Synthesis and antioxidant properties of pulvinic acids analogues

Nadal, Brice; Thétiot-Laurent, Sophie; Pin, Serge; Renault, Jean Philippe; Cressier, Damien; Rima, G.; Roux, Antoine Le; Meunier, Stéphane; Wagner, Alain; Lion, Claude; Gall, Thierry Le

doi:10.1016/j.bmc.2010.09.037

Cited by 21 publications

(12 citation statements)

References 40 publications

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“…Substitution of arylamino group (6-9) for 4-hydroxyl group (1) maintained the potency or showed a mild increase in activity, while the 2-bromoethoxy group is present at this place, leading to an inactive compound (2). However, the bromine atom in the side chain of 2 was replaced by an aliphatic amino group (3)(4)(5), resulting in a 3-to 10-fold increase in activity, with compound 5 being the most active (MIC 50 = 7.3 lg/mL).…”

Section: Resultsmentioning

confidence: 93%

“…Compounds with c-butyrolactone-core show diverse biological activities such as anti-oxidative, anti-inflammatory and antibacterial activity [1][2][3], and have been receiving increasing attention in recent years [4,5]. In 2006, Lattmann et al [6] reported 5-alkoxy-4-aminofuran-2(5H)-ones (Scheme 1) showing good antibacterial activity against multiresistant Staphylococcus aureus.…”

Section: Introductionmentioning

confidence: 97%

“…As a part of our ongoing studies on furan-2(5H)-ones, we designed and synthesized a series of 3-(3,4-dimethoxyphenyl)-furan-2(5H)-ones for screening antibacterial activity. For confirmation of the structure the obtained compounds (1)(2)(3)(4)(5)(6)(7)(8)(9), the single crystal structure of 3-(3,4-dimethoxyphenyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy) furan-2(5H)-one (5) was selected to determine.…”

Section: Introductionmentioning

confidence: 99%

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Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones

Zhang

et al. 2011

J Chem Crystallogr

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Crystalline hydrate of the title compound (5), C 19 H 26 N 2 O 5 Á2(H 2 O), was structurally characterized by single crystal X-ray diffraction. It crystallizes in monoclinic system space group P 21/c with a = 7.3987(7) Å , b = 17.8691(16) Å , c = 17.0022(13) Å , b = 112.944(3)°, V = 2070.0(3) Å 3 , Z = 4, R 1 = 0.0592, wR 2 = 0.1016, and T = 298(2) K. The X-ray structure determination revealed that the center furanone ring is nearly coplanar with 3,4-dimethoxybenzene ring, making a dihedral angle of 0.860(69)°. Two kinds of centrosymmetric tetramers characterized by graph-set motifs of R 7 8 (36) and R 4 6 (32) are formed through O-HÁÁÁO, O-HÁÁÁN and C-HÁÁÁO hydrogen bonding interactions, which generate a sheet of edge-fused rings parallel to the (011) plane. These sheets are further linked into a three dimensional network by C-HÁÁÁp interactions. Nine 3-(3,4-dimethoxyphenyl)furan-2(5H)-ones were synthesized and fully characterized by elemental analysis, MS and 1 H NMR. All of them were evaluated for antimicrobial activities against three Gram-positive organisms and a Gram-negative organism, and compound 5 was the most active against Staphylococcus aureus ATCC 25923.

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Section: Resultsmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones

Zhang

et al. 2011

J Chem Crystallogr

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“…We can speculate that the mycobiont culture chemosyndrome could be very similar to the chemosyndrome of aposymbiotic pre-thallus stage in nature being related to adaptation to different habitats and different ecological valence. In this case make sense that Parmelina carporrhizans inhabiting more oceanic habitats is producing confluentic acid with biocide properties [42] very useful in humid places while P. quercina inhabiting continental drier habitat is producing pulvininic acid as major compound, which confers vantage by its photoprotective properties and DNA protection against oxidative stress [43] as an adaptation to drought and insolation.…”

Section: Discussionmentioning

confidence: 99%

Chemosyndrome Variation in Mycobiont Culture and Thallus of <em>Parmelina carporrhizans</em> and <em>Parmelina quercina</em>

Alors¹,

Divakar²,

Anjuli³

et al. 2017

Preprint

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Abstract:We cultured Parmelina carporrhizans and P. quercina in Corn Meal Agar and 0.2% glucose Malt Yeast Agar for 160 days. Chemosyndrome of natural thalli and mycobiont cultures were analyzed by HPLC. Lecanoric acid, atranorin, chloratranorin and ergosterol were detected in P. carporrhizans thalli, while lecanoric acid, chloratranorin and aliphates were found in P. quercina thalli. The secondary methabolites pattern between thalli and mycobiont culture was completely different in both species. Both species secreted the phenalenone myeloconone C in culture media and was also detected in P. quercina mycobiont aggregates. Interestingly, the phenolic compounds produced by the mycobiont culture of P. carporrhizans are related to those produced by natural thallus by the same biosynthetic pathway, while the chemosyndrome of P. quercina mycobiont implies switch of biosynthetic pathway from acetate-polymalonate pathway to shikimic acid pathway, with pulvinic acid as major compound of mycobiont culture. The role of Myelochonone C, confluentic acid and pulvinic acid produced by mycobiont culture is discussed as possible adaptive vantage in field as photoprotective agent or as byproduct result of stressing artificial culture conditions.

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“…In our group, derivatives as 3-aryl-4-aminofuran-2(5H)-ones, 3-aryl-4-acyloxyethoxyfuran-2(5H)-ones and 3-arylfuran-2(5H)-one-fluoroquinolone hybrids have been previously reported to exhibit excellent inhibition activity against pathogenic bacteria. [23][24][25][26][27][28][29] However, the anti-H. pylori activity of them was not included.…”

Section: Introductionmentioning

confidence: 99%