In addition to six known phenanthroindolizidine alkaloids, eight new alkaloids, namely, ficuseptines B-D (1-3), 10R,13aR-tylophorine N-oxide (4), 10R,13aR-tylocrebrine N-oxide (5), 10S,13aR-tylocrebrine N-oxide (6), 10S,13aR-isotylocrebrine N-oxide (7), and 10S,13aS-isotylocrebrine N-oxide (8), were isolated from a methanol extract of the stems of Ficus septica. The structures of the new compounds were elucidated by means of spectroscopic data interpretation. Cytotoxicity of some of these alkaloids was assessed in vitro using the HONE-1 and NUGC cell lines.
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http://dx.doi.org/10.1021/np050095o | DOI Listing |
J Food Drug Anal
December 2023
School of Pharmacy, College of Medicine, National Taiwan University, Taipei 10050, Taiwan.
Phytochemistry
May 2024
Vineland Research and Innovation Centre, 4890 Victoria Ave North, Box 4000, Vineland Station, Ontario, L0R 2E0, Canada; Department of Biological Sciences, Brock University, 1812 Sir Isaac Brock Way, St Catharines, Ontario, L2S 3A1, Canada. Electronic address:
Front Chem
September 2023
College of Pharmacy, Seoul National University, Seoul, Republic of Korea.
The formation of -heterocycles with multiple substituents is important in organic synthesis. Herein, we report a novel method for the construction of functionalized dihydropyridinone rings through the annulation of an amide -carbon with a tethered alkyne moiety. The reaction of the amide with the alkyne was achieved via -silyl ,-ketene acetal formation and silver-mediated addition.
View Article and Find Full Text PDFOrg Biomol Chem
October 2023
Department of Chemistry & Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada.
A rapid total synthesis of seco-phenanthroindolizidine alkaloids was achieved involving a one-pot acid catalyzed deprotection- condensation-electrocyclization strategy. This synthetic route provided a concise synthesis of (±)-seco-antofine and (±)-septicine in only 4 steps with an overall yield of 22% and 17%, respectively.
View Article and Find Full Text PDFOrg Lett
July 2023
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
We report a concise approach to phenanthroindolizidine alkaloids, wherein strained azacyclic alkynes are intercepted in Pd-catalyzed annulations. Two types of strained intermediates were evaluated: a functionalized piperidyne and a new strained intermediate, an indolizidyne. We show that each can be employed, ultimately allowing access to three natural products: tylophorine, tylocrebine, and isotylocrebine.
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