查看更多>>摘要：Phaeosphspirone, an undescribed polyketide with a unique 6/5/5/6-fused tetracyclic system, and two known analogues, herbarin and O-methylherbarin, were purified from the endophytic fungus Phaeosphaeriaceae sp. isolated from the desert plant Bassia dasyphylla. The connectivity and relative configuration of phaeosphspirone was elucidated by comprehensive HR-ESI-MS and NMR analysis together with a computer-assisted structure elucidation (CASE) method. A pair of enantiomers existing in phaeosphspirone were separated by HPLC chromatography after reacting with chiral reagents, from which the absolute configuration of phaeosphspirone was simultaneously determined based on Mosher's rule. This tandem strategy provides a useful approach for the separation and stereochemical determination of enantiomers possessing secondary hydroxyl groups. The structural feature of phaeosphspirone, herbarin and O-methylherbarin together with gene cluster analysis suggested their polyketide biosynthetic origin. Herbarin and O-methylherbarin exhibited moderate cytotoxicity against three cancer cell lines.
查看更多>>摘要：Ganorbifates C-I, seven undescribed biosynthetically related polyoxygenated 3,4-seco-27-norlanostanoid congeners, were isolated from the edible mushroom, Ganoderma orbiforme. Ganorbifate C features a unique cyclo-butene ring constructed at C19/C11, and both D and E incorporate an unusual cyclopropane ring formed by C -19/C-9 linkage. Their structures, including the absolute configurations, were determined by spectroscopic methods and ECD calculations. The proposed Norrish-Yang cyclization-based key biosynthetic pathway for ganorbifates C-E is revealed by density functional theory (DFT) calculations. The computational studies uncover the formation of both cyclobutene and cyclopropane rings in the isolates and the stereoselectivity centers of these steps are consistent with those in the natural products. All compounds exhibited NO generation inhibition in LPS-induced BV-2 microglial cells, among them ganorbifate C was the most promising one with the IC50 values of 4.37 mu M.
Asl, Saeed SoleimaniKarkhane, Ali AsgharAmirzakaria, Javad ZamaniNoghabi, Kambiz Akbari...
10页
查看更多>>摘要：Demands for peroxidases (POX)s with diverse physicochemical properties have steadily grown as more applications of POXs are demonstrated. Plants are among the best sources of versatile POXs, and plant biotechnology, as an agricultural hassle-free technology, promises to circumvent the limitations of natural resource exploitation and to address the demands. Following this trend, it was shown that POX production steadily increased during the 31-day subculture of Alkanna frigida (from Boraginaceae) callus on Murashige-Skoog medium containing 2,4dichlorophenoxyacetic acid (10-6 M) and kinetin (10-5 M). The purified cationic enzyme (POXalf) maintained its optimal activity over pH 4-7 for 2 years. It was resistant to H2O2 high concentrations (IC50 = 543.7 mM) and showed high specific activity in the reaction with phenol (4320.5 AU mg-1 > 20-fold of HRP AU). Furthermore, the specificity constant ratio of guaiacol to phenol indicated a 100 times faster reaction of POXalf with guaiacol. However, in contrast to HRP, it had little effect on diazo derivatives of aniline and meta-diaminobenzene. Based on the resulting primary structure from the tandem mass analysis, the POXalf 3D structure was constructed via homology modelling. Despite the high topological similarity between the HRP and POXalf structures, there were important differences between the active site pockets that could explain the observed differences in the corresponding substrate spectra and the specific activities. Considering the dynamics of POXalf production, its inactivity towards IAA and its high affinity for guaiacol, POXalf may have associated roles with A. frigida cell wall construction and monolignol metabolism.
查看更多>>摘要：Eight undescribed polyhydroxylated bergamotane-type sesquiterpenoids with bicyclic, tricyclic and tetracyclic systems, namely sporulamides A-D, sporulosoic acids A-B and sporuloketals A-B, along with three known analogs were isolated from cultures of the marine mud-associated fungus Paraconiothyrium sporulosum YK-03. The chemical structures of these sesquiterpenoids were elucidated by the extensive spectroscopic techniques of NMR and HR-ESI-MS. Assisted by the X-ray crystallography analysis and electronic circular dichroism (ECD) spectroscopic calculation and comparison, their absolute configurations were established. Sporuloketals A-B represent two rare tetracyclic bergamotanes. It's the first time that ECD empirical rules have been successfully verified and applied for determining the absolute configurations of these bergamotane-type sesquiterpenoids.
查看更多>>摘要：Seven undescribed pregnane glycosides named amurensides A-G and two known aglycones were isolated from the whole herb of Adonis amurensis Regel & Radde. Their structures were established based on 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and acid hydrolysis. The cytotoxicity of all compounds against three tumor cell lines (HepG2, Caco-2, and A549) were evaluated. Among them, amurensides A-C and E showed moderate inhibitory effects on the growth of HepG2 cells, with IC50 values ranging from 15.6 to 48.7 mu M (sorafenib, 7.5 +/- 1.9 mu M). Amurensides A, D and F displayed inhibitory effects on the growth of A549 cells with IC50 values of 18.8 +/- 1.2, 12.4 +/- 0.6, and 30.4 +/- 0.1 mu M (cis-platinum, 6.1 +/- 0.1 mu M), respectively.
