title: Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum.
abstract: The chemical reactions carried out by microorganisms have been used as a tool in modern chemistry. This paper reports the production of mycophenolic acid and a new phthalide by the endophytic fungus Penicillium crustosum obtained from coffee seeds. The fungus was cultivated in a liquid medium for a period of seven days and after that the culture medium was divided into four treatments: A, B, C and D, to which different organic substances were added. Treatment A was maintained as the control to evaluate the occurrence of biotransformation. Organic acids were added to the culture media of treatments B (ferulic and quinic acids) and C [cinnamic and 3,4-(methylenedioxy) cinnamic acids], and caffeine was added in the treatment D. All these organic compounds were dissolved in DMSO, and the fermentation was maintained for more 13 days, totalizing 20 days. Mycophenolic acid was isolated from the culture with no added acids (treatment A). Mycophenolic acid and a new phthalide, 5-hydroxy-7-methoxy-4-methylphthalide were isolated from treatments B and C, and mycophenolic acid and caffeine (added to the culture medium) were isolated from treatment D. The structures were determined by NMR techniques and confirmed by MS and MS/MS techniques.
authors.affiliation: Embrapa Meio Ambiente, Laboratório de Microbiologia Ambiental, Jaguariúna, SP, Brasil. angvalente@gmail.com
authors.forename: Angela M M P
authors.initials: AM
authors.lastname: Valente
authors.forename: Antonio G
authors.initials: AG
authors.lastname: Ferreira
authors.forename: Cristina
authors.initials: C
authors.lastname: Daolio
authors.forename: Edson
authors.initials: E
authors.lastname: Rodrigues Filho
authors.forename: Elisangela F
authors.initials: EF
authors.lastname: Boffo
authors.forename: Antonia Q L
authors.initials: AQ
authors.lastname: Souza
authors.forename: Fernanda L S
authors.initials: FL
authors.lastname: Sebastianes
authors.forename: Itamar S
authors.initials: IS
authors.lastname: Melo
mesh_terms: D001572:Benzofurans / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D003069:Coffee / Q000382:microbiology; D003470:Culture Media; D009682:Magnetic Resonance Spectroscopy; D009173:Mycophenolic Acid / Q000096:biosynthesis* / Q000737:chemistry; D010407:Penicillium / Q000378:metabolism*; D053719:Tandem Mass Spectrometry; D013997:Time Factors
chemical_list: C529015:5-hydroxy-7-methoxy-4,6-dimethylphthalide; D001572:Benzofurans; D003069:Coffee; D003470:Culture Media; D009173:Mycophenolic Acid