論文 - 荻原　和仁

Flavonoids and Isoflavonoids from the Fresh Immature Seeds of Sophora tomentosa L.

Kazuhito OGIHARA,* Takerou OOYA, Eiken KUNIYOSHI, Toshimasa SUZUKA, and Matsutake HIGA

Bulletin of Faculty ofScience University of Ryukyus   ( 108 ) 27 - 32   2020年03月

掲載種別: 研究論文（学術雑誌）

Friedel–Crafts-Type Alkylation of Indoles in Water Using Amphiphilic Resin-Supported 1,10-Phenanthroline–Palladium Complex under Aerobic Conditions

Suzuka Toshimasa, Ooshiro Yuto, Ogihara Kazuhito

Catalysts ( MDPI )  10   193 - 203   2020年02月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

Polymer-Supported Terpyridine–Palladium Complex for the Allylic Alkylation with Arylboronic Acid in Water

Suzuka Toshimasa, Takayama Naoki, Unten Masanori, Onda Kaoru, Ogihara Kazuhito

Transactions of the Materials Research Society of Japan ( 一般社団法人 日本MRS )  44 ( 1 ) 41 - 44   2019年01月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

　概要を見る

<p>  A novel homogeneous transition-metal catalyst, a polymer-supported terpyridine–palladium(II) complex, was found to promote the allylic alkylation with phenylborinic acid under phosphine-free conditions in water with good yield. The catalyst was recovered and reused several times without loss of catalytic activity. To our knowledge, this is the first example of the allylic alkylation with pheylboronic acid in water using a polymer-supported terpyridine–palladium(II) complex under aerobic conditions. The stereochemistry of the allylic alkylation with phenylboronic acid was demonstrated to be not net retention. </p>

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Naphthoquinone Derivatives from Diospyros maritima.

Higa M, Takashima Y, Yokaryo H, Harie Y, Suzuka T, Ogihara K

Chemical & pharmaceutical bulletin ( 公益社団法人 日本薬学会 )  65 ( 8 ) 739 - 745   2017年08月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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<p>From the chloroform extract of the fresh fruits of <i>Diospyros maritima</i> BLUME (Ebenaceae), five new naphthoquinone derivatives, 2,7′-dimethyl-2′,3-bijuglone (27), 2,7′-dimethyl-3,3′-bijuglone (28), 2,7′-dimethyl-6,8′-bijuglone (29), 7,7′-dimethyl-3,3′-ethylidenebijuglone (30), and 2′,7-dimethyl-3,6′-ethylidenebijuglone (31), were isolated, in addition to twenty-one known naphthoquinone derivatives: plumbagin (4), droserone (5), 2,3-epoxyplumbagin (8), 3,3′-biplumbagin (9), chitranone (10), 3,8′-biplumbagin (11), elliptinone (12), maritinone (13), isozeylanone (14), methylene-3,3′-biplumbagin (15), ethylidene-3,3′-biplumbagin (16), ethylidene-3,6′-biplumbagin (17), ethylidene-6,6′-biplumbagin (18), 7-methyl-β-dihydrojuglone (19), 7-methyljuglone (20), 2,3-epoxy-7-methyljuglone (21), neodiospyrin (22), mamegakinone (23), ehretione (24), isoxylospyrin (25) and β-dihydroplumbagin (26). The structures of the new compounds were established by spectral analysis. The quinones obtained from the chloroform extract of the fruits were compared with previously reported quinones obtained from ethanol extracts. The quinones in the fruits were categorized in three groups: quinones from ethanol extract only, quinones from chloroform extract only, and quinones from both extracts. The six naphthoquinones, 19–21, 25, 26, and 29, were examined for their ichthyotoxic activity and germination inhibitory activity. Quinones 19–21, 26, and 29 showed ichthyotoxic activity against Japanese killifish (<i>Oryzias latipes</i> var.) at 10 ppm; quinones 19 to 21 and 26 showed germination inhibitory activity toward lettuce seeds (<i>Lactuca sativa</i> L. var. Great Lakes) at 100 ppm.</p>