查看更多>>摘要：This work focusses on the chemical diversification of an Ambrosia tenuifolia extract and its bioguided fractionation, aiming to unveil the chemical entity responsible for the trypanocidal activity. Besides, a revision of the phytochemical study of this species, based on previous reports of the antiparasitic psilostachyins A and C as main compounds, was conducted. To improve the biological properties of a plant extract through a simple chemical reaction, the oxidative diversification of the dichloromethane extract of this plant species was carried out. A bioguided fractionation of a chemically modified extract was performed by evaluating the inhibitory activity against Trypanosoma cruei trypomastigotes. This experiment led to the isolation of one of the most active compounds. In general terms, epoxidized metabolites were obtained as a result of the oxidation of the major metabolite of the species. The trypanocidal activity of some tested metabolites overperformed the reference drug, benznidazole, displaying no cytotoxicity at trypanocidal concentrations. Key structure-activity relationships were obtained for designing previously undescribed antiparasitic sesquiterpene lactones.
Jo, Yang HeeLee, SolipYeon, Sang WonRyu, Se Hwan...
9页
查看更多>>摘要：The composition of a plant, together with its efficacy, vary depending on its maturity and plant parts. In this study, the chemical constituents of immature fruits of Maclura tricuspidata (Moraceae) were investigated together with their anti-diabetic and antioxidant effects. A total of 34 compounds were isolated from the immature fruits of M. tricuspidata using various chromatographic methods. Structure elucidation using extensive spectroscopic analysis led to the characterization of isolated compounds as isoflavonoids with prenyl substituents. Among them, macluraisoflavones A-O were first isolated from nature. The anti-diabetic and antioxidant activity of the isolated compounds were also suggested by alpha-glucosidase inhibitory activity and DPPH radical scavenging activity, respectively. In particular, macluraisoflavone I, an isoflavonoid with 2,2-dimethylpyran and 2-hydroperoxy-3-methylbut-3-enyl moieties, showed potent alpha-glucosidase inhibitory activity and DPPH radical scavenging activity. Further molecular docking analysis suggested hydrogen bond and alkyl interactions between alpha-glucosidase and macluraisoflavone I. Therefore, the immature fruits of M. tricuspidata can be used as an important natural product with antioxidant and anti-diabetic properties.
查看更多>>摘要：The Gretchen Hagen 3 (GH3) genes encoding proteins belonging to the ANL superfamily are widespread in the plant kingdom. The ANL superfamily consists of three groups of adenylating enzymes: aryl- and acyl-CoA synthetases, firefly luciferase, and amino acid-activating adenylation domains of the nonribosomal peptide synthetases (NRPS). GH3s are cytosolic, acidic amidosynthetases of the firefly luciferase group that conjugate auxins, jasmonates, and benzoate derivatives to a wide group of amino acids. In contrast to auxins, which amide conjugates mainly serve as a storage pool of inactive phytohormone or are involved in the hormone degradation process, conjugation of jasmonic acid (JA) results in biologically active phytohormone jasmonyl-isoleucine (JAIle). Moreover, GH3s modulate salicylic acid (SA) concentration by conjugation of its precursor, isochorismate. GH3s, as regulators of the phytohormone level, are crucial for normal plant development as well as plant defense response to different abiotic and biotic stress factors. Surprisingly, recent studies indicate that FIN219/JAR1/ GH3.11, one of the GH3 proteins, may act not only as an enzyme but is also able to interact with tau-class glutathione S-transferase (GSTU) and constitutive photomorphogenic 1 (COP1) proteins and regulate light and stress signaling pathways. The aim of this work is to summarize our current knowledge of the GH3 family.
查看更多>>摘要：During our continuous investigation of natural, herbal inhibitors of microglial over-activation in the Euphorbiaceae family, two plants of the Vernicia genus showed remarkable inhibitory effects on nitric oxide (NO) production in over-activated microglia. In this study, bioactivity-guided phytochemical research on the active fraction of the roots of V. montana was carried out. As a result, seven undescribed terpenoids and lignans, together with thirty-one known components, were isolated and identified using comprehensive spectral analysis. All the identified compounds were evaluated for their inhibitory effects on NO production in lipopolysaccharidestimulated BV-2 cells. Combined with our previous research on the Vernicia genus, the effective material basis of different plants and medicinal components was analyzed systematically.
查看更多>>摘要：Nauclea pobeguinii is traditionally used for treatment of malaria. Previous studies on the plant extract and strictosamide, the putative active constituent, showed a profound in vivo activity of the extract but no in vitro activity of strictosamide. This might indicate that one or more compounds present in the extract, most likely alkaloids, act as prodrugs undergoing biotransformation after oral administration resulting in the active compounds. The phytochemical composition of a N. pobeguinii extract was characterized using UHPLC-UV-HRMS (Ultrahigh-Performance Liquid Chromatography-Ultraviolet-High Resolution Mass Spectrometry) data. An in vitro gastrointestinal model was used to simulate biotransformation of the extract allowing monitoring of the relative abundances of individual constituents over time on one hand, while antiplasmodial activity and cytotoxicity of the biotransformed extract could be evaluated on the other hand. A diversity of compounds was (tentatively) identified in the extract, mainly saponins and alkaloids, including 32 compounds that have not been reported before in N. pobeguinii. The automated data analysis workflow used for unbiased screening for metabolites showed that glycosylated compounds decreased in intensity over time. Alkaloids containing no sugar moieties, including angustine-type alkaloids, showed no gastrointestinal biotransformation. In vitro gastrointestinal biotransformation of strictosamide did not result in a major metabolite. Moreover, multivariate data analysis using Orthogonal Partial Least Square-Discriminant Analysis (OPLS-DA) showed no in vitro activity of strictosamide or its metabolites suggesting that other compounds or metabolites present in the extract are responsible for the antiplasmodial effect of the N. pobeguinii extract. The OPLS-DA proposes alkaloids with a beta-carboline moiety as active principles, suggesting that antiplasmodial activity of N. pobeguinii derives from an additive or synergistic effect of multiple minor alkaloids and their metabolites present in the bark extract of N. pobeguinii.
NSTL
Elsevier