New Ansamycins from the Deep-Sea-Derived Bacterium Ochrobactrum sp. OUCMDZ-2164.
ABSTRACT: Two new ansamycins, trienomycins H (1) and I (2), together with the known trienomycinol (3), were isolated from the fermentation broth of the deep-sea-derived bacterium Ochrobactrum sp. OUCMDZ-2164. Their structures, including their absolute configurations, were elucidated based on spectroscopic analyses, ECD spectra, and Marfey's method. Compound 1 exhibited cytotoxic effects on A549 and K562 cell lines with IC50 values of 15 and 23 ?M, respectively.
Project description:Four new azaphilones, sclerotiorins A-D (1-4), as well as the dimeric sclerotiorin E (5) of which we first determined its absolute configuration, and 12 known analogues (5-16) were isolated from the fermentation broth of Penicillium sclerotiorum OUCMDZ-3839 associated with a marine sponge Paratetilla sp.. The new structures, including absolute configurations, were elucidated by spectroscopic analyses, optical rotation, ECD spectra, X-ray single-crystal diffraction, and chemical transformations. Compounds 11 and 14 displayed significant inhibitory activity against α-glycosidase, with IC50 values of 17.3 and 166.1 μM, respectively. In addition, compounds 5, 7, 10, 12-14, and 16 showed moderate bioactivity against H1N1 virus.
Project description:A new hybrid polyketide, cladodionen (1), together with a new abscisic acid analogue, cladosacid (2), were isolated from the marine-derived fungus, Cladosporium sp. OUCMDZ-1635. Their structures, including the absolute configurations, were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Cladodionen (1) showed cytotoxic activities against MCF-7, HeLa, HCT-116, and HL-60 human cancer cell lines with IC50 values of 18.7, 19.1, 17.9, and 9.1 µM.
Project description:A chemical-epigenetic method was used to enhance the chemodiversity of a marine algicolous fungus. Apart from thirteen known compounds, (+)-brevianamide R ((+)-3), (?)-brevianamide R ((?)-3), (+)-brevianamide Q ((+)-4), (?)-brevianamide Q ((?)-4), brevianamide V ((+)-5), brevianamide W ((?)-5), brevianamide K (6), diorcinol B (7), diorcinol C (8), diorcinol E (9), diorcinol J (10), diorcinol (11), 4-methoxycarbonyldiorcinol (12), two new compounds, (+)- and (?)-brevianamide X ((+)- and (?)- 2)), as well as a new naturally occurring one, 3-[6-(2-methylpropyl)-2-oxo-1H-pyrazin-3-yl]propanamide (1), were isolated from chemical-epigenetic cultures of Aspergillus versicolor OUCMDZ-2738 with 10 µM vorinostat (SAHA). Compared to cultures in the same medium without SAHA, compounds 1?4, 8, 9, 11, and 12 were solely observed under SAHA condition. The structures of these compounds were elucidated based on spectroscopic analysis, specific rotation analysis, ECD, and X-ray crystallographic analysis. (±)-3, (±)-4, and (±)-5 were further resolved into the corresponding optically pure enantiomers and their absolute configurations were determined for the first time. Compounds 11 and 12 showed selective antibacterial against Pseudomonas aeruginosa with a minimum inhibitory concentration (MIC) of 17.4 and 13.9 ?M, respectively. Compound 10 exhibited better ?-glucosidase inhibitory activity than the assay control acarbose with IC50 values of 117.3 and 255.3 ?M, respectively.
Project description:A potential degrader of paraffinic and aromatic hydrocarbons was isolated from oil-contaminated soil from steel plant effluent area in Burnpur, India. The strain was investigated for degradation of waste lubricants (waste engine oil and waste transformer oil) that often contain EPA (Environmental Protection Agency, USA) classified priority pollutants and was identified as Ochrobactrum sp. C1 by 16S rRNA gene sequencing. The strain C1 was found to tolerate unusually high waste lubricant concentration along with emulsification capability of the culture broth, and its degradation efficiency was 48.5 ± 0.5 % for waste engine oil and 30.47 ± 0.25 % for waste transformer oil during 7 days incubation period. In order to get optimal degradation efficiency, a three level Box-Behnken design was employed to optimize the physical parameters namely pH, temperature and waste oil concentration. The results indicate that at temperature 36.4 °C, pH 7.3 and with 4.6 % (v/v) oil concentration, the percentage degradation of waste engine oil will be 57 % within 7 days. At this optimized condition, the experimental values (56.7 ± 0.25 %) are in a good agreement with the predicted values with a calculated R <sup>2</sup> to be 0.998 and significant correlation between biodegradation and emulsification activity (E <sub>24</sub> = 69.42 ± 0.32 %) of the culture broth toward engine oil was found with a correlation coefficient of 0.972. This is the first study showing that an Ochrobactrum sp. strain is capable of degrading waste lubricants, which might contribute to the bioremediation of waste lubricating oil-contaminated soil.
