Band 72, Heft 5-6

During the systematic search of active compounds from endophytic fungi, two new butyrolactones, namely aspernolides L ( 2 ) and M ( 4 ), together with four known compounds: 1- O -acetylglycerol ( 1 ), butyrolactone I ( 3 ), butyrolactone VI ( 5 ), and (+) alantrypinone ( 6 ) were characterized from the EtOAc extract of the endophytic fungus Aspergillus versicolor isolated from the roots of Pulicaria crispa (Asteraceae). Extensive spectroscopic analysis, including 1D, 2D NMR, and HRESIMS, was used to elucidate their structures. Compounds 1 , 5 , and 6 are reported for the first time from this fungus.

A series of 1 H -benzo[ f ]chromene-2-carbonitriles was synthesized and evaluated for their cytotoxic activities against MCF-7, HCT-116, and HepG-2 cancer cells. The SAR studies reported that the substitution in the phenyl ring at 1-position of 1 H -benzo[ f ]chromene nucleus with the specific group, H atom, or methoxy group at 9-position increases the ability of the molecule against the different cell lines.

Pharmaceuticals are widely used for treating human and animal diseases. Naproxen [(S) 6-methoxy-α-methyl-2-naphthalene acetic acid] and its sodium salt are members of the α-arylpropionic acid group of nonsteroidal anti-inflammatory drugs. Due to excessive usage of naproxen, this drug has been determined even in drinking water. In this study, four fungal strains Phanerochaete chrysosporium , Funalia trogii , Aspergillus niger , and Yarrowia lipolytica were investigated in terms of naproxen removal abilities. According to LC/MS data, A. niger was found the most efficient strain with 98% removal rate. Two main by-products of fungal transformation, O -desmethylnaproxen and 7-hydroxynaproxen, were identified by using LC/MS, 1 HNMR, and 13 CNMR. Our results showed that O -demethylation and hydroxylation of naproxen is catalyzed by cytochrome P450 enzyme system.

Adventitious roots (ARs) directly affect lotus seedling growth and product quality because principal root is not well developed. However, the details of AR formation at the molecular level have not been determined in lotus. Therefore, three stages were chosen to identify the change of proteins abundant during rhizome formation, using isobaric tags for relative and absolute quantization coupled with liquid chromatography–tandem mass spectrometry to gain insight into the molecular mechanisms involved in AR formation. We totally obtained 323,375 spectra during AR formation. After filtering to eliminate low-scoring spectra, 66,943 spectra, including 53,106 unique spectra, were identified. These unique spectra matched 28,905 peptides, including 24,992 unique peptides, which were assembled into 6686 proteins. In the C0/C1 and C1/C2 stages, 66 and 32 proteins showed enhanced abundance, and 173 and 73 proteins showed decreased abundance, respectively. Seventeen important AR formation-related proteins from the three stages were identified, and the expressions of nine genes from the above-identified proteins were assessed by qRT-PCR. This article provides a comprehensive understanding of the changes in metabolism during AR formation, and is helpful to accelerate the progress of breeding in fulture in lotus root.

The naphthalene glycosidecurviflorside [1,5-dihydroxy-8-methoxynaphthalene-2- O -β-D-xylopyranoside] ( 3 ) and the flavanol curviflorin [(+)-catechin-7- O -3″,4″-dihydroxybenzoate] ( 4 ), along with two known flavonoids: (+)-catechin ( 1 ) and quercetin ( 2 ) were isolated from the shoots of Plicosepalu scurviflorus Benth. (Loranthaceae) growing in Saudi Arabia and the chemical structures were elucidated by 2D-NMR spectroscopy.

