Nematicidal Alkaloids and Related Compounds Produced by the FungusPenicilliumcf.simplicissimum

Abstract

A new nematicidal alkaloid, peniprequinolone (1), together with the known alkaloids penigequinolones A and B (2a, 2b), 3-methoxy-4-hydroxy-4-(4'-methoxyphenyl)quinolinone (3), and 3-methoxy-4,6-dihydroxy-4-(4'-methoxyphenyl)quinolinone (4), were isolated from Penicillium cf. simplicissimum (Oudemans) Thom. Cyclopenin (5) and a compound (6a/6b) structurally related to cyclopenin also were isolated from the fungus, and their structures were established by spectroscopic analysis. The biological activities of 1, 2, 3, 4, and 5 were examined by a bioassay with root-lesion nematodes.

Yaequinolones, New Insecticidal Antibiotics Produced by Penicillium sp. FKI-2140

“…NOE experiments for 3 to 7 showed similar results to those for 2, indicating that the stereochemistry of their quinolinone skeleton is 3R*, 4R*. Biosynthetic studies of this series of compounds have not been reported so far, but the biosynthetic pathway could be speculated to be as follows [5]. First, diketodiazepins 15 and 16 are biosynthesized from anthranilic acid and tyrosine, which are de-and re-cyclized to form the fundamental phenylquinolinones (1, 2, 10 and 11).…”

“…1 H and 13 C NMR data of 13 and 14 are also shown for comparison. From the MS, 1 H and 13 C NMR (data not shown), 10 to 16 were identified as 4-hydroxy-3,4-dihydro-3-methoxy-4-(4Ј-methoxyphenyl)-2(1H)-quinolinone (quinolinone A, 10) [4], 4,5-dihydroxy-3,4-dihydro-3-methoxy-4-(4Ј-methoxyphenyl)-2(1H)-quinolinone (quinolinone B, 11) [4], peniprequinolone (12) [5], penigequinolones A and B (13, 14) [5,6], 4Ј-methoxycyclopeptin (15) [5] and transdehydro-4Ј-methoxycyclopeptin (16) [7]. Compounds 1 and 2 were named yaequinolones A1 and A2 in this study, therefore these structural elucidations were described blow.…”

Yaequinolones, New Insecticidal Antibiotics Produced by Penicillium sp. FKI-2140

“…4-Hydroxy-3,4-dihydro-3-methoxy-4-(4Ј-methoxyphenyl)-2(1H)-quinolinone (abbreviated quinolinone A in this study) (10) [10] and 4,5-dihydroxy-3,4-dihydro-3-methoxy-4-(4Ј-methoxyphenyl)-2(1H)-quinolinone (quinolinone B) (11) [10], were originally isolated as insecticidal antibiotics against A. salina from Penicillium simplicissimum. Peniprequinolone (12) [11] was isolated as a nematicidal antibiotic against root-lesion nematode Pratylenchus penetras from Penicillium cf. simplicissimum.…”

“…simplicissimum. Penigequinolones A and B (13, 14) [11,12], isolated as a mixture from Penicillium sp. NO.…”

“…410, were reported to show pollengrowth inhibitory activity and nematicidal activity against P. penetrans. 4Ј-Methoxycyclopeptin (15) [11] was isolated along with 12. trans-Dehydro-4Ј-methoxycyclopeptine (16) [13] was previously reported as a synthetic intermediate of cyclopeptin. The structural elucidation of the yaequinolones is described in the accompanying paper [14] and elsewhere [3].…”