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Characterization of Alcohol-Absorption Inhibitors from Chinese Traditional Medicines with Anti-Alcoholic Activity

Research Project

Project/Area Number 07557292
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

YOSHIKAWA Masayuki  Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (90116129)

Co-Investigator(Kenkyū-buntansha) SHIMADA Hiromi  Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Research As, 薬学部, 助手 (90268102)
MURAKAMI Toshiyuki  Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Research As, 薬学部, 助手 (40278445)
MATSUDA Hisashi  Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Associate P, 薬学部, 助教授 (40288593)
村上 啓寿  京都薬科大学, 薬学部, 助教授 (00210013)
Project Period (FY) 1995 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1997: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordsalcohol-absorption inhibitor / anti-alcoholic principle / Chinese traditional medicine / elatoside / escin / camelliasaponin / senegasaponin / scoparianoside / 西洋トチノキ / 地膚子 / 抗潰瘍活性 / scoparianoside / kochianoside / アルコール吸収抑制物質 / 枳 子 / アルコール性筋弛緩抑制成分 / 肝障害抑制成分 / ヒスタミン遊離抑制成分 / hovenitin / ジヒドロフラボノール / ムクロジ / ツバキ / サポニン / 構造活性相関
Research Abstract

Alcoholism, which is a major health problem in the world, causes as much trouble physiologically as it dose socially. Excessive consumption of ethanol is known to affect profoundly nearly every organ in the body. In order to relieve ethanol toxicity in acute alcohol in ingestion, a couple of methods using an accelerator of ethanol metabolism and the sequestering of acetaldehyde have hitherto been reported. In addition, dehydrogenase inhibitors such as cyanamide and disulfiram have been used clinically for chronic alcoholics. It is known that dehydrogenase inhibitors force alcoholics to quit drinking based on the fear of unpleasant reaction elicited after ethanol intake, but these drugs are also reported to show many strong side effects.
On the other hand, many Chinese traditional medicines have been known to have preventive and therapeutic effects for ethanol intoxication, but their active components have not been identified so far. In the course of our screening to find anti-alcoholic … More active principles contained in traditional medicines, several natural medicines were found to contain inhibitors of ethanol absorption. By monitoring the inhibitory effect on ethanol absorption in the rat, we have characterized new active triterpene oligoglycosides from Aralia elata (elatosides), Aesculus hippocastanum, A.turbinata (escins), Camellia japonica (camelliasaponins), Polygala senega var.latifolia (E,Z-senegasaponins, Z-senegins), Sapindus mukurossi (sapindosides), Kochia scoparia (kochianosides, scoparianosides), and Beta vulgaris (betavulgarosides). Furthermore, by examination of the structure requirement for the activity, it has been found that the active saponins can be classified into the following three types of structure : 1) Oleanen-28-oic acid 3-O-monodesmosides such as elatosides, sapindosides, kochianosides, scoparianosides, and betavulgarosides, 2) Acylated polyhydroxyoleanene 3-O-monodesmosides such as escine and camelliasaponins, and 3) Oleanene acylated bisdesmosides such as senegasaponins and senegins. Less

Report

(4 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (39 results)

All Other

All Publications (39 results)

