Naoki Abe

Naoki Abe
Tokyo University of Agriculture · Department of Nutritional Science and Food Safty

Ph.D.

About

82
Publications
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2,026
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April 2014 - March 2016
Tokyo University of Agriculture
Position
  • Head of Department

Publications

Publications (82)
Article
The patients of type I allergic diseases were increased in the developed countries. Recently, many studies have focused on food factors with anti-allergic activities. Enzymatically synthesized glycogen, a polysaccharide with a multi-branched α-1,4 and α-1,6 linkages, is a commercially available product from natural plant starch, and has immunostimu...
Article
Variegatic acid, isolated from Tylopilus ballouii dry fruiting bodies, is an inhibitor of β-hexosaminidase release and tumor necrosis factor (TNF)-α secretion from rat basophilic leukemia (RBL-2H3) cells, with IC50 values of 10.4 μM and 16.8 μM, respectively. On the other hand, it inhibits PKCβ1 activity with an IC50 value of 36.2 μM.
Article
Interaction between foods and drugs is an important consideration in pharmaceutical therapy. Therefore, here, we examined the suppressive effects of the extracts from seven edible herbs on the induction of CYP3A4 gene expression in rifampicin-treated HepG2 cells. We evaluated the structure and suppressive activity of the most effective active compo...
Article
Bisorbicillinol, which is isolated from Trichoderma sp. USF2690, is an inhibitor of β-hexosaminidase release and tumor necrosis factor (TNF)-α and Interleukin (IL)-4 secretion from rat basophilic leukemia (RBL-2H3) cells, with IC50 values of 2.8 μM, 2.9 μM and 2.8 μM respectively. We showed that the inhibitory mechanism of β-hexosaminidase release...
Article
Palytoxin analogs are marine toxins with large complex polyol structures. A benthic dinoflagellate Ostreopsis siamensis produces more than ten palytoxins (ostreocins, OSTs). The limited sample availability of minor OSTs restricts the definition of their chemical structures. The present investigation characterizes structures of two minor OSTs, i.e.,...
Article
Rationale Ostreocin‐B is a new palytoxin congener of comparable complexity. Elucidation of the chemical structure by nuclear magnetic resonance has been hampered due to limited sample availability. More importantly, the dihedral angles of protons at the base of hydroxyls on ring structures are predicted to produce little couplings and thus disrupt...
Article
Several p-terphenyl compounds have been isolated from the edible Chinese mushroom Thelephora vialis. Vialinin A, a p-terphenyl compound, strongly inhibits tumor necrosis factor-α production and release. Vialinin A inhibits the enzymatic activity of ubiquitin-specific peptidase 5, one of the target molecules in RBL-2H3 cells. Here we examined the in...
Article
A new inhibitor of TNF-α production (IC50=0.89μM) named vialinin C (1) was isolated from dry fruiting bodies of an edible Chinese mushroom, Thelephora vialis. The structure of 1 was determined by high-resolution MS, NMR spectroscopic analysis, and confirmed by synthesis. Synthesis of ganbajunin B (5) obtained from the same origin was also described...
Article
Full-text available
Tumor necrosis factor alpha (TNF-α), a central mediator of the inflammatory response, is released from basophilic cells and other cells in response to a variety of proinflammatory stimuli. Vialinin A is a potent inhibitor of TNF-α production and is released from RBL-2H3 cells. Ubiquitin-specific peptidase 5 (USP5), a deubiquitinating enzyme, was id...
Article
Abstract The first total syntheses of 5′-O-desmethylterphenyllin and three related p-terphenyls have been achieved. The methodology features a Suzuki–Miyaura coupling reaction with a hindered aryl chloride as the key step. Two of the four synthesized 5′-O-desmethylterphenyllins exhibit moderate TNF-α release-inhibitory activity toward RBL-2H3 cells...
Article
We identified epicatechin-(4 β→6)-epicatechin-(2 β→O→7, 4 β→8)-catechin (EEC) in the skin of the peanut (Arachis hypogaea L.). EEC (a trimer) showed more potent cholesterol micelle-degrading activity than procyanidin A1 (a dimer) did in vitro. The hypercholesterolemia suppressing effect of a peanut skin polyphenol on rats fed high-cholesterol diet...
Article
Vialinin A, a small compound isolated from the Chinese mushroom Thelephora vialis, exhibits more effective anti-inflammatory activity than the widely used immunosuppressive drug tacrolimus (FK506). Here, we show that ubiquitin-specific peptidase 5/isopeptidase T (USP5/IsoT) is a target molecule of vialinin A, identified by using a beads-probe metho...
