Fumihiko Yoshizaki

Tohoku Pharmaceutical University, Miyagi, Japan

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Publications (51)89.94 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: To identify antibacterial components in traditional Mongolian medicinal plant Caryopteris mongolica, an ortho-quinone abietane caryopteron A (1) and three its derivatives caryopteron B-D (2-4) were isolated from the roots of the plant together with three known abietanes demethylcryptojaponol (5), 6α-hydroxydemethyl cryptojaponol (6), and 14-deoxycoleon U (7). The chemical structures of these abietane derivatives were elucidated on the basis of spectroscopic data. Compounds 1-4 had C-13 methylcyclopropane substructures, and 2-4 had a hexanedioic anhydride ring C instead of ortho-quinone in 1. The stereochemistry of these compound was assumed from NOE spectra and ECD Cotton effects. Compounds 1 and 5-7 showed antibacterial activities against the Gram-positive bacteria Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, and Micrococcus luteus, being 1 the more potent. Copyright © 2015 Elsevier Ltd. All rights reserved.
    Bioorganic & medicinal chemistry letters 04/2015; 25(12). DOI:10.1016/j.bmcl.2015.04.048 · 2.33 Impact Factor
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    ABSTRACT: A diterpenoid diglucoside (12,19-di-O-β-D-glucopyranosyl-11-hydroxyabieta-8,11,13-triene-19-one), isoscutellarein 7-O-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranoside, isoscutellarein 7-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7-O-[6″-O-(p-E-coumaroyl)]-β-D-glucopyranoside, hypolaetin 7-O-[6″-O-(E-caffeoyl)]-β-D-glucopyranoside, and 15 known compounds were isolated from aerial parts of the Mongolian medicinal plant Caryopteris mongolica. The cholinesterase-inhibitory activities of the constituents were estimated. The abietane diterpenoids (12-O-demethylcryptojaponol and 6α-hydroxydemethylcryptojaponol) showed potent inhibitory activity against acetylcholinesterase from human erythrocytes and electric eel, and against butyrylcholinesterase from horse serum.
    Journal of Natural Medicines 04/2015; DOI:10.1007/s11418-015-0908-6 · 1.45 Impact Factor
  • Kenroh Sasaki, Syuko Chiba, Fumihiko Yoshizaki
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    ABSTRACT: The aim of the present study was to identify the inhibitory activity of natural flavonoids, stilbenes and caffeic acid oligomers on protein glycation. Antioxidant activity was evaluated using 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity. The production of 3-deoxyglucosone (3-DG) and advanced glycation end products (AGEs) by glycation reactions were determined by high-performance liquid chromatography and fluorescence, respectively. Certain flavonoids, stilbenes and caffeic acid oligomers prevented AGE production and the IC50 values of the compounds were compared. These examined compounds are assumed to suppress AGE generation by inhibiting the increase in 3-DG production through a specific unknown mechanism in the early phase of the Maillard reaction, by inhibiting the generation of active oxygen in the later phase and by suppressing the progression of the reaction. Regular, daily consumption of these compounds in the form of a food or extract is expected to aid in the prevention or inhibition of non-enzymatic amino acid glycation in the living body, which is possibly associated with aging, diabetic complications, arteriosclerotic diseases and Alzheimer's disease, and they may also be effective agents in cosmetics promoting anti-aging.
    09/2014; 2(5):628-632. DOI:10.3892/br.2014.304
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    ABSTRACT: Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.
    Phytochemistry 05/2014; 101. DOI:10.1016/j.phytochem.2014.02.007 · 3.35 Impact Factor
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    ABSTRACT: An extract of whole plants of Pycnanthemum flexuosum showed an inhibitory effect on hyaluronidase activity. From an 80% acetone extract of aerial parts, 3-[(3E)-4-phenylbut-3-enoylamino]propionic acid, 3-O-β-D-glucuronopyranosyl- echinocystic acid 28-O-β-D-xylopyranosyl-(1→3)-[3,4-diacetyl-β-D-xylopyranosyl- (1→4)]-a-L-rhamnopyranosyl-(1→2)-a-L-arabinopyranosyl ester, vanillic acid 1-O-[(5-O-syringoyl)-β-D-apiofuranosyl]-(1→2)-β-D-glucopyranoside, and (4S,5R)-4-hydroxy-5-phenyl-tetrahydrofuran-2-one were isolated together with 30 known compounds. Six known compounds were isolated from an 80% acetone extract of roots, and eritrichin was revealed as a hyaluronidase inhibitor in P. flexuosum.
