AI Article Synopsis

  • Two new phenanthroquinolizidine alkaloids and a new piperidine derivative were isolated from plant leaves, along with three known alkaloids, and their structures were characterized using advanced spectral techniques.
  • The absolute configurations of the new compounds were confirmed through comparison of experimental and calculated circular dichroism data.
  • The isolated compounds were tested for cytotoxicity against various cancer cell lines, with the new alkaloid showing particularly strong inhibition against KB and HepG-2 cancer cells.

Article Abstract

Two new phenanthroquinolizidine alkaloids (1: and 2: ) and a new piperidine derivative (3: ) were isolated from the leaves of aff. together with 3 known alkaloids: julandine (4: ), cryptopleurine (5: ), and 1,3,6,6-tetramethyl-5,6,7,8-tetrahydro-isoquinolin-8-one (6: ). Their structures were determined by spectral data analyses including mass spectrometry and 2-dimensional nuclear magnetic resonance data. The absolute configurations of 1: -3: were established by comparison of their experimental circular dichroism data with the calculated electronic circular dichroism spectra. The isolated compounds were evaluated for their cytotoxicity against 4 cancer cell lines: KB (mouth epidermal carcinoma cells), HepG-2 (human liver hepatocellular carcinoma cells), LU-1 (human lung adenocarcinoma cells), and MCF-7 (human breast cancer cells). The new phenanthroquinolizidine pileamartine D (2: ) showed strong and selective proliferation inhibition toward KB and HepG-2 cells with IC values of 25 and 27 nM, respectively. Pileamartine C (1: ), julandine (4: ), and cryptopleurine (5: ) exhibited cytotoxicity against 4 tested cancer cell lines with IC values less than 1 µM.

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http://dx.doi.org/10.1055/a-0826-0483DOI Listing

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Article Synopsis
  • Two new phenanthroquinolizidine alkaloids and a new piperidine derivative were isolated from plant leaves, along with three known alkaloids, and their structures were characterized using advanced spectral techniques.
  • The absolute configurations of the new compounds were confirmed through comparison of experimental and calculated circular dichroism data.
  • The isolated compounds were tested for cytotoxicity against various cancer cell lines, with the new alkaloid showing particularly strong inhibition against KB and HepG-2 cancer cells.
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An efficient synthesis of functionalized quinolizidines was developed from an enantiomerically enriched γ-nitroketone, which is easily prepared by an organocatalytic ketone-nitroalkene Michael addition. Oxidative ring expansion of the nitroketone followed by reductive ring-opening leads to a suitably functionalized nitrodiol which is an intermediate to the title compounds.

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Four enantiomerically pure monoseco-analogues, 5, 7, 9, and 11, of the phenanthroquinolizidine alkaloid julandine (1) and four of congener cryptopleurine (2), viz. compounds 6, 8, 10, and 12, have been prepared and subjected to preliminary biological evaluation. These analogues show dramatically reduced cytotoxicity compared with the parent system 2 but they are, nevertheless, potent anti-angiogenic agents.

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