The structure of coronatine

Abstract

Coronatine (1), produced by Pseudomonas coronafacience var. atropurpúrea, is a toxin which induces chlorosis on the leaves of Italian ryegrass; it also expands potato cells at concentrations of 1 X 10-7 mol/1.1 In this communication, we forward structure 1 for coronatine on the basis of spectroscopic data of the derivatives and x-ray crystallographic analysis of coronafacic acid (2b). 151-153 °C was formulated as C18H25O4N {m/e M+ found, 319.1753; caled, 319.1731) and shows the following spectral data, UV XmaxEtOH 208 nm (e 8378); IR iwKBr 1740 (fivemembered ring C=0), 1620 (C=C), 3270,1645,1525 cm-1 (-CONH-); NMR (90 MHz) ¿Me4SiCD3COCD3 0.94 (6 H, t, J = 7 Hz, CH2C//3), 3.15 (1 H, br. q, -CHCO), 6.50 (1 H, s, =CH). The high resolution mass spectrum of 1 indicates

Differential Expression of a Novel Gene in Response to Coronatine, Methyl Jasmonate, and Wounding in the Coi1Mutant of Arabidopsis1

“…Coronatine is a phytotoxin produced by several pathovars of Pseudomonas syringae (Ichihara et al, 1977;Mitchell and Young, 1978;Mitchell, 1982). Its biological effects include induction of leaf chlorosis and inhibition of root growth (Nishiyama et al, 1976;Ferguson and Mitchell, 1985;Kenyon and Turner, 1990), and it has been suggested to play a role in disease development as a virulence factor produced by the bacteria during infection.…”

COI1-Dependent Expression of an Arabidopsis Vegetative Storage Protein in Flowers and Siliques and in Response to Coronatine or Methyl Jasmonate

“…The phytotoxin coronatine produced by pathovars of Pseudomonas syringae (Ichihara et al, 1977;Mitchell and Young, 1978) causes diverse responses in plants. Coronatine causes chlorosis and promotes senescence in tobacco leaves (Kenyon and Turner, 1990), inhibits root growth in wheat (Sakai, 1980), stimulates ethylene production by leaves of bean (Ferguson and Mitchell, 1985) and tobacco (Kenyon and Turner, 1992), increases amylase activity in potato tubers (Sakai et al, 1979a), and causes hypertrophy of potato tubers (Sakai et al, 1979b).…”

Induction of Chlorosis, ROS Generation and Cell Death by a Toxin Isolated fromPyricularia oryzae

“…17) Coronatine, which had been isolated from a liquid culture of Pseudomonas syringae pv. atropurpurea 20) induced chlorosis on the leaves of its host plant, Italian ryegrass. 21) Coronatine was also subsequently shown to be an octadecanoid analog that could mediate and induce defense reactions.…”

“…The Iowa X469 cultivar from oat [Avena sativa (L.)] was used. Oat seeds were sown in vermiculite and grown in a growth chamber at 20 C with a 12-h photoperiod of photosynthetic photon flux (PPF). The primary leaves of 9-d-old seedlings were used for a bioassay of the toxin.…”