Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities

Marine Pharmacology in 2014–2015: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, Antiviral, and Anthelmintic Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…Quang con colleagues determined that tanzawaic acid A (163), isolated from a marine fungus Penicillium sp. SF-6013 derived from the Pacific sea urchin Brisaster latifrons, inhibited both NO and PGE 2 production from LPS-activated murine BV-2 microglia cells and RAW 264.7 murine macrophages, while suppressing iNOS and COX-2 expression and inhibiting protein tyrosine phosphatase 1B [183]. In contrast to the marine compounds with described anti-inflammatory mechanisms of action described in the preceding paragraph, and as shown in Table 2, for marine compounds , only anti-inflammatory activity (IC 50 ) was reported, but the molecular mechanism of action of these marine-derived compounds remained undetermined at the time of publication: a new highly oxygenated meroterpene aspertetranone D (164) isolated from the marine algal-associated fungus Aspergillus sp.…”

Secondary metabolites from the marine‐derived fungus Paraconiothyrium sp. VK‐13

“…Thus, the marine-derived fungal strain VK-13 was characterized as Paraconiothyrium sp. 13 C) and chemical shifts were referenced relative to the corresponding residual solvents signals (δ H 4.80 and 3.30/δ C 49.0). HMQC and HMBC experiments were optimized for 1 J CH = 140 Hz and n J CH = 8 Hz, respectively.…”

“…for C 10 H 14 NaO 3 , 205.0841) in the HRESIMS. Analysis of the 1 H, 13 C NMR, and DEPT spectra of 5 led to identification of two double bonds (including one cis-and one trans-configured), one carbonyl carbon, two oxygenated methines, two methylene groups, and one methyl group. Comparative analysis of the 1 H and 13 C NMR data of 5 with those of 4 suggested that the structures of these compounds are nearly identical, except for the replacement of an oxymethine group in 4 by a methylene group [ H 2.37 and 2.15/  C 32.1 (C-7)] in 5 (table 2).…”

“…[11] Some compounds have been reported to possess cytotoxicity [1,3,7] and antibacterial activities [2,9] . In the course of our ongoing search for new and bioactive compounds from marine-derived fungi [12][13][14][15] , we conducted a chemical investigation of the EtOAc extract of the fungal strain Paraconiothyrium sp. VK-13.…”

Inhibitors of Protein Tyrosine Phosphatase 1B from Marine Natural Products

“…They were isolated from the sea urchin Brisaster latifrons , collected from the Sea of Okhotsk (N 53°22.626′ E 144°24.200′). The assay based on structural–activity relationships between tanzawaic acids and its derivatives suggested that the presence of the hydroxy group at C(10) might be the important structure in diminishing PTP1B inhibitory …”