    Chemical & pharmaceutical bulletin 03/2014; DOI:10.1248/cpb.c14-00123 · 1.38 Impact Factor
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    ABSTRACT: Two new chromone acyl glucosides, 5-hydroxy-7-O-(6-O-p-cis-coumaroyl-β-D-glucopyranosyl)-chromone (1) and 5-hydroxy-7-O-(6-O-p-trans-coumaroyl-β-D-glucopyranosyl)-chromone (2), and a new flavonoid glucoside, ayanin 3′-O-β-D-glucopyranoside (3) were isolated from aerial parts of Dasiphora parvifolia, together with flavonoid glycosides (4–10), catechins (11, 12), and hydrolysable tannins (13, 14). The chemical structures of these compounds were elucidated on the basis of spectroscopic data. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and the hyaluronidase inhibitory activity of these compounds were evaluated.
    Phytochemistry Letters 11/2013; 6(4):552–555. DOI:10.1016/j.phytol.2013.07.004 · 1.54 Impact Factor
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    ABSTRACT: Monardic acids A (1) and B (2), which are (7R,8R) diastereomers of lithospermic acid (LA) and lithospermic acid B, respectively, were isolated from Monarda fistulosa. A (7S,8R) isomer (3) of LA was also isolated from this plant, and a (7R,8S) isomer (7) of LA was obtained from Lithospermum erythrorhizon. The absolute configuration of 1 was confirmed by analysis of its hydrolysates, 7-epiblechnic acid and 2R-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid. The configuration in the dihydrobenzofuran moieties of 2, 3, and 7 were extrapolated by using the phenylglycine methyl ester method and a Cotton effect at approximately 250-260nm in their electronic circular dichroism spectra. Diastereomers (1-3 and 7) displayed moderate hyaluronidase inhibitory and histamine release inhibitory activities.
    Fitoterapia 08/2013; 91. DOI:10.1016/j.fitote.2013.08.009 · 2.22 Impact Factor
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    ABSTRACT: Activity-guided isolation of the n-butanol fraction of Chamaerhodos erecta and water soluble fraction of C. altaica resulted in the isolation of 39 compounds, including new compounds identified as 4,5-dihydroxybenzaldehyde-3-O-β-D-glucopyranoside (1) from C. erecta and quercetin-3-O-β-D-glucuronopyranosyl-4'-O-β-D-glucopyranoside (2) from C. altaica. A total of 37 other compounds were identified based on physico-chemical properties and spectroscopic data. Antioxidative activity was evaluated using a DPPH radical-scavenging method, hyaluronidase inhibitory activity, and advanced glycation end products production inhibitory activity of isolated compounds. Some flavonols (4, 6, 9-11, 14, 15), catechins (18, 19), an amino acid (20), a lignan glucoside (23), and tannins (29-39) exhibited potential a free radical scavenging activity while the new compound (1) showed weak activity. A catechin (18) and some of the tannins (32, 33, 35, 36, 38) had moderate hyaluronidase inhibitory activity. Some of flavonoids and tannins prevented advanced glycation end products production, and the IC(50) of compounds 3, 9, 14-16, 33, 34, 36, 38, and 39 were determined.
