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Article: Prenylflavonoids from propolis collected in Chiang Mai, Thailand

Mukaide, Kazuma / Honda, Sari / Vongsak, Boonyadist / Kumazawa, Shigenori

Phytochemical Society of Europe Phytochemistry letters. 2021 June, v. 43

2021

Abstract: Three new prenylflavonoids, 3-hydroxy-5′-methoxy-licoflavanone (12), 3′-hydroxy-5′-methoxy-glabranin (13), and 5′-methoxy-lespedezaflavanone C (17) were isolated for the first time from propolis collected from Chiang Mai in northern Thailand. The ... ...

Abstract	Three new prenylflavonoids, 3-hydroxy-5′-methoxy-licoflavanone (12), 3′-hydroxy-5′-methoxy-glabranin (13), and 5′-methoxy-lespedezaflavanone C (17) were isolated for the first time from propolis collected from Chiang Mai in northern Thailand. The structures of the new compounds were determined by MS and NMR spectroscopy. Seventeen other known compounds, including 4′-methyl-8-prenyltaxifolin (1), 6-prenyleriodictyol (2), abyssinone V (3), munduleaflavanone B (4), euchrestaflavanone A (5), cathayanon H (6), licoflavanone (7), 8-prenylnaringenin (8), exiguaflavanone K (9), flowerine (10), 8-dimethylallyltaxifolin (11), isolicoflavonol (14), (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-hydroxy-3-methylbutyl)chroman-4-one (15), lespedezaflavanone C (16), gancaonin E (18), 5,3′-dihydroxyisobavachin-7-O-methyl ether (19), and carphorin B (20) were also identified based on their MS, NMR, and electronic circular dichroism spectra.
Keywords	circular dichroism spectroscopy ; nuclear magnetic resonance spectroscopy ; plant biochemistry ; propolis ; Thailand
Language	English
Dates of publication	2021-06
Size	p. 88-93.
Publishing place	Elsevier Ltd
Document type	Article
ISSN	1874-3900
DOI	10.1016/j.phytol.2021.03.015
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Identification of Pyrogallol in the Ethyl Acetate-Soluble Part of Coffee as the Main Contributor to Its Xanthine Oxidase Inhibitory Activity.

Honda, Sari / Masuda, Toshiya

Journal of agricultural and food chemistry

2016 Volume 64, Issue 41, Page(s) 7743–7749

Abstract: In this study, ethyl acetate-soluble parts of hot-water extracts from roasted coffee beans were found to demonstrate potent xanthine oxidase (XO) inhibition. The XO inhibitory activities and chlorogenic lactone contents (chlorogenic lactones have ... ...

Abstract	In this study, ethyl acetate-soluble parts of hot-water extracts from roasted coffee beans were found to demonstrate potent xanthine oxidase (XO) inhibition. The XO inhibitory activities and chlorogenic lactone contents (chlorogenic lactones have previously been identified as XO inhibitors in roast coffee) were measured for ethyl acetate-soluble parts prepared from coffee beans roasted to three different degrees. Although chlorogenic lactone contents decreased with higher degrees of roasting, the XO inhibitory activity did not decrease. These data led us to investigate new potent inhibitors present in these ethyl acetate-soluble extracts. Repeated assay-guided purifications afforded a highly potent XO inhibitor, which was eluted before chlorogenic lactones via medium-pressure chromatography using an octadecylsilica gel column. The obtained inhibitor was identified as pyrogallol (1,2,3-trihydroxybenzene), which had an IC
Language	English
Publishing date	2016-10-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.6b03339
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Article: Identification of Pyrogallol in the Ethyl Acetate-Soluble Part of Coffee as the Main Contributor to Its Xanthine Oxidase Inhibitory Activity

