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Literature summary extracted from

  • Yamazaki, Y.; Yasuda, K.; Matsuyama, T.; Ishihara, T.; Higa, R.; Sawairi, T.; Yamaguchi, M.; Egi, M.; Akai, S.; Miyase, T.; Ikari, A.; Miwa, M.; Sugatani, J.
    A Penicillium sp. F33 metabolite and its synthetic derivatives inhibit acetyl-CoA:1-O-alkyl-sn-glycero-3-phosphocholine acetyltransferase (a key enzyme in platelet-activating factor biosynthesis) and carrageenan-induced paw edema in mice (2013), Biochem. Pharmacol., 86, 632-644.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.3.1.67 medicine inhibitors 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone and 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone at 2.5 mg/kg shod significant, 47.9-51.7%, inhibition in the carrageenan-induced mouse paw edema test, stronger than that of prednisolone at 10 mg/kg Mus musculus

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.67 gene Lpcat2, quantitative realtime PCR exprssion analysis Mus musculus

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.23 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone potent inhibitor Rattus norvegicus
2.3.1.23 3,4-dihydroxy-1,2-dimethoxy-5-methylbenzene
-
 Rattus norvegicus
2.3.1.23 3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone
-
 Rattus norvegicus
2.3.1.23 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone potent inhibitor Rattus norvegicus
2.3.1.23 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
-
 Rattus norvegicus
2.3.1.23 dihydrofumigatin i.e. 2-methoxy-1,3,4- trihydroxy-5-methylbenzene Rattus norvegicus
2.3.1.23 fumigatin i.e. 3-hydroxy-2-methoxy-5-methyl-1,4-benzoquinone Rattus norvegicus
2.3.1.23 additional information not inhibited by 2-methoxy-5-methyl-1,3,4-triacetoxybenzene and 1,4-diacetoxy-2-methoxy-5-methyl-3-tetradecanoyloxybenzene Rattus norvegicus
2.3.1.67 1,4-diacetoxy-2-methoxy-5-methyl-3-tetradecanoyloxybenzene
-
 Mus musculus
2.3.1.67 2-methoxy-1,3,4-trihydroxy-5-methylbenzene i.e. 2-methoxy-1,3,4-trihydroxy-5-methylbenzene, isolated from Penicillium sp. strain F33 Mus musculus
2.3.1.67 2-methoxy-5-methyl-1,3,4-triacetoxybenzene
-
 Mus musculus
2.3.1.67 2-methoxy-5-methyl-3-octadecanoyloxy-1,4-benzoquinone
-
 Mus musculus
2.3.1.67 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone derivative of a metabolite from Penicillium sp. F33 , strong inhibition. Compound also significantly suppresses the gene expression of lyso-PAF acetyltransferase/LPCAT2 in mouse bone marrow-derived macrophages stimulated by lipopolysaccharide Mus musculus
2.3.1.67 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone derivative of a metabolite from Penicillium sp. F33 , strong inhibition. Compound also significantly suppresses the gene expression of lyso-PAF acetyltransferase/LPCAT2 in mouse bone marrow-derived macrophages stimulated by lipopolysaccharide Rattus norvegicus
2.3.1.67 3,4-dihydroxy-1,2-dimethoxy-5-methylbenzene
-
 Mus musculus
2.3.1.67 3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone
-
 Mus musculus
2.3.1.67 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone derivative of a metabolite from Penicillium sp. F33 , strong inhibition. Compound also significantly suppresses the gene expression of lyso-PAF acetyltransferase/LPCAT2 in mouse bone marrow-derived macrophages stimulated by lipopolysaccharide; not active against lipoxygenase and cyclooxygenases Mus musculus
2.3.1.67 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone derivative of a metabolite from Penicillium sp. F33 , strong inhibition. Compound also significantly suppresses the gene expression of lyso-PAF acetyltransferase/LPCAT2 in mouse bone marrow-derived macrophages stimulated by lipopolysaccharide Rattus norvegicus
2.3.1.67 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
-
 Mus musculus
2.3.1.67 3-hydroxy-2-methoxy-5-methyl-1,4-benzoquinone
-
 Mus musculus
2.3.1.67 Decanoic acid
-
 Mus musculus
2.3.1.67 dihydrofumigatin i.e. 2-methoxy-1,3,4-trihydroxy-5-methylbenzene, isolated from Penicillium sp. strain F33 Mus musculus
2.3.1.67 dodecanoic acid
-
 Mus musculus
2.3.1.67 additional information inhibition of lipopolysaccharide-induced platelet activating factor production and gene expression of lysophosphatidylcholine acyltransferase (LPCAT2)/lyso-PAF acetyltransferase by synthetic fumigatin derivatives, compound stability and inhibitory potencies, synthesis and evaluation, overview. Dihydrofumigatin is isolated and identified from Penicillium sp. strain F33. In addition to the efficacy to inhibit the function of lyso/PAF acetyltransferase/LPCAT2, 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone, 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone, and 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone also inhibit the expression of LPCAT2 mRNA Mus musculus
2.3.1.67 myristic acid
-
 Mus musculus
2.3.1.67 octanoic acid
-
