Resorcinolic Lipids, the Natural Non-isoprenoid Phenolic Amphiphiles and Their Biological Activity

Kozubek, Arkadiusz; Tyman, J. H. P.

doi:10.1021/cr970464o

Cited by 511 publications

(466 citation statements)

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“…Most of the biological functions of phenolic lipids are related to modification of the physical properties of biomembranes [2]. As an amphiphilic compound, PDP can easily incorporate into the lipid bilayer, change the physicochemical properties of biomembranes, and alter the activities of different membrane proteins.…”

Section: Figurementioning

confidence: 99%

“…Many long-hydrocarbon-chain phenolic lipids can induce in higher concentrations non-layered structures of the micellar or H II type in lipid membranes [28]. This is responsible for the increase in permeability of a biomembrane in the presence of phenolic lipids and it changes the activities of membrane proteins [2]. PDP molecules create …”

Section: Accepted M Manuscriptmentioning

confidence: 99%

“…It is a large group of compounds of natural origin [1][2][3][4][5] which can interact with proteins, DNA, and biomembranes and they are antibacterial, fungicidic, and cytotoxic agents [2,6,7]. Phenolic lipids compose of an aromatic headgroup related to phenol or dihydroxybenzene connected to a hydrophobic hydrocarbon chain.…”

Section: Introductionmentioning

confidence: 99%

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The effect of 3-pentadecylphenol on DPPC bilayers ATR-IR and 31P NMR studies

Cieślik-Boczula¹,

Koll²

2009

Biophysical Chemistry

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To cite this version:Katarzyna Cieślik-Boczula, Aleksander Koll. The effect of 3-pentadecylphenol on DPPC bilayers ATR-IR and P NMR studies. Biophysical Chemistry, Elsevier, 2009, 140 (1-3) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. e-mail address: kasia_cieslik0@yahoo.com A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT3 AbstractThe influence of 3-pentadecylphenol (PDP) on the structure and physicochemical properties of the lipid bilayers of DPPC liposomes was studied using ATR-IR and 31 P NMR methods. On the basis of analysis of the bands assigned to the CH 2 stretching, CH 2 scissoring, C=O stretching, and PO 2 -stretching vibrations it was revealed that PDP influences both the hydrophobic and hydrophilic parts of the DPPC liposome bilayer. Analysis of the 31 P NMR line-shape indicated a lamellar to non-lamellar phase transition in PDP-doped DPPC dispersions. It was shown that PDP/DPPC isotropic aggregates have similar νC=O and ν as PO 2 -band positions and lower gauche populations in the hydrophobic chain region compared with the DPPC bilayer in the liquid-crystal phase.

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Section: Figurementioning

confidence: 99%

Section: Accepted M Manuscriptmentioning

confidence: 99%

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The effect of 3-pentadecylphenol on DPPC bilayers ATR-IR and 31P NMR studies

Cieślik-Boczula¹,

Koll²

2009

Biophysical Chemistry

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“…The most possible pathway is that bis-5-alkylresorcinols are synthesized by alkylresorcinols, which are known to be distributed widely in plants. 2 In this pathway, alkylresorcinols are first produced from acyl-CoAs. Next, the o-carbon of the alkyl chain of alkylresorcinols is oxidized, and the CoA is attached to the newly formed carboxyl group.…”

Section: Discussionmentioning

confidence: 99%

“…One class of the products of type III PKSs includes alkylresorcinols that consist of polar dihydroxybenzene rings and hydrophobic alkyl chains, and exhibit a wide variety of biological and biochemical activities. [2][3][4][5][6] For example, ArsB, a bacterial type III PKS from Azotobacter vinelandii, catalyzes three condensations of malonyl-CoA with a long-chain acyl starter substrate and subsequently cyclizes the resultant tetraketide intermediate by aldol condensation to yield alkylresorcinol. 3,4 ORAS, a fungal type III PKS from Neurospora crassa, synthesizes tetraketide and pentaketide alkylresorcylic acids from a long-chain acyl starter substrate such as stearoyl-CoA.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of bis-5-alkylresorcinols by resorcinol-producing type III polyketide synthases

Miyanaga

Horinouchi

2009

J Antibiot

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No enzyme systems responsible for the biosynthesis of structurally and biosynthetically intriguing bis-5-alkylresorcinols produced by plants have been identified. Herein, we show that bacterial, fungal and plant alkylresorcinol-producing type III polyketide synthases (PKSs), such as ArsB in the Gram-negative bacterium Azotobacter vinelandii, ORAS in the fungus Neurospora crassa and ARAS2 in the rice plant Oryza sativa, can synthesize bis-5-alkylresorcinol from alkanedioic acid N-acetylcysteamine dithioester as a starter substrate and from malonyl-CoA as an extender substrate by two-step conversion. Plants presumably use a type III PKS for the biosynthesis of bis-5-alkylresorcinols. Keywords: bis-5-alkylresorcinol; enzymatic synthesis; polyketide synthase INTRODUCTION Type III polyketide synthases (PKSs) are structurally simple enzymes that catalyze the synthesis of aromatic polyketides in bacteria, fungi and plants. 1 Type III PKSs catalyze iterative decarboxylative condensations of an extender substrate such as malonyl-CoA with a starter substrate such as acyl-CoA, and subsequently cyclize the resultant polyketide chain to yield various bioactive natural compounds with great structural diversity. This structural diversity of polyketide scaffolds is governed mainly by the selectivity of starter and extender substrates, the number of condensation reactions and the mode of ring closure of the resultant polyketide chains. One class of the products of type III PKSs includes alkylresorcinols that consist of polar dihydroxybenzene rings and hydrophobic alkyl chains, and exhibit a wide variety of biological and biochemical activities. [2][3][4][5][6] For example, ArsB, a bacterial type III PKS from Azotobacter vinelandii, catalyzes three condensations of malonyl-CoA with a long-chain acyl starter substrate and subsequently cyclizes the resultant tetraketide intermediate by aldol condensation to yield alkylresorcinol. 3,4 ORAS, a fungal type III PKS from Neurospora crassa, synthesizes tetraketide and pentaketide alkylresorcylic acids from a long-chain acyl starter substrate such as stearoyl-CoA. 5 ARAS2 (Oryza sativa genome DB os10g08620, alkylresorcylic acid synthase 2), a plant type III PKS from the rice plant O. sativa, also produces a tetraketide alkylresorcylic acid from a longchain acyl starter substrate, as does ORAS (our unpublished data). The alkylresorcylic acids produced by ORAS and ARAS2 are immediately converted into alkylresorcinols by non-enzymatic decarboxylation.Bis-5-alkylresorcinol, having a dihydroxybenzene ring at both terminal ends of an alkyl chain, has a relatively uncommon chemical structure (Figure 1a). The alkyl chain length of the bis-5-alkylresorcinols so far

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