title: Tulipaline A: structure-activity aspects as a nematicide and V-ATPase inhibitor.
abstract: Carbonyl groups are known to form covalent adducts with endogenous proteins, but so far, their nematicidal mechanism of action of has been overlooked. The nematicidal activity of ten lactones was tested in vitro against the root knot nematodes Meloidogyne incognita and Meloidogynearenaria. In particular, the saturated lactones α-methylene-γ-butyrolactone or tulipaline A (1) and γ-butyrolactone (3) were active against M. incognita with an EC50/48h of 19.3±10.0 and 40.0±16.2mg/L respectively. Moreover the α, β-unsaturated lactone 5,6-dihydro-2H-pyran-2-one (2) exhibited the strongest nematicidal activity against the two species with EC50/48h 14.5±5.3 and 21.2±9.7mg/L respectively. Here we propose that the toxic effects of lactones and aldehydes on M.incognita and M. arenaria might be a consequence of their vacuolar-type H(+)-ATPase (V-ATPase) inhibition activity; in fact α-methylene-γ-butyrolactone (1) and salicylaldehyde (12) produced an increased pH in lysosomal-like organelles on HeLa human cell line and this alteration was most likely related to a V-ATPase impairment.
authors: Department of Life and Environmental Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, Italy. Electronic address: caboni@unica.it.
authors: Pierluigi
authors: P
authors: Caboni
authors: Department of Life and Environmental Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, Italy.
authors: Laura
authors: L
authors: Tronci
authors: Department of Life and Environmental Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, Italy.
authors: Barbara
authors: B
authors: Liori
authors: Department of Life and Environmental Sciences, University of Cagliari, via Ospedale 72, 09124 Cagliari, Italy.
authors: Graziella
authors: G
authors: Tocco
authors: Institute for Plant Protection, C.N.R., via G. Amendola 122/D, 70126 Bari, Italy.
authors: Nicola
authors: N
authors: Sasanelli
authors: Department of Biomedical Sciences, University of Cagliari, Monserrato, Italy.
authors: Andrea
authors: A
authors: Diana
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000447:Aldehydes / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006367:HeLa Cells; D015801:Helminth Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D006863:Hydrogen-Ion Concentration / Q000187:drug effects; D007783:Lactones / Q000737:chemistry / Q000494:pharmacology; D008247:Lysosomes / Q000187:drug effects / Q000378:metabolism; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D015388:Organelles / Q000187:drug effects / Q000378:metabolism; D013045:Species Specificity; D013329:Structure-Activity Relationship; D014431:Tylenchoidea / Q000145:classification / Q000187:drug effects / Q000201:enzymology; D025262:Vacuolar Proton-Translocating ATPases / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D000447:Aldehydes; D000969:Antinematodal Agents; D015801:Helminth Proteins; D007783:Lactones; C014096:alpha-methylene gamma-butyrolactone; D025262:Vacuolar Proton-Translocating ATPases; D015107:4-Butyrolactone
keywords: Carbonyl compounds; HeLa cells; M. arenaria; M. incognita; Vacuolar-type H(+)-ATPase; α-Methylene-γ-butyrolactone