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Recyclable polymer-supported terpyridine–palladium complex for the tandem aminocarbonylation of aryl iodides to primary amides in water using NaN<inf>3</inf> as ammonia equivalent

Suzuka T. Hiromu Sueyoshi, Kazuhito Ogihara

Catalysts ( Catalysts )  7 ( 4 )   2017年04月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Flavonoids, isoflavonoids and other constituents from the fresh mature seeds of Sophora tomentosa L.

Ogihara Kazuhito,Kuniyoshi　Eiken,Suzuka　Toshimasa,Higa　Matsutake,

BULLETIN OF THE FACULTY OF SCIENCE UNIVERSITY OF THE RYUKYUS ( 琉球大学理学部 )  ( 101 ) 1 - 7   2016年03月

掲載種別: 研究論文（大学，研究機関紀要）

　概要を見る

The chloroform-soluble fraction in a methanol extract from mature seeds of Sophora tomentosa L.was subjected to chromatographic separation and purification to give two flavonoids (4 and 5), two isoflavonoids (3 and 6), one lupin alkaloid (1) and one polyphenol (2), respectively. These compounds were identified as 7,4’-dihydroxy- 3’-methoxyflavone (4, geraldone), 7,3’-dihydroxy-4’-methoxyflavone (5, farnisin), 7,3’-dihydroxy-5’-methoxyisoflavone (3), 7,4’-dihydroxy- 3’-methoxyisoflavone (6), N-methylcytisine (1) and methyl 3,4- dihydroxybenzoate (2, methyl protocatechuate), respectively, by spectroscopic methods. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Polymer-Supported Terpyridine–Palladium Complex for the Aminocarbonylation in Water of Aryl Iodines Using Methoxylamine Hydrochloride as an Ammonia Equivalent

Suzuka Toshimasa, Sueyoshi Hiromu, Ogihara Kazuhito

Transactions of the Materials Research Society of Japan ( 一般社団法人 日本MRS )  41 ( 3 ) 225 - 228   2016年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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<p>  A novel homogeneous transition-metal catalyst, a polymer-supported terpyridine–palladium(II) complex, was found to promote the aminocarbonylation of aryl iodines using methoxylamine under phosphine-free conditions in water with good yield. The catalyst was recovered and reused several times without loss of catalytic activity. To our knowledge, this is the first example of polymer-supported, palladium-catalyzed synthesis of primary amides by aminocarbonylation of aryl iodides and methoxylamine under phosphine-free conditions in water.</p>

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Phenylethanoid Glycosides from the fresh immature legumes of Golden Trumpet Tree (Tabebuia chrysotricha)

Ogihara Kazuhito, Murata　Masayuki, Sasamoto　Shohei, Suzuka　Toshimasa, Higa　Matsutake

No.100 (2015/9) ( 琉球大学理学部 )  ( 100 ) 13 - 19   2015年11月

掲載種別: 研究論文（大学，研究機関紀要）

　概要を見る

Three phenylethanoid glycosides were isolated from a 1-butanol soluble fraction of a methanol extract of the fresh immature legumes of Tabebuia chrysotricha. These glycosides were identified to be 2-(3,4-dihydroxypheny1)ethy1 Ｏ-α-L-rhamnopyranosy1-(1 → 3)-(4-Ｏ-caffeoy1)-β-D-glucopyranoside (acteoside), 2-(3,4-dihydroxypheny1)ethy1 Ｏ-α-L-rhamnopyranosy1-(1 → 3)-(4-Ｏ-caffeoy1)-2-Ｏ-acety1-β-D-glucopyranoside (2'-acety1acteoside), and 2-(3,4-dihydroxyphenyl)ethy1 Ｏ-α-L-rhamnopyranosy1-(1→3)-(6-Ｏ-cafeoy1)-β-D-glucopyranoside (isoacteoside), respectively, by spectroscopic methods and chemical evidences. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Use of Polymer-Supported Terpyridine-Palladium Complex for Mizoroki-Heck Reaction in Water under Aerobic Conditions