 Mus musculus
2.3.1.67 palmitic acid
-
 Mus musculus
2.3.1.67 tetradecanoic acid
-
 Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
2.3.1.23 microsome
-
 Rattus norvegicus
-
-
2.3.1.67 microsome
-
 Rattus norvegicus
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.23 acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine Rattus norvegicus
-
 CoA + 1,2-diacyl-sn-glycero-3-phosphocholine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.23 Rattus norvegicus
-
-
-
2.3.1.67 Mus musculus
-
-
-
2.3.1.67 Mus musculus Q8BYI6 gene Lpcat2; gene Lpcat2
-
2.3.1.67 Rattus norvegicus
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.23 spleen
-
 Rattus norvegicus
-
2.3.1.67 macrophage bone marrow-derived Mus musculus
-
2.3.1.67 spleen
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.23 acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine
-
 Rattus norvegicus CoA + 1,2-diacyl-sn-glycero-3-phosphocholine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.23 acetyl-CoA:1-O-alkyl-sn-glycero-3-phosphocholine acetyltransferase
-
 Rattus norvegicus
2.3.1.23 lyso-PAF acetyltransferase
-
 Rattus norvegicus
2.3.1.67 acetyl-CoA:1-O-alkyl-sn-glycero-3-phosphocholine acetyltransferase
-
 Mus musculus
2.3.1.67 acetyl-CoA:lyso-PAF acetyltransferase
-
 Mus musculus
2.3.1.67 acetyl-CoA:lyso-PAF acetyltransferase
-
 Rattus norvegicus
2.3.1.67 LPCAT2
-
 Mus musculus
2.3.1.67 LPCAT2
-
 Rattus norvegicus
2.3.1.67 lyso-PAF acetyltransferase
-
 Mus musculus
2.3.1.67 lysophosphatidylcholine acyltransferase (LPCAT2)/lyso-PAF acetyltransferase
-
 Mus musculus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.67 37
-
 assay at Mus musculus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.67 6.9
-
 assay at Mus musculus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.3.1.23 0.003
-
 at pH 6.9 and 37°C Rattus norvegicus 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.23 0.02
-
 at pH 6.9 and 37°C Rattus norvegicus 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone
2.3.1.23 0.101
-
 at pH 6.9 and 37°C Rattus norvegicus dihydrofumigatin
2.3.1.23 0.109
-
 at pH 6.9 and 37°C Rattus norvegicus fumigatin
2.3.1.23 0.139
-
 at pH 6.9 and 37°C Rattus norvegicus 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.23 0.166
-
 at pH 6.9 and 37°C Rattus norvegicus 3,4-dihydroxy-1,2-dimethoxy-5-methylbenzene
2.3.1.23 0.391
-
 at pH 6.9 and 37°C Rattus norvegicus 3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.67 0.003
-
 pH 6.9, 37°C Rattus norvegicus 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.67 0.003
-
 pH 6.9, 37°C Mus musculus 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.67 0.02
-
 pH 6.9, 37°C Rattus norvegicus 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone
2.3.1.67 0.02
-
 pH 6.9, 37°C Mus musculus 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone
2.3.1.67 0.101
-
 pH 6.9, 37°C Mus musculus 2-methoxy-1,3,4-trihydroxy-5-methylbenzene
2.3.1.67 0.109
-
 pH 6.9, 37°C Mus musculus 3-hydroxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.67 0.121
-
 pH 6.9, 37°C Mus musculus 3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.67 0.139
-
 pH 6.9, 37°C Mus musculus 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone
2.3.1.67 0.166
-
 pH 6.9, 37°C Mus musculus 3,4-dihydroxy-1,2-dimethoxy-5-methylbenzene
2.3.1.67 0.183
-
 pH 6.9, 37°C Mus musculus myristic acid
2.3.1.67 0.183
-
 pH 6.9, 37°C Rattus norvegicus tetradecanoic acid
2.3.1.67 0.391
-
 pH 6.9, 37°C Mus musculus 2-methoxy-5-methyl-3-octadecanoyloxy-1,4-benzoquinone
2.3.1.67 0.419
-
 pH 6.9, 37°C Mus musculus dodecanoic acid
2.3.1.67 0.5
-
 pH 6.9, 37°C Mus musculus palmitic acid
2.3.1.67 0.5
-
 pH 6.9, 37°C Mus musculus octanoic acid
2.3.1.67 0.5
-
 pH 6.9, 37°C Mus musculus Decanoic acid
2.3.1.67 0.5
-
 pH 6.9, 37°C Mus musculus 2-methoxy-5-methyl-1,3,4-triacetoxybenzene
2.3.1.67 0.5
-
 pH 6.9, 37°C Mus musculus 1,4-diacetoxy-2-methoxy-5-methyl-3-tetradecanoyloxybenzene

Expression

EC Number Organism Comment Expression
2.3.1.67 Mus musculus 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone, 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone, and 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone also inhibit the expression of the enzyme mRNA down
2.3.1.67 Mus musculus fatty acid esters of fumigatin reduce lipopolysaccharide-stimulated transcription of lyso-PAF acetyltransferase/LPCAT2 mRNA in bone marrow-derived macrophages additional information
2.3.1.67 Mus musculus stimulation of enzyme expression by lipopolysaccharides up

General Information

EC Number General Information Comment Organism
2.3.1.23 metabolism key enzyme in platelet-activating factor biosynthesis Rattus norvegicus
2.3.1.67 physiological function in inflammatory and allergic processes, platelet-activating factor, PAF, is biosynthesized in specific enzymatic reactions, which involve acetyl-CoA:lyso-PAF acetyltransferases Mus musculus