Mycophenolic Derivatives from Eupenicillium parvum

Abstract

A new compound, euparvic acid (1, C14H16O6), and the known compounds 5,7-dihydroxy-4-methylphthalide (2), 6-(3-carboxybutyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (3), 6-(5-carboxy-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (4), and 6-(5-carboxy-4-hydroxy-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (5) were isolated from the EtOAc extract of Eupenicillium parvum. The structure of 1 was determined by interpretation of MS and homo- and heteronuclear 2D NMR spectroscopic data and confirmed by X-ray crystallography. The absolute configuration of 5 was determined via MPA ester derivatization.

Two new members of mycophenolic acid family from Penicillium brevicompactum Dierckx

“…The 1 H-, 13 C-and 2D-NMR data of 2 suggested the presence of a phthalan-1-one system with a long aliphatic chain, and indicated that 2 should be a mycophenolic derivative. 10 This partial structure of phthalan-1-one was established by spectral data in comparison with those of MPA (1) and supported by its heteronuclear multiple bond coherence (HMBC) correlations from H-3 to C-1, 4, 7a, 3a, CH 3 -8 to C-4, C-5, C-3a and CH 3 -9 to C-5. This result was further supported by the UV absorption at 250 and 304 nm, which was very similar to that of MPA (1).…”

Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens

“…The following known compounds were also identified; flavoglaucin ( 3 ), 9 tetrahydroauroglaucin ( 4 ), 10 dihydroauroglaucin ( 5 ), 11 auroglaucin ( 6 ), 11 and 2-(2′,3-epoxy-1′,3′-heptadienyl)- 6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde ( 7 ), 9 echinulin ( 8 ), 12 and 5,7-dihydroxy-4-methylphthalide ( 9 ), 13 and this was confirmed by comparison of physical and spectroscopic data (UV, 1 H and 13 C NMR, and MS) with corresponding authentic samples or literature values.…”

Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum

“…However, natural phthalides such as (5,7-dihydroxy-4-methylphthalide) and (5,7-dimethoxyisobenzofuran-1(3H)-one) have already been reported (Puel et al 2005, Fujimoto et al 1999, Habib et al 2008, Sun et al 2009). That ANGELA M.M.P.…”