1998 Fiscal Year Annual Research Report

和漢薬の伝承薬効解明を基盤とした高次機能サポニン類の探索と応用

Research Project

Project/Area Number	09672177
Research Institution	Kyoto Pharmaceutical University
Principal Investigator	松田久司京都薬科大学, 薬学部, 助教授 (40288593)
Co-Investigator(Kenkyū-buntansha)	村上敏之京都薬科大学, 薬学部, 助手 (40278445) 吉川雅之京都薬科大学, 薬学部, 教授 (90116129)
Keywords	伝承薬効解明 / 高次機能サポニン / 和漢薬 / 柴胡 / 西洋トチノキ種子 / 肝保護作用 / 抗アレルギー作用 / アジュバント活性
Research Abstract	平成10年度は、抗アレルギー作用、免疫系に及ぼす作用および肝保護について人参、アメリカ人参、三七人参、.酸棗仁、柴胡、西洋トチノキ種子および豆類(三度豆、大豆、白扁豆)などの天然薬物を広範にスクリーニングした。ラット腹腔肥満細胞を用いたヒスタミン遊離試験において、三度豆から強いヒスタミン遊離抑制活性を有するsandosaponinAおよびBを単離し、それらの化学構造を明らかにした。白扁豆に含まれるlablabosideA〜Fの化学構造を明らかにするとともに、酸棗仁に含まれるjujuboside類および食用種子に含まれるsoyasaponin類に抗体産生能増強活性、すなわちアジュバンド活性を見い出した。西洋トチノキ種子からescin類およびisoescin類12種を単離し、それらの化学構造を明らかにするとともに、主成分escin Ia,Ib,IIa及びIIbの抗炎症作用を明らかにした。アメリカ人参から新規dammarane系サポニン,qinquenosideI,IIおよびIII、柴胡からbupleurosideI〜XIIIおよびscorzonerosideA〜Cの化学構造を明らかにするとともに、D-ガラクトサミン・リポ多糖誘発急性肝障害モデルにおいて人参、アメリカ人参および三七人参および柴胡に抑制効果を見いだした。柴胡に含まれるサポニンは、初代培養肝細胞を用いたD-ガラクトサミンによる細胞毒性を強く抑制し、関連サポニンおよびそれらの誘導体について検討した結果、活性発現には3位の糖鎖構造、11位酸素官能基および16位β-OHが活性発現に必須であることなどを明らかにした。以上、今回、アメリカ人参、豆類、柴胡、西洋トチノキ種子などに含まれる新規サポニン類の化学構造の解明と薬理活性に関する興味深い知見を得るなど平成10年度当初計画をほぼ完全に達成することができた。

Research Products

(26 results)

All Other

All Publications (26 results)

