TY - JOUR
T1 - New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.
AU - Shang, Zhuo
AU - Li, Li
AU - Espósito, Breno P.
AU - Salim, Angela A.
AU - Khalil, Zeinab G.
AU - Quezada, Michelle
AU - Bernhardt, Paul V.
AU - Capon, Robert J.
PY - 2015/7/28
Y1 - 2015/7/28
N2 - Chemical analysis of a marine-derived fungus, Chaunopycnis sp. (CMB-MF028), isolated from the inner tissue of a pulmonate false limpet Siphonaria sp., collected from rock surfaces in the intertidal zone of Moora Park, Shorncliffe, Queensland, yielded the tetramic acid F-14329 (1) and new analogues, chaunolidines A-C (2-4), together with the new pyridinone chaunolidone A (5), and pyridoxatin (6). Structures inclusive of absolute configurations were assigned to 1-6 on the basis of detailed spectroscopic analysis, X-ray crystallography, electronic circular dichroism (ECD), biosynthetic considerations and chemical interconversion. Chaunolidine C (4) exhibits modest Gram-positive antibacterial activity (IC50 5-10 μM), while chaunolidone A (5) is a selective and potent inhibitor (IC50 0.09 μM) of human non-small cell lung carcinoma cells (NCI-H460). Tetramic acids 1-4 form metal chelates with Fe(iii), Al(iii), Cu(ii), Mg(ii) and Zn(ii).
AB - Chemical analysis of a marine-derived fungus, Chaunopycnis sp. (CMB-MF028), isolated from the inner tissue of a pulmonate false limpet Siphonaria sp., collected from rock surfaces in the intertidal zone of Moora Park, Shorncliffe, Queensland, yielded the tetramic acid F-14329 (1) and new analogues, chaunolidines A-C (2-4), together with the new pyridinone chaunolidone A (5), and pyridoxatin (6). Structures inclusive of absolute configurations were assigned to 1-6 on the basis of detailed spectroscopic analysis, X-ray crystallography, electronic circular dichroism (ECD), biosynthetic considerations and chemical interconversion. Chaunolidine C (4) exhibits modest Gram-positive antibacterial activity (IC50 5-10 μM), while chaunolidone A (5) is a selective and potent inhibitor (IC50 0.09 μM) of human non-small cell lung carcinoma cells (NCI-H460). Tetramic acids 1-4 form metal chelates with Fe(iii), Al(iii), Cu(ii), Mg(ii) and Zn(ii).
UR - http://www.scopus.com/inward/record.url?scp=84936861738&partnerID=8YFLogxK
U2 - 10.1039/c5ob01058f
DO - 10.1039/c5ob01058f
M3 - Article
C2 - 26107107
AN - SCOPUS:84936861738
VL - 13
SP - 7795
EP - 7802
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
SN - 1477-0520
IS - 28
ER -
