from shellfish waste was promising. RESULTS: A mutant C81 was obtained from Chitinolyticbacter meiyuanensis SYBC-H1 via 60Co-γ irradiation. This mutant C81 showed the highest chitinase activity of 9.8 U/mL that was 85% higher than the parent strain. The mutant C81 exhibted improved antioxidant activities, including total antioxidant capacity, superoxide radical ability, and hydroxyl radical scavenging ability, compared to that of the parent strain. Four out of nine organic solvents increased the chitinase activity by 1.9%, 6.8%, 11.7%, and 15.8%, corresponding to methylbenzene, n-heptane, petroleum ether, and n-hexane, respectively. The biphase system composed of aqueous and hexane presented a five-fold reduction of cell viability compared to the control. Using a continuous fermentation bioconversion process, 4.2 g/L GlcNAc was produced from crayfish shell powder with a yield of 80% of the chitin content. CONCLUSIONS: This study demonstrated that the mutant C81 is suitable for converting crayfish shell powder into GlcNAc in an aqueous-organic system.

Two new threonine-containing metabolites from fungus Curvularia inaequalis strain HS-FG-257.

Two new threonine-containing metabolites, N-[4-hydroxy-3-prenyl-benzoyl]-L-threonine (1) and N-[2,2-dimethyl-2H-chromene-6-carbonyl]-L-threonine (2), were isolated from the fermentation broth of the soil fungus Curvularia inaequalis strain HS-FG-257. Their structures were elucidated through the interpretation of HR-ESIMS and extensive NMR spectroscopic data. Both compounds exhibited no cytotoxic activity against the test cell lines A549 and HCT-116.

Two new 13-hydroxylated milbemycin metabolites from the genetically engineered strain Streptomyces avermitilis AVE-H39.

Two new milbemycin metabolites, 13α-hydroxymilbemycin ß13 (1) and 26-methyl-13α-hydroxymilbemycin ß13 (2), were isolated from the fermentation broth of a genetically engineered strain Streptomyces avermitilis AVE-H39. Their structures were determined by the comprehensive spectroscopic data, including 1 D, 2 D NMR, MS spectral analysis and the comparison with data from the literature. Compounds 1 and 2 not only exhibited potent acaricidal activities against Tetranychus cinnabarinus, but also had nematocidal activity against Bursaphelenchus xylophilus.

Two new milbemycin derivatives from a genetically engineered strain Streptomyces bingchenggensis.

Two new milbemycin derivatives, milbemycin M (1) and milbemycin N (2), were isolated from the culture of a genetically engineered strain Streptomyces bingchenggensis BCJ60. Their structures were elucidated through the interpretation of NMR and HR-ESI-MS spectroscopic data, as well as comparison with previous reports. The acaricidal and nematicidal activities of them against Tetranychus cinnabarinus and Bursaphelenchus xylophilus were tested. The results showed that compounds 1-2 possessed potent acaricidal and nematocidal activities.

Two novel milbemycin derivatives from the genetically engineered strain Streptomyces avermitilis AVE-H39.

Two novel milbemycin derivatives, 5,27-epoxy-13α-hydroxy milbemycin ß11 (1) and 5,27-epoxy-13α-hydroxy-25-ethyl milbemycin ß11 (2), were isolated from the genetically engineered strain Streptomyces avermitilis AVE-H39. Their structures were elucidated through the interpretation of HR-ESIMS and extensive NMR spectroscopic data. Compounds 1 and 2 exhibited moderate acaricidal and nematicidal activities.

Two new glutarimide antibiotics from Streptomyces sp. HS-NF-780.

Two new glutarimide antibiotics, 9-methylstreptimidone 2-α-D-glucopyranoside (1), and hydroxyiso-9-methylstreptimidone (2), along with a known compound, 9-methylstreptimidone (3), have been isolated from the broth of Streptomyces sp. HS-NF-780. Their structures were determined on the basis of spectroscopic analysis, including 1D and 2D NMR techniques as well as ESI-MS and comparison with data from the literature. By modified Mosher's method and acid hydrolysis, the absolute configurations of compounds 1 and 2 were established. Compounds 1 and 2 exhibited moderate cytotoxic activity.

