Anti-Inflammatory Activity of Tanzawaic Acid Derivatives from a Marine-Derived Fungus Penicillium steckii 108YD142

Chemical investigation of a marine-derived fungus, Penicillium steckii 108YD142, resulted in the discovery of a new tanzawaic acid derivative, tanzawaic acid Q (1), together with four known analogues, tanzawaic acids A (2), C (3), D (4), and K (5). The structures of tanzawaic acid derivatives 1–5 were determined by the detailed analysis of 1D, 2D NMR and LC-MS data, along with chemical methods and literature data analysis. These compounds significantly inhibited nitric oxide (NO) production and the new tanzawaic acid Q (1) inhibited the lipopolysaccharide (LPS)-induced inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins and mRNA expressions in RAW 264.7 macrophages. Additionally, compound 1 reduced the mRNA levels of inflammatory cytokines. Taken together, the results of this study demonstrated that the new tanzawaic acid derivative inhibits LPS-induced inflammation. This is the first report on the anti-inflammatory activity of tanzawaic acid Q (1).

• Publication year

  2016

• Venue

  Marine Drugs

• Publication date

  2016-01-01

• Fields of study

  Biology, Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.3390/md14010014PMID 26761016PMCID 4728511
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities.

  2015cited by this paper
• Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06

  2014cited by this paper
• Sensitivity of Neurospora crassa to a Marine-Derived Aspergillus tubingensis Anhydride Exhibiting Antifungal Activity That Is Mediated by the MAS1 Protein

  2014cited by this paper
• Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities.

  2014influential reference
• Natural products containing 'decalin' motif in microorganisms.

  2014influential reference
• Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua.

  2013cited by this paper
• Anti-inflammatory effect of sargachromanol G isolated from Sargassum siliquastrum in RAW 264.7 cells

  2012cited by this paper
• Secondary metabolites of fungi from marine habitats.

  2011cited by this paper
• The anti-inflammatory effects of Pyrolae herba extract through the inhibition of the expression of inducible nitric oxide synthase (iNOS) and NO production.

  2007cited by this paper
• Drugs from the seas – current status and microbiological implications

  2002cited by this paper
• Secondary metabolites characteristic of Penicillium citrinum, Penicillium steckii and related species.

  2000cited by this paper
• In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa.

  2000cited by this paper
• Antileishmanial cyclic peroxides from the Palauan sponge Plakortis aff. angulospiculatus

  1998cited by this paper
• Synthesis and absolute stereochemistry of tanzawaic acid (GS-1302)

  1998cited by this paper
• Tanzawaic Acids A, B, C, and D : Inhibitors of Superoxide Anion Production from Penicillium citrinum

  1997cited by this paper

• Recent advances in chemistry and bioactivity of decalin-containing natural products (2014-2025).

  2026cites this paper
• [The genus Penicillium: Ecology, secondary metabolites and biotechnological applications].

  2025cites this paper
• Antimicrobial Isochroman‐Derived Atropo‐Diastereomeric Dimers from Penicillium Steckii SCISO 41228

  2024cites this paper
• In vivo anti-inflammatory activity of M116, one extract obtained from the marine bacterium Bacillus amyloliquefaciens

  2023cites this paper
• Antibacterial and cytotoxic secondary metabolites from endophytic fungi associated with Antidesma bunius leaves

  2023cites this paper
• First Total Synthesis of Tanzawaic Acid B

  2023cites this paper
• New Fusarin Derivatives from the Marine Algicolous Fungus Penicillium steckii SCSIO41040

  2023cites this paper
• Endophytic Fungus Penicillium steckii DF33 Promoted Tanshinones Biosynthesis in Salvia miltiorrhiza by Regulating the Expression of CYP450 genes.

  2023cites this paper
• Time for a change! A spotlight on the many neglected facets of sponge microbial biotechnology.

  2022cites this paper
• Identification of the polyketide synthase gene responsible for the synthesis of tanzawaic acids in Penicillium steckii IBWF104-06.

  2022cites this paper
• Tanzawaic Acids from a Deep-Sea Derived Penicillium Species.

