Abstract Phytochemical investigation of the stem bark of Diospyros longiflora yielded longiflorol ( 1 ), a new bergenin α - d -apioside, together with bergenin ( 2 ) and five known compounds: lupeol ( S1 ), betulin ( S2 ), betulinic acid ( S3 ), stigmasterol ( S4 ) and stigmasterol glucoside ( S5 ). Their structures were determined by one-dimensional (1D) and 2D nuclear magnetic resonance experiments along with electrospray ionization high-resolution mass spectrometry and extended density-functional theory calculations of chiroptical properties. Longiflorol ( 1 ) and bergenin ( 2 ) were evaluated for their DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidant activity, with the crude extract for comparison and ascorbic acid as standard. The results showed that the extract and 2 had good antioxidant activity, whereas 1 showed only moderate activity at high concentration (>2 mg mL −1 ).
Three new alkaloids, janetinine (1a), pleiokomenine A (2), and huncaniterine B (3a), and 13 known compounds, pleiomutinine (3b), huncaniterine A (3c), 1-carbomethoxy-β-carboline (4), evoxanthine (5), deformyltalbotine acid lactone (6), pleiocarpamine (7), N4-methyl-10-hydroxygeissoschizol (8), spegatrine (9), neosarpagine (10), aspidofractinine (11), N1-methylkopsinin (12), pleiocarpine (13), and N1-methylkopsinin-N4-oxide (14), were isolated from the stem bark of Pleiocarpa pycnantha. Janetinine (1a) is a carbazole alkaloid; in pleiokomenine A (2), two aspidofractinine-type alkaloids are bridged by a methylene unit in an unprecedented way, and huncaniterine B (3a) is a pleiocarpamine–aspidofractinine-type dimer. The structures and relative configurations of these compounds were elucidated on the basis of NMR and MS analyses. Their absolute configurations were defined by means of experimental and calculated ECD data, and additionally, the structures of 5 and 13 were determined by single crystal X-ray diffraction. Compounds 1a, 2, 3b, 4, 6, 9, and 12 displayed cancer chemopreventive properties through either quinone reductase induction (CD = 30.7, 30.2, 29.9, 43.5, and 36.7 μM for 1a, 4, 6, 9, and 12, respectively) and/or NF-κB inhibition with IC50 values of 13.1, 8.4, 9.4, and 8.8 μM for 2, 3b, 6, and 12, respectively.
An enzyme-catalyzed synthesis of rhododendrol, an intermediate in the production of raspberry ketone, was investigated. The approach involves the enzymatic hydrolysis of rhododendrol glycosides into rhododendrol and a glycosidic residue. Rhododendrol glycosides, which are naturally derived from the inner bark of birch trees─a renewable resource─vary considerably in composition depending on the origin of the plants. In this study, mixtures of betuloside and apiosylrhododendrin from natural resources were used in different proportions. An in-depth study was conducted to assess the feasibility of the process. A mathematical model was developed based on studies of the kinetics and operational stability of the enzyme. The model for betuloside hydrolysis catalyzed by β-glucosidase was validated in batch, repetitive batch, and ultrafiltration membrane reactors. The highest productivity, ranging from 83.9 to 94.5 g L–1 day–1, was achieved in the latter. After screening nearly 50 enzymes, RAPIDASE emerged as a solution for the hydrolysis of apiosylrhododendrin, and the model was validated in a batch reactor. Model-based optimization enabled the prediction of input parameters for different compositions of biogenic rhododendrol glycosides to obtain consistent process output metrics.
Many secondary metabolites derived from Rumex extracts exhibited potent activities against a panel of phytopathogens including those of Phytophthora spp. Phytochemical investigation of Rumex abyssinicus has led to the isolation of nine compounds, including one phenolic acid (1), five anthraquinones (2–6) and three flavanols (7–9). Compounds 1, 4, 6–9 are reported here from R. abyssinicus for the first time. The isolated compounds were evaluated for their inhibitory activity against zoospores of the oomycete phytopathogen Phytophthora capsici. Physcion (3) displayed strongest motility inhibitory activity with a MIC value of 15 μg mL− 1, and showed lytic activities against zoospores at 500 μg mL− 1.
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