Isolation of the trimer of compound 48/80 and determination of its histamine-releasing activity.

Katsu, Takashi; Ono, Hiroko; Tasaka, Kenji; Fujita, Yuzuru

doi:10.1248/cpb.32.4185

Cited by 9 publications

(4 citation statements)

References 1 publication

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“…This finding supported that mastoparans increased the permeability of the erythrocyte membrane as proposed by the carpet model [4,31]. The structural requirement for making the crenated form was further investigated with the use of compound 48/80 and its constituents (monomer, dimer, and trimer) [32], changing systematically the number of cationic charges of the molecules.…”

Section: Introductionsupporting

confidence: 59%

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Comparative study of the membrane-permeabilizing activities of mastoparans and related histamine-releasing agents in bacteria, erythrocytes, and mast cells

Nakao

Komagoe

Inoue

et al. 2011

Biochimica et Biophysica Acta (BBA) - Biomembranes

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The membrane-permeabilizing activities of mastoparans and related histamine-releasing agents were compared through measurements of K(+) efflux from bacteria, erythrocytes, and mast cells. Changes in bacterial cell viability, hemolysis, and histamine release, as well as in the shape of erythrocytes were also investigated. The compounds tested were mastoparans (HR1, a mastoparan from Polistes jadwagae, and a mastoparan from Vespula lewisii), granuliberin R, mast cell-degranulating peptide, and compound 48/80, as well as antimicrobial peptides, such as magainin I, magainin II, gramicidin S, and melittin. We used a K(+)-selective electrode to determine changes in the permeability to K(+) of the cytoplasmic membranes of cells. Consistent with the surface of mast cells becoming negatively charged during histamine release, due to the translocation of phosphatidylserine to the outer leaflet of the cytoplasmic membrane, histamine-releasing agents induced K(+) efflux from mast cells, dependent on their ability to increase the permeability of bacterial cytoplasmic membranes rich in negatively charged phospholipids. The present results demonstrated that amphiphilic peptides, possessing both histamine-releasing and antimicrobial capabilities, induced the permeabilization of the cytoplasmic membranes of not only bacteria but mast cells. Mastoparans increased the permeability of membranes in human erythrocytes at higher concentrations, and changed the normal discoid shape to a crenated form. The structural requirement for making the crenated form was determined using compound 48/80 and its constituents (monomer, dimer, and trimer), changing systematically the number of cationic charges of the molecules.

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Section: Introductionsupporting

confidence: 59%

“…The sources of reagents were as follows: mastoparan HR1 (named mast Institute (Osaka, Japan); dioctyl phthalate from Tokyo Kasei (Tokyo, Japan); and poly(vinyl chloride) (PVC) (degree of polymerization, 1020) from Nacalai Tesque (Kyoto, Japan). The monomer, dimer, and trimer of compound 48/80 were prepared as reported previously [32].…”

Section: Reagentsmentioning

confidence: 99%

Comparative study of the membrane-permeabilizing activities of mastoparans and related histamine-releasing agents in bacteria, erythrocytes, and mast cells

Nakao

Komagoe

Inoue

et al. 2011

Biochimica et Biophysica Acta (BBA) - Biomembranes

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“…A solution of NaHCO 3 (2.8 g) and Na 2 SO 3 ؒ7H 2 O (1.0 g) in water (20 cm 3 ) was magnetically stirred under an atmosphere of nitrogen. Toluene (50 cm 3 ) was added followed by N-methyl-4methoxyphenylethylamine hydrochloride 25 (3.0 g) and then 4bromophenacyl bromide (2.9 g). After further stirring (4 h) the organic phase was separated, washed with saturated Na 2 HPO 4 solution (50 cm 3 ) and then stirred with aqueous HBr (3 cm 3 of 49% HBr made to 15 cm 3 ).…”

Section: Preparation Of N-(4-bromobenzoylmethyl)-n-[2-(4-hydroxypheny...mentioning

confidence: 99%

Oxidative cyclisation of N,N-dialkylcatechol amines to heterocyclic betaines via o-quinones: synthetic, pulse radiolytic and enzyme studies

Clews

Cooksey²,

Garratt³

et al. 2000

J. Chem. Soc., Perkin Trans. 1

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“…The antiallergic reaction of compounds (2-7) was investigated based on the expression of histamine against the allergy suppression involved in the onset of hay fever causing many diseases in recent years. As a comparison substance, a basic polymer compound 48/80 (an itch inducing agent) 30 causing mast cell degranulation in rat peritoneal was added, then method (histamine release inhibition test) was used to liberate histamine. As a result, it was shown (Table-7) that histamine release inhibitory effects of compound (2) and (4) were with values of (24.21± 2.08) % and (21.08 ± 3.76) %, respectively, compared with values of 35.23 ± 4.53 % of the control group.…”

Section: Resultsmentioning

confidence: 99%

Physiological Activity of Chinese Lichen (Gyrophora esculenta) Component, Methyl 2,4-Dihydroxy-6-methylbenzoate and the Related Compounds

Wu¹,

Zhao²,

Okada³

et al. 2014

Asian J. Chem.

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It was confirmed that there was a higher expression of antioxidant potential in methyl 2,4-dihydroxy-6-methylbenzoate (orsellinic acid methyl ester) (2), which was isolated from methanol extract oil of Chinese lichen Gyrophora esculenta rather than from commercialized ascorbic acid. Taking this into account, 4 types of compounds-(4-7) which are known to be related to compound (2)-have been synthesized by using 2,4-dihydroxy benzoic acid (3) as starting material. After that, some physiological activity tests on these compounds have been conducted in the following aspects: antioxidant potential, cytotoxicity, cytokine suppressant effect and histamine liberation inhibition and the effects have been evaluated, respectively. The result shows that (2) and methyl 2,4-dihydroxybenzoate (4) showed high radical expression in both antioxidant potential and histamine liberation inhibition. It was also found that none of these compounds expresses cytotoxicity.

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Isolation of the trimer of compound 48/80 and determination of its histamine-releasing activity.

Cited by 9 publications

References 1 publication

Comparative study of the membrane-permeabilizing activities of mastoparans and related histamine-releasing agents in bacteria, erythrocytes, and mast cells

Comparative study of the membrane-permeabilizing activities of mastoparans and related histamine-releasing agents in bacteria, erythrocytes, and mast cells

Oxidative cyclisation of N,N-dialkylcatechol amines to heterocyclic betaines via o-quinones: synthetic, pulse radiolytic and enzyme studies

Physiological Activity of Chinese Lichen (Gyrophora esculenta) Component, Methyl 2,4-Dihydroxy-6-methylbenzoate and the Related Compounds

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