[Publications] Masayuki Yoshikawa: "Absolute Stereostructures of Betavulgarosides III and IV, Inhibitors of Glucose Absorption,from the Roots of Beta vulgaris L.(Sugar Beet)." Chem.Pharm.Bull.vol.45. 561-563 (1997)
[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.VI.Histamine Release Inhibitors from Kidney Bean,the Seeds of Phaseolus vulgaris L. : Chemical Structures of Sandosaponins A and B." Chem.Pharm.Bull.vol.45. 877-882 (1997)
[Publications] Masayuki Yoshikawa: "Studies on Kochiae Fructus.II.On the Saponin Constituents from the Fruit of Chinese Kochia scoparia (Chenopodiaceae) : Chemical Structures of Kochianosides I,II,III,and IV." Chem.Pharm.Bull.vol.45. 1052-1055 (1997)
[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs. IX.The Inhibitors of Glucose Absorption from the Leaves of Gymnema sylvestre R.BR.(Asclepiadaceae) : Structures of Gymnemosides a and b." Chem.Pharm.Bull.vol.45. 1671-1676 (1997)
[Publications] Hisashi Matsuda: "Antiinflammatory Effects of Escins Ia,Ib,IIa,and IIb from Horse Chestnut, the Seeds of Aesculus hippocastanum L." Bioorg.Med.Chem.Lett.vol.7. 1611-1616 (1997)
[Publications] Masayuki Yoshikawa: "ギムネマ葉含有成分Gymnemic acid IVの血糖下降作用." 和漢医薬学雑誌. vol.14. 418-419 (1997)
[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.VIII.Fenugreek Seed. (2) : Structures of Six New Furostanol Saponins,Trigoneosides IVa,Va,Vb,VI,VIIb,and VIIIb,from the Seeds of Indian Trigonella foenum-graecum L." Heterocycles. vol.47. 397-405 (1998)
[Publications] Hajime Komatsu: "Medicinal Foodstuffs.XIII.Saponin Constituents with Adiuvant Activity from Hyacinth Bean,the Seeds of Dolichos lablab L. (2) : Structures of Lablabosides D,E,and F." Heterocycles. vol.48. 703-710 (1998)
[Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glysosides. XI.Structures of New Dammarane-Type Triterpene Oligoglycosides,Quinquenosides I,II,III,IV,and V.from American Ginseng,the Roots of Panax quinguefolium L." Chem.Pharm.Bull.vol.46. 647-654 (1998)
[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.XIII.Saponin Constituents with Adiuvant Activity from Hyacinth Bean,the Seeds of Dolichos lablab L. (1) : Structures of Lablabosides A,B,and C." Chem.Pharm.Bull.vol.46. 812-816 (1998)
[Publications] Hisashi Matsuda: "Mode of Action of Escins Ia and IIa and E,Z-Senegin II on Glucose Absorption in Gastrointestinal Tract." Bioorg.Med.Chem.vol.6. 1019-1023 (1998)
[Publications] Hisashi Matsuda: "Antidiabetic Principles of Natural Medicines. III.Structure-Related Inhibitory Activity and Action Mode of Oleanolic Acid Glycosides on Hypoglycemic Activity." Chem.Pharm.Bull.vol.46. 1399-1403 (1998)
[Publications] Hisashi Matsuda: "Protective Effects of Oleanolic Acid Oligoglycosides on Ethanol-or Indomethacin-Induced Gastric Mucosal Lesions in Rats." Life Sci.vol.63. PL245-250 (1998)
[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.XV.Suger Beet.(2) : Structures of Betavulgarosides V,VI,VII,VIII,IX,and X from the Roots and Leaves of Suger Beet (Beta Vulgaris L.,Chenopodiaceae)." Chem.Pharm.Bull.vol.46. 1758-1763 (1998)
[Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glycosides. XII.Horse Chestnut.(2) : Structures of Escins IIIb,IV,V,and VI and Isoescins Ia,Ib,and V,Acylated Polyhydroxyoleanene Triterpene Oligoglycosides,from the Seeds of Horse Chestnut Tree (Aesculus hippocastanum L.,Hippocastanaceae)." Chem.Pharm.Bull.vol.46. 1764-1769 (1997)
[Publications] Hideaki Matsuda: "Studies on Kochiae Fructus.V.Antipruritic Effects of Oleanolic Acid Glycosides and the Structure-Requirement." Biol.Pharm.Bull.vol.21. 1231-1232 (1998)
[Publications] Masayuki Yoshikawa: "Absolute Stereostructures of Spinacosides C and D with a Novel Acetal Type Substituent from Spinacia oleracea (Spinach) and Basella rubra (Indian Spinach)." Heterocycles. vol.49. 93-96 (1998)
[Publications] Hisashi Matsuda: "薬用食物のサポニン成分の免疫機能に及ぼす作用-Soyasaponin類のアジュバント活性-" 和漢医薬学雑誌. vol.15. 278-279 (1998)
[Publications] Masayuki Yoshikawa: "生物活性サポニン及び配糖体(13報)西洋トリノキ種子サポニン(3):高速液体クロマトグラフィーを用いたEscin Ia,Ib,IIa,およびIIbの定量分析." 薬学雑誌. vol.119. 81-87 (1999)
[Publications] Hisashi Matsuda: "Structure-Related Inhibitory Activity of Oleanolic Acid Glycosides." Bioorg.Med.Chem.vol.7(in press). (1999)
[Publications] Hisashi Matsuda: "Effects of Escins Ia,Ib,IIa,and IIb from horse chestnuts on gastric emptying in mice." Eur.J.Pharmacol.(in press). (1999)
[Publications] Yuhao Li: "Effects of Oleanolic Acid Glycosides on Gastrouitestinal Transit and Ileus in Mice." Bioorg.Med.Chem.vol.7(in press). (1999)
[Publications] Hisashi Matsuda: "Inhibition of Gastric Emptying by Triterpene Saponin,Momordin Ic,in Mice : Reles Blood Glucose,Capsaicin-Sensitive Sensory Nerves,and Central Nervous System." J.Pharmacol.Exp.Ther.(in press). (1999)
[Publications] Hisashi Matsuda: "Roles of Capsaicin-Sensitive Sensory Nerves,Endogenous Nitric Oxide,Sulfhysryls,and Prostaglandins in Gastroprotection by Momordin Ic,an Oleanolic Acid Olgoglycoside,on Ethanol-Induced Gastric Mucosal Lesions in Rats." Life Sci.(in press). (1999)
[Publications] Masayuki Yoshikawa: "Towards Natural Medicine Research in the 21st Century" Elsevier, 585 (1998)
[Publications] Masayuki Yoshikawa: "Advances in Plant Glycosides,Chemistry and Biology" Elsevier, 556 (1999)