Termiglaucescin ( 1 ), a new triterpene glucoside, has been isolated from the ethyl acetate extract of the root bark of Terminalia glaucescens Planch. ex Benth, together with 11 known compounds, β -D-glucopyranosyl 2 α ,3 β ,6 β -trihydroxy-23-galloylolean-12-en-28-oate ( 2 ), arjunglucoside I ( 3 ), sericoside ( 4 ), arjungenin ( 5 ), sericic acid ( 6 ), arjunetin ( 7 ), chebuloside II ( 8 ), 3,3′,4-tri- O -methylelagic acid ( 9 ), 3,3′-di- O -methylelagic acid ( 10 ), β -sitosterol ( 11 ) and stigmasterol ( 12 ). Compounds 2 , 3 , 7 , 8 and 9 are reported from the plant for the first time. The structures of the isolated compounds were characterized by spectroscopic data interpretations, especially 1D and 2D NMR. The triterpenic isolates showed potent antioxidant and anti-inflammatory activities.

The aim of this article is influence of the structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity. This work was based on the general remark that even the smallest change in the structure of a compound can affect its biological properties. The results of the biotransformation of four bicyclic unsaturated lactones with one or two methyl groups in the cyclohexene ring was tested using fifteen fungal strains ( Fusarium species, Penicillium species, Absidia species, Cunninghamella japonica , and Pleurotus ostreatus ) and five yeast strains ( Yarrowia lipolytica , Rhodorula marina, Rhodorula rubra , Candida viswanathii , and Saccharomyces cerevisiae ). During these transformations, new epoxylactone and hydroxylactone were obtained. The relationship between the substrate structure and the ability of the microorganisms to transform them were analysed. Only compounds with C–O bond of lactone ring in the equatorial position were transformed by fungus. All presented here lactones were examined also for their antimicrobial activity. It turned out that these compounds exhibited growth inhibition of bacteria and fungi, mainly Bacillus subtilis , Candida albicans , Aspergillus niger, and Penicillium expansum.

Hypericum perforatum L. has been used for centuries as a natural remedy for the treatment of many disorders. Neuropathic pain is a common side effect of oxaliplatin-based chemotherapy and often the cause of therapy discontinuation. Thanks to its anti-inflammatory and analgesic effects, the use of H. perforatum may be a novel therapeutic strategy for neuropathy. The aim of this paper was to evaluate the effect of H. perforatum hydrophilic extract on an in vitro model of oxaliplatin-induced neurotoxicity. The antioxidant potential of extract was first evaluated in cell-free models by the thiobarbituric acid-reactive substances assay and nitro blue tetrazolium oxidation test; the ability of H. perforatum extract to reduce oxaliplatin-induced caspase-3 activity in rat astrocytes and its potential interference with the cytotoxic effects of oxaliplatin in a colorectal cancer in vitro model (HT-29 cells) were also evaluated. The extract showed a significant antioxidant effect and was able to reduce caspase-3 activity in rat astrocytes. Of note, the extract alone exerted a cytotoxic effect in HT-29 cells and did not reduce the cytotoxicity of oxaliplatin in HT-29 cells. These data suggest that H. perforatum could be used as a novel therapeutic strategy for counteracting chemotherapy-induced neuropathy.

Olive mill wastewater has significant polluting properties due to its high phenolic content [mainly tyrosol (trs) and hydroxytyrosol (htrs)]. Growth kinetics and a series of fluorescence induction measurements for Scenedesmus obliquus cultures showed that microalgae can be tolerant of these phenolic compounds. Changes in the cellular energy reserves and concentration of the phenolic compounds adjust the “toxicity” of these compounds to the microalgae and are, therefore, the main parameters that affect biodegradation. Autotrophic growth conditions of microalgae and high concentrations of trs or htrs induce higher biodegradation compared with mixotrophic conditions and lower phenolic concentrations. When microalgae face trs and htrs simultaneously, biodegradation begins from htrs, the more energetically demanding compound. All these lead to the conviction that microalgae have a “rational” management of cellular energy balance. Low toxicity levels lead to higher growth and lower biodegradation, whereas higher toxicity levels lead to lower growth and higher biodegradation. The selection of appropriate conditions (compatible to the bioenergetic strategies of microalgae) seems to be the key for a successful biodegradation of a series of toxic compounds, thus paving the way for future biotechnological applications for solving complicated pollution problems, like the detoxification of olive mill wastewater.