Higher Cardol Homologues (5-Alkenylresorcinols) from Rye Affect the Red Cell Membrane-Water Transport

Kozubek, Arkadiusz

doi:10.1515/znc-1985-1-216

Cited by 13 publications

(2 citation statements)

References 10 publications

(25 reference statements)

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“…Phenolic lipids (especially resorcinolic lipids) are indicated for the prevention and/or treatment of cancer. The amphiphilic property of these compounds, which is attributed to the presence of non-isoprenoid side chains bound to the hydroxybenzene ring, permits their interaction with the lipid bilayer [ 4 – 6 ], the formation of liposomes [ 7 ], protection against oxidative stress [ 8 ] and the inhibition of bacterial [ 9 – 11 ] and tumor cell growth [ 12 , 13 ]. Particularly interesting are phenolic lipids of the cytosporone class, which present allelopathic activity [ 14 ] and can interact with the orphan nuclear receptor Nur77, triggering apoptosis [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

A novel cytosporone 3-Heptyl-4,6-dihydroxy-3H-isobenzofuran-1-one: synthesis; toxicological, apoptotic and immunomodulatory properties; and potentiation of mutagenic damage

et al. 2015

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BackgroundA large number of studies are attempting to identify alternative products from natural sources or synthesized compounds that effectively interact with cancer cells without causing adverse effects on healthy cells. Resorcinolic lipids are a class of bioactive compounds that possess anticancer activity and are able to interact with the lipid bilayer. Therefore, the objective of this study was to synthesize a novel resorcinolic lipid and test its biological proprieties.MethodsWe aimed to synthesize a novel resorcinolic lipid belonging to the class of cytosporones, AMS049 (3-Heptyl-4,6-dihydroxy-3H-isobenzofuran-1-one) and to evaluate the toxicity of two concentrations of this lipid (7.5 and 10 mg/kg) by determining its genotoxic, mutagenic, immunomodulatory, and apoptotic effects, as well as any biochemical and histopathological alterations in mice treated with cyclophosphamide. The results were analyzed by ANOVA followed by the Tukey test A . level of significance of p < 0.05 was adopted.ResultsThe new cytosporone AMS049 was synthesized in only three steps and in satisfactory yields. The results indicate that the compound is neither genotoxic nor mutagenic and does not alter biochemical parameters. The histological alterations observed in the liver and kidneys did not compromise the function of these organs. Histology of the spleen suggested immunomodulation, although no changes were observed in splenic phagocytosis or differential blood cell count. The results also show that AMS049 potentiates the mutagenic effect of the chemotherapy drug cyclophosphamide and that the combination induces apoptosis.ConclusionThese facts indicate a potential therapeutic application of this novel cytosporone as an important chemotherapeutic adjuvant.Electronic supplementary materialThe online version of this article (doi:10.1186/s12885-015-1532-2) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

A novel cytosporone 3-Heptyl-4,6-dihydroxy-3H-isobenzofuran-1-one: synthesis; toxicological, apoptotic and immunomodulatory properties; and potentiation of mutagenic damage

et al. 2015

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“…If added before phospholipid vesicles are formed, ARs showed a stabilizing effect on phospholipid bilayers. The membrane becomes more resistant to the permeation of small solutes, such as water, ions, and glucose (9)(10)(11)(12), and vesicles are more resistant to osmotic stress (13).…”

Section: Introductionmentioning

confidence: 99%

Disturb or Stabilize? A Molecular Dynamics Study of the Effects of Resorcinolic Lipids on Phospholipid Bilayers

Siwko

Vries

Mark

et al. 2009

Biophysical Journal

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Resorcinolic lipids, or resorcinols, are commonly found in plant membranes. They consist of a substituted benzene ring forming the hydrophilic lipid head, attached to an alkyl chain forming the hydrophobic tail. Experimental results show alternative effects of resorcinols on lipid membranes. Depending on whether they are added to lipid solutions before or after the formation of the liposomes, they either stabilize or destabilize these liposomes. Here we use atomistic molecular dynamics simulations to elucidate the molecular nature of this dual effect. Systems composed of either one of three resorcinol homologs, differing in the alkyl tail length, interacting with dimyristoylphosphatidylcholine lipid bilayers were studied. It is shown that resorcinols preincorporated into bilayers induce order within the lipid acyl chains, decrease the hydration of the lipid headgroups, and make the bilayers less permeable to water. In contrast, simulations in which the resorcinols are incorporated from the aqueous solution into a preformed phospholipid bilayer induce local disruption, leading to either transient pore formation or even complete rupture of the membrane. In line with the experimental data, our simulations thus demonstrate that resorcinols can either disturb or stabilize the membrane structure, and offer a detailed view of the underlying molecular mechanism.

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Biological activity of phenolic lipids

Stasiuk

Kozubek

2009

Cell. Mol. Life Sci.

229

158

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Phenolic lipids are a very diversified group of compounds derived from mono and dihydroxyphenols, i.e., phenol, catechol, resorcinol, and hydroquinone. Due to their strong amphiphilic character, these compounds can incorporate into erythrocytes and liposomal membranes. In this review, the antioxidant, antigenotoxic, and cytostatic activities of resorcinolic and other phenolic lipids are described. The ability of these compounds to inhibit bacterial, fungal, protozoan and parasite growth seems to depend on their interaction with proteins and/or on their membrane-disturbing properties.

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Higher Cardol Homologues (5-Alkenylresorcinols) from Rye Affect the Red Cell Membrane-Water Transport

Cited by 13 publications

References 10 publications

A novel cytosporone 3-Heptyl-4,6-dihydroxy-3H-isobenzofuran-1-one: synthesis; toxicological, apoptotic and immunomodulatory properties; and potentiation of mutagenic damage

A novel cytosporone 3-Heptyl-4,6-dihydroxy-3H-isobenzofuran-1-one: synthesis; toxicological, apoptotic and immunomodulatory properties; and potentiation of mutagenic damage

Disturb or Stabilize? A Molecular Dynamics Study of the Effects of Resorcinolic Lipids on Phospholipid Bilayers

Biological activity of phenolic lipids

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