查看更多>>摘要：Five undescribed triterpenoids, two unusual omphalane-type sesquiterpenoids together with twenty-five known compounds were isolated from the leaves and stems of Rhododendron minutiflorum Hu. The absolute configurations of 1-3 and 6 were established by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD). Compounds 6-7 feature the rare omphalane-type sesquiterpene skeleton and are verified by single-crystal X-ray diffraction analysis for the first time. In the biological activity assay, most of the triterpenoids have different degrees of inhibitory effects on alpha-glucosidase, with IC50 values ranging from 6.97 to 229.3 mu M (the positive control drug acarbose has an IC50 value of 3.07 x 10 3 mu M). Structure and activity relationship (SAR) study reveals that the oxidation degrees of C-3, C-8, or C-11 to C-13 of the ursane-type triterpenoid influence the inhibitory activity dramatically.
查看更多>>摘要：A reinvestigation of the chemical constituents of the stem barks of Scutia buxifolia, a member of the Rhamnaceae, resulted, along with the known alkaloids scutianine C and scutianene L, in the isolation of three undescribed diastereoisomeric alkaloids - scutianine N, 27-epi-scutianine N and 3, 4, 7-tri-epi-scutianine N -, one undescribed non macrocyclic alkaloid - scutianine Q - and a neutral compound -scutianene M. Their structures were determined using extensive NMR techniques and HRMS. The absolute configurations of the stereogenic centers of the three diastereoisomeric alkaloids have been assigned by gas chromatography employing modified cyclodextrins as chiral stationary phases. Scutianine Q had its structure and stereochemistry defined by single crystal X-ray crystallographic analysis. All tested compounds showed good to moderate antibacterial activity (MICs between 1.56 and 100 mu g mL-1) when evaluated in vitro against a panel of Gram-positive and Gram-negative bacteria. Some stereochemistry-activity relationships have been identified for the antibacterial activity of diastereoisomeric alkaloids against the Gram-negative bacteria Enterobacter aerogenes. The alkaloid 27-epi-scutianine N was as active as the standard antibiotic chloramphenicol (MIC = 1.56 mu g mL-1), while scutianine N and 3,4,27-tris-epi-Scutianine N were inactive (>100 mu g mL-1).
查看更多>>摘要：(+/-)-trichodermatrione A, a pair of cyclobutane-containing enantiomers with an undescribed tricyclic 6/4/6 skeleton, was isolated from Trichoderma sp. EFT2, an endophytic fungus from Euonymus fortunei (Turcz.) Hand.-Mazz (Celastraceae). The racemates were separated by chiral HPLC with the structures elucidated by a combination of MS, NMR, ECD calculation and X-ray crystallography analyses. (+/-)-trichodermatrione A and enantiomers were found to be antibacterial against phytopathogenic bacteria Xanthomonas oryzae pv. oryzae (Xoo) and X. oryzae pv. oryzicola (Xoc).
查看更多>>摘要：Seven previously undescribed cadinane sesquiterpenoids, albocinnamins A.G, were isolated from the fungus Antrodiella albocinnamomea. Their structures with absolute configurations were elucidated on the basis of extensive spectroscopic methods, as well as single crystal X-ray diffraction. Cadinane sesquiterpenoids were reported from A. albocinnamomea for the first time. All of these sesquiterpenoids possess an unusual ether ring with minor modifications. Albocinnamins D and G showed certain inhibitory activities against nitric oxide production in LPS-activated RAW264.7 macrophages with IC50 values of 26.1 and 19.2 mu M, respectively.
查看更多>>摘要：Seasonal variations of phenolic compounds, in leaves of Zostera marina L. from the Baltic Sea near Kiel/Germany were investigated. Dominant compounds were mono- and disulfated flavonoids and phenylpropanoic acids, in particular luteolin 7,3'-O-disulfate and diosmetin 7-O-sulfate as well as rosmarinic acid, a dimeric phenylpropanoid. All detected sulfated flavones showed similar seasonal trends: there were two significant concentration peaks in June and November. Moreover, two geographically distinct flavonoid chemotypes were identified based on their respective main flavonoid; one chemotype was characterized by the prevalence of luteolin 7,3'-O-disulfate (German Baltic Sea), and the other by the prevalence of diosmetin 7-O-sulfate (Norwegian North Sea). Furthermore, an undescribed tetrameric phenylpropanoid, 7 '',8 ''-didehydrosalvianolic acid B, was isolated and its structure was established by extensive NMR, MS, and CD experiments. This compound inhibited activity of Na+/K+-ATPase in the micro-molar range without any cytotoxic effects against human cancer and normal cells.
查看更多>>摘要：Four undescribed regular rosane-type diterpenoids euphominoids M-P and three undescribed rearranged rosane-type diterpenoids euphomilones C-E were isolated from the whole plants of Euphorbia milii Des Moul., along with nine known compounds. Their structures were elucidated by detailed interpretation of the NMR and mass spectroscopy. The absolute configurations were established by single-crystal X-ray diffraction experiments, as well as comparative analyses of calculated and experimental ECD spectra. Euphominoid M featured a highly oxygenated ring A and a rare four-membered oxygen ring while euphomilones C-E possessed 7/5/6 or 5/7/6 fused ring systems, which were rarely occurring in rosane-type diterpenoids. In the in-vitro bioassays, 19-norrosa1,3,5(10),15-tetraene-2,3-diol and antiquorin showed more potent alpha-glucosidase inhibitory activity than the positive control acarbose while euphominoid C exhibited significant inhibitory activity against both alpha-glucosi-dase and beta-glucuronidase. To the best of our knowledge, it was the first time that rosane-type diterpenoids were reported as beta-glucuronidase inhibitors.
