Secondary metabolites of Pyricularia oryzae I. o-Nitrophenol derivatives

Naturally-occurring nitro compounds

“…4-Hydroxy-3-nitrobenzyl alcohol (10) has been found in the marine bryozoan Phidolophora pacifica and the deuteromycete Pyricularia oryzae. 5,6 P. pacifica also produces 4-methoxymethyl-2-nitrophenol (12), while P. oryzae produces 4-hydroxy-3nitrophenethyl alcohol (7), 4-hydroxy-a-methyl-3-nitrobenzyl alcohol (11), 4-hydroxy-3-nitrophenylacetic acid (2), and Nacetyl-4-hydroxy-3-nitrophenethylamine (8). 5 A facultatively anaerobic, halophilic bacterium isolated from the Great Salt Plains of Oklahoma produces the N-acylated 4-hydroxy-3-nitrophenethylamines 23 and 24 as well as 4-hydroxy-3-nitrophenyl acetic acid (2).…”

“…5,6 P. pacifica also produces 4-methoxymethyl-2-nitrophenol (12), while P. oryzae produces 4-hydroxy-3nitrophenethyl alcohol (7), 4-hydroxy-a-methyl-3-nitrobenzyl alcohol (11), 4-hydroxy-3-nitrophenylacetic acid (2), and Nacetyl-4-hydroxy-3-nitrophenethylamine (8). 5 A facultatively anaerobic, halophilic bacterium isolated from the Great Salt Plains of Oklahoma produces the N-acylated 4-hydroxy-3-nitrophenethylamines 23 and 24 as well as 4-hydroxy-3-nitrophenyl acetic acid (2). 7 Unacylated 4-hydroxy-3-nitrophenethylamine (25) has been isolated from the cactus Cereus validus.…”

“…The 2,5-diketopiperazine pyriculamide ( 82) is produced by the fungus Pyricularia oryzae. 5 Its biological activity has not been assessed. The endophytic fungus Coniothryium produces four nitrated naphthalene derivatives (83)(84)(85)(86).…”

Griseaketides A–D, New Aromatic Polyketides from the Pathogenic Fungus Magnaporthe grisea

“…Each year rice blast causes losses of 10-30% of the rice harvest and therefore poses a threat to the world's most important food security crop [6]. Previous, studies have shown that aromatic polyketide phytotoxins [7], O-nitrophenol derivatives [8], and naphthalenones [9] are the typical secondary metabolites of M. grisea. Some secondary metabolites (such as melanin, siderophores and fumonisin) of pathogenic fungi often function as essential determinants of pathogenicity and are involved in the infection process [10,11].…”

“…Thus, examining their secondary metabolism leads to the discovery of novel compounds with interesting structures or modes of action that could be useful for agrochemistry or pharmacology [5]. In the work, chemical investigations of a strain M. grisea M639 have led to the discovery of four new aromatic polyketides griseaketides A-D (1-4), as well as 15 known compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). Herein, we describe the isolation, structural elucidation and nematicidal activities of these compounds.…”