Suzuka Toshimasa, Adachi Mika, Nakamoto Yuki, Ogihara Kazuhito

Transactions of the Materials Research Society of Japan ( The Materials Research Society of Japan )  40 ( 1 ) 77 - 80   2015年

掲載種別: 研究論文（学術雑誌）

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  A novel heterogeneous transition-metal catalyst, a polymer-supported terpyridine-palladium(II) complex, was prepared from 4-methoxycarbonylbenzaldehyde, 2-acetylpyridine, NH₄OAc according to the reported procedures and found to promote the Mizoroki-Heck reaction in water between aryl halides and styrenes under aerobic conditions with high to excellent yield. The catalyst was recovered and reused several times without loss of catalytic activity.

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Sonogashira Coupling Reaction in Water Using a Polymer-Supported Terpyridine–Palladium Complex under Aerobic Conditions

Suzuka Toshimasa, Adachi Mika, Ogihara Kazuhito

Transactions of the Materials Research Society of Japan ( 一般社団法人 日本MRS )  40 ( 2 ) 103 - 106   2015年

掲載種別: 研究論文（学術雑誌）

　概要を見る

The palladium-catalyzed coupling reaction between an aryl halide and a terminal alkyne, the so-called Sonogashira coupling reaction, was found to occur in water under copper-free conditions using an amphiphilic polystyrene–poly(ethylene glycol) (PS-PEG) resin-supported palladium–terpyridine complex, giving the corresponding aryl-substituted alkyne in high yield. The PS-PEG resin-supported palladium–terpyridine catalyst was recovered simply by filtering the product mixture under air and could be reused three times with only slightly decreased catalytic activity after each use.

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Constituents from the fruits of Messerschmidia argentea (4)

Ogihara Kazuhito, Kuwae　Mariko, Suzuka　Toshimasa, Higa　Matsutake,

No.93 (2012/3) ( 琉球大学理学部 )  ( 93 ) 47 - 54   2012年12月

掲載種別: 研究論文（大学，研究機関紀要）

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Four pyrocatechol derivatives and two flavone glycosides were isolated from a methanol extract of the fruits of Messerschmidia argentea, in addition to two pyrrolidizine alkaloids, hydrocarbons, and fatty acid methyl esters. These pyrocatechol derivatives were identified as methyl caffeate, methyl 3, 4-dihydroxybenzoate, methyl 2-(3,4-dihydroxyphenyl) acetate, and rosmarinic acid, these flavone glycosides as kaempferol 3-O-B-D-glucopyranoside and quercetin 3-O-B-glucopyranoside, and the alkaloids as 3'-acetylindicine and indicine, respectively, by spectroscopic methods. It is found that the hydrocarbons and the fatty acid methyl esters were mainly composed of tricosane and methyl linoleate, respectively. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Anthraquinones and other constituents from the roots of Hemerocallis fulva L. var. sempervirona M. Hotta

Kikushima　Fumito,Matsui　Shunsuke,Shinyashiki　Hiroto,Suzuka　Toshimasa,Higa　Matsutake,

No.90 (2010/9) ( 琉球大学理学部 )  ( 90 ) 11 - 16   2010年11月

掲載種別: 研究論文（大学，研究機関紀要）

　概要を見る

Four anthraquinone derivatives were isolated from n-hexane- and chloroform-soluble fractions in a methanol extract from the roots of Hemerocallis fulva L. var. sempervirona M. Hotta, in addition to aliphatic hydrocarbons, fatty acid methyl esters, and phytosterols. The anthraquinone derivatives were identified as chrysophanol (1), kwanzoquinone B (2), obtusifolin (3), and aloe-emodin(4), respectively, by spectroscopic methods. It is found that the aliphatic hydrocarbons, the fatty acid methyl esters, and the phytosterols, were mainly composed of pentacosane, methyl parmitate, and stigmasterol, respectively, on the basis of these GC/MS analyses. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Glucosides from the Leaves of Cynanchum liukiuense (2)