  2022cites this paper
• Antimicrobial tanzawaic acid derivatives from the endophytic Penicillium citrinum BCC71086

  2022cites this paper
• Targeted Isolation of Two New Anti-inflammatory and UV-A Protective Dipyrroloquinones from the Sponge-associated Fungus Aspergillus tamarii MCCF102

  2021cites this paper
• Discovery of Survivin Inhibitors Part 1: Screening the Harbor Branch Pure Compound Library

  2021cites this paper
• Diversity, Phylogenetic Profiling of Genus Penicillium, and Their Potential Applications

  2021cites this paper
• Bioactive compounds from marine-derived fungi and their potential applications

  2021cites this paper
• Two New Phomaligols from the Marine-Derived Fungus Aspergillus flocculosus and Their Anti-Neuroinflammatory Activity in BV-2 Microglial Cells

  2021cites this paper
• Trends in Development of Marine‐based Anti‐inflammatory Pharmaceuticals

  2020cites this paper
• Effects of whole plant brown algae (Laminaria japonica) on zootechnical performance, apparent total tract digestibility, faecal characteristics and blood plasma urea in weaned piglets

  2020cites this paper
• Marine‐derived Potential Anti‐inflammatory Agents

  2020cites this paper
• A Review of Anti-Inflammatory Compounds from Marine Fungi, 2000–2018

  2019influential citation
• Pharmacological Potential of Marine Microbes

  2019cites this paper
• Therapeutic Potential of Endophytic Compounds: A Special Reference to Drug Transporter Inhibitors.

  2019cites this paper
• Pharmacological significance of marine microbial bioactive compounds

  2019cites this paper
• Antioxidant and cytotoxic activity of three Turkish marine-derived fungi

  2019cites this paper
• ISOLATION, IDENTIFICATION AND BIOACTIVITY SCREENING OF TURKISH MARINE-DERIVED FUNGI

  2019cites this paper
• Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp.

  2018cites this paper
• Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

  2018cites this paper
• Lipid-Lowering Polyketides from the Fungus Penicillium Steckii HDN13-279

  2018cites this paper
• Marine natural products.

  2018cites this paper
• Marine macroalgae as sources of protein and bioactive compounds in feed for monogastric animals

  2018cites this paper
• Effects of Vegetable Proteins on Hypercholesterolemia and Gut Microbiota Modulation

  2018cites this paper
• Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

  2017cites this paper
• Identification and function analysis of an anti‐lipopolysaccharide factor from the ridgetail prawn Exopalaemon carinicauda

  2017cites this paper
• A review and outlook in the treatment of osteosarcoma and other deep tumors with photodynamic therapy: from basic to deep

  2017cites this paper
• Inhibitory effect of ethanol extract of Nannochloropsis oceanica on lipopolysaccharide-induced neuroinflammation, oxidative stress, amyloidogenesis and memory impairment

  2017cites this paper
• Fucoxanthin prevents H2O2-induced neuronal apoptosis via concurrently activating the PI3-K/Akt cascade and inhibiting the ERK pathway

  2017cites this paper
• TXNIP overexpression suppresses proliferation and induces apoptosis in SMMC7221 cells through ROS generation and MAPK pathway activation.

  2017cites this paper
• Glycerolipid Characterization and Nutrient Deprivation-Associated Changes in the Green Picoalga Ostreococcus tauri1

  2017cites this paper
• Chemical diversity from the Tibetan Plateau fungi Penicillium kongii and P. brasilianum

  2017cites this paper
• Asperflavin, an Anti-Inflammatory Compound Produced by a Marine-Derived Fungus, Eurotium amstelodami

  2017cites this paper
• The PI3K/Akt pathway: a critical player in intervertebral disc degeneration

  2017cites this paper
• Genome-wide analysis of differentially expressed lncRNAs and mRNAs in primary gonadotrophin adenomas by RNA-seq

  2016cites this paper
• Macrolactins from Marine-Derived Bacillus subtilis B5 Bacteria as Inhibitors of Inducible Nitric Oxide and Cytokines Expression

  2016cites this paper
• miR-138-5p suppresses autophagy in pancreatic cancer by targeting SIRT1

  2016cites this paper
• marine drugs

  year unknowncites this paper