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•Proteomics was used to investigate proteome changes in germinating M. oleifera seeds.•The DEPs within the molecular weight range of 10–60 kDa were most abundant.•A peptidase and ...three types of endopeptidases were identified during germination.•M. oleifera germinating seeds contained a mixture of milk-clotting proteases.•The highly expressed proteases have potential application in the food industry.
This study is the first to apply label-free based proteomics to investigate the proteome changes during Moringa oleifera seed germination. In total, 1267 proteins were identified, with proteins within the molecular weight range of 10–60 kDa being most abundant. Among the 174 differentially expressed proteins (DEPs), 42 were upregulated and 26 downregulated, whereas 45 and 61 were uniquely expressed in the matured dry and germinating seeds, respectively. Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analysis revealed that the main DEPs had significant molecular functions related to catalytic activity and were involved in metabolism, degradation and biosynthesis, with 49 enzymes highly expressed in germination, including 9 proteases with hydrolytic activity, of which a peptidase and three types of endopeptidases were associated with milk-clotting activity. We further demonstrated that proteolytic activity (PA) and milk-clotting specific activity (MCSA) of protease extracts from M. oleifera seeds were increased during germination, particularly for samples from the ammonium sulfate (AS) fractionation that were statistically significance (p value < 0.05). Overall, proteases derived from germinating M. oleifera seeds can be used in the food industry, especially for potential application in the production of bioactive peptides and cheese processing.
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•25 novel N-(1,3-thiazol-2-yl)carboxamides of fraxinellone were prepared.•Compounds 6b and 6i exhibited potent insecticidal activities against two insect pests.•Compound 6b and 6i ...showed low cytotoxicity to noncancerous mammalian cells.•The interesting structure–activity relationships were also discussed.
To improve the insecticidal activities of fraxinellone, two series of fraxinellone-based N-(1,3-thiazol-2-yl)carboxamides containing 25 compounds were prepared by structural modification. Their structures were determined by melting point, optical rotation, IR, 1H NMR and ESI-MS. The steric configurations of compounds 6i, 7d and 7i were unambiguously confirmed by X-ray diffraction further. The bioassay showed that compounds 6b and 6i exhibited more potent larvicidal and growth inhibitory activities against Plutella xylostella Linnaeus and Mythimna separata Walker, respectively. Moreover, compounds 6b and 6i also displayed low cytotoxicity to noncancerous mammalian cells. The structure–activity relationships (SARs) of all target compounds were also observed.
The present study aimed to investigate the biological functions of germinated M. oleifera seed proteins and to identify the identity of milk-clotting proteases. A total of 963 proteins were ...identified, and those with molecular weights between 10 and 30 kDa were most abundant. The identified proteins were mainly involved in energy-associated catalytic activity and metabolic processes, and carbohydrate and protein metabolisms. The numbers of proteins associated with the hydrolytic and catalytic activities were higher than the matured dry M. oleifera seeds reported previously. Of the identified proteins, proteases were mainly involved in the milk-clotting activity. Especially, a cysteine peptidase with a molecular mass of 17.727 kDa exhibiting hydrolase and peptidase activities was purified and identified. The identified cysteine peptidase was hydrophilic, and its secondary structure consisted of 27.60% alpha helix, 9.20% beta fold, and 63.20% irregular curl; its tertiary structure was also constructed using M. oleifera seed 2S protein as the protein template. The optimal pH and temperature of the purified protease were pH 4.0 and 60 °C, respectively. The protease had high acidic stability and good thermostability, thus could potentially be applied in the dairy industry.
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•Biofunctions of germinated M. oleifera seeds were investigated by proteomics.•Proteases with MWs of 10–30 kDa were likely responsible for milk-clotting activity.•The cysteine peptidase with a molecular mass of 17.727 kDa was purified.•The protease had high acidic stability and good temperature stability.
