Basidalin,a new antibiotic from basidiomycetes.

Iinuma, Hisae; Nakamura, Hikaru; Naganawa, Hiroshi; Masuda, Tohru; Takano, S; Takeuchi, Tomio; Umezawa, Hamao; Iitaka, Yōichi; Ôbayashi, Akira

doi:10.7164/antibiotics.36.448

Cited by 17 publications

(17 citation statements)

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“…cinereus inhibited E. coli. Basidalin, isolated from L. naucinus showed weak antibacterial activity against Aeromonas salmonicida (MIC 100 µg/ml), Vibrio anguillarum (MIC 100 µg/ml), and inhibited the synthesis of protein, RNA and DNA in cultured L1210 cells, the IC 50 were 0.4-0.6 µg/ml (Iinuma et al 1983). To the best of our knowledge, the species Climacodon pulcherrimus and Tyromyces duracinus are cited here for the first time as producers of antimicrobial compounds.…”

Section: Resultsmentioning

confidence: 99%

Screening of Brazilian basidiomycetes for antimicrobial activity

Rosa

Machado

Jacob

et al. 2003

Mem. Inst. Oswaldo Cruz

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Section: Resultsmentioning

confidence: 99%

Screening of Brazilian basidiomycetes for antimicrobial activity

Rosa

Machado

Jacob

et al. 2003

Mem. Inst. Oswaldo Cruz

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“…This natural product exhibits antibacterial and antitumor activities, and its structure was elucidated in 1983 by X-ray diffraction analysis. 9 To the best of our knowledge only the synthesis of the non-natural E isomer has been described. 10 Thiobasidalin, the thiolactone analogue of basidalin, has been synthesized by Stachel and co-workers.…”

Section: Methodsmentioning

confidence: 99%

Decarboxylative Knoevenagel-Type Reactions on Tetronamides: Synthesis of 5-Ylidene-4-Amino-2(5H)-Furanones

Ear

Toum

Thorimbert

et al. 2014

Synlett

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A detailed account regarding the synthesis of 5-ylidene-2(5H)-furanones is given. The key step is a decarboxylative Knoevenagel-type reaction of tetronamides with various α-functionalized aldehydes. The synthesis of protected basidalin is presented.Amino-2(5H)-furanones, commonly referred to as tetronamides, are important intermediates in the synthesis of natural products, 1 and they are also of interest in the pharmaceutical and agrochemical arenas. 2 Most methods reported for the preparation of substituted tetronamides are based on the nucleophilicity of the enamine function. 3 A sequence involving condensation of primary or secondary amines with tetronic acid followed by alkylation or aldolization using, most generally, tert-butyllithium as a base furnishes 5-substituted tetronamides. 4 We have described a novel N-bromosuccinimide (NBS) 5 -promoted cyclization of enaminoesters 6 1 to 4-amino-5-carboxymethyl-2(5H)-furanones 2 and subsequent C5-alkylation to prepare 5-substituted tetronamides 3 in an overall three-step approach (Scheme 1). 7 Scheme 1In our continuing efforts to develop efficient C5 modifications of tetronamides, we were interested in the possibility of preparing 5-ylidene-4-amino-2(5H)-furanones 6. Though the synthesis of these heterocyclic derivatives have been described (most often obtained as unexpected products through thermal rearrangements of azido-or isoxazoloquinones), 8 no direct methylene insertion onto the C5 position of tetronamides has been reported. Moreover, this structural framework is found in basidalin, a natural product isolated from the mushroom Leucoagaricus naucina. This natural product exhibits antibacterial and antitumor activities, and its structure was elucidated in 1983 by X-ray diffraction analysis. 9 To the best of our knowledge only the synthesis of the non-natural E isomer has been described. 10 Thiobasidalin, the thiolactone analogue of basidalin, has been synthesized by Stachel and co-workers. 11 Therefore, it was of interest to evaluate the preparation of basidalin by means of a process that would make use of glyoxal derivatives and the pivotal tetronamide 2 as reaction partners in a Knoevenagel-Doebnertype reaction (Scheme 2). 12

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“…) is a key structural feature of an increasing number of bioactive molecules, nearly all of them being of synthetic origin. In fact, the only tetronamide known to occur in nature is basidalin ( 2 ), an antitumor antibiotic isolated from terrestrial fungi . Synthetic tetronamides are frequently used as building blocks for the construction of complex molecules, as well as in chemical, medicinal and agrochemical research .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new tetronamides displaying inhibitory activity against bloom‐forming cyanobacteria

Acosta

Karak

Barbosa

et al. 2019

Pest Management Science

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BACKGROUND: The increasing frequency and intensity of cyanobacterial blooms pose a serious threat to aquatic ecosystems. These blooms produce potent toxins that can contaminate drinking water and endanger the life of wild and domestic animals as well as humans. Consequently, the development of effective methods for their control is a matter of high priority. We have previously shown that some -benzylidenebutenolides, related to the rubrolide family of natural products, are capable of inhibiting the photosynthetic electron transport chain (Hill reaction), a target of commercial herbicides. Here we report the synthesis and biological properties of a new class of rubrolide-inspired molecules featuring a tetronamide motif.RESULTS: A total of 47 N-aryl tetronamides, including 38 aldol adducts, were prepared bearing phenyl, biphenyl, naphthyl, aliphatic and heteroaromatic groups. Some of the aldol adducts were dehydrated to the corresponding -benzylidenetetronamides, although satisfactory yields were obtained in only three cases (52-97%). None of the synthesized compounds were capable of blocking the Hill reaction. This notwithstanding, several aldol adducts equipped with a biphenyl substituent displayed excellent inhibitory activity against Synechococcus elongatus and other cyanobacterial strains (IC 50 = 1-5 M). Further, these tetronamides were found to be essentially inactive against eukaryotic microorganisms. CONCLUSION: Several newly synthesized biphenyl-containing tetronamides were shown to display potent and selective inhibitory activity against cyanobacteria. These compounds appear to exert their biological effects without interfering with the Hill reaction. As such, they represent novel leads in the search of environmentally benign agents for controlling cyanobacterial blooms.

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Basidalin,a new antibiotic from basidiomycetes.

Cited by 17 publications

References 0 publications

Screening of Brazilian basidiomycetes for antimicrobial activity

Screening of Brazilian basidiomycetes for antimicrobial activity

Decarboxylative Knoevenagel-Type Reactions on Tetronamides: Synthesis of 5-Ylidene-4-Amino-2(5H)-Furanones

Synthesis of new tetronamides displaying inhibitory activity against bloom‐forming cyanobacteria

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