Article
Full-text available
The chemical composition of Salicornia herbacea L. a food plant belonging to Chenopodiaceae was investigated based on its mineral composition, proteins and carbohydrates contents. The phenolic composition analysed by high performance liquid chromatography with diode array detection (HPLC-DAD) showed the presence of eight phenolic acids and eight fl...
Article
Vialinin A is an extremely potent inhibitor of tumor necrosis factor (TNF)-α release from RBL-2H3 cells. The present study investigated in detail the inhibitory effects of vialinin A and its analog, 5',6'-dimethyl-1,1':4',1″-terphenyl-2',3',4,4″-tetraol (DMT), on TNF-α. Vialinin A and DMT inhibited the release of TNF-α from RBL-2H3 cells in a dose-...
Article
Two effective cytochrome P450 (CYP) inhibitors were isolated from tarragon, Artemisia dracunculus. Their structures were spectroscopically identified as 2E,4E-undeca-2,4-diene-8,10-diynoic acid isobutylamide (1) and 2E,4E-undeca-2,4-diene-8,10-diynoic acid piperidide (2). Both compounds had dose-dependent inhibitory effects on CYP3A4 activity with...
Article
Vialinin A (1) is an extremely potent inhibitor against tumor necrosis factor (TNF)-α production in rat basophilic leukemia (RBL-2H3) cells. This Letter describes the design and synthesis of its advanced analog, 5',6'-dimethyl-1,1':4'1″-terphenyl-2',3',4,4″-tetraol (2) with a comparable inhibitory activity (IC(50)=0.02 nM) to that of 1. The synthes...
Article
A highly polymethylated flavone that effectively inhibited cytochrome P450s (CYPs) 1A2 and 3A4 (IC(50) = 2.41 and 1.71 µM) in vitro was isolated from thyme leaves (Thymus saturoides) purchased from a Japanese market. Its structure was spectroscopically identified as 4',5-dihydroxy-3',6,7,8-tetramethoxy flavone (8-methoxycirsilineol, 1). This is the...
Article
Full-text available
Peanut skin contains large amounts of polyphenols having antiallergic effects. We found that a peanut-skin extract (PSE) inhibits the degranulation induced by antigen stimulation of rat basophilic leukemia (RBL-2H3) cells. A low-molecular-weight fraction from PSE, PSEL, also had inhibitory activity against allergic degranulation. A main polyphenol...
Article
The benzothiazol-2-ylcarboxylic acids, with diverse spacers between the carboxy group and the benzothiazole ring, were synthesized and evaluated for their ability to inhibit aldose reductase (AR). The phenylacetic acids 6 which have a less complex structure than that of existing AR inhibitors were found to be highly potent, orally active AR inhibit...
Article
Full-text available
The structure of a long-known natural pigment, atromentin, was established by a total synthesis based on double Suzuki-Miyaura coupling and by a single-crystal X-ray analysis of the synthetic sample thereby obtained. A similar strategy including ceric ammonium nitrate (CAN) oxidation was applied to prepare 2-O-methoxyatromentin and thelephantin I.
Article
Aspernolide A and butyrolactones I and II showed inhibitory activities against soybean lipoxygenase. All of them also had DPPH (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging activity. An analysis of the mechanism for radical scavenging allowed us to deduce that aspernolide A was converted to a quinone methide by a reaction with two molecules of...
Article
A powerful inhibitor of TNF-alpha production, vialinin A, was synthesized from sesamol through a series of reactions involving double Suzuki-Miyaura coupling, 2,3-dichloro-5,6-dicyano-1,4-benzoquino (DDQ) mediated de-methoxymethylation and oxidative removal of methylene acetal by lead tetraacetate. The synthetic method also made it possible to prep...
Article
A first total synthesis of vialinin B, a powerful inhibitor (IC(50) 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps...
Article
In our searching program for novel sorbicillin related compounds, three novel compounds, spirosorbicillinols A (1), B (2), and C (3), were isolated from the fermentation broth of the USF-4860 strain isolated from a soil sample. The planar structures of compounds 1-3 were determined from spectroscopic evidence and degradation reaction, and that of 1...
Article
This paper describes the total synthesis of thelephantin G, thus revising the proposed structure 1 to 2. The key steps involved a double Suzuki-Miyaura coupling and an esterification reaction. By a similar strategy, ganbajunins D and E (3 and 4) were also prepared. Compound 2 strongly inhibited TNF (tumor necrosis factor)-alpha production in rat ba...
