New Furan and Cyclopentenone Derivatives from the Sponge-Associated Fungus Hypocrea Koningii PF04

Abstract

Two new furan derivatives, hypofurans A and B (1 and 2), and three new cyclopentenone derivatives, hypocrenones A–C (3–5), along with seven known compounds (6–12), were isolated from a marine fungus Hypocrea koningii PF04 associated with the sponge Phakellia fusca. Among them, compounds 10 and 11 were obtained for the first time as natural products. The planar structures of compounds 1–5 were elucidated by analysis of their spectroscopic data. Meanwhile, the absolute configuration of 1 was determined as 2R,3R by the comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. All the isolates were evaluated for their antibacterial and antioxidant activity. Compounds 1, 10, and 12 all showed modest antibacterial activity against Staphylococcus aureus ATCC25923 (MIC, 32 μg/mL). In addition, compounds 1, 10 and 11 exhibited moderate DPPH radical scavenging capacity with IC50 values of 27.4, 16.8, and 61.7 µg/mL, respectively.

Marine natural products

“…205 Interestingly, compounds with the same planar structures as chaunolidines A 259 and C 261 were simultaneously reported as metabolites of the terrestrial fungus Tolypocladium cylindrosporum. 208 An OSMAC approach was utilised in the isolation of polyketides 264 and 265 from Cladosporium sphaerospermum 209 227 Two of these compounds, N-isobutyl-2-phenylacetamide 228 337 and N-(2-methylbutyl)-2phenylacetamide 229 338 were rst time NPs. 227 New natural products were isolated from the genera Lophiostoma (merosesquiterpenoids craterellin D 339 and craterellin A 230 340; rst marine isolation for the latter), 231 and Nectria (monoterpenoid a-pyrones 341 and 342).…”

“…208 An OSMAC approach was utilised in the isolation of polyketides 264 and 265 from Cladosporium sphaerospermum 209 227 Two of these compounds, N-isobutyl-2-phenylacetamide 228 337 and N-(2-methylbutyl)-2phenylacetamide 229 338 were rst time NPs. 227 New natural products were isolated from the genera Lophiostoma (merosesquiterpenoids craterellin D 339 and craterellin A 230 340; rst marine isolation for the latter), 231 and Nectria (monoterpenoid a-pyrones 341 and 342). 232 Of these, nectriapyrone D 232 342 was simultaneously isolated from a terrestrial fungus as gulpyrone B.…”

3,5‐Dimethylorsellinic Acid Derived Meroterpenoids from Eupenicillium sp. 6A‐9, a Fungus Isolated from the Marine Sponge Plakortis simplex

“…[5,6,43] The final concentrations of each compound in the wells were 64, 32, 16, 8, 4, 2, 1, 0.5, 0.25, and 0.125 μg/mL. Chloramphenicol was used as the positive control and exhibited MICs of 4, 4, and 4 μg/mL, respectively, against the above-mentioned bacteria.…”

“…[2][3][4] As part of our efforts to discover structurally diverse and novel bioactive fungal metabolites, investigations of fungi isolated from several marine sponges collected from Yongxing Island were initiated. [5,6] In the course of TLC-, HPLC-PDA-, LC-MS-, and 1 H-NMR-guided screening, [7] a fungal strain, Eupenicillium sp. 6A-9 (KM582643), with 98 % sequence identity with the closest rela-tive Eupenicillium sp.…”

Antibiotic Resistance of Symbiotic Marine Bacteria Isolated from Marine Organisms in Jeju Island of South Korea

“…Pseudovibrio isolates originating from marine invertebrates such as tunicates, corals, and sponges showed antimicrobial activity [24][25][26]. The antioxidants generally produced by marine environment include polyphenolic metabolites such as flavonoids, cinnamic acid, furan, and phlorotannins [27,28]. So, we are doing to search bioactive compounds from these results now.…”