Chinen　Ryouko,Suzuka　Toshimasa,Higa　Matsutake,Yogi　Seiichi

No.89 (2010/3) ( 琉球大学理学部 )  ( 89 ) 59 - 64   2010年07月

掲載種別: 研究論文（大学，研究機関紀要）

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Three glucosides were isolated from an n-BuOH soluble fraction in a methanol extract of the leaves of Cynanchum liukiuense Werb. These compounds were identified as (1R, 6R)-3-oxo-6-hydroxy-α-ionol 11-O-β-D-glucopyranoside (9), quercetin 3-O-β-D-glucopyranoside (10), and kaempferol 3-O-β-D-glucopyranoside (11), respectively, by spectroscopic methods and chemical evidences. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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リュウキュウウマノスズクサ(Aristolochia liukiuensis)の成分研究（第2報）

趙　嘉平,比嘉　松武,与儀　誠一,

No.54 (1992/10) ( 琉球大学理学部 )  ( 54 ) 17 - 28   2010年01月

掲載種別: 研究論文（大学，研究機関紀要）

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The chemical constituents in the roots of Aristolochia liukiuensis Hatsusima were examined. Aristolactone (1), mansonone G (3), dehydrooxoperezinone (4), aristololactam D2 (6), 3,4 - methylenedioxy - 8 - methoxyphenanthrene - 1 - carboxylic acid (8), aristolochic acid 2 (10), and aristolochic acid 4 methyl ester (11) were isolated from the roots, in addition to already isolated constituents from the leaves and the stems, such as sitosterol (2), 2-hydroxy-1-methoxy-4,5-dioxo-6,7-dehydroaporphine (5), aristololactam A2 (7), aristolochic acid 1 (9), and sitosterolfl-β-glucoside (12). This is the first report of 4 in natural sources. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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DPPH-radical Scavenging Constituents from the Twigs of Messerschmidia argentea (3)

Nakazato　Risa,Nishi　Yuka,Higa　Matsutake,Yogi　Seiichi

No.74 (2002/9) ( 琉球大学理学部 )  ( 74 ) 73 - 80   2010年01月

掲載種別: 研究論文（大学，研究機関紀要）

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Five aromatic compounds possessing DPPH-radical scavenging activity were isolated from a water extract of the twigs of Messerschmidia argentea. These compounds were identified as rosmarinic acid and its methyl ester, cafferic acid and its methyl ester, and 3-(3', 4'-dihydroxyphenyl)lactic acid, respectively. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Studies on Constituents from the Twigs of Messerschmidia argentea 2

Iraha　Rumiko,Higa　Matsutake,Yogi　Seiichi,

No.64 (1997/9) ( 琉球大学理学部 )  ( 64 ) 53 - 59   2010年01月

掲載種別: 研究論文（大学，研究機関紀要）

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Four triterpenoids and an aromatic carboxylic acid methyl ester were isolated from a chloroform-soluble fraction in a methanol extract of the twigs of Messerschmidia argentea. These compounds were identified as olean-12-en-3β-ol acetate (β-amyrin acetate), 3β-acetyloxy-olean-12-en-28-al (3-O-acetyloleanolic aldehyde), 3β-acetyloxy-olean-12-en-28-ol (erythrodiol 3-acetate), 3β-acetyloxy-olean-12-en-28-oic acid (oleanolic acid acetate), and methyl 3, 4-dihydroxycinnamate respectively. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Triterpenoids and Phytosteroids from the Leaves of Cynanchum liukiuense

