研究等業績 - 原著論文 - 菊地 正史
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ムラサキハシドイの葉のセコイリドイド配糖体の構造並びにヒトがん細胞株に対する増殖阻害活性について
八百板 康範, 菊地 正史, 菊地 正雄
東北薬科大学研究誌 ( 東北医科薬科大学 ) ( 57 ) 47 - 50 2010年12月 [査読有り]
研究論文（学術雑誌）
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Three new glycosides from the leaves of Hydrangea macrophylla subsp serrata (THUNB.) MAKINO
Masao Kikuchi, Rie Kakuda, Masafumi Kikuchi, Yasunori Yaoita
CHEMICAL & PHARMACEUTICAL BULLETIN ( PHARMACEUTICAL SOC JAPAN ) 56 ( 4 ) 610 - 611 2008年04月 [査読有り]
研究論文（学術雑誌）
Three new glycosides, 7-deoxyloganic acid beta-D-glueopyranosyl ester (1), (3R)-hydrangenol 8,4'-di-O-beta-D-glu-copyranoside (2), and (6R,7E,9R)-megastigma-4,7-dien-3-one 9,13-di-O-beta-D-glueopyranoside (3), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO (Saxifragaceae). The structures of 1-3 were elucidated on the basis of spectral data and chemical evidence.
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Monohydroxy-Substituted Polyunsaturated Fatty Acids from Swertia japonica
Masafumi Kikuchi, Yasunori Yaoita, Masao Kiknchi
HELVETICA CHIMICA ACTA ( WILEY-V C H VERLAG GMBH ) 91 ( 10 ) 1857 - 1862 2008年 [査読有り]
研究論文（学術雑誌）
Fourteen monohydroxy-substituted polyunsaturated fatty acids, including two new compounds. (9Z,12S,13E,15Z)-12-hydroxyoetadeca-9,13,15-trienoic acid (10) and (9Z,12Z,14E,16R)-16-hydroxyoctadeca-9,12,14-trienoic acid acid (13), and 12 known ones. i.e., 1-9, 11, 12, and 14, were isolated from the whole plants of Swertia japonica MAKINO, and characterized as the corresponding methyl esters 1a- 14a. Their structures were elucidated by analysis of the corresponding spectroscopic data, and the absolute configurations of 10a and 13a were determined by the Mosher-ester method. The CD spectra (Table) of compounds 1a-14a are briefly discussed. This IS the first report oil the isolation of monohydroxy-substituted polyunsaturated fatty acids from the Swertia genus in Gentianaceae.
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New secoiridoid glucosides from Swertia japonica
Masafumi Kikuchi, Rie Kakuda, Yasunori Yaoita, Masao Kikuchi
HELVETICA CHIMICA ACTA ( WILEY-V C H VERLAG GMBH ) 91 ( 7 ) 1236 - 1243 2008年 [査読有り]
研究論文（学術雑誌）
Four new secoiridoid glucosides, swertiajaposides C-F (1-4, resp.), were isolated from the whole plant of Swertia japonica MAKINO together with two known compounds, 8-hydroxy-10-hydrosweroside (5) and senburiside IV (6). The structures of 1-4 were elucidated on the basis of spectroscopic, chemical, and physicochemical evidence.
