Organochlorine compounds from a terrestrial higher plant: structures and origin of chlorinated orcinol derivatives from diseased bulbs of Lilium maximowiczii.
Seven chlorine-containing orcinol derivatives (2-8) and orcinol (9) have been isolated from diseased bulbs of the edible lily Lilium maximowiczii, and their structures have been elucidated. Six of the chlorinated orcinol derivatives (2, 4-8) showed antifungal activity. Because organochlorine compounds are rare in terrestrial higher plants, their biosynthetic origin was examined. These compounds were shown to be induced in intact bulb scales by UV irradiation or by inoculation with the pathogenic fungus Fusarium oxysporum f. sp. lilii. Biosynthetic studies suggested that these "natural organochlorine pesticides" are produced by enzymatic chlorination of orcinol (9) with chloroperoxidase and hydrogen peroxide, which are both induced in the plant tissue under stress conditions.
Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan. kmonde@icrs.tohku.ac.jp
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Monde
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Satoh
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Nakamura
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Tamura
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Takasugi
D000935:Antifungal Agents / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000302:isolation & purification / Q000494:pharmacology; D005670:Fusarium / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D006843:Hydrocarbons, Chlorinated / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000378:metabolism; D010544:Peroxidases / Q000037:antagonists & inhibitors; D010935:Plant Diseases; D018517:Plant Roots / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D012118:Resorcinols / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D006843:Hydrocarbons, Chlorinated; D012118:Resorcinols; C005282:orcinol; D010544:Peroxidases