Restricticin, a novel glycine-containing antifungal agent.

Schwartz, Robert E.; Dufresne, Claude; Flor, James E.; Kempf, August J.; Wilson, Kenneth E.; Lam, Thientu; Onishi, Janet C.; Milligan, James A.; Fromtling, Robert A.; Abruzzo, George K.; Jenkins, Rosalind G.; Glazomitsky, Konstantin; Bills, Gerald F.; Zitano, Lauretta; Val, Sagrario Mochales del; Omstead, Mary Nallin

doi:10.7164/antibiotics.44.463

Cited by 32 publications

(19 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Isofumigaclavine A and citrinin were extrolites of P. improvisum . Restricticins are broad spectrum antifungal polyenes previously only identified in cultures of P. restrictum ( Hensens et al 1991 , Schwartz et al 1991 ) and Penicillium sp. NR6564 ( Matsukuma et al 1992 ).…”

Section: Discussionmentioning

confidence: 99%

Fifteen new species of <I>Penicillium</I>

et al. 2016

View full text Add to dashboard Cite

We introduce 15 new species of Penicillium isolated from a diverse range of locations, including Canada, Costa Rica, Germany, Italy, New Zealand, Tanzania, USA and the Dry Valleys of Antarctica, from a variety of habitats, including leaf surfaces in tropical rain forests, soil eaten by chimpanzees, infrabuccal pockets of carpenter ants, intestinal contents of caterpillars and soil. The new species are classified in sections Aspergilloides (1), Canescentia (2), Charlesia (1), Exilicaulis (3), Lanata-Divaricata (7) and Stolkia (1). Each is characterised and described using classical morphology, LC-MS based extrolite analyses and multigene phylogenies based on ITS, BenA and CaM. Significant extrolites detected include andrastin, pulvilloric acid, penitrem A and citrinin amongst many others.

show abstract

Section: Discussionmentioning

confidence: 99%

Fifteen new species of <I>Penicillium</I>

et al. 2016

View full text Add to dashboard Cite

show abstract

“…According to the results, restricticin derivatives have the most potent anti-inflammatory effect among the treated compounds without cytotoxicity. Therefore, restricticin B (1) and N-acetyl restricticin (2) were selected to further investigate the effects on the LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNA and protein expression, and the production of LPS-stimulated proinflammatory cytokines in BV-2 microglia cells. Two restricticin class compounds (1 and 2) at the concentrations of 50 μM and 100 μM inhibited the NO production in BV-2 cells in a dose-dependent manner ( Figure 6A).…”

Section: Resultsmentioning

confidence: 99%

“…The novel class of potent antifungal agents, restricticin and restricticinol, were first isolated from the fermentation broth of Penicillium restrictum [1,2]. These compounds contain a tetrahydropyran ring and triene side chains in common and restricticin possesses a glycine unit linked to the tetrahydropyran ring [3].…”

Section: Introductionmentioning

confidence: 99%

“…These compounds contain a tetrahydropyran ring and triene side chains in common and restricticin possesses a glycine unit linked to the tetrahydropyran ring [3]. The initial biological activity study of restricticin derivatives displayed that only restricticin exhibited potent antifungal activity against both yeast and filamentous fungi [1,4]. The very closely related compounds with a shorter polyene chain, lanomycin and lanomycinol, were isolated from Pycnidiophora dispersa in 1992 and chaunopyran A possessing a same polyene chain and 2-alkenyl-tetrahydropyran was reported in 2017 [5,6].…”

Section: Introductionmentioning

confidence: 99%

“…1 H and13 C NMR data for 1 and 2 at 500 MHz and 125 MHz in CD 3 OD (δ in ppm, J in Hz).The assignments were aided by COSY, NOESY, HSQC, and HMBC NMR spectra. a Measured in CDCl 3 b NMR chemical shifts recorded for the minor signals observed for compound 1.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

Choi

et al. 2020

Marine Drugs

View full text Add to dashboard Cite

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2–5) were obtained from the EtOAc extract of the marine-derived fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via the analyses of NOESY spectroscopy data, the comparison of optical rotation values with those of reported restricticin derivatives and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

show abstract

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

2021

View full text Add to dashboard Cite

Structures of several dozen of known antibacterial, antifungal or antiprotozoal agents are based on the amino acid scaffold. In most of them, the amino acid skeleton is of a crucial importance for their antimicrobial activity, since very often they are structural analogs of amino acid intermediates of different microbial biosynthetic pathways. Particularly, some aminophosphonate or aminoboronate analogs of protein amino acids are effective enzyme inhibitors, as structural mimics of tetrahedral transition state intermediates. Synthesis of amino acid antimicrobials is a particular challenge, especially in terms of the need for enantioselective methods, including the asymmetric synthesis. All these issues are addressed in this review, summing up the current state‐of‐the‐art and presenting perspectives fur further progress.

show abstract

Restricticin, a novel glycine-containing antifungal agent.

Cited by 32 publications

References 5 publications

Fifteen new species of <I>Penicillium</I>

Fifteen new species of <I>Penicillium</I>

Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

Contact Info

Product

Resources

About