Article
Increasing attention has been focused on food-drug interactions. We have investigated the inhibitory effect of Chinese edible mushrooms, Boletus calopus and Suillus bovinus, on cytochrome P450 (CYP) 1A2, 2C9, 2D6, and 3A4, the main drug-metabolizing enzymes. Three pulvinic acid derivatives, atromentic acid (1), variegatic acid (2), and xerocomic ac...
Article
Thelephora vialis is a mushroom that grows in symbiosis with pine trees found in Yunnan province, China. It is one of the most favorite edible mushrooms due to its special flavor and taste. Several compounds were isolated from the Thelephoraceae family. For example, ganbanjuns B, C, D and Ε were isolated from the fresh fruiting body of Thelephora g...
Article
Thelephora vialis is a mushroom that grows in symbiosis with pine trees in Yunnan, China, a place known to have some of the richest and most diverse bioresources in the world. This is one of the most favored edible mushrooms, due to its flavor. Our screening for bioactive compounds from these mushrooms isolated a novel potent antioxidant, vialinin...
Article
Thelephora vialis is a mushroom that grows in symbiosis with pine trees in Yunnan, China, a place known to have some of the richest and most diverse bioresources in the world. This is one of the most favored edible mushrooms, due to its flavor. Our screening for bioactive compounds from these mushrooms isolated a novel potent antioxidant, vialinin...
Article
Biosynthetic feeding studies of [1-13C], [2-13C], and [1,2-13C2]-labeled sodium acetates into 5-epihydroxyvertinolide, a new sorbicillinoid, gives an incorporation pattern that proves the c-lactone ring formation associated with a ring cleavage reaction of the precursor, a potential intermediate of sorbicillinol biosynthesis.
Article
Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the...
Article
In our screening program for antioxidants with 1,1-diphenyl-2-picrylhydrazyl (DPPH)-radical scavenging activity, two novel compounds, demethylbisorbibutenolide (1) and trichopyrone (2), were isolated from the fermentation broth of the fungus of USF-4860 strain isolated from a soil sample. The structures of these compounds were determined from spect...
Article
A novel dibenzofuran compound designated vialinin B was isolated from dry fruiting bodies of an edible mushroom, Thelephora vialis, and potently inhibits TNF-alpha production in RBL-2H3 cells (IC(50)=0.02nM) and is a promising anti-allergic agent.
Article
Full-text available
While screening for bioactive compounds from edible mushrooms, a new potent antioxidant, vialinin A (1), together with a known compound, ganbajunin B (2), and a mixture of ganbajunins D (3) and E (4), were isolated from the dry fruiting bodies of Thelephora vialis. The structure of 1, 5',6'-bis(phenylacetoxy)-1,1':4',1''-terphenyl-2',3',4,4''-tetra...
Article
Full-text available
Dou-chi, a traditional soybean food fermented with Aspergillus sp., is usually used as a seasoning in Chinese food, and has also been used as a folk medicine in China and Taiwan. As 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavengers, four phenol compounds, one isoflavanone, eight isoflavones and one 4-pyrone have been isolated from dou-chi. Am...
Article
In the course of our screening to find 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavengers, we isolated eleven sorbicillin-related compounds, including seven novel compounds, from the fermentation broth of Trichoderma sp. USF-2690. The "bisorbicillinoids" was recently defined by Nicolaou as the term used to designate a group composed of dimeri...
Article
Full-text available
We isolated from soybean miso 8-hydroxyglycitein and 6-hydroxydaidzein as DPPH-radical scavengers, and elucidated their chemical structures by mass spectrometric, and (1)H- and (13)C-NMR spectrosopic analyses. These compounds showed DPPH-radical scavenging activity as high as that of alpha-tocopherol, 8-hydroxygenistein and 8-hydroxydaidzein. This...
Article
Three novel lipoxygenase inhibitors, tetrapetalone B (2, C(28)H(35)NO(9)), C (3, C(26)H(34)NO(8)), and D (4, C(28)H(36)NO(10)), were isolated from a culture broth of Streptomyces sp. USF-4727 that produced a lipoxygenase inhibitor tetrapetalone A (1) simultaneously. Each chemical structure was revealed by spectroscopic evidence, this suggests that...
Article
A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C26H33NO7, was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of...