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•Two series of fraxinellone-based N-phenylpyrazole compounds were prepared.•Compounds 7g–i and 8g–j exhibited potent insecticidal activity against M. separata.•Compound 8g displayed ...promising larvicidal activity against P. xylostella.•The interesting structure-activity relationship was also discussed.
Fraxinellone, a degraded limonoid, has been mainly isolated from some renewable plants in Meliaceae and Rutaceae. In a continuous effort to discover new natural products-based pesticides, two series of fraxinellone derivatives containing N-phenylpyrazole moiety were designed, synthesized and evaluated for their pesticidal activities against Mythimna separata Walker and Plutella xylostella Linnaeus. Two structures of compounds 7g and 8k were unambiguously determined by X-ray diffraction further. The bioassay showed that over half of the target compounds exhibited better insecticidal activity against M. separata than the precursor fraxinellone. Among all the target compounds, the compounds 7g–i and 8g–j exhibited more potent insecticidal activity than toosendanin, a commercial botanical pesticide. Furthermore, the compound 8g displayed more promising larvicidal activity with the LC50 value of 0.31 μmol mL−1 than the toosendanin against P. xylostella. The structure–activity relationship (SAR) revealed that introduction of polyhalogenated phenylpyrazole ring on furyl-ring of fraxinellone could lead more potent compounds both against M. separata and P. xylostella than that of monohalogenated phenylpyrazole ring or electron-donating groups substituted phenylpyrazole ring.
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•Two series of novel 4-(aminoalkyl)-6-allyl-sesamols were prepared from sesamol.•An efficient way for the synthesis of these sesamol derivatives was developed.•The sesamol derivative ...7i displayed excellent antioxidant activity.•The interesting structure-activity relationships (SARs) were also discussed.•Compounds 7a, 7g and 7i showed very low toxicity to normal cells.
Sesamol, a natural phenolic compound with good antioxidant activity, is a nonoil component of sesame seed oil. Two series of novel Mannich bases, 4-(aminoalkyl)-6-allyl-sesamols were synthesized from sesamol, substituted benzaldehydes and piperidine/morpholine via the one-pot reaction. An efficient way using toluene as solvent, catalyst-free and one-pot reaction for the synthesis of these sesamol derivatives was developed. The structures of all 4-(aminoalkyl)-6-allyl-sesamols were determined by spectral analysis. Compound 6f was unambiguously confirmed by X-ray diffraction further. The antioxidant assays have demonstrated that the sesamol derivative 7i displayed excellent antioxidant activity. The structure–activity relationships (SARs) of these sesamol derivatives were also observed. Further, the representative compounds 7a, 7g and 7i exhibited relative low toxicity to normal cells. Based on these characteristics, these sesamol derivatives will have great potential application in food and drugs.
2-(2-Phenylethyl)chromones (PECs) are the primary constituents responsible for the promising pharmacological activities and unique fragrance of agarwood. However, the O-methyltransferases (OMTs) ...involved in the formation of diverse methylated PECs have not been reported. In this study, we identified one Mg2+-dependent caffeoyl-CoA-OMT subfamily enzyme (AsOMT1) and three caffeic acid-OMT subfamily enzymes (AsOMT2–4) from NaCl-treated Aquilaria sinensis calli. AsOMT1 not only converts caffeoyl-CoA to feruloyl-CoA but also performs nonregioselective methylation at either the 6-OH or 7-OH position of 6,7-dihydroxy-PEC. On the other hand, AsOMT2–4 preferentially utilizes PECs as substrates to produce structurally diverse methylated PECs. Additionally, AsOMT2–4 also accepts nonPEC-type substrates such as caffeic acid and apigenin to generate methylated products. Protein structure prediction and site-directed mutagenesis revealed that residues of L313 and I318 in AsOMT3, as well as S292 and F313 in AsOMT4 determine the distinct regioselectivity of these two OMTs toward apigenin. These findings provide important biochemical evidence of the remarkable structural diversity of PECs in agarwood.
