Tanzawaic Acids A, B, C, and D: Inhibitors of Superoxide Anion Production from Penicillium citrinum

Abstract

Tanzawaic acids have been isolated from Penicillium citrinum and their structures were elucidated by spectroscopic analysis. Their relative stereochemistries were also clarified by detailed analyses of 1H–1H coupling constants and NOE data. Tanzawaic acid B (GS-1302-1) significantly inhibits superoxide anion production in human neutrophils.

A New Antioxidant Decalin Polyketide from Freshwater‐Sediment‐Derived Fungus Penicillium sp. Strain S1a1

“…Results revealed that compound 1 possess a pronounced antioxidant activity with IC 50 value of 2.8 μM (compared to quercetin which possesses IC 50 of 5.72 μM). This antioxidant activity was similar to its related congeners tanzawaic acid A−D . Moreover, compound 1 proved to have a weak antibacterial activity against Staphylococcus aureus with a MIC of 64 μg/mL and no cytotoxic effect.…”

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

“…[2][3][4][5][6][7][8] Structurally, these compounds possess a highly reduced polyunsaturated octaketide backbone derived from the condensation of 8 mol of acetate, plus the addition of two methyl groups at C-8 and C-10, predictably from methionine, as frequently occurs in fungal metabolism. 2,5,7,8 Here we describe the chemical structure and relative stereochemistry, propose a biogenetic hypothesis and investigate the antimicrobial and cytotoxic activities of four novel tanzawaic acids M-P (1-4) (Fig. Some of these compounds display anticoccidial activity, inhibition of superoxide anion production, inhibition of NO production or inhibition of protein tyrosine phosphatase 1B (PTP1B).…”

“…Some of these compounds display anticoccidial activity, inhibition of superoxide anion production, inhibition of NO production or inhibition of protein tyrosine phosphatase 1B (PTP1B). 2,3 Results and discussion 1).…”

Screening for Sulfur Compounds by Molybdenum-Catalyzed Oxidation Combined with Liquid Chromatography-Mass Spectrometry

“…Next, we investigated the possibility of selectively identifying sulfur compounds from a mixture containing 1.0 mg each of six microbial compounds: outovirin A and nanaomycin K as sulfur compounds, and acremolin B [21], SF-227 [22], beauvericin [23] and tanzawaic acid B [24] as non-sulfur compounds. This mixture was oxidized as described above using H 2 O 2 and (NH 4 ) 6 Mo 7 O 24 •4H 2 O as a catalyst.…”