Article
There is a need for simple rapid tests for evaluating the carcinogenic potential of the thousands of chemical compounds that are developed each year. The DNA-damaging effects of 83 National Toxicology Program (NTP) chemicals, including noncarcinogens and carcinogens, were examined in the umu test by measuring the expression of the umuDC-lacZ genes...
Article
Tetrapetalone A (I), C26H33O7N, is a novel lipoxygenase inhibitor isolated from a culture filtrate of Streptomyces sp. USF-4727 strain. Its chemical structure was determined by its spectroscopic evidence and methylation with diazomethane. The stereochemistry was investigated by the coupling constant in 1H NMR, NOESY data and modified Mosher’s method....
Article
Full-text available
The antimutagenic activity of four isoflavones isolated from soybean miso toward three kinds of mutagens, AF-2, MNNG, and Trp-P-1, was evaluated by the Ames test. 8-Hydroxyisoflavones had greater suppressive potency than that of daidzein, and 6-hydroxydaidzein had almost the same activity as daidzein. These results indicated the number of hydroxy a...
Article
The antimutagenic activity of four isoflavones isolated from soybean miso toward three kinds of mutagens, AF-2, MNNG, and Trp-P-1, was evaluated by the Ames test. 8-Hydroxyisoflavones had greater suppressive potency than that of daidzein, and 6-hydroxydaidzein had almost the same activity as daidzein. These results indicated the number of hydroxy a...
Article
An incorporation study of [1-(13)C] and [1,2-(13)C2] labeled sodium acetates into sorbicillinol 1 established a ring closure system between C-1 and C-6 and the positions that were oxidized and/or methylated on a hexaketide chain. Subsequent investigations, using 13C-labeled 1 prepared from [1-(13)C] labeled sodium acetate, clearly demonstrated that...
Article
A potent antioxidant, bisorbicillinol, which is a member of the bisorbicillinoid family isolated from the culture broth of Trichoderma sp. USF-2690, produces a stable radical-terminated symmetric dimer by donating two hydrogen atoms to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.
Article
Biosynthetic incorporation of labeled sodium acetate into oxosorbicillinol in Trichoderma sp. USF-2690 suggests that oxosorbicillinol is derived from six acetate units, and subsequent bioconversion of the labeled oxosorbicillinol to bisvertinolone in the fermentation of the strain suggests that bisvertinolone is biosynthesized from oxosorbicillinol...
Article
Full-text available
In the course of our screening program for free radical scavengers from Trichoderma sp. USF-2690, we found an unidentified metabolite (1) that appeared by the method used for HPLC analysis. Metabolite 1 gradually decreased with the production of bisorbicillinoids and was easily missed during the general isolation procedure. The LC-ESI-MS (negative)...
Article
Biosynthetic incorporation of labelled sodium acetates into bisorbicillinol in Trichoderma sp. USF-2690 suggests that bisorbicillinol is derived from 12 acetate units. Successful bioconversion of the labelled bisorbicillinols to bisorbibutenolides (bislongiquinolides) and bisorbicillinolides using the washed mycelium of the strain suggests tha...
Article
Guided by their DPPH radical-scavenging activity, nine compounds were isolated from soybean miso. Of these, 8-hydroxydaidzein, 8-hydroxygenistein and syringic acid had as high DPPH radical-scavenging activity as that of alpha-tocopherol. The antiproliferative activity of four of the isolated isoflavones toward three cancer cell lines was examined....
Article
Guided by their DPPH radical-scavenging activity, nine compounds were isolated from soybean mise. Of these, 8-hydroxydaidzein, 8-hydroxygenistein and syringic acid had as high DPPH radical-scavenging activity as that of alpha-tocopherol. The antiproliferative activity of four of the isolated isoflavones toward three cancer cell lines was examined....
Article
Full-text available
The novel compounds, demethylsorbicillin (1) and oxosorbicillinol (2), were isolated from a fermentation broth of Trichoderma sp. USF-2690. The structures of these compounds, which were determined from spectroscopic evidence, suggest the possibility that methylation at C-6 and oxidation at C-1 and C-6 of sorbicillin were controlled in the early pol...
Article
The radical scavenging mechanisms for the 2-pyrone compound, 4-hydroxy-3,6-dimethyl-2H-pyrane-2-one (1), and the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical (4) in several solvent systems were evaluated by the quantitative change in compounds detected at 270 nm and subsequent HPLC analyses. The HPLC profile for each condition suggested that the re...