1998 Fiscal Year Annual Research Report

和漢薬の伝承薬効解明を基盤とした高次機能サポニン類の探索と応用

Principal Investigator

松田 久司 京都薬科大学, 薬学部, 助教授 (40288593)

Research Products

[Publications] Masayuki Yoshikawa: "Absolute Stereostructures of Betavulgarosides III and IV, Inhibitors of Glucose Absorption,from the Roots of Beta vulgaris L.(Sugar Beet)." Chem.Pharm.Bull.vol.45. 561-563 (1997)

[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.VI.Histamine Release Inhibitors from Kidney Bean,the Seeds of Phaseolus vulgaris L. : Chemical Structures of Sandosaponins A and B." Chem.Pharm.Bull.vol.45. 877-882 (1997)

[Publications] Masayuki Yoshikawa: "Studies on Kochiae Fructus.II.On the Saponin Constituents from the Fruit of Chinese Kochia scoparia (Chenopodiaceae) : Chemical Structures of Kochianosides I,II,III,and IV." Chem.Pharm.Bull.vol.45. 1052-1055 (1997)

[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs. IX.The Inhibitors of Glucose Absorption from the Leaves of Gymnema sylvestre R.BR.(Asclepiadaceae) : Structures of Gymnemosides a and b." Chem.Pharm.Bull.vol.45. 1671-1676 (1997)

[Publications] Hisashi Matsuda: "Antiinflammatory Effects of Escins Ia,Ib,IIa,and IIb from Horse Chestnut, the Seeds of Aesculus hippocastanum L." Bioorg.Med.Chem.Lett.vol.7. 1611-1616 (1997)

[Publications] Masayuki Yoshikawa: "ギムネマ葉含有成分Gymnemic acid IVの血糖下降作用." 和漢医薬学雑誌. vol.14. 418-419 (1997)

[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.VIII.Fenugreek Seed. (2) : Structures of Six New Furostanol Saponins,Trigoneosides IVa,Va,Vb,VI,VIIb,and VIIIb,from the Seeds of Indian Trigonella foenum-graecum L." Heterocycles. vol.47. 397-405 (1998)

[Publications] Hajime Komatsu: "Medicinal Foodstuffs.XIII.Saponin Constituents with Adiuvant Activity from Hyacinth Bean,the Seeds of Dolichos lablab L. (2) : Structures of Lablabosides D,E,and F." Heterocycles. vol.48. 703-710 (1998)

[Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glysosides. XI.Structures of New Dammarane-Type Triterpene Oligoglycosides,Quinquenosides I,II,III,IV,and V.from American Ginseng,the Roots of Panax quinguefolium L." Chem.Pharm.Bull.vol.46. 647-654 (1998)

