Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis.
A new meroditerpene, sartorypyrone C (5), was isolated, together with the known tryptoquivalines L (1a), H (1b), F (1c), 3'-(4-oxoquinazolin-3-yl) spiro [1H-indole-3,5']-2,2'-dione (2) and 4(3H)-quinazolinone (3), from the culture of the marine sponge-associated fungus Neosartorya paulistensis (KUFC 7897), while reexamination of the fractions remaining from a previous study of the culture of the diseased coral-derived fungus N. laciniosa (KUFC 7896) led to isolation of a new tryptoquivaline derivative tryptoquivaline T (1d). Compounds 1a-d, 2, 3, and 5, together with aszonapyrones A (4a) and B (4b), chevalones B (6) and C (7a), sartorypyrones B (7b) and A (8), were tested for their antibacterial activity against four reference strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa), as well as the environmental multidrug-resistant isolates. Only aszonapyrone A (4a) and sartorypyrone A (8) exhibited significant antibacterial activity as well as synergism with antibiotics against the Gram-positive multidrug-resistant strains. Antibiofilm assays of aszonapyrone A (4a) and sartorypyrone A (8) showed that practically no biofilm was formed in the presence of their 2× MIC and MIC. However, the presence of a sub-inhibitory concentration of ½ MIC of 4a and 8 was found to increase the biofilm production in both reference strain and the multidrug-resistant isolates of S. aureus.
ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, Porto 4050-313, Portugal. ngomes@ciimar.up.pt.
Nelson M
NM
Gomes
ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, Porto 4050-313, Portugal. lbessa@ciimar.up.pt.
Lucinda J
LJ
Bessa
ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, Porto 4050-313, Portugal. nokrari_209@hotmail.com.
Suradet
S
Buttachon
ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, Porto 4050-313, Portugal. pmcosta@icbas.up.pt.
Paulo M
PM
Costa
Division of Environmental Science, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand. jbuaruang@ru.mail.go.th.
Jamrearn
J
Buaruang
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand. agrtdd@ku.ac.th.
Tida
T
Dethoup
Departamento de Química, Universidade de Aveiro, Aveiro 4810-1933, Portugal. artur.silva@ua.pt.
Artur M S
AM
Silva
ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, Porto 4050-313, Portugal. ankijjoa@icbas.up.pt.
Anake
A
Kijjoa
D000818:Animals; D000900:Anti-Bacterial Agents / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D018441:Biofilms / Q000187:drug effects; D004224:Diterpenes / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D024901:Drug Resistance, Multiple, Bacterial; D004357:Drug Synergism; D007211:Indoles / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D055326:Neosartorya / Q000737:chemistry; D011161:Porifera / Q000382:microbiology; D012988:Soil Microbiology
D000900:Anti-Bacterial Agents; D004224:Diterpenes; D007211:Indoles; C010522:tryptoquivaline