Honda, Sari / Toshiya Masuda

Journal of agricultural and food chemistry. 2016 Oct. 19, v. 64, no. 41

2016

Abstract	In this study, ethyl acetate-soluble parts of hot-water extracts from roasted coffee beans were found to demonstrate potent xanthine oxidase (XO) inhibition. The XO inhibitory activities and chlorogenic lactone contents (chlorogenic lactones have previously been identified as XO inhibitors in roast coffee) were measured for ethyl acetate-soluble parts prepared from coffee beans roasted to three different degrees. Although chlorogenic lactone contents decreased with higher degrees of roasting, the XO inhibitory activity did not decrease. These data led us to investigate new potent inhibitors present in these ethyl acetate-soluble extracts. Repeated assay-guided purifications afforded a highly potent XO inhibitor, which was eluted before chlorogenic lactones via medium-pressure chromatography using an octadecylsilica gel column. The obtained inhibitor was identified as pyrogallol (1,2,3-trihydroxybenzene), which had an IC50 of 0.73 Î¼mol Lâ1, much stronger than that of other related polyphenolic compounds. Quantitative analysis of pyrogallol and chlorogenic lactones revealed that pyrogallol (at concentrations of 33.9 Â± 4.2 nmol mLâ1 in light roast coffee and 39.4 Â± 3.9 nmol mLâ1 in dark roast coffee) was the main XO inhibitor in hot-water extracts of roasted coffee beans (i.e., drinking coffee).
Keywords	chromatography ; coffee (beverage) ; coffee beans ; gels ; inhibitory concentration 50 ; lactones ; polyphenols ; pyrogallol ; quantitative analysis ; roasting ; xanthine oxidase
Language	English
Dates of publication	2016-1019
Size	p. 7743-7749.
Publishing place	American Chemical Society, Books and Journals Division
Document type	Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.6b03339
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Article ; Online: Correction to Propolis Components from Stingless Bees Collected on South Sulawesi, Indonesia, and Their Xanthine Oxidase Inhibitory Activity.

Miyata, Ryo / Sahlan, Muhamad / Ishikawa, Yoshinobu / Hashimoto, Hiroshi / Honda, Sari / Kumazawa, Shigenori

Journal of natural products

2020 Volume 83, Issue 4, Page(s) 1356

Language	English
Publishing date	2020-03-31
Publishing country	United States
Document type	Journal Article ; Published Erratum
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.0c00282
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Article: Neuroprotection and axon regeneration by novel low-molecular-weight compounds through the modification of DOCK3 conformation.

Namekata, Kazuhiko / Tsuji, Naoki / Guo, Xiaoli / Nishijima, Euido / Honda, Sari / Kitamura, Yuta / Yamasaki, Atsushi / Kishida, Masamichi / Takeyama, Jun / Ishikawa, Hirokazu / Shinozaki, Youichi / Kimura, Atsuko / Harada, Chikako / Harada, Takayuki

Cell death discovery

2023 Volume 9, Issue 1, Page(s) 166

Abstract: Dedicator of cytokinesis 3 (DOCK3) is an atypical member of the guanine nucleotide exchange factors (GEFs) and plays important roles in neurite outgrowth. DOCK3 forms a complex with Engulfment and cell motility protein 1 (Elmo1) and effectively activates ...

Abstract	Dedicator of cytokinesis 3 (DOCK3) is an atypical member of the guanine nucleotide exchange factors (GEFs) and plays important roles in neurite outgrowth. DOCK3 forms a complex with Engulfment and cell motility protein 1 (Elmo1) and effectively activates Rac1 and actin dynamics. In this study, we screened 462,169 low-molecular-weight compounds and identified the hit compounds that stimulate the interaction between DOCK3 and Elmo1, and neurite outgrowth in vitro. Some of the derivatives from the hit compound stimulated neuroprotection and axon regeneration in a mouse model of optic nerve injury. Our findings suggest that the low-molecular-weight DOCK3 activators could be a potential therapeutic candidate for treating axonal injury and neurodegenerative diseases including glaucoma.
Language	English
Publishing date	2023-05-15
Publishing country	United States
Document type	Journal Article
ISSN	2058-7716
ISSN	2058-7716
DOI	10.1038/s41420-023-01460-8
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Article ; Online: Carob pod polyphenols suppress the differentiation of adipocytes through posttranscriptional regulation of C/EBPβ.

Fujita, Kasumi / Norikura, Toshio / Matsui-Yuasa, Isao / Kumazawa, Shigenori / Honda, Sari / Sonoda, Takumi / Kojima-Yuasa, Akiko

PloS one

2021 Volume 16, Issue 3, Page(s) e0248073

Abstract: Obesity is a major risk factor for various chronic diseases such as diabetes, cardiovascular disease, and cancer; hence, there is an urgent need for an effective strategy to prevent this disorder. Currently, the anti-obesity effects of food ingredients ... ...