Bioactive naphthoquinone and anthrone derivatives from endophytic Micromonospora sp. NEAU-gq13.

Two new naphthalenone derivatives, 5-hydroxy-4-oxo-2-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-yl acetate (1) and 5-hydroxy-2-(2-hydroxypropyl)naphthalene-1,4-dione (2), together with two new anthrone derivatives, (S)-2,5-dihydroxy-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione (3) and 4,5-dihydroxy-2-methyl-9H-xanthen-9-one (4), were isolated from the fermentation broth of endophytic Micromonospora sp. NEAU-gq13. Their structures were determined by 1D-NMR, 2D-NMR, and HR-ESI-MS analysis. Compounds 2 and 3 exhibited strong cytotoxic activity against human central nervous system cancer (SF-268) with the IC50 values of 3.04 and 5.66 µg/ml, respectively. Moreover, compound 2 also displayed potent activity against human liver cancer (HepG2) with an IC50 value of 1.01 µg/ml.

New milbemycin metabolites from the genetically engineered strain Streptomyces bingchenggensis BCJ60.

Two new milbemycin derivatives, 27-methoxylmilbemycin α31 (1) and 27-oxomilbemycin α31 (2), were isolated from the genetically engineered strain Streptomyces bingchenggensis BCJ60. Their structures were determined by 1D NMR, 2D NMR and HR-ESI-MS spectral analysis, and comparison with previous reports. The acaricidal and nematocidal capacities of compounds 1 and 2 were evaluated against Tetranychus cinnabarinus and Bursaphelenchus xylophilus, respectively. The results showed that the two new macrocyclic lactones 1 and 2 possessed potent acaricidal and nematocidal activities.

A new tetrahydrobenzofuranone metabolite from Streptomyces sp. HS-NF-853.

A new tetrahydrobenzofuranone derivative, strefuranone A (1), was isolated from Streptomyces sp. HS-NF-853. The structure of the compound was elucidated on the basis of MS and extensive NMR analysis.

New macrocyclic lactones with acaricidal and nematocidal activities from a genetically engineered strain Streptomyces bingchenggensis BCJ60.

Two new macrocyclic lactones, 4,25-diethyl-4,25-demethyl-milbemycin ß3 (1) and 27-formaldehyde-milbemycin ß14 (2), were isolated from a genetically engineered strain Streptomyces bingchenggensis BCJ60. Their structures were determined on the basis of spectroscopic analysis, including 1D and 2D NMR techniques as well as ESI-MS and comparison with data from the literature. The acaricidal and nematocidal capacities of compounds 1 and 2 were evaluated against Tetranychus cinnabarinus and Bursaphelenchus xylophilus, respectively. The results showed that the two new macrocyclic lactones 1 and 2 possessed potent acaricidal and nematocidal activities.

A new naphthalenepropanoic acid analog from the marine-derived actinomycetes Micromonospora sp. HS-HM-036.

A new naphthalenepropanoic acid analog (1) was isolated from the broth of the actinomycetes Micromonospora sp. HS-HM-036. The structure of compound 1 was determined based on MS and extensive NMR analysis. A preliminary investigation of the biological activity of compound 1 was also described.

A new spectinabilin derivative with cytotoxic activity from ant-derived Streptomyces sp. 1H-GS5.

A new spectinabilin derivative (1) was isolated from the fermentation broth of the ant-derived Streptomyces sp. 1H-GS5, and the structure was elucidated by extensive spectroscopic analysis. Compound 1 showed cytotoxicity against human tumor cell lines A549, HCT-116, and HepG2 with IC50 values of 9.7, 12.8, and 9.1 µg/ml, respectively, which was relative higher than that of spectinabilin.