Populations of bloodroot [Sanguinaria canadensis L. (Papaveraceae)] are found throughout the eastern forests of North America, with particular abundance in the southern Appalachian Mountains. Increasingly, it is finding use in Europe as a nonantibiotic animal feed supplement to promote weight gain. As efforts to cultivate this herb are underway, there is a need to understand the effect of agronomic permutations on both the dry mass rhizome yield and the yield of benzophenanthridine alkaloids. Month-to-month variability of the concentration of the alkaloids sanguinarine and chelerythrine in both cultivated and wildcrafted bloodroot was examined. The alkaloid yield was consistently higher, but more variable, in wildcrafted plants. On average, cultivated rhizomes were both larger and more consistently sized than those that were wildcrafted. The concentration of a suite of trace elements was measured in soil that was collected concomitantly with each plant accession. Differences in element profiles were compared against alkaloid yields.
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http://dx.doi.org/10.1021/jf062498f | DOI Listing |
Microb Cell Fact
June 2024
State Key Laboratory of Microbial Metabolism, School of Life Sciences and Biotechnology, Shanghai Jiao Tong University, 800 Dongchuan Rd, Shanghai, 200240, China.
Background: Chelerythrine is an important alkaloid used in agriculture and medicine. However, its structural complexity and low abundance in nature hampers either bulk chemical synthesis or extraction from plants. Here, we reconstructed and optimized the complete biosynthesis pathway for chelerythrine from (S)-reticuline in Saccharomyces cerevisiae using genetic reprogramming.
View Article and Find Full Text PDFMolecules
July 2022
College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024, China.
Chelerythrine (CH) and ethoxychelerythrine (ECH) are chemical reference substances for quality control of Chinese herbal medicines, and ECH is the dihydrogen derivative of CH. In this study, their fluorescence and absorption spectra, as well as their structural changes in different protic solvents were compared. It was observed that their emission fluorescence spectra in methanol were almost the same (both emitted at 400 nm), which may be attributed to the nucleophilic and exchange reactions of CH and ECH with methanol molecules with the common product of 6-methoxy-5,6-dihydrochelerythrine (MCH).
View Article and Find Full Text PDFJ Org Chem
November 2021
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600036, India.
The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes.
View Article and Find Full Text PDFFitoterapia
October 2020
Department of Chemistry, Maseno University, Maseno, Kenya.
A systematic analysis of the root bark of Zanthoxylum chalybeum was conducted to establish the antidiabetic potential of isolated compounds based on its ethnomedicinal use to manage diabetes. Chromatographic separation of alkaloid extracts led to isolation of three undescribed amides, chaylbemide A (1), chalybemide B (2) and chalybemide C (3) alongside the known fagaramide (4); four known benzophenanthridine alkaloids skimmianine (5), norchelerythrine (6), 6-acetonyldihydrochelerythrine (7) and 6-hydroxy-N-methyl decarine (8). The alkaloid free extracts yielded three known lignans, ailanthoidol (9), 2,3-epoxy-6,7-methylenedioxy coniferyl alcohol (10), sesamine (11), together with five known triterpenoids, lupeol (12), lupanone (13), 3α,20-dihydroxy-28-lupanoic acid (14), 20-hydroxy-3-oxo-28-lupanoic acid (15) and 3α,20,28-trihydroxylupane (16).
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2020
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN, 47405, USA.
We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent.
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