Seven rarely spirooxindole alkaloids, voagafricines A-G (1-7) were isolated from the stem barks of Voacanga africana. Their structures were unambiguously elucidated by comprehensive spectroscopic data and electronic circular dichroism (ECD) analyses. 1 and 2 possess a unique indoleone system in conjugation with a 3,4'-decahydroquinoline spiral ring originating from seco-quinolhiddin core of the precursor, furthermore 1 undergo decarburization formed a novel C-3-nor monoterpenoid indole. All isolates were evaluated for their antibacterial activities against MBLs producing Escherichia coli strains. Compounds 1 and 7 were found to be potent inhibitors against E. coli 298 and 140 by targeting biofilm. Possible interaction sites of 1 and 7 with biofilm were preliminarily explored by means of molecular docking.
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http://dx.doi.org/10.1016/j.bioorg.2023.106780 | DOI Listing |
Phytochemistry
March 2025
School of Pharmaceutical Science & Yunnan Provincial Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, 650500, China; Yunnan College of Modern Biomedical Industry, Kunming Medical University, Kunming, 650500, China. Electronic address:
Voagafries A-E, five undescribed monoterpenoid indole alkaloids (MIAs), were isolated from the stem bark of Voacanga africana. Voagafrie A (1) has a unique 6/5/5/6/6 spiral ring skeleton with an indolone-fused 9-oxo-3-aza-tricyclo[6,3,1,0]-12-alkane-10-carbonyllactone. Voagafrie B (2) is a rare 5,6-seco diazine scaffold, whereas voagafrie C (3) possesses an octahydropyrrolo[2,3-b] pyrrole-fused 2,8-diazabicyclo[3.
View Article and Find Full Text PDFBioorg Chem
November 2023
School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650500, China. Electronic address:
Seven rarely spirooxindole alkaloids, voagafricines A-G (1-7) were isolated from the stem barks of Voacanga africana. Their structures were unambiguously elucidated by comprehensive spectroscopic data and electronic circular dichroism (ECD) analyses. 1 and 2 possess a unique indoleone system in conjugation with a 3,4'-decahydroquinoline spiral ring originating from seco-quinolhiddin core of the precursor, furthermore 1 undergo decarburization formed a novel C-3-nor monoterpenoid indole.
View Article and Find Full Text PDFACS Omega
August 2023
Department of Chemistry, University at Albany, State University of New York, 1400 Washington Ave, Albany, New York 12222, United States.
Plant seeds are a renewable resource that can furnish access to medicinal natural products that can only otherwise be isolated from aerial or root parts, the harvest of which may be destructive to the plant or threaten its viability. However, optimization of the isolation of such compounds from seeds would be greatly assisted if the spatial distribution of the molecules of interest within the plant tissue were known. For example, iboga alkaloids that hold promise for the treatment of opioid use disorder are typically isolated from the leaves, bark, or roots of or spp.
View Article and Find Full Text PDFInsects
November 2022
Department of Animal Biology and Physiology, Faculty of Science, University of Yaounde I, Yaoundé P.O. Box 812, Cameroon.
and several Africa-native species are serious constraints to fruit production in sub-Saharan Africa. A long-term trapping and fruit collection study was conducted (2011-2016) in two contrasting agro-ecological zones (AEZs) of Cameroon to determine fruit fly species composition, seasonality, attraction to various lures and baits, and fruit infestation levels. Ten tephritid species from genera , , , and were captured in traps.
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September 2022
Department of Chemistry, University of California-Davis, Davis, California 95616, United States.
The energetic viability of the previously proposed biogenetic pathway for the formation of two unique monoterpenoid indole alkaloids, voacafricine A and B, which are present in the fruits of , was investigated using density functional theory computations. The results of these calculations indicate that not only is the previously suggested pathway not energetically viable but also that an alternative biosynthetic precursor is likely.
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