Abstract	Obesity is a major risk factor for various chronic diseases such as diabetes, cardiovascular disease, and cancer; hence, there is an urgent need for an effective strategy to prevent this disorder. Currently, the anti-obesity effects of food ingredients are drawing attention. Therefore, we focused on carob, which has high antioxidant capacity and various physiological effects, and examined its anti-obesity effect. Carob is cultivated in the Mediterranean region, and its roasted powder is used as a substitute for cocoa powder. We investigated the effect of carob pod polyphenols (CPPs) on suppressing increases in adipose tissue weight and adipocyte hypertrophy in high fat diet-induced obesity model mice, and the mechanism by which CPPs inhibit the differentiation of 3T3-L1 preadipocytes into adipocytes in vitro. In an in vivo experimental system, we revealed that CPPs significantly suppressed the increase in adipose tissue weight and adipocyte hypertrophy. Moreover, in an in vitro experimental system, CPPs acted at the early stage of differentiation of 3T3-L1 preadipocytes and suppressed cell proliferation because of differentiation induction. They also suppressed the expression of transcription factors involved in adipocyte differentiation, thereby reducing triacylglycerol synthesis ability and triglycerol (TG) accumulation. Notably, CPPs regulated CCAAT/enhancer binding protein (C/EBP)β, which is expressed at the early stage of differentiation, at the posttranscriptional level. These results demonstrate that CPPs suppress the differentiation of adipocytes through the posttranscriptional regulation of C/EBPβ and may serve as an effective anti-obesity compound.
MeSH term(s)	3T3-L1 Cells ; Adipocytes/metabolism ; Animals ; CCAAT-Enhancer-Binding Protein-beta/metabolism ; Cell Differentiation/drug effects ; Cell Proliferation/drug effects ; Fabaceae/chemistry ; Galactans/chemistry ; Male ; Mannans/chemistry ; Mice ; Plant Gums/chemistry ; Polyphenols/chemistry ; Polyphenols/pharmacology
Chemical Substances	CCAAT-Enhancer-Binding Protein-beta ; Cebpb protein, mouse ; Galactans ; Mannans ; Plant Gums ; Polyphenols ; locust bean gum (V4716MY704)
Language	English
Publishing date	2021-03-08
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1932-6203
ISSN (online)	1932-6203
DOI	10.1371/journal.pone.0248073
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Effective Conversion of Metmyoglobin to Oxymyoglobin by Cysteine-Substituted Polyphenols.

Honda, Sari / Miura, Yukari / Masuda, Toshiya / Masuda, Akiko

Journal of agricultural and food chemistry

2016 Volume 64, Issue 4, Page(s) 806–811

Abstract: Reaction products from the peroxidase-catalyzed oxidation of polyphenols in the presence of cysteine showed a potent activity for reducing metmyogolobin (MetMb) to bright-colored oxymyogolobin (MbO2). High-performance liquid chromatography (HPLC) ... ...

Abstract	Reaction products from the peroxidase-catalyzed oxidation of polyphenols in the presence of cysteine showed a potent activity for reducing metmyogolobin (MetMb) to bright-colored oxymyogolobin (MbO2). High-performance liquid chromatography (HPLC) purification of the reaction products from catechin, chlorogenic acid, dihydrocaffeic acid, hydroxytyrosol, nordihydroguaiaretic acid, and rosmarinic acid afforded corresponding S-cysteinyl compounds, the structures of which were determined by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). The isolated cysteinyl polyphenols showed a concentration-dependent reducing activity for MetMb to MbO2 for the initial 1 h. However, after 1 h, some of them decreased the amount of MbO2 produced. The effect of the number of cysteinyl sulfur substitutions in polyphenols on both MetMb reduction and MbO2 maintenance was examined using hydroxytyrosols with different numbers of cysteine substitutions; these hydroxytyrosols were synthesized from hydroxytyrosol and an N-acetylcysteine methyl ester. The hydroxytyrosol derivative substituted with two N-acetylcysteine esters exhibited the most effective reducing activity without any effect on MbO2.
MeSH term(s)	Chromatography, High Pressure Liquid ; Cysteine/chemistry ; Magnetic Resonance Spectroscopy ; Metmyoglobin/chemistry ; Molecular Structure ; Myoglobin/chemistry ; Oxidation-Reduction ; Polyphenols/chemistry
Chemical Substances	Myoglobin ; Polyphenols ; oxymyoglobin ; Metmyoglobin (12772-23-5) ; Cysteine (K848JZ4886)
Language	English
Publishing date	2016-02-03
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.5b05511
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Article: Effective Conversion of Metmyoglobin to Oxymyoglobin by Cysteine-Substituted Polyphenols

