Purpurenol, a highly oxygenated coumarin from Pterocaulon purpurascens

Debenedetti, Sílvia; Nadinic, Elena L.; Coussio, J.; Kimpe, Norbert De; Dupon, Jeanine Feneau; Declercq, J.P.

doi:10.1016/0031-9422(91)85138-p

Cited by 35 publications

(10 citation statements)

References 4 publications

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“…Malme. Algumas cumarinas isoladas de espécies de Pterocaulon podem ser citadas: 6,7-dimetoxicumarina de P. sphacelatum, oito cumarinas do extrato etéreo das partes aéreas de P. balansae e P. lanatum (MA-GALHÃES et al, 1981) e uma cumarina 5,6,7,8-tetraoxigenada, denominada purpurenol de P. purpurascens (Debenedetti et al, 1991). Debenedetti et al (1997) realizaram uma revisão estrutural das cumarinas denominadas sabandinol e sabandinona e a descrição de mais duas novas cumarinas denominadas de virgatenol e virgatol (Debenedetti et al, 1998).…”

Section: Introductionunclassified

Estudo fitoquímico da espécie Pterocaulon interruptum DC. (Asteraceae)

Heemann¹,

Miguel²,

Miguel³

et al. 2006

Rev. Bras. Cienc. Farm.

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Section: Introductionunclassified

Estudo fitoquímico da espécie Pterocaulon interruptum DC. (Asteraceae)

Heemann¹,

Miguel²,

Miguel³

et al. 2006

Rev. Bras. Cienc. Farm.

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“…Wagner et al 10 later reported isosilybin (11b), a congener of silybin. Eusiderin (12) is a rare example of a neolignan with a 1,4-benzodioxan nucleus and was isolated by Hobbs and King 11 from Eusideroxylon zwageri. Purpurenol (13) l2 is a new 5,6,7,8-tetraoxygenated coumarin derivative that was isolated from the aerial parts of Pterocaulon purpurascens, the plant used in folk medicine in Argentina for various purposes, e.g.…”

Section: 3-dihydro-14-benzodioxin Derivativesmentioning

confidence: 99%

Perspectives on 1,4-Benzodioxins, 1,4-Benzoxazines and their 2,3-Dihydro Derivatives

Achari¹,

Mandal²,

Dutta³

et al. 2004

Synlett

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The origin and growth of the chemistry of 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives are briefly described. This class of compounds has attracted special attention due to their natural occurrence and important biological activities. The structural scaffolds of these heterocycles serve as building blocks in various useful syntheses. The introduction of palladium-catalyzed reactions has added a new dimension to this field by making the synthesis more convenient and general. The purpose of this account is to facilitate and revitalize interest in this field within the synthetic community. Conclusions

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“…It can also be acquired from more common natural sources. [13][14][15][16][17] It was reported that various derivatives of 1,4-benzodioxan show biological activities, [18][19][20] some of which are anticancer agents 21) or new anti-inflammatory compounds.…”

Section: )mentioning

confidence: 99%

Synthesis and Antibacterial Activity of Cinnamaldehyde Acylhydrazone with a 1,4-Benzodioxan Fragment as a Novel Class of Potent β-Ketoacyl–Acyl Carrier Protein Synthase III (FabH) Inhibitor

et al. 2014

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Fatty acid biosynthesis is essential for bacterial survival. β-Ketoacyl-acyl carrier protein (ACP) synthase III (FabH), is a particularly attractive antibacterial target, since it is central to the initiation of fatty acid biosynthesis. Three series of 21 cinnamaldehyde acylhydrazone derivatives, A3-9, B3-9, and C3-9, were synthesized and evaluated for FabH-inhibitory activity. Compound B6 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis (minimum inhibitory concentrations (MICs) values: 1.56-3.13 µg/mL) and was comparable with the positive control. Docking simulation by positioning compound B6 in the FabH structure active site was performed to explore the possible binding model. Key words cinnamaldehyde; acylhydrazone; benzodioxan; antibacterial; structure-activity relationship; FabH inhibitor Bactria has become a greater threat to human beings as antibiotic resistance sweeps the world.1) Fatty acid biosynthesis (FAB) is an essential metabolic process for prokaryotic organisms and is required for cell viability and growth.2) The significant differences between human and prokaryotic FAB systems render prokaryotic FAB to be an attractive target.3)The β-ketoacyl-acyl carrier protein (ACP) synthase III (FabH) has no homologs in human and is one of essential functional enzymes in bacterial FAB system. FabH initiates the FAB cycle by catalyzing the first condensation step between acetylCoA and malonyl-ACP, playing a key regulatory role in the bacterial FAB cycle.4) Many kinds of compounds harbored Schiff base motif or hydrozone motif was screened for antimicrobial activity, some of which are potent inhibitors of FabH. 5)For example, compounds 1-8 (Fig. 1A) reported as inhibitors of Escherichia coli FabH showed the most potent FabH inhibitory activity in each article respectively. [6][7][8][9][10][11][12] 1,4-Benzodioxan is an important frame for medicine and widely found in natural products, e.g. silybin, purpurenol, 3,4-dihydroxystyrene dimmers (shown in Fig. 1B). It can also be acquired from more common natural sources. [13][14][15][16][17] It was reported that various derivatives of 1,4-benzodioxan show biological activities, [18][19][20] some of which are anticancer agents 21) or new anti-inflammatory compounds.18) The aim of this study is to design a series of hydrazide-Schiff bases with a spectrum of antibactrial applications. In view of the findings mentioned above, we report in this present work the synthesis of a series of 1,4-benzodioxan acylhydrazone derivatives (showed in Fig. 1C) to achieve new potential antibacterial FabH inhibitors. Results and DiscussionChemistry In this study, twenty-one cinnamaldehydeacylhydrazone derivatives were designed and synthesized. The synthesis of compounds A3-9; B3-9 and C3-9 followed the general pathway outlined in Chart 1. All of them were prepared in three steps, which is based on our previous research. with 85% hydrazine monohydrate in ethanol. The synthesis of compounds A3-9, B3-9...

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Purpurenol, a highly oxygenated coumarin from Pterocaulon purpurascens

Abstract: A new 5,6,7,8-tetraoxygenated coumarin, named purpurenol, was isolated from aerial parts of Pterocaulon purpurascens. Its structure was elucidated on the basis of the spectral data and was confirmed by X-ray analysis

Cited by 35 publications

References 4 publications

Estudo fitoquímico da espécie Pterocaulon interruptum DC. (Asteraceae)

Estudo fitoquímico da espécie Pterocaulon interruptum DC. (Asteraceae)

Perspectives on 1,4-Benzodioxins, 1,4-Benzoxazines and their 2,3-Dihydro Derivatives

Synthesis and Antibacterial Activity of Cinnamaldehyde Acylhydrazone with a 1,4-Benzodioxan Fragment as a Novel Class of Potent β-Ketoacyl–Acyl Carrier Protein Synthase III (FabH) Inhibitor

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