Article
A novel indophenol-reducing and DPPH radical-scavenging compound (1) was isolated from a fungal metabolite. The structure of 1 was determined by a spectroscopic analysis, and the absolute configuration of 1 was determined by the modified Mosher's method. Compound 1 showed slow-reacting DPPH radical-scavenging activity (ED50 value of 298 μM after 96...
Article
A novel indophenol-reducing and DPPH radical-scavenging compound (1) was isolated from a fungal metabolite. The structure of 1 was determined by a spectroscopic analysis, and the absolute configuration of 1 was determined by the modified Mosher’s method. Compound 1 showed slow-reacting DPPH radical-scavenging activity (ED50 value of 298 μM after 96...
Article
We isolated a novel oxidized sorbicillin dimer (1) as yellowish amorphous powder from the fermentation broth of Trichoderma sp. USF-2690 strain isolated from a soil sample. The structure of the compound was determined by elucidation of spectroscopic evidence. The compound was revealed to possess a new carbon skeleton in the group of oxidized sorbic...
Article
The indophenol-reducing compound, 4-hydroxy-3,6-dimethyl-2 H-pyrane-2-one (I), was isolated from the culture filtrate of an unidentified fungus. I also reacted with the DPPH radical to form a reaction product IV which was determined to be 1-[4-(3,4-dihydro-3,6-dimethyl-2,4-dioxo- 2 H-pyran-3-yl)phenyl]-1-phenyl-2-picrylhydrazine. This is the first...
Article
Full-text available
In our screening program for antioxidants with DPPH radical scavenging activity, we isolated four yellowish compounds from the fermentation broth of Trichoderma sp. USF-2690 strain isolated from a soil sample: two were novel compounds designated bisorbicillinol (1) and demethyltrichodimerol (2), and two were known compounds bisvertinolone (3) and t...
Article
The benzothiazol-2-ylcarboxylic acids, with diverse spacers between the carboxy group and the benzothiazole ring, were synthesized and evaluated for their ability to inhibit aldose reductase (AR). The phenylacetic acids 6 which have a less complex structure than that of existing AR inhibitors were found to be highly potent, orally active AR inhibit...
Article
GP-1447 {3-[(4,5,7-trifluorobenzothiazol-2-yl) methyl]-5-methylphenylacetic acid}, a novel aldose reductase (AR) inhibitor, exhibited highly potent and specific inhibition of AR activity from human placenta, human muscle, porcine and rat lens with IC50 values ranging from 3 to 10 nM. Lineweaver-Burk plots revealed non-competitive inhibition between...
Article
Three novel antibiotics, named chrymutasins A, B and C, were isolated from the fermentation products of a mutant strain obtained by NTG (N-methyl-N'-nitro-N-nitrosoguanidine) treatment. The mutant strain produced the chrymutasins, which differed in the aglycone moiety from chartreusin, and related compounds. The production of these compounds needed...
Article
Chrymutasins A, B and C are glycosidic antibiotics produced by a mutant of the chartreusin producer-organism Streptomyces chartreusis. We report here the structure elucidation of these compounds. The sugar moieties involved were determined by comparison with the related chartreusins. The structure of the aglycone, the same in all three compounds, w...
Article
The structure of chrymutasin A, B and C are determined from spectral studies, incorporation studies of 13C-labelled sodium acetates and an aglycone derivative.
Article
In the course of our investigation aimed at the discovery of novel antitumor antibiotics from microorganisms, Streptomyces sp. G324 was found to produce the antitumor antibiotic, lavendamycin, and also, to yield the novel beta-carboline compounds, oxopropalines. We isolated five compounds as oxopropalines A, B, D, E and G. Oxopropalines B, D and G...
Article
Novel cytocidal compounds designated oxopropalines A, B, D, E and G were isolated from the fermentation of an actinomycete named Streptomyces sp. G324, a strain that also produced an antitumor antibiotic, lavendamycin. All these compounds possessed a beta-carboline chromophore. The structures of the oxopropalines were elucidated by several NMR spec...
Article
Streptomyces sp. HP530 was found to produce novel antitumor antibiotics, saptomycins, closely related to the pluramycin-group and was further found to mutate frequently. The natural mutant produced several new saptomycins as determined by HPLC analyses. We isolated saptomycins A, B, C1, C2 and F from the parent strain and saptomycins D, E, G and H...
Article
A complex of novel antitumor antibiotics related to the pluramycin-group was isolated from the fermentation of actinomycete, named Streptomyces sp. HP530. The producing strain mutated frequently. The products isolated from the parent strain were designated saptomycins A, B, C1, C2 and F, while those of the mutant were named saptomycins D, E, G and...