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•Thirty novel (+)- nootkatone derivatives were prepared by molecular hybridization.•Compounds B9 and B21 displayed more potent insecticidal activities than azadirachtin.•B9 and B21 ...also showed low cytotoxic activities on normal mammalian cells.•Inhibition of acetylcholinesterase may be the mode of insecticidal action of B9.
(+)-Nootkatone, a non-food bioactive natural bicyclic sesquiterpene ketone, is isolated from Chamaecyparis nootkatensis D. Don Spach as a renewable forest resource. In continuation of our effort to develop synthetic natural derived insecticides from non-food bioactive products, a small library of thirty N-(1,3- thiazol-2-yl)carboxamides fused (+)-nootkatone was prepared by molecular hybridization and characterized by 1H/13C NMR, HR-MS, and IR spectroscopy. Their insecticidal activities against Mythimna separata Walker and Plutella xylostella Linnaeus were evaluated. Compounds B6, B7, B9, B19–21 and B24 showed better insecticidal activity against M. separata than the botanical insecticide azadirachtin, and their LC50 values ranged from 0.55−0.68 mg/mL. Particularly, compound B9 exhibited 1.87-fold more pronounced insecticidal activity against M. separata than azadirachtin. The insecticidal activity of B21 against P. xylostella was 1.37-fold of that of azadirachtin. Through acetylcholinesterase (AChE) inhibitory activity and molecular docking studies, AChE may be the insecticidal target of B9 against M. separata. In addition, three pronounced compounds B9, B21 and B24 exhibited low hemolytic and cytotoxic activities on normal mammalian cells. These findings will give insights into the further development of (+)-nootkatone derivatives as potentially synthetic natural derived insecticides for pest management.
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•Thirty novel (+)-nootkatone derivatives were prepared as α-glucosidase inhibitors.•II7 and II14 displayed about 3-fold higher α-glucosidase inhibitory activity than acarbose.•II7 and ...II14 were noncompetitive inhibitors and low cytotoxic to red and LO2 cells.•Molecular docking results further validated II7 and II14 were noncompetitive inhibitors.
Nowadays, the discovery and development of α-glucosidase inhibitors from natural products or their derivatives represents an attractive approach. Here we reported studies on a series of novel N-acyl-2-aminothiazoles fused (+)-nootkatone and evaluation for their α-glucosidase inhibitory activities. Most of (+)-nootkatone derivatives exhibited more potent α-glucosidase inhibitory ability than the positive drug acarbose. In particular, compounds II7 and II14 showed the most promising α-glucosidase inhibitory ability with IC50 values of 13.2 and 13.8 µM. II7 and II14 also exhibited relatively low cytotoxicities towards normal LO2 cells. Kinetic study indicated that compounds II7 and II14 inhibited the α-glucosidase in a noncompetitive manner, and molecular docking results were in line with the noncompetitive characteristics that II7 and II14 did not bind to the known active sites (Asp214, Glu276 and Asp349). Based on our findings, these (+)-nootkatone derivatives could be used as antidiabetic candidates.
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•New N-phenylpyrazole-containing 8-hydroxyquinaldine derivatives were prepared.•An efficient way for one pot synthesis of the target compounds was developed.•Compounds 8g and 9f ...exhibited potent pesticidal activities.•The structure-activity relationships were also discussed.
In continuation of our research aimed at discovery and development of new pesticidal agents, a series of new 8-hydroxyquinaldine derivatives containing a N–phenylpyrazole moiety were prepared and their structures were characterized by 1H NMR, IR, ESI-MS and mp. Meanwhile, an efficient way of using iodine-mediated oxidative cyclization for one pot synthesis of these 8-hydroxyquinaldine derivatives containing a N–phenylpyrazole moiety was developed. The bioassay showed that compounds 8g and 9f exhibited potent pesticidal activities against both Mythimna separata Walker and Plutella xylostella Linnaeus. The structure–activity relationships were also discussed.