    Journal of Natural Medicines 02/2013; 67(4). DOI:10.1007/s11418-013-0748-1 · 1.45 Impact Factor
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    ABSTRACT: From an extract of the aerial parts of Dracocephalum ruyschiana, five new flavone tetraglycosides, five new benzyl alcohol glycosides, and 19 known compounds were isolated. The tetraglycosides contain a 7-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranosyl moiety. The benzyl alcohol glycosides had acyl groups on their glycosyl or aglycone moieties. The compounds were tested for antioxidant activity using DPPH. Although the new compounds were not active, phenylpropanoylquinic acid derivatives were revealed as radical scavengers in D. ruyschiana.
    Journal of Natural Products 01/2013; 76(2). DOI:10.1021/np300609u · 3.95 Impact Factor
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    ABSTRACT: A methanol extract of Abies sibirica Ladeb, a Mongolian medicinal plant, had an inhibitory effect on both lipase activity in mouse plasma and LDL anti-oxidative activity, which are preventative factors for arteriosclerosis. The extract was fractionated by column chromatography and its active constituents were sought. From lipid soluble fractions, 20 terpenoids including seven hitherto unknown triterpenes were isolated. The latter triterpenes had either a γ-lactone ring with a lactol or a derivative thereof. Their chemical structures were determined by spectroscopic methods. The lipase inhibitory activity and LDL anti-oxidative activity of these compounds were evaluated. Some constituents (either lipase inhibitory or LDL anti-oxidative activities) had moderate inhibitory activities.
    Phytochemistry 12/2012; 86. DOI:10.1016/j.phytochem.2012.11.017 · 3.35 Impact Factor
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    ABSTRACT: An extract of Clethra barbinervis with an inhibitory effect on hyaluronidase activity was fractionated guided by the results of an assay. From the active fractions, seven new triterpene saponins (1-4 and 6-8) and a new lignan glycoside (14) were isolated together with 14 known compounds (5, 9-13, and 15-22). Some of the saponins (2, 3, and 9) were revealed as hyaluronidase inhibitors similar to epicatechin (17).
    Chemical & pharmaceutical bulletin 12/2012; DOI:10.1248/cpb.c12-00566 · 1.38 Impact Factor
  • Toshihiro Murata, Toshio Miyase, Fumihiko Yoshizaki
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    ABSTRACT: Nine new compounds, shimobashiric acid A (I), C (IIa), D (IIb), shimobashiraside A (IIIa), B (IIIb), C (IV), D (V), E (VI) and F (VII), are isolated together with 20 known compounds.
    ChemInform 07/2012; 43(28):no-no. DOI:10.1002/chin.201228218
  • Toshihiro Murata, Toshio Miyase, Fumihiko Yoshizaki
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    ABSTRACT: An extract of Keiskea japonica MIQ. showed an inhibitory effect on hyaluronidase activity. From the extract, four new phenylpropanoids, two new maltol glycosides, two new monoterpene glycosides, and two new phenolic compounds were isolated together with 19 known compounds. Among these constituents, two phenylpropanoids and a flavone glucuronide were revealed as hyaluronidase inhibitors.
    Chemical & pharmaceutical bulletin 01/2012; 60(1):121-8. DOI:10.1248/cpb.60.121 · 1.38 Impact Factor
  • Food Science and Technology Research 01/2012; 18(2):309-313. DOI:10.3136/fstr.18.309 · 0.36 Impact Factor
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    Toshihiro Murata, Toshio Miyase, Fumihiko Yoshizaki
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    ABSTRACT: Nine new phenylpropanoids, rashomonic acids A-D (1-4) and meehaniosides A-E (5-9), along with four known compounds were isolated from Meehania urticifolia. The structure of each new compound was elucidated based on the results of spectroscopic analyses. Compounds 3-8 showed moderate hyaluronidase inhibitory activity with IC(50) values of 183-1049 µM.
    Chemical & pharmaceutical bulletin 08/2011; 59(1):88-95. DOI:10.1002/chin.201131209 · 1.38 Impact Factor
  • Toshihiro Murata, Toshio Miyase, Fumihiko Yoshizaki
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    ABSTRACT: A new phenylethanoid glycoside, rashomoside A (1), a new phenolic glucoside, rashomoside B (2), and a new shikimic acid derivative (3) were isolated from Meehania urticifolia together with 12 known flavones (4-15), three known phenylethanoid glycosides (16-18), and 13 other compounds (19-31). The structure of each of these compounds was elucidated based on the results of spectroscopic analysis.