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Neuritogenesis of herbal geniposide-related compounds in PC12h cells
Kenzo Chiba, Matsumi Yamazaki, Masafumi Kikuchi, Koichi Machida, Masao Kikuchi
JOURNAL OF HEALTH SCIENCE ( PHARMACEUTICAL SOC JAPAN ) 52 ( 6 ) 743 - 747 2006年12月 [査読有り]
研究論文（学術雑誌）
Previously, we have reported that geniposide, a compound isolated from an extract of Gardenia fructus, has neuritogenic activity in PC12h cells, a subclone of the rat pheochromocytoma cell. In this study, we have examined the effects of seven geniposide-related compounds (S-1, 6 alpha-hydroxygeniposide; S-2, 6 beta-hydroxygeniposide; S-3, 6 alpha-methoxygeniposide; S-4, 6 beta-methoxygeniposide; S-5, loganin; S-6, 7-ketologanin; and S-7, syringopicroside) isolated from various medicinal herbs. The geniposide-type iridoids S-1, S-2, S-3, and S-4, and S-7 induced neurite outgrowth that was similar or more potent to that of geniposide. S-2 and S-4, which are optical isomers of S-1 and S-3, respectively, were particularly potent. The 2 loganin-type iridoids, S-5 and S-6, showed less activity than geniposide. The neuritogenic activity of geniposide-type iridoids appears to be not necessarily correlated directly to their hydrophobicity. These results suggest that geniposide-type iridoids have potent neuritogenic activity and that specific configurations for the interactions between iridoid compounds and the target molecule are necessary for neuritogenic function.
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A new iridoid diglycoside from Gentianae Scabrae Radix
Tomoko Kyoya, Masafumi Kikuchi, Rie Kakuda, Yasunori Yaoita, Masao Kikuchi
Natural Medicines ( 日本生薬学会 ) 59 ( 4 ) 178 - 180 2005年08月 [査読有り]
研究論文（学術雑誌）
A new iridoid diglycoside, gentianaside (1), was isolated together with two known compounds, 6'-O-β-D-glucopyranosylloganic acid (2) and 8-epikingiside (3), from Gentianae Scabrae Radix. The structure of the new compound was elucidated on the basis of spectral data.
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Secoiridoid glycosides from Gentiana scabra
M Kikuchi, R Kakuda, M Kikuchi, Y Yaoita
JOURNAL OF NATURAL PRODUCTS ( AMER CHEMICAL SOC ) 68 ( 5 ) 751 - 753 2005年05月 [査読有り]
研究論文（学術雑誌）
Six new secoiridoid glycosides, gentiascabraside A (1), 6 beta-hydroxyswertiajaposide A (2), 1-O-beta-D-glucopyranosyl-4-epiamplexine (3), and scabrans G(3) (4), G(4) (5), and G(5) (6), have been isolated from the rhizomes and roots of Gentiana scabra together with a known compound, swertiajaposide A (7). The structures of the new Compounds were determined by spectroscopic (NMR, MS) and chemical means.
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Studies on the constituents of Swertia japonica MAKINO II.(1)) - On the structures of new glycosides
M Kikuchi, M Kikuchi
CHEMICAL & PHARMACEUTICAL BULLETIN ( PHARMACEUTICAL SOC JAPAN ) 53 ( 1 ) 48 - 51 2005年01月 [査読有り]
研究論文（学術雑誌）
Two new secoiridoid glycosides, swertiajaposide A (1) and swertiajaposide B (2), a new unsaturated alcohol glycoside, 3-butenyl 6'-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (3), and a new lignan glycoside, 7R,7'R,8S,8'S-(+)-neo-olivil-4-O-beta-D-glucopyranoside (4), were isolated together with six known compounds from the whole plants of Swertia japonica MAKINO. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.
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Studies on the constituents of Swertia japonica MAKINO I. On the structures of new secoiridoid diglycosides
M Kikuchi, M Kikuchi
CHEMICAL & PHARMACEUTICAL BULLETIN ( PHARMACEUTICAL SOC JAPAN ) 52 ( 10 ) 1210 - 1214 2004年10月 [査読有り]
研究論文（学術雑誌）
Eight new secoiridoid diglycosides, 6'-O-alpha-L-arabinopyranosylswertiamarin (1), 3'-O-P-D-glUeopyranosylswertiamarin (2), 4'-O-beta-D-glucopyranosylswertiamarin (3), 3'-O-beta-D-galactopyranosylswertiamarin (4), 6'-O-alpha-D-galactopyranosylswertiamarin (5), 6'-O-beta-D-mannopyranosylswertiamarin (6), 6'-O-beta-D-fructofuranosylswertiamarin (7) and 5"-O-beta-D-glucopyranosylamaroswerin (12), were isolated, together with five known compounds from the whole plants of Swertia japonica MAKINO. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. Compounds 6 and 7 are the first naturally occuring iridoid diglycosides having an alpha-D-mannopyranosyl unit and beta-D-fructofuranosyl unit, respectively.
