Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs

Grossmann, Gilles; Poncioni, Marc; Bornand, Marc; Jolivet, Benoît; Neuburger, Markus; Séquin, Urs

doi:10.1016/s0040-4020(03)00483-6

Cited by 44 publications

(31 citation statements)

References 15 publications

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“…In particular, the synthesis of four 2[5H]-furanones with antibiotic activity against Pseudomonas aeruginosa has been reported previously for Streptomyces antibioticus (5). Some of these compounds proved to be active in the quorum-sensing system of Chromobacterium violaceum (16). Moreover, five 2[5H]-furanones, the aporpinones, were reported to be secondary metabolites of Aspergillus terreus (45) and Aporpium caryae (27).…”

Section: Discussionmentioning

confidence: 91%

“…While the biosynthesis of the 2[3]-furanones and of AHLs has been deeply studied (57), the biosynthesis mechanisms of the abovementioned 2[5H]-furanones and their precursors are almost unknown. However, some bioactive 2[5H]-furanones endowed with pharmacological properties have been obtained through chemical synthesis (16). These synthetic compounds were able to simulate AHL activity and induce violacein formation in Chromobacterium violaceum (31).…”

Section: Discussionmentioning

confidence: 99%

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Two 2[5H]-Furanones as Possible Signaling Molecules inLactobacillus helveticus

Ndagijimana

Vallicelli

Cocconcelli

et al. 2006

Appl Environ Microbiol

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Two 2[5H]-furanones, in association with medium-chain fatty acids, were released in whey by Lactobacillus helveticus exposed to oxidative and heat stresses. This species plays an important role in cheese technology, particularly for Swiss-type cheeses and Grana cheese. Moreover, it significantly contributes to cheese ripening by means of an early autolysis and the release of enzymes during processing. Experimental evidence of the involvement of the two 2[5H]-furanones, detected by a gas chromatography-mass spectrometry/solid-phase microextraction technique, in the autolysis phenomenon has been obtained. Zymograms performed by using renaturing sodium dodecyl sulfate-polyacrylamide gels were used to detect the bioactivity of the supernatants containing the two furanones on fresh cells of the same strain. In addition to bands corresponding to known autolysins, new autolysins were detected concomitant with the exposure of Lactobacillus helveticus to the supernatants, which can be regarded as conditioned media (CM), and to a commercial furanone, 5-ethyl-3-hydroxy-4-methyl-2[5H]-furanone (HEMFi), having spectral data similar to those of the newly described 2[5H]-furanones. Morphological changes were observed when fresh cells were exposed to CM containing the two 2[5H]-furanones and HEMFi. The two furanones produced by Lactobacillus helveticus, which met a number of criteria to be included in cell-cell signaling molecules, have a presumptive molecular mass lower than those of already known 3[2H]-furanones having an autolytic activity and being produced by gram-negative bacteria. Moreover, they present a different chemical structure with respect to the furanones already identified as products of Lactococcus lactis subsp. cremoris or to those identified in some cheeses with Lactobacillus helveticus as a starter culture.

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Section: Discussionmentioning

confidence: 91%

Section: Discussionmentioning

confidence: 99%

Two 2[5H]-Furanones as Possible Signaling Molecules inLactobacillus helveticus

Ndagijimana

Vallicelli

Cocconcelli

et al. 2006

Appl Environ Microbiol

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“…for C 24 H 25 NO 4 : C,73.64;H,6.44;N,3.58 (%). Found: C,73.66;H,6.40;N,3.60 (%) 2,29.2,34.8,52.9,67.8,115.3,123.4,134.5,137.9,145.1,158.3,196.1,206.7. Anal.…”

Section: -(Tert-butylimino)-67-dihydro-2h-spiro[benzofuran-33´-indmentioning

confidence: 99%

“…1 They have been shown wide range of biological activities such as antimicrobial, 2 antifungal, 3 anti-inflammatory, 4 anticancer, 5 and antiviral. 6 Moreover, iminolactones have been used for the synthesis of sphingofungin F 7a that exhibits inhibitory effects toward serine palmitoyl transferase (SPT), which induces apoptosis in both yeast and mammalian cells by blocking the sphingosine biosynthesis pathway.…”

Section: Introductionmentioning

confidence: 99%

Eco-Friendly Multi-Component Synthesis of γ-Spiroiminolactones in Water

Safaei¹,

Shekouhy

2017

ACSi

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Abstractγ-Spiroiminolactone derivatives can be synthesized through an one-pot three-component reaction of cyclic carbonyl compounds (isatin, acenaphthoquinone, ninhydrin), activated α-methylene carbonyl groups and isocyanides in water using sodium dodecyl sulfate (SDS) as a commercially available and cheap surfactant compound. All products were obtained in good to excellent yields without formation of any by-products in water as a green and benign reaction medium. Moreover, presented method was successfully applied for the synthesis of some novel bis(spiroiminolactone) derivatives.

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“…The widespread distribution of butenolides in naturally occurring [1][2][3] and synthetic bioactive substances strongly motivate an interest for improving the methodology of the selective synthesis of butenolide functionalized spirooxindoles in high yield [4,5]. Such developments are of interest not only for the possible total synthesis of therapeutically useful spirooxindoles [6][7][8][9][10][11][12][13][14][15], but also for the preparation of synthetic analogs [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] in order to improve our knowledge in structure-activity relationships [12-14, 31, 32].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of New Spirolactones from Substituted Isatins

Sucman¹,

Pogrebnoi²,

Обушак³

et al. 2015

ChemJMold

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Abstract. Interaction of N-ethyl isatin 3 with dimethyl acetylenedicarboxylate in the presence triphenylphosphine has led to good selectivity of methyl 1'-ethyl-4-methoxy-2',5-dioxo-5H-spiro[furan-2,3'-indoline]-3-carboxylate 4 formation. Similar yields of spirolactones 6,8 were obtained by addition of dimethyl acetylenedicarboxylate to 5-bromo functionalized isatins 5,7. However, reaction of N-butyl isatin 9 resulted in formation of an inseparable mixture of compounds. Treatment of N-benzyl isatin 10 and dimethyl acetylenedicarboxylate with triphenylphosphine proceeded with reduced selectivity of the spirooxindole 11 formation.Keywords: spirolactones, isatins, triphenylphosphine, dimethyl acetylenedicarboxylate. IntroductionThe widespread distribution of butenolides in naturally occurring [1-3] and synthetic bioactive substances strongly motivate an interest for improving the methodology of the selective synthesis of butenolide functionalized spirooxindoles in high yield [4,5]. Such developments are of interest not only for the possible total synthesis of therapeutically useful spirooxindoles [6][7][8][9][10][11][12][13][14][15], but also for the preparation of synthetic analogs [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] in order to improve our knowledge in structure-activity relationships [12-14, 31, 32]. So-called butenolide functionalized spirooxindoles 1 provide the most interesting subject for synthetic investigations in view of the large and ever increasing number of the members of this family which have furan-2(5H)-one 2 as a building block (Scheme 1).

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Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs

Cited by 44 publications

References 15 publications

Two 2[5H]-Furanones as Possible Signaling Molecules inLactobacillus helveticus

Two 2[5H]-Furanones as Possible Signaling Molecules inLactobacillus helveticus

Eco-Friendly Multi-Component Synthesis of γ-Spiroiminolactones in Water

The Synthesis of New Spirolactones from Substituted Isatins

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