    Journal of Natural Medicines 04/2011; 65(2):385-90. DOI:10.1007/s11418-010-0501-y · 1.45 Impact Factor
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    ABSTRACT: This paper summarizes our research for herbal extracts with potent antioxidant activity obtained from a large scale screening based on superoxide radical (O2•−) scavenging activity followed by characterization of antioxidant properties. Firstly, scavenging activity against O2•− was extensively screened from ethanol extracts of approximately 1000 kinds of herbs by applying an electron spin resonance (ESR)-spin trapping method, and we chose four edible herbal extracts with prominently potent ability to scavenge O2•−. They are the extracts from Punica granatum (Peel), Syzygium aromaticum (Bud), Mangifera indica (Kernel), and Phyllanthus emblica (Fruit). These extracts were further examined to determine if they also scavenge hydroxyl radical (•OH), by applying the ESR spin-trapping method, and if they have heat resistance as a desirable characteristic feature. Experiments with the Fenton reaction and photolysis of H2O2 induced by UV irradiation demonstrated that all four extracts have potent ability to directly scavenge •OH. Furthermore, the scavenging activities against O2•− and •OH of the extracts of P. granatum (peel), M. indica (kernel) and P. emblica (fruit) proved to be heat-resistant. The results of the review might give useful information when choosing a potent antioxidant as a foodstuff. For instance, the four herbal extracts chosen from extensive screening possess desirable antioxidant properties. In particular, the extracts of the aforementioned three herbs are expected to be suitable for food processing in which thermal devices are used, because of their heat resistance.
    Journal of Clinical Biochemistry and Nutrition 01/2011; 48(1):78-84. DOI:10.3164/jcbn.11-013FR · 2.29 Impact Factor
  • Toshihiro Murata, Toshio Miyase, Fumihiko Yoshizaki
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    ABSTRACT: The dried whole plant of Meehania fargesii (H. LéV.) C. Y. WU is utilized as an antipyretic and antidote for poison in China. Water soluble fractions, obtained from an 80% acetone extract of the whole plant, showed hyaluronidase inhibitory activity. From these fractions, hyaluronidase inhibitors were isolated along with two new spermidine alkaloids (meefarnines A and B), four new flavone glycosides (fargenins A-D), and 10 known compounds. The structure of each was elucidated by spectroscopic methods.
    Chemical & pharmaceutical bulletin 11/2010; 58(5):696-702. DOI:10.1248/cpb.58.696 · 1.38 Impact Factor
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    ABSTRACT: An 80% acetone extract of Monarda punctata showed an inhibitory effect on lipase activity in isolated mouse plasma in vitro and carvacrol was obtained as the active constituent. It had an IC₅₀ value of 4.07 mM invitro and suppressed elevations in blood triacylglycerol levels in olive oil-loaded mice. Furthermore, from the whole plant, 22 compounds were isolated. Six monoterpene glycosides, a flavone glucuronide, and other known compounds were identified based on the results of spectroscopic analyses.
    Phytochemistry 11/2010; 71(16):1884-91. DOI:10.1016/j.phytochem.2010.08.009 · 3.35 Impact Factor

Publication Stats

349 Citations
89.94 Total Impact Points


  • 2001–2015
    • Tohoku Pharmaceutical University
      Miyagi, Japan
  • 2010–2011
    • Tohoku University
      • Department of Pharmacology
      Miyagi, Japan
    • Kanazawa University
      Kanazawa, Ishikawa, Japan
  • 2008
    • Kanazawa Medical University
      • Department of General Internal Medicine
      Kanazawa-shi, Ishikawa-ken, Japan
    • University of Shizuoka
      Sizuoka, Shizuoka, Japan
  • 2007
    • Nihon Pharmaceutical University
      Komoro, Nagano, Japan