Phenopyrrozin, a New Radical Scavenger Produced by Penicillium sp. FO-2047.

Metabolites from the Marine-Derived Fungus Chromocleista sp. Isolated from a Deep-Water Sediment Sample Collected in the Gulf of Mexico

“…The structure of compound 1 was confirmed as 5,6,7,7a(S)-tetrahydro-2-hydroxy-1-(p-hydroxyphenyl)-3H-pyrrolizin-3-one ( Figure 1) by single-crystal X-ray diffraction. 14 Comparison of the NMR and mass spectroscopic data of 2 with those of compound 1 and with literature reported data 5,6 identified compound 2 as 5,6,7,7a-tetrahydro-2-hydroxy-1-phenyl-3H-pyrrolizin-3-one. This compound was previously isolated from a Penicillium sp., and its absolute configuration at 7a was not reported in these publications.…”

“…isolated from a marine sediment sample collected at a depth of 70 m in the Gulf of Mexico. In addition, the same fungus yielded the known compounds phenopyrrozine (2), 5 a radical scavenger, 6 cyclo(L-Pro-L-Tyr) 7 (6), cyclo(L-Pro-L-Phe) 8 (7), cyclo(L-Pro-L-Val) 9 (8), and cyclo(L-Pro-D-Leu) 10 9, N b -acetyltryptamine (10), 11 and agathic acid (11). 12,13 The structures of all of the known compounds have been confirmed by comparison with spectroscopic data reported in the literature.…”

“…In addition, the fungus gave the known compound phenopyrrozin (2), four known diketopiperazines (6)(7)(8)(9), N-acetyltryptamine (10), and agathic acid (11). Another new diketopiperazine (5) was separated and identified as a decomposition product of 3 and 4. The structures of the new metabolites were determined on the basis of mass spectroscopy, NMR experiments, and derivatization methods.…”

Genome screening for reducing type I polyketide synthase genes in tropical fungi associated with medicinal plants

“…Previously, phenopyrrozin had been isolated from Penicillium sp. FO-2047(Shiomi et al 1995. In 2006, p-hydroxyphenopyrrozin and phenopyrrozin had been elucidated from the marine fungus Chromocleista sp.…”

“…corresponding to the molecular formula C 13 H 13 NO 2 . According to database search with the 1 H, 13 C NMR, 2D-NMR and ESI data (supplement data), compound 2 was identified as 5,6,7,7a-tetrahydro-2-hydroxy-1-phenyl-3H-pyrrolizin-3-one (Shiomi et al 1995). In this study, kojic acid (30 mg), a white crystalline material was recovered from fraction 6.…”