Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

Martinková, Miroslava; Gonda, Jozef; Raschmanová, Jana Špaková; Slaninková, Michaela; Kuchár, Juraj

doi:10.1016/j.carres.2010.09.016

Cited by 26 publications

(5 citation statements)

References 39 publications

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“…The use of endophytic microorganisms has the advantage of being safe for humans; however, they may occasionally elicit various adverse effects such as phytotoxicity or environmental dependence for adequate biological activity [23], which is why the use of bioactive extracts and metabolites of these endophytes, including P. variotii, is of considerable interest [39]. A multitude of compounds synthesised by this fungus and able to act as microbial control agents has been described, such as 6-decyl salicylic acid [40], phenopicolinic acid [25], eicosenoic acid [41], ascofuranone [42], betulin [34], sphingofungin E and F [43,44], lawsozaheer [45], paecilaminol [20], paecilocin A-D [40], paeciloxazine [44,46], peptaibols [47], chitinases [39], varioxepine A and B [22,48], viriditin A and B [49], viriditoxin, semi-viriditoxin, and semi-viriditoxic acid [16,23,50].…”

Section: Introductionmentioning

confidence: 99%

Biocontrol Effects of Paecilomyces variotii against Fungal Plant Diseases

Moreno-Gavíra

Diánez

Sánchez-Montesinos

et al. 2021

JoF

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The genus Paecilomyces is known for its potential application in the control of pests and diseases; however, its use in agriculture is limited to few species. Research interest in new formulations based on microorganisms for the control of pathogens is growing exponentially; therefore, it is necessary to study new isolates, which may help control diseases effectively, and to examine their compatibility with established agricultural control methods. We analysed in vitro and in vivo the antagonistic capacity of Paecilomyces variotii against seven phytopathogens with a high incidence in different crops, and we examined its compatibility with 24 commercial fungicides. P. variotii was applied in the following pathosystems: B. cinereal—melon, Sclerotinia sclerotiorum—pepper, R. solani—tomato, F. solani—zucchini, P. aphanidermatum—melon, M. melonis—melon, and P. xanthii—zucchini. The results showed strong control effects on M. melonis and P. xanthii, reducing the disease severity index by 78% and 76%, respectively. The reduction in disease severity in the other pathosystems ranged from 29% to 44%. However, application of metabolites alone did not cause any significant effect on mycelial growth of phytopathogens, apart from F. solani, in which up to 12% inhibition was observed in vitro when the extract was applied at a concentration of 15% in the medium. P. variotii was compatible with most of the tested fungicides, and of the 24 fungicides tested at the maximum authorised dose, 6 acted as fungicides, 4 as fungistatics, and the remaining showed inhibition rates ranging from 18.2% to 95.8%. These results indicate that P. variotii is a potential biological control agent to be used against several aerial and soil diseases, thus it should be integrated into modern pest management strategies.

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Section: Introductionmentioning

confidence: 99%

Biocontrol Effects of Paecilomyces variotii against Fungal Plant Diseases

Moreno-Gavíra

Diánez

Sánchez-Montesinos

et al. 2021

JoF

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“…Like sphingofungin B, both compounds inhibited serine palmitoyltransferase at nanomolar levels. Furthermore, sphingofungin E showed fungicidal activity against several human pathogens [37].…”

Section: Sphingolipidsmentioning

confidence: 99%

The Chemical Diversity of the Ascomycete Fungus Paecilomyces variotii

Mioso

Marante

Laguna

2015

Appl Biochem Biotechnol

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Paecilomyces variotii isolated from a broad range of habitats drives the diversification of new high-value-added secondary metabolites that could potentially play an important role in human and animal health. These metabolites include the anhydride metabolite of the nonadride family, as well as the following compounds: naphthopyranone metabolites, sphingofungins, eicosenoic acids, new branched fatty acids, ascofuranone, polyketides, an anacardic acid analogue, straight-chain peptides, and volatile compounds. These natural products show that P. variotii can provide leading compounds for new drug discoveries, which may include herbicide agents, some of which are important in the agrochemical market. Finally, this review outlines recent developments, trends, and prospects for the chemistry of this ascomycete.

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“…Due to their intriguing structural features and important pharmacological properties, sphingofungins became quickly popular total synthetic targets. Until today, 14 distinct synthetic strategies have been applied in the total synthesis of sphingofungins B, D, E, and F,[ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ] with the last syntheses of sphingofungin E and F being reported in 2017 by Noda et al. [35] and Sugai et al.…”

Section: Introductionmentioning

confidence: 99%

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

et al. 2021

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Sphingofungins are fungal natural products known to inhibit the biosynthesis of sphingolipids which play pivotal roles in various cell functions.H ere,w er eport as hort and flexible synthetic approach towards the sphingofungin family. Keystep of the synthesis was adecarboxylative cross-coupling reaction of chiral sulfinyl imines with afunctionalizedtartaric acid derivative,whichyielded the core motif of sphingofungins carrying four consecutive stereocenters and at erminal double bond. Subsequent metathesis reaction allowed for the introduction of different side chains of choice resulting in atotal of eight sphingofungins,i ncluding for the first time sphingofungin C( eight steps from commercially available protected tartaric acid with an overall yield of 6%)and sphingofungin A (ten steps). All newly synthesized derivatives were tested for their antifungal, cell-proliferative and antiparasitic activity unraveling their structure-activity relations.

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Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

Cited by 26 publications

References 39 publications

Biocontrol Effects of Paecilomyces variotii against Fungal Plant Diseases

Biocontrol Effects of Paecilomyces variotii against Fungal Plant Diseases

The Chemical Diversity of the Ascomycete Fungus Paecilomyces variotii

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

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