Nishizato　Saori,Ishigaki　Masashi,Higa　Matsutake,Yogi　Seiichi

No.70 (2000/9) ( 琉球大学理学部 )  ( 70 ) 83 - 92   2010年01月

掲載種別: 研究論文（大学，研究機関紀要）

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Five triterpenoids were isolated from a chloroform-soluble fraction in a methanol extract of the leaves of Cynanchum liukiuense Werb, in addition to methyl stearate, phytosterols, and phytosterol glycosides. These triterpenoids were identified as 3β- acetyloxy-urs-12-ene (α-amyrin acetate), 3β-acetyloxy-olean-12-ene (β-amyrin acetate), (4β)-D-friedoolean-14-en-3β-ol (taraxerol), olean-12-en-3β-ol (β-amyrin), and lup-20(29)-en-β-ol(lupeol), respectively. The phytosterols consisted of stigmastanol, stigmasterol, and campesterol by co-GC and GC-MS analyses and the phytosterol glycosides mainly did of the glucosides of stigmastanol, β-sitosterol, stigmasterol, and campesterol. （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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マダラチョウのメスとモンパノキとの相関に関する研究

その他の著者

研究報告書（理） ( 荻原和仁 )    2009年12月

掲載種別: 研究論文（その他学術会議資料等）

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平成10年度～平成12年度科学研究費補助金[基盤研究(C)(2)]研究成果報告書 （管理者追加）リポジトリ登録情報を移行しました。確認のうえ、加除修正をしてください。

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Three New Naphthoquinone Derivatives from Diospyros maritima

Matsutake Higa, Nobue Noha, Hiroto Yokaryo, Kazuhito Ogihara, Seiichi Yogi

Chemical and Pharmaceutical Bulletin   50 ( 5 ) 590 - 593   2002年05月 [ 査読有り ]

掲載種別: 研究論文（その他学術会議資料等）

　概要を見る

Three new naphthoquinone derivatives, 6-(1-ethoxyethyl)plumbagin (16), ethylidene-3,3′-biplumbagin (17), and ethylidene-3,6′-biplumbagin (18), were isolated, in addition to six known naphthoquinones, isozeylanone (10), 3,3′-biplumbagin (11), chitranone (12), methylene-3,3′-biplumbagin (13), 2,3-epoxyplumbagin (14), and 3,8′-biplumbagin (15), from the fruits of Diospyros maritima BLUME (Ebenaceae). The structures of the new compounds were established by spectroscopic methods. The eight naphthoquinones 11—18 were examined for ichthyotoxic activity and germination inhibitory activity. The quinones 11, 12, and 14—16 showed strong ichthyotoxic activity and the quinone 14 mild germination inhibitory activity.

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Bioactive Naphthoquinone Derivatives from Diospyros maritima Blume

Matsutaka HIGA, Kazuhito OGIHARA, Seiichi YOGI

Chemical and pharmaceutical Bulletin ( その他の出版社 )  46 ( 8 ) 1189 - 1193   1998年08月 [ 査読有り ]

掲載種別: 研究論文（その他学術会議資料等）

　概要を見る

From the fresh fruits of Diospyros maritima BLUME (Ebenaceae) three new naphthoquinones, 3-bromoplumbagin (1), ethylidene-6, 6'-biplumbagin (2), and 3-(2-hydroxyethyl)plumbagin (3), were isolated, in addition to six known naphthoquinones, 3-chloroplumbagin (4), 3-methylplumbagin (5), plumbagin (6), droserone (7), elliptinone (8), and maritinone (9). The structures of the new compounds were established by chemical and spectroscopic means.The 21 compounds isolated from this plant were examined for ichthyotoxic activity, germination inhibitory activity, and antifugal activity. The naphthoquinone derivatives from the fruits of Diospyros maritima showed a variety of biological activities, especially plumbagin (6), which showed strong activity in these three bioassays.

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