  • [Publications] Masayuki Yoshikawa: "New Hepatoprotective Saponins Buoleurosides III,VI,IX,and XIII, from Chinese Bupleuri Radix:Structure-Requirements for the Cytoprotective Activity in Primary Cultured Rat Hepatosytes." Bioorganic & Medicinal Chemistry Letters. 7. 2193-2198 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Scorzonerosides A,B,and C, Novel Triterpene Oligoglycosides with Hepatoprotective Effect from Chinese Bupleuri Radix、 the Roots of Bupleurum scorzonerifolium WILLD." Tetrahedron Letters. 38. 7395-7398 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs. VII. On the Saponin Constituents with Glucose and Alcohol Absorption-Inhibitory Activity from a Food Garnish “Tonburi"the Fruit of Japanese Kochia scoparia(L.) SCHARAD:Structures of Scoparianosides A.B. and C." Chemical & Pharmaceutical Bulletin. 45. 1300-1305 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glycosides.VI.Elatosides A and B,Potent Inhibitors of Ethanol Absorption,from the Bark of Aralia slata SEEM.(Araliaceae):The Structure-Requirement in Oleanolic Acid Glucuronide-Saponins for the Inhibitory Activity" Chemical & Pharmaceutical Bulletin. 44. 1915-1922 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glycosides.V.Acylated Polyhydroxolean-12-ene Triterpene Oligoglycosides,Camelliasaponins A1,A2,B1,B2,C1, and C2, from the Seeds of Camellia japonica L.:Structures and Inhibitory Activity on Alcohol Absorption." Chemical & pharmaceutical Bulletin. 44. 1899-1907 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glycosides.III.Horse Chestnut.(I):The Structures,Inhibitory Effects on Ethanol Absorption. and Hypoglycemic Activity of Escins Ia,Ib,IIa,IIb,and IIIa from the Seeds of Aesculus hippocastanum L." Chemical & Pharmaceutical Bulletin. 44. 1454-1464 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Saponins used in Traditional and Modern Medicine" G.R.Waller,K.Yamasaki,Plenum Press., 606 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Emiko Harada, Toshiyuki Murakami, Hisashi Matsuda, Johji Yamahara, and Nobutoshi Murakami: "Camelliasaponins B_1, B_2, C_1 and C_2, New Type Inhibitors of Ethanol Absorption in Rats from the Seeds of Camellia japonica L." Chem.Pharm.Bull. 42(3). 742-744 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Emiko Harada, Toshiyuki Murakami, Hisashi Matsuda, Noriko Wariishi, Johji Yamahara, Nobutoshi Murakami and Isao Kitagawa: "Escins-Ia, Ib, IIa, IIb, and IIIa, Bioactive Triterpene Oligoglycosides from the Seeds of Aesculus hippocastanum L./Their Inhibitory Effects on Ethanol Absorption and Hypoglycemic Activity on Glucose Tolerance Test." Chem.Pharm.Bull. 42(6). 1357-1359 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Takahiro Ueno, Masashi Kadoya, Hisashi Matsuda, Johji Yamahara, and Nobutoshi Murakami: "E-Senegasaponins a and b, Z-senegasaponins a and b, Z-senegins II and III,New Type Inhibitors of Ethanol Absorption in Rats from Senegae Radix, the Roots of Polygala Senega L.var.latiofolia TOOREY et GRAY." Chem.Pharm.Bull. 43(2). 350-352 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Takahiro Ueno, Masashi Kadoya, Hisashi Matsuda, Johji Yamahara, and Nobutoshi Murakami: "Bioactive Saponins and Glycosides.I.Senegae Radix (I) : E-Senegasaponins a and b and Z-Senegasaponins a and b, their Inhibitory Effect on Alcohol Absorption and Hypoglycemic Activity." Chem.Pharm.Bull. 43(12). 2115-2122 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Hisashi Matsuda, Takahiro Ueno, Masashi Kadoya, Johji Yamahara, and Nobutoshi Murakami: "Bioactive Saponins and Glycosides. II.Senegae Radix (2) : Chemical Structures, Hypoglycemic Activity, and Ethanol Absorption-inhibitory Effect of E-Senegasaponin c, Z-Senegasaponin c, and Z-Senegins II,III,and IV." Chem.Pharm.Bull. 44(7). 1305-1313 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Hisashi Matsuda, Johji Yamahara, Nobutoshi Murakami, and Isao Kitagawa: "Bioactive Saponins and Glycosides. III.Horse Chestnut (1) : The Structures, Inhibitory Effects on Ethanol Absorption, and Hypoglycemic Activity of Escins Ia, Ib, IIa, IIb, and IIIa from the Seeds of Aesculus hippocastanum L." Chem.Pharm.Bull. 44(8). 