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Triterpenoids from Gentianae Scabrae Radix and Gentianae Radix
Rie Kakuda, Chie Ueno, Nagisa Kobayashi, Masafumi Kikuchi, Yasunori Yaoita, Masao Kikuchi
Natural Medicines ( 日本生薬学会 ) 58 ( 1 ) 22 - 26 2004年02月 [査読有り]
研究論文（学術雑誌）
For new triterpenoids, uvaol 3-O-linoleate (1), uvaol 3-O-stearate (2), erythrodiol 3-O-linoleate (3) and erythrodiol 3-O-stearate (4), were isolated from Gentianae Scabrae Radix. Compounds 1 and 2, and an inseparable mixture of the new triterpenoids, α-amyrin 3-O-coriolate (5) and α-amyrin 3-O-dimorphecolate (6), were obtained from Gentianae Radix. The structures of the new compounds were elucidated on the basis of spectral data.
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Studies on the constituents of Gentiana species. II. A new triterpenoid, and (S)-(+)- and (R)-(-)-gentiolactones from Gentiana lutea
R Kakuda, K Machida, Y Yaoita, M Kikuchi, M Kikuchi
CHEMICAL & PHARMACEUTICAL BULLETIN ( PHARMACEUTICAL SOC JAPAN ) 51 ( 7 ) 885 - 887 2003年07月 [査読有り]
研究論文（学術雑誌）
A new triterpenoid, 12-ursene-3beta, 11alpha-diol 3-O-palmitate (1), has been isolated from the rhizomes and roots of Gentiana lutea, together with the artificial diene derivative, 9 (11), 12-ursadien-3beta-ol 3-O-palmitate (1a) and five known compounds (3-7). Their structures were established on the basis of spectral analysis. In addition, (+/-)-gentiolactone [(+/-)-2], isolated from this plant, was successfully separated into its enantiomers [(+)-2, (-)-2] for the first time, and the absolute configurations at C-9 of (+)-2, (-)-2 were assigned as S and R, respectively, from the optical rotations and the circular dichroism (CD) spectral data.
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New triterpenoids from Gentiana lutea
Y Toriumi, R Kakuda, M Kikuchi, Y Yaoita, M Kikuchi
CHEMICAL & PHARMACEUTICAL BULLETIN ( PHARMACEUTICAL SOC JAPAN ) 51 ( 1 ) 89 - 91 2003年01月 [査読有り]
研究論文（学術雑誌）
Three new triterpenoids, 2,3-seco-3-oxours-12-en-2-oic acid, 2,3-seco-3-oxoolean-12-en-2-oic acid, and betulin 3-O-palmitate, have been isolated from the rhizomes and roots of Gentiana lutea, together with five known ones. The structures of the new compounds were determined by spectral and chemical methods.
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ゲンチアナの化学成分について(第3報)
上野稚恵, 角田利枝, 菊地正史, 八百板康範, 町田浩一, 菊地正雄
東北薬科大学研究誌 ( 50 ) 81 - 84 2003年 [査読有り]
研究論文（学術雑誌）
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リュウタンの化学成分について(第3報)
小林渚, 角田利枝, 菊地正史, 八百板康範, 町田浩一, 菊地正雄
東北薬科大学研究誌 ( 50 ) 85 - 88 2003年 [査読有り]
研究論文（学術雑誌）
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Sterol constituents from Poria cocos
Yasunori Yaoita, Masafumi Kikuchi, Masao Kikuchi
Natural Medicines ( 日本生薬学会 ) 56 ( 2 ) 63 - 63 2002年01月 [査読有り]
研究論文（学術雑誌）