Project description:Wailupemycins H (1) and I (2) with a new skeleton coupled two 6-(2-phenylnaphthalene-1-yl)pyrane-2-one nuclei to a -CH2- linkage were identified from the culture of Streptomyces sp. OUCMDZ-3434 associated with the marine algae, Enteromorpha prolifera. Compounds 1 and 2 are two new ?-glucosidase inhibitors with the Ki/IC50 values of 16.8/19.7 and 6.0/8.3??M, respectively. In addition, the absolute configurations of wailupemycins D (3) and E (4) are also resolved in this paper for the first time.
Project description:Two new indole-diterpenoids (1 and 2) and a new isocoumarin (3), along with the known ?-aflatrem (4), paspalinine (5), leporin B (6), ?-cyclopiazonic acid (7), iso-?-cyclopiazonic acid (8), ditryptophenaline (9), aflatoxin B1 (10), 7-O-acetylkojic acid (11) and kojic acid (12), were isolated from the fermentation broth of the marine-derived fungus, Aspergillus flavus OUCMDZ-2205. The structures of Compounds 1-12 were elucidated by spectroscopic analyses, quantum ECD calculations and the chemical method. New Compound 1 exhibited antibacterial activity against Staphylococcus aureus with a MIC value of 20.5 ?M. Both new Compounds 1 and 2 could arrest the A549 cell cycle in the S phase at a concentration of 10 ?M. Compound 1 showed PKC-beta inhibition with an IC50 value of 15.6 ?M. In addition, the absolute configurations of the known compounds, 4-6 and leporin A (6a), were also determined for the first time.
Project description:<i>Ochrobactrum</i> species are non-enteric, Gram-negative organisms that are closely related to the genus <i>Brucella</i>. Since the designation of the genus in 1988, several distinct species have now been characterised and implicated as opportunistic pathogens in multiple outbreaks. Here, we examine the genus, its members, diagnostic tools used for identification, data from recent <i>Ochrobactrum</i> whole genome sequencing and the pathogenicity associated with reported <i>Ochrobactrum</i> infections. This review identified 128 instances of <i>Ochrobactrum</i> spp. infections that have been discussed in the literature. These findings indicate that infection review programs should consider investigation of possible <i>Ochrobactrum</i> spp. outbreaks if these bacteria are clinically isolated in more than one patient and that <i>Ochrobactrum</i> spp. are more important pathogens than previously thought.
Project description:Under the guidance of global natural product social molecular networking, three new indolocarbazoles named streptocarbazoles F–H (1-3), along with staurosporine (4) were isolated from the marine-derived Streptomyces sp. OUCMDZ-5380. Structures of streptocarbazoles F–H were, respectively, determined as N-demethyl-N-hexanoylstaurosporine (1), N-demethyl-N-(2-methyl-3-methoxypyridin-4-yl) staurosporine staurosporine (2), and 4-(N-demethylstaurosporine-N-yl)-1,2-dimethyl-3-methoxypyridinium (3) by spectroscopic analysis and electronic circular dichroism comparison with staurosporine. Compared with staurosporine (4), streptocarbazoles F–H (1-3) showed a selective antiproliferation of the acute myeloid leukemia cell line MV4-11 with the IC50 values of 0.81, 0.55, and 1.88 μM, respectively. GRAPHICAL ABSTRACT
Project description:Four new ansamycins, named divergolides T-W (1-4), along with two known analogs were isolated from the fermentation broth of the mangrove-derived actinomycete Streptomyces sp. KFD18. The structures of the compounds, including the absolute configurations of their stereogenic carbons, were determined by spectroscopic data and single-crystal X-ray diffraction analysis. Compounds 1-4 showed cytotoxic activity against the human gastric cancer cell line SGC-7901, the human leukemic cell line K562, the HeLa cell line, and the human lung carcinoma cell line A549, with 1 being the most active while compounds 5 and 6 were inactive against all the tested cell lines. Compounds 1 and 3 showed very potent and specific cytotoxic activities (IC50 2.8 and 4.7 µM, respectively) against the SGC-7901 cells. Further, the apoptosis-inducing effect of 1 and 3 against SGC-7901 cells was demonstrated by two kinds of staining methods for the first time.