1454-1464 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Tomohiko Ueda, Hisashi Matsuda, Johji Yamahara, and Nobutoshi Murakami: "Bioactive Saponins and Glycosides. IV.Four Methyl-Migrated 16,17-seco-Dammarane Triterpene Glycosides from Chinese Natural Medicine, Hoveniae Semen Seu Fructus, the Seeds and Fruit of Hovenia dulcis THUNB. : Absolute Stereostructures and Inhibitory Activity on Histamine Release of Hovenidulciosides A_1, A_2, B_1, and B_2." Chem.Pharm.Bull. 44(9). 1736-1743 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Satoshi Yoshizumi, Nobutoshi Murakami, Johji Yamahara, and Hisashi Matsuda: "Bioactive Saponins and Glycosides. V.Acylated Polyhydroxyolean-12-ene Triterpene Oligoglycosides, Camelliasaponins A_1, A_2, B_1, B_2, C_1, and C_2, from the Seeds of Camellia japonica L. : Structures and Inhibitory Activity on Alcohol Absorption" Chem.Pharm.Bull. 44(10). 1899-1907 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Emiko Harada, Nobutoshi Murakami, Johji Yamahara, and Hisashi Matsuda: "Bioactive Saponins and Glycosides. VI.Elatosides A and B,Potent Inhibitors of Ethanol Absorption, from the Bark of Aralia elata SEEM.(Araliaceae) : The Structure-Requirement in Oleanolic Acid Glucuronide-Saponins for the Inhibitory Activity." Chem.Pharm.Bull. 44(10). 1915-1922 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Tomohiko Ueda, Satoshi Yoshizumi, Kiyofumi Ninomiya, Nobutoshi Murakami, Hisashi Matsuda, Masayuki Saito, Wataru Fujii, Takaharu Tanaka, Johji Yamahara: "Bioactive Constituents of Chinese Natural Medicines. III.Absolute Stereostructures of New Dihydroflavonols, Hovenitins I,II,and III,Isolated from Hoveniae Semen Seu Fructus, the Seed and Fruit of Hovenia dulcis THUNB.(Rhamnaceae) : Inhibitory Effect on Alcohol-induced Muscular Relaxation and Hepatoprotective Activity" Yakugaku Zasshi. 117(2). 108-118 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Yue Dai, Hiromi Shimada, Toshio Morikawa, Narumi Matsumura, Satoshi Yoshizumi, Hisashi Matsuda, Hideaki Matsuda, and Michinori Kubo: "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. 45(6). 1052-1055 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Hiromi Shimada, Toshio Morikawa, Satoshi Yoshizumi, Narumi Matsumura, Toshiyuki Murakami Hisashi Matsuda, Kazuyuki Hori, and Johji Yamahara: "Medicinal Foodstuffs. VII.On the Saponin Constituents with Glucose and Alcohol Absorption-Inhibitory Activity from a Food Garnish "Tonburi", the Fruit of Japanese Kochia scoparia (L.) SCHARD. : Structures of Scoparianosides A,B,and C." Chem.Pharm.Bull. 45(8). 1300-1305 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hisashi Matsuda, Yuhao Li, Toshiyuki Murakami, Kiyofumi Ninomiya, Johji Yamahara, and Masayuki Yoshikawa: "Effects of Escins Ia, Ib, IIa, and IIb from Horse Chestnut, the Seeds of Aesculus hippocastanum L., on Acute Inflammation in Animals." Biol.Pharm.Bull. 20(10). 1092-1095 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa, Toshiyuki Murakami, Kazuhiro Hirano, Masahiro Inadzuki, Kiyofumi Ninomiya, and Hisashi Matsuda: "Scorzonerosides A,B,and C,Novel Triterpene Oligoglycosides with Hepatoprotective Effect from Chinese Bupleuri Radix, the Roots of Bupleurum scorzonerifolium WILLD." Tetrahedron Lett. 38(42). 7395-7398 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hisashi Matsuda, Yuhao Li, Toshiyuki Murakami, Kiyofumi Ninomiya, Nobuharu Araki, Masayuki Yoshikawa, and Johji Yamahara: "Antiinflammatory Effects of Escins Ia, Ib, IIa, and IIb from Horse Chestnut, the Seeds of Aesculus hippocastanum L." Bioorg.Med.Chem.Lett. 7(13). 1611-1616 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hisashi Matsuda, Toshiyuki Murakami, Kiyofumi Ninomiya, Masahiro Inadzuki, and Masayuki Yoshikawa: "New Hepatoprotective Saponins, Bupleurosides III,VI,IX,and XIII,from Chinese Bupleuri Radix : Structure-Requirements for the Cytoprotective Activity in Primary Cultured Rat Hepatocytes." Bioorg.Med.Chem.Lett. 7(17). 2193-2198 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Masayuki Yoshikawa: "Studies on Kochiae Fructus.II.On the Spaponin Constituents from the Fruit of Chinese Kochia scoparia (Chenopodiaceae):Chemical Structures of Kochianosides I,II,III,and IV." Chemical & Pharmaceutical Bulletin. 45・6. 1052-1055 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Medicinal Foodstuffs. VII. On the Saponin Constituents with Glucose and Alcohol Absorption-Inhibitory Activity from a Food Garnish "Tonburi",the Fruit of Japanese Kochia scoparia (L.)SCHARD.:Structures of Scoparianosides A,B,and C." Chemical &Pharmaceutical Bulletin. 