[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.XIII.Saponin Constituents with Adiuvant Activity from Hyacinth Bean,the Seeds of Dolichos lablab L. (1) : Structures of Lablabosides A,B,and C." Chem.Pharm.Bull.vol.46. 812-816 (1998)

[Publications] Hisashi Matsuda: "Mode of Action of Escins Ia and IIa and E,Z-Senegin II on Glucose Absorption in Gastrointestinal Tract." Bioorg.Med.Chem.vol.6. 1019-1023 (1998)

[Publications] Hisashi Matsuda: "Antidiabetic Principles of Natural Medicines. III.Structure-Related Inhibitory Activity and Action Mode of Oleanolic Acid Glycosides on Hypoglycemic Activity." Chem.Pharm.Bull.vol.46. 1399-1403 (1998)

[Publications] Hisashi Matsuda: "Protective Effects of Oleanolic Acid Oligoglycosides on Ethanol-or Indomethacin-Induced Gastric Mucosal Lesions in Rats." Life Sci.vol.63. PL245-250 (1998)

[Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs.XV.Suger Beet.(2) : Structures of Betavulgarosides V,VI,VII,VIII,IX,and X from the Roots and Leaves of Suger Beet (Beta Vulgaris L.,Chenopodiaceae)." Chem.Pharm.Bull.vol.46. 1758-1763 (1998)

[Publications] Hideaki Matsuda: "Studies on Kochiae Fructus.V.Antipruritic Effects of Oleanolic Acid Glycosides and the Structure-Requirement." Biol.Pharm.Bull.vol.21. 1231-1232 (1998)

[Publications] Masayuki Yoshikawa: "Absolute Stereostructures of Spinacosides C and D with a Novel Acetal Type Substituent from Spinacia oleracea (Spinach) and Basella rubra (Indian Spinach)." Heterocycles. vol.49. 93-96 (1998)

[Publications] Hisashi Matsuda: "薬用食物のサポニン成分の免疫機能に及ぼす作用-Soyasaponin類のアジュバント活性-" 和漢医薬学雑誌. vol.15. 278-279 (1998)

[Publications] Masayuki Yoshikawa: "生物活性サポニン及び配糖体(13報)西洋トリノキ種子サポニン(3):高速液体クロマトグラフィーを用いたEscin Ia,Ib,IIa,およびIIbの定量分析." 薬学雑誌. vol.119. 81-87 (1999)

[Publications] Hisashi Matsuda: "Structure-Related Inhibitory Activity of Oleanolic Acid Glycosides." Bioorg.Med.Chem.vol.7(in press). (1999)

[Publications] Hisashi Matsuda: "Effects of Escins Ia,Ib,IIa,and IIb from horse chestnuts on gastric emptying in mice." Eur.J.Pharmacol.(in press). (1999)

[Publications] Yuhao Li: "Effects of Oleanolic Acid Glycosides on Gastrouitestinal Transit and Ileus in Mice." Bioorg.Med.Chem.vol.7(in press). (1999)

[Publications] Hisashi Matsuda: "Inhibition of Gastric Emptying by Triterpene Saponin,Momordin Ic,in Mice : Reles Blood Glucose,Capsaicin-Sensitive Sensory Nerves,and Central Nervous System." J.Pharmacol.Exp.Ther.(in press). (1999)

[Publications] Hisashi Matsuda: "Roles of Capsaicin-Sensitive Sensory Nerves,Endogenous Nitric Oxide,Sulfhysryls,and Prostaglandins in Gastroprotection by Momordin Ic,an Oleanolic Acid Olgoglycoside,on Ethanol-Induced Gastric Mucosal Lesions in Rats." Life Sci.(in press). (1999)

[Publications] Masayuki Yoshikawa: "Towards Natural Medicine Research in the 21st Century" Elsevier, 585 (1998)

[Publications] Masayuki Yoshikawa: "Advances in Plant Glycosides,Chemistry and Biology" Elsevier, 556 (1999)

松田久司京都薬科大学, 薬学部, 助教授 (40288593)