5-Alkylresorcinols from Hakea trifurcata, that cleave DNA.

Lytollis, W.; Scannell, Ralph T.; An, Hongyu; Murty, V. S.; Reddy, K. Sambi; Barr, John R.; Hecht, Sidney M.

doi:10.1021/ja00156a004

Cited by 74 publications

(36 citation statements)

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“…Many biologically active compounds belonging to this class of derivatives also include other functional groups in the aromatic ring as well as in the 526 D. Petrelli et al alkyl chain. Antimicrobial, antiparasitic, anticancer and genotoxic activities have been reported to date for this group of compounds (Lytollis et al 1995;Singh et al 1995;Kozubek et al 2001).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

et al. 2012

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Climacostol is a defense toxin produced by the ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that shows antimicrobial, antiparasitic, and cytotoxic activities. In this study we investigate the antimicrobial activity of climacostol and its alkyl and alkynyl derivatives against a panel of bacterial and fungal pathogens. Our results show a good and comparable antimicrobial activity of the three compounds, which have resulted effective against Gram-positive bacteria and Candida with MIC and MBC ranging from 8 to 32 mg L −1 , whereas no significant effect against Gram-negative species has been observed. Taken as a whole, the experimental data reported in the current study suggest that differences in the saturation rate of the lateral chain of climacostol are not related to the activity of the molecule. Therefore, it is likely that the general structure of the two moieties, i.e., the di-hydroxy-phenyl group and the alkenyl chains, contributes to the overall antibiotic behaviour.

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Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

et al. 2012

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“…To date, several compounds that show antimicrobial, antiparasitic, antitumoral and genotoxic activities have been identified among the alkylresorcinols (Picardo et al 1987;Lytollis et al 1995;Singh et al 1995;Kozubek et al 2001). In addition, their potential use in the therapy and/or prevention of specific classes of diseases has attracted particular attention (Itokawa et al 1989;Suresh & Ray 1990;Gasiorowsky et al 1996;Kozubek et al 2001;Filip et al 2002;Barbini et al 2006).…”

Section: Introductionmentioning

confidence: 99%

The protozoan toxin climacostol and its derivatives: Cytotoxicity studies on 10 species of free-living ciliates

Buonanno

Ortenzi

2010

Biologia

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Climacostol (5-(Z)-non-2-enyl-benzene-1,3-diol) is a natural toxin isolated from the freshwater ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that show antimicrobial, antiparasitic, and anticancer activities. We investigated the cytotoxic activity of the chemically synthesized toxin and its alkyl and alkynyl derivatives on C. virens and nine other common species of free-living freshwater ciliates. Our results show that the cytotoxic potency of climacostol can be modulated by the substitution of the double bond present in the aliphatic chain of the toxin with a single or a triple one that was previously obtained during the synthesis of the unsaturated and saturated derivatives of the parent molecule. We demonstrated that the cytotoxicity level of the molecules considered in this study appears to be inversely correlated to the unsaturation level of their aliphatic chains, and that the potency of their action is also related to the target organism.

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“…6 Furthermore, reaction with 0.5 equivalents of 1,12-dibromododecane afforded the tetramethyl ether 3f (Table 1, entry 7); the latter compound, according to a literature procedure, can be converted into 1,3-dihydroxy-5-[14 -(3 ,5 -dihydroxyphenyl)tetradecyl]-benzene, a natural lipidic resorcinol able to cleave DNA in the presence of Cu 2+ . 12,13 As an approach to the synthesis of resorcinols bearing an additional functional group on the alkyl chain, suitable for further elaboration, we investigated the reactivity of intermediate 2 with functionalized alkyl halides and with an epoxide. Accordingly, reaction with 10-bromodecanol (0.5 equivalents), 2-bromoethyl-1,3-dioxolane (1.1 equivalents), and 1-butene oxide (2.2 equivalents) led to the recovery of the dimethyl ethers of functionalized resorcinols 3g, 3h and 3i respectively in satisfactory yields (Table 1, entries 8-10).…”

Section: Main Group Metal Compoundsmentioning

confidence: 99%

Practical generation of 3,5‐dimethoxybenzyllithium: application to the synthesis of 5‐substituted‐resorcinols

Azzena

Dettori

Idini

et al. 2003

Applied Organom Chemis

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Reductive lithiation of 3,5-dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at −15 • C, leading to the quantitative generation of 3,5-dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non-functionalized and functionalized alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5-substituted natural and non-natural resorcinols.

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5-Alkylresorcinols from Hakea trifurcata, that cleave DNA.

Cited by 74 publications

References 1 publication

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

The protozoan toxin climacostol and its derivatives: Cytotoxicity studies on 10 species of free-living ciliates

Practical generation of 3,5‐dimethoxybenzyllithium: application to the synthesis of 5‐substituted‐resorcinols

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