45・8. 1330-1305 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Effect of Escines Ia,Ib,IIa,and IIb from Horse Chestnut,the Seeds of Aesculus hippocastanum L.,on Acute Inflammation in Animals." Biological & Pharmaceutical Bulletin. 20・10. 1092-1095 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Scorzonerosides A,B,and C,Novel Triterpene Oligoglycosides with Hepatoprotective Effext from Chinese Bupleuri Radix,the Roots of Bupleurum scorzonerifolium WILLD." Tetrahedron Letters. 38・42. 7395-7398 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Antiinflammatory Effexts of Escins Ia,Ib,IIa,and IIb from Horse Chestnut,the Seeds of Aesculus hippocastanum L." Bioorganic & Medicinal Chemistry Letters. 7・13. 1611-1616 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "New Hepatoprotective Saponins,Bupleurosides III,VI,IX,and XIII,from Chinese Bupleuri Radix:Structure-Requirements for the Cytoprotective Activity in Primary Cultured Rat Hepatocytes." Bioorganic & Medicinal Chemistry Letters. 7・17. 2193-2198 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 吉川雅之: "漢薬の生物活性成分(第3報)枳 子(Hoveniae Semen Seu Fructus)のアルコール性筋弛緩抑制及び肝保護作用成分:新規Dihydroflavonolo,Hovenitin I,II,IIIの絶対構造" 薬学雑誌. 117・2. 108-118 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki,Yoshikawa: "Bioactive Saponins and Glycosides. VI.Elatosides A and B,Potent Inhibitors of Ethanol Absorption,from the Band of Aralia elata SEEM.Glucuronide-Saponins for the Inhibitory Activity" Chemical & Pharmaceutical Bulletin. 44・10. 1915-1922 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki,Yoshikawa: "Bioactive Saponins and Glycosides.V.Acylated Polyhydroxyolean-12-ene Triterpene Oligoglycosides,Camelliasaponins A_1,A_2,B_1,B_2,C_1 and C_2,from the Seeds of Camellia japonica L. : Structures and Inhibitory Activity on Alcohol Absorption" Chemical & Pharmaceutical Bulletin. 44・10. 1899-1907 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki,Yoshikawa: "Bioactive Saponins and Glycosides.IV.Four Methyl-Migrated 16,17-seco-Dammarane Triterpene Glycosides from Chinese Natural Medicine,Hoveniae Semen Seu Fructus,the Seeds and Fruit of Hovenia dulcis THUNB. : Absolute Stereostructures and Inhibitory Activity on Histamine Release of Hovenidulciosides A_1,A_2,B_1,and B_2" Chemical & Pharmaceutical Bulletin. 44・9. 1736-1743 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki,Yoshikawa: "Bioactive Saponins and Glycosides.III.Horse Chestnut.(1) : The Structures,Inhibitory Effects on Ethanol Absorption,and Hypoglycemic Activity of Escins Ia,Ib,IIa,IIb,and IIIa from the Seeds of Aesculus hippocastanum L." Chemical & Pharmaceutical Bulletin. 44・8. 1454-1464 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki,Yoshikawa: "Bioactive Saponins and Glycosides.II.Senege Radix.: Chemical Structures,Hypoglycemic Activity,and Ethanol Absorption-Inhibitory Effect of E-Senegasaponin C,Z-Senegasapoin c,and Z-Senegins II,III,and IV" Chemical & Pharmaceutical Bulletin. 44・7. 1345-1313 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Bioactive Saponins and Glycosides. I. Senegac Radix(I): E-Senegasaponins a and b and Z-Senegasaponins a and b, Their Inhibitory Effect on Alcohol Absorption and Hypoglycemic Activity" Chemical & Pharmaceutical Bulletin. 43. 2115-2122 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "E-Senegasaponins a and b, Z-Senegasaponins a and b, Z-Senegins II and III, New Type Inhibitors of Ethanol Absorption in Rats from Senegae Radix, the Roots of Polygala Senega L. var latiofolia TORREY et GRAY" Chemical & Pharmaceutical Bulletin. 43. 350-352 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Escins-Ia, Ib, IIa, IIb, and IIIa, Bioactive Triterpene Oligoglycosides from the Seeds of Aesculus hippocastanum L. : Their Inhibitory Effects on Ethanol Absorption and Hypoglycemic Activity on Glucose Tolerance Test" Chemical & Pharmaceutical Bulletin. 42. 1357-1359 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masayuki Yoshikawa: "Camelliasaponins B_1, B_2, C_1, and C_2, New Type Inhibitors of Ehanol Absorption in Rats from the Seeds of Camellia japonica L." Chemical & Pharmaceutical Bulletin. 42. 742-744 (1994)

    • Related Report
      1995 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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