TY - JOUR
T1 - Synthesis, Characterization, and Bioactivity of the Lichen Pigments Pulvinamide, Rhizocarpic Acid, and Epanorin and Congeners
AU - James, Patrick J.C.
AU - Vuong, Daniel
AU - Moggach, Stephen A.
AU - Lacey, Ernest
AU - Piggott, Matthew J.
N1 - Funding Information:
We thank Dr. G. Nealon of the Centre for Microscopy Characterisation and Analysis, University of Western Australian, for assistance with NMR spectra, and S. Sala for help acquiring mass spectra. This research was funded, in part, by the Australian Cooperative Research Centres Projects scheme (CRCPFIVE000119).
Publisher Copyright:
© 2023 American Chemical Society and American Society of Pharmacognosy.
PY - 2023/3/24
Y1 - 2023/3/24
N2 - The lichen natural products pulvinamide, rhizocarpic acid, and epanorin have been synthesized and characterized spectroscopically and by X-ray crystallography. The syntheses, by ring-opening of pulvinic acid dilactone (PAD), may well be biomimetic, given the well-known occurrence of PAD in lichen. The enantiomers, ent-rhizocarpic acid and ent-epanorin, and corresponding carboxylic acids, norrhizocarpic acid and norepanorin, were similarly prepared. All compounds were assessed for growth inhibitory activity against selected bacteria, fungi, a protist, a mammalian tumor cell line, and normal cells. Rhizocarpic acid is weakly antibacterial (Bacillus subtilis MIC = 50 μg/mL) and possesses modest but selective antitumor activity (NS-1 murine myeloma MIC = 3.1 μg/mL) with >10-fold potency relative to its enantiomer (MIC = 50 μg/mL).
AB - The lichen natural products pulvinamide, rhizocarpic acid, and epanorin have been synthesized and characterized spectroscopically and by X-ray crystallography. The syntheses, by ring-opening of pulvinic acid dilactone (PAD), may well be biomimetic, given the well-known occurrence of PAD in lichen. The enantiomers, ent-rhizocarpic acid and ent-epanorin, and corresponding carboxylic acids, norrhizocarpic acid and norepanorin, were similarly prepared. All compounds were assessed for growth inhibitory activity against selected bacteria, fungi, a protist, a mammalian tumor cell line, and normal cells. Rhizocarpic acid is weakly antibacterial (Bacillus subtilis MIC = 50 μg/mL) and possesses modest but selective antitumor activity (NS-1 murine myeloma MIC = 3.1 μg/mL) with >10-fold potency relative to its enantiomer (MIC = 50 μg/mL).
UR - http://www.scopus.com/inward/record.url?scp=85149939192&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.2c01013
DO - 10.1021/acs.jnatprod.2c01013
M3 - Article
C2 - 36897305
AN - SCOPUS:85149939192
SN - 0163-3864
VL - 86
SP - 550
EP - 556
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 3
ER -