查看更多>>摘要：Auxin regulates root development and is considered a potential target for improving crop yield. In this study, we identified 22 basic leucine zipper transcription factors (bZIP TFs) that responded to two concentrations (1 and 50 mu M) of indole-acetic acid (IAA) during wheat root development by transcriptome analysis. In addition, we identified 176 TabZIP genes from the wheat genome. Phylogenetic classification and gene structure analysis indicated that the 22 auxin-responsive TabZIPs were divided into groups 1 to 9 (except group 3) with different functions. Phenotypic analysis showed that knocking out Arabidopsis AtHY5, which is the homologous gene of TabZIP6D_147 (one of the downregulated auxin-responsive TabZIPs under both 1 and 50 mu M IAA that belonged to group 4), resulted in insensitivity to IAA, while the phenotype of TabZIP6D_147/hy5 complementary lines recovered to that of the wild type, suggesting that downregulated TabZIP6D_147 plays a negative role in the auxin signalling pathway. These results revealed that auxin-responsive TabZIP genes may play different roles in root architecture in the response to the two concentrations of auxin.
查看更多>>摘要：Ten siderophore-related compounds were isolated by MS/MS-based molecular networking from a mesophotic sponge-associated Streptomyces diastaticus NBU2966. Among them, there were three kinds of siderophores including three undescribed phenol/thiazoline-type compounds, thiazostatin C, methyl thiazostatin B, and pulicatin J, one undescribed phenol/oxazoline-type compound, spoxazomicin E, and one undescribed phenol/ oxazoline/thiazoline-type compound, streptochelin A, as well as five known compounds. Pulicatin J and spoxazomicin E were both isolated as a pair of inseparable epimers. The planar structures of all these compounds were determined based on the detailed NMR and HRESIMS spectroscopic analysis, and the absolute configurations of them were assigned by ECD and NMR quantum chemical calculations. Additionally, in vitro antibacterial activities, inhibition of MRSA biofilm formation, and neuroprotective activity for these compounds were tested.
查看更多>>摘要：Differences in phenolic composition across different ontogenic stages can be crucial in determining the interaction outcomes between plants and their surrounding biotic environment. In seagrasses, specific phenolic compounds have rarely been analyzed and remain unexplored in ontogenic stages other than non-reproductive adults. Furthermore, it is generally accepted that plants would prioritize defense (e.g., through increased phenolic content) on tissues or stages that are critical for plant fitness but how this affects nutritional quality or plant resources has been scarcely explored. We analyzed how phenolic composition, N and C content and carbohydrate resources varied among different life stages (i.e. old and young leaves of reproductive and nonreproductive plants, and leaves of seedlings) in the seagrass Posidonia oceanica. We identified five phenolic compounds, whose structures were established as hydroxycinnamate esters of tartaric acid. Also, our results show that in all examined ontogenic stages phenolic compounds have the same qualitative composition but inflorescences exhibit higher contents than vegetative tissues. We did not find a reduction in stored resources in reproductive plants, pointing to some kind of compensatory mechanism in the production or storage of resources. In contrast, seedlings seemed to have less phenolic compounds than reproductive plants, perhaps due to limited resources available to allocate to phenolic production. Our results demonstrate how different ontogenic stages change their investment in specialized phenolic compounds prioritizing different functions according to the needs and limitations of that stage.
查看更多>>摘要：Sixteen cassane diterpenoids (CAs), including four undescribed lactam-type, four unreported lactone-type, along with eight known ones, were isolated from the aerial parts of Caesalpinia pulcherrima (L.) Sw. Their structures were characterized by comprehensive spectroscopic analyses (including NMR and HRESIMS). The absolute configuration of pulcherritam A was finally established by single-crystal X-ray diffraction with Cu K alpha radiation. Notably, pulcherritam s A-D were elucidated as a group of rare CAs bearing an alpha, beta-unsaturated gamma-lactam ring rather than a typical lactone moiety. Almost all compounds were examined for their antibacterial. The results reveal that pulcherritam H exhibited significant antibacterial activities against Bacillus cereus, Staphylococcus aureus, as well as Pseudomonas syringae pv. actinidae (Psa) with the MIC from 6.25 to 12.5 mu M, while pulcherritams A and C displayed potent antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA). Then, all isolates were evaluated for their anti-glioblastoma activities. Pulcherritam A and Pulcherrimin G illustrated moderate inhibitory activity against glioblastoma multiforme (GBM) U87MG cell, and the other compounds did not show obvious inhibitory activity against GBM U87MG cell. Furthermore, the preliminary structure-activity relationship and their biosynthetic pathway were also discussed.
NSTL
Elsevier