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

Kuramoto, Makoto; Yamada, Kazutoyo; Shikano, Mayumi; Yazawa, Kazunaga; Arimoto, Hirokazu; Okamura, Takuya; Uemura, Daisuke

doi:10.1002/chin.199804235

Cited by 10 publications

(21 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Extensive NMR experiments ( 1 H NMR, 13 CNMR, 1 H- 1 H COSY, gHSQC, gHMBC and NOESY) indicate that TZA-B has three methyl groups, two methylenes, twelve methines (six of them olefinic), one quaternary carbon and one exchangeable proton. These data were identical with those for TZA-B, previously reported in the literature [ 23 ]. 1 H-NMR and 13 C-NMR data ( Fig 1 ) were recorded on a Varian “Mercury 400” spectrometer (Agilent Technologies) at 400 and 100 MHz, respectively.…”

Section: Methodssupporting

confidence: 91%

“…Guided fractionation of P605 allowed the purification of one active compound, whose structure was elucidated by nuclear magnetic resonance ( Fig 1 ). The new COIN was identified as TZA-B, a polyketide previously described as inhibitor of superoxide anion production from Penicillium citrinum [ 23 , 24 ]. Dose/response analysis of TZA-B was also performed by fluorescence-based HTC assay.…”

Section: Resultsmentioning

confidence: 99%

“…In the same way as TZA-B, two of its structural analogs, namely TZAs A and E ( Fig 3A ), are also inhibitors of superoxide anion production [ 23 , 24 ]. They were also checked as possible COINs.…”

Section: Resultsmentioning

confidence: 99%

“…TZAs were previously reported to inhibit superoxide anion production [ 23 , 24 ], nitric oxide production and protein tyrosine phosphatase 1B activity in inflammatory cells [ 26 ]. In addition, two recent studies analyzed antimicrobial and cytotoxic effects of these fungal polyketides.…”

Section: Discussionmentioning

confidence: 99%

See 3 more Smart Citations

Tanzawaic Acids, a Chemically Novel Set of Bacterial Conjugation Inhibitors

et al. 2016

View full text Add to dashboard Cite

Bacterial conjugation is the main mechanism for the dissemination of multiple antibiotic resistance in human pathogens. This dissemination could be controlled by molecules that interfere with the conjugation process. A search for conjugation inhibitors among a collection of 1,632 natural compounds, identified tanzawaic acids A and B as best hits. They specially inhibited IncW and IncFII conjugative systems, including plasmids mobilized by them. Plasmids belonging to IncFI, IncI, IncL/M, IncX and IncH incompatibility groups were targeted to a lesser extent, whereas IncN and IncP plasmids were unaffected. Tanzawaic acids showed reduced toxicity in bacterial, fungal or human cells, when compared to synthetic conjugation inhibitors, opening the possibility of their deployment in complex environments, including natural settings relevant for antibiotic resistance dissemination.

show abstract

Section: Methodssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Tanzawaic Acids, a Chemically Novel Set of Bacterial Conjugation Inhibitors

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The evolution of these biosynthetic genes remains unknown and more research is needed. Besides citrinin and a series of derivates or precursors of citrinin (Clark et al 2006;Wakana et al 2006;Lu et al 2008;Zhu et al 2009), several other metabolites are also claimed to be produced by P. citrinum, including compactins ), agroclavine-1 and epoxyagroclavine-1 (Kozlovskiĭ et al 2003a(Kozlovskiĭ et al , 2005, asterric acid (Turner 1971;Turner and Aldridge 1983), cathestatins (Woo et al 1995), citrinadin A (Tsuda et al 2004;Mugishima et al 2005), quinocitrinines and ergot alkaloids (Kozlovskiĭ et al 2005), quinolactacins Takahashi et al 2000;Kim et al 2001), quinolactacide (Abe et al 2005), tanzawaic acids (Kuramoto et al 1997), scalusamides A-C , perinadine A , cyclocitrinols (Kozlovskiĭ et al 2000a;Amagata et al 2003), ergosta-4,6,8 (14),22-tetraen-3-one (Price and Worth 1974), 2,3,4-trimethyl-5,7-dihydroxybenzofuran (Chen et al 2002) and gibberellins (Khan et al 2008). Of these metabolites, we have confirmed the production of citrinin and some of its derivatives, quinolactacins (= quinocitrinins), and citrinadins.…”

Section: Discussionmentioning

confidence: 99%

Taxonomy of Penicillium citrinum and related species

2010

View full text Add to dashboard Cite

Penicillium citrinum and related species have been examined using a combination of partial β-tubulin, calmodulin and ITS sequence data, extrolite patterns and phenotypic characters. It is concluded that seven species belong to the series Citrina. Penicillium sizovae and Penicillium steckii are related to P. citrinum, P. gorlenkoanum is revived, Penicillium hetheringtonii sp. nov. and Penicillium tropicoides sp. nov. are described here as new species, and the combination Penicillium tropicum is proposed. Penicillium hetheringtonii is closely related to P. citrinum and differs in having slightly broader stipes, metulae in verticils of four or more and the production of an uncharacterized metabolite, tentatively named PR1-x. Penicillium tropicoides resembles P. tropicum, but differs in the slow maturation of the cleistothecia, slower growth at 30°C and the production of isochromantoxins. The type strain of P. hetheringtonii is CBS 122392 T (=IBT 29057 T ) and the type strain of P. tropicoides is CBS 122410 T (=IBT 29043 T ).

show abstract

The anti-infective potential of the endophytic fungi associated with Allium cepa supported by metabolomics analysis and docking studies

Hassan

Abdelhafez

Shady

et al. 2023

Natural Product Research

View full text Add to dashboard Cite

Endophytic fungi are known to be a rich source for anti-infective drugs. In our study, Allium cepa was investigated for fungal diversity using different media to give eleven isolates which were identified morphologically. Out of the isolated fungal strains, Penicillium sp. (LCEF10) revealed potential anti-infective activity against the tested microbes (Fusarium solani ATTC 25922, Pseudomonas aeruginosa ATTC 29213, Staphylococcus aureus ATTC 27853, Candida albicans ATTC 10231), besides, their MICs were measured by well diffusion method therefore it was subjected to molecular identification in addition to phylogenetic analysis. Moreover, the ITS sequence of strain LCEF10 showed a consistent assignment with highest sequence similarity (99.81%) to Penicillium oxalicum NRRL 787. The crude ethyl acetate extract of Penicillium sp. LCEF10 was investigated for metabolomic analysis using LC-HR-ESI-MS. The metabolic profiling revealed the presence of polyketides, macrolides, phenolics, and terpenoids. Furthermore, in silico molecular docking study was carried out to predict which compounds most likely responsible for the anti-infective activity.

show abstract

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

Cited by 10 publications

References 1 publication

Tanzawaic Acids, a Chemically Novel Set of Bacterial Conjugation Inhibitors

Tanzawaic Acids, a Chemically Novel Set of Bacterial Conjugation Inhibitors

Taxonomy of Penicillium citrinum and related species

The anti-infective potential of the endophytic fungi associated with Allium cepa supported by metabolomics analysis and docking studies

Contact Info

Product

Resources

About