Biotransformation of Ethinylestradiol by Whole Cells of Brazilian Marine-Derived Fungus Penicillium oxalicum CBMAI 1996

Anti-Inflammatory Ergosteroid Derivatives from the Coral-Associated Fungi Penicillium oxalicum HL-44

“…The presence of a palmitic acid residue was proven with an MS analysis and comparison of the spectroscopic data with those reported data [34]. The existence of the fatty acyl moiety was indicated by the characteristic 13 Derivatives of 15α-hydroxy steroids serve as key intermediates in the production of contraceptives [35,36]. A P450 enzyme, which is composed of the cytochrome P450 hydroxylase and the NADPH-cytochrome P450 reductase (CPR), has been reported to be associated with the 15α-hydroxylation reaction in P. raistrickii [37].…”

“…The crude extract was subjected to column chromatography (CC) silica gel, Sephadex LH-20, and reversed phase HPLC to afford compounds 1-16 (Figure 1). On the basis of spectroscopic techniques ( 1 H-NMR, 13 C-NMR) and comparison with data recorded in the references, compounds 2-16 were determined as (22E,24R)-9α,15α-dihydroxyergosta-4,6,8( 14),22-tetraen-3-one (2) [17], ganodermaside D (3) [18], (22E,24R)-ergosta-4,6,8( 14),22-tetraen-3-one (4) [19], isocyathisterol (5) [20], herbarulide (6) [21], dankasterones A (7) [22], (22E,24R)-ergosta-7,22-dien-3β,5α-diol-6-one (8) [23], (22E,24R)-ergosta-7,22-dien-3β,5α,9α-trihydroxy-6-one (9) [24], (22E,24R)-3β-hydroxyergosta-5,8,22-trien-7-one (10) [25], (22E,24R)-5α,9α-epidioxyergosta-6,8( 14),22-triene-3β-ol (11) [26], (22E, 24R)-7α-methoxy-5α,6α-epoxyergosta-8( 14),22-dien-3β-ol (12) [27], (22E,24R)-6-acetoxy-ergosta-7,22-dien-3β,5α,6β-triol (13) [28], (22E,24R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol (14) [29], (22E,24R)-5α,8α-epidioxyergosta-6,22dien-3β-ol (15) [30], and demethylincisterol A3 (16) [31]. Compound 1 was obtained as an optically yellowish oil.…”

“…P. oxalicum is known for its ability in biotransformation. The fungi were found to be able to act as hyperproducers of chitin deacetylase for converting chitin to chitosan, transforming protopanaxadiol-type saponins to ginsenoside compound K, and promoting the biotransformation of ethinylestradiol 1 [12,13].…”

“…As part of ongoing screening for bioactive metabolites from China marine sources, a fungus strain of P. oxalicum HL-44 was isolated from the soft coral Sinularia gaweli collected from the Xisha area of the South China Sea. Chemical investigation of this fungi led to the isolation of a new ergostane-type sterol ester (1) and fifteen known derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16). Their structures were determined with extensive spectroscopic analyses and comparisons with reported data.…”

Marine-derived fungi as biocatalysts

“…This indicates that a biodegradation process was occurring at the same time as the biotransformation. It is worth noting that marine-derived fungi can play a relevant role in the biodegradation of steroidal compounds in the ocean and in wastewater due to their inappropriate disposal (de Queiroz et al, 2020).…”