Honda, Sari / Yukari Miura / Toshiya Masuda / Akiko Masuda

Journal of agricultural and food chemistry. 2016 Feb. 3, v. 64, no. 4

2016

Abstract	Reaction products from the peroxidase-catalyzed oxidation of polyphenols in the presence of cysteine showed a potent activity for reducing metmyogolobin (MetMb) to bright-colored oxymyogolobin (MbO2). High-performance liquid chromatography (HPLC) purification of the reaction products from catechin, chlorogenic acid, dihydrocaffeic acid, hydroxytyrosol, nordihydroguaiaretic acid, and rosmarinic acid afforded corresponding S-cysteinyl compounds, the structures of which were determined by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). The isolated cysteinyl polyphenols showed a concentration-dependent reducing activity for MetMb to MbO2 for the initial 1 h. However, after 1 h, some of them decreased the amount of MbO2 produced. The effect of the number of cysteinyl sulfur substitutions in polyphenols on both MetMb reduction and MbO2 maintenance was examined using hydroxytyrosols with different numbers of cysteine substitutions; these hydroxytyrosols were synthesized from hydroxytyrosol and an N-acetylcysteine methyl ester. The hydroxytyrosol derivative substituted with two N-acetylcysteine esters exhibited the most effective reducing activity without any effect on MbO2.
Keywords	acetylcysteine ; catechin ; chlorogenic acid ; cysteine ; high performance liquid chromatography ; mass spectrometry ; nordihydroguaiaretic acid ; nuclear magnetic resonance spectroscopy ; oxidation ; polyphenols ; rosmarinic acid ; sulfur
Language	English
Dates of publication	2016-0203
Size	p. 806-811.
Publishing place	American Chemical Society, Books and Journals Division
Document type	Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.5b05511
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Article ; Online: Propolis Components from Stingless Bees Collected on South Sulawesi, Indonesia, and Their Xanthine Oxidase Inhibitory Activity.

Miyata, Ryo / Sahlan, Muhamad / Ishikawa, Yoshinobu / Hashimoto, Hiroshi / Honda, Sari / Kumazawa, Shigenori

Journal of natural products

2019 Volume 82, Issue 2, Page(s) 205–210

Abstract: Three new compounds, namely, 4-(4'-hydroxy-3'-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesins A (2) and B (3), were isolated from the propolis of stingless bees ( Tetragonula aff. biroi) collected on South Sulawesi, Indonesia. In addition, ... ...

Abstract	Three new compounds, namely, 4-(4'-hydroxy-3'-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesins A (2) and B (3), were isolated from the propolis of stingless bees ( Tetragonula aff. biroi) collected on South Sulawesi, Indonesia. In addition, five known compounds, glyasperin A, broussoflavonol F, (2 S)-5,7-dihydroxy-4'-methoxy-8-prenylflavanone, (1' S)-2- trans,4- trans-abscisic acid, and (1' S)-2- cis,4- trans-abscisic acid, were identified. The structures of the new compounds were determined by a combination of methods that included mass spectrometry and NMR spectroscopy. The absolute configuration of sulawesin A (2), a new podophyllotoxin derivative, was determined by X-ray crystallography. The absolute configuration of sulawesin B (3) was also determined by the ECD calculation. 4-(4'-Hydroxy-3'-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesin A (2) were examined for xanthine oxidase (XO) inhibitory activity; 1 exhibited XO inhibitory activity, with an IC
MeSH term(s)	Animals ; Bees ; Coumarins/chemistry ; Coumarins/isolation & purification ; Coumarins/pharmacology ; Indonesia ; Molecular Structure ; Propolis/analysis ; Sesterterpenes/chemistry ; Sesterterpenes/isolation & purification ; Sesterterpenes/pharmacology ; Xanthine Oxidase/antagonists & inhibitors
Chemical Substances	Coumarins ; Sesterterpenes ; sulawesin A ; sulawesin B ; Propolis (9009-62-5) ; Xanthine Oxidase (EC 1.17.3.2)
Language	English
Publishing date	2019-02-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.8b00541
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Article ; Online: Conversion to purpurogallin, a key step in the mechanism of the potent xanthine oxidase inhibitory activity of pyrogallol.

Honda, Sari / Fukuyama, Yuya / Nishiwaki, Hisashi / Masuda, Akiko / Masuda, Toshiya

Free radical biology & medicine

2017 Volume 106, Page(s) 228–235

Abstract: In this study, the mechanism of the xanthine oxidase (XO) inhibitory activity of pyrogallol, the main inhibitor found in roasted coffee, was investigated. Pyrogallol was unstable and readily converted to purpurogallin in a pH 7.4 solution, a ... ...

Abstract	In this study, the mechanism of the xanthine oxidase (XO) inhibitory activity of pyrogallol, the main inhibitor found in roasted coffee, was investigated. Pyrogallol was unstable and readily converted to purpurogallin in a pH 7.4 solution, a physiological model of human body fluids. The XO inhibitory activity of the produced purpurogallin was higher than that of pyrogallol, as evidenced by comparing their IC
Language	English
Publishing date	2017-05
Publishing country	United States
Document type	Journal Article
ZDB-ID	807032-5
ISSN	1873-4596 ; 0891-5849
ISSN (online)	1873-4596
ISSN	0891-5849
DOI	10.1016/j.freeradbiomed.2017.02.037
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