Acacia concinna Saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction

Fumiyuki Kiuchi, Abdul Gafur, Tohoru Obata, Akiko Tachibana, Yoshisuke Tsuda

研究成果: Article

33 引用 (Scopus)

抄録

From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid- 6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.

元の言語English
ページ(範囲)807-812
ページ数6
ジャーナルChemical and Pharmaceutical Bulletin
45
発行部数5
出版物ステータスPublished - 1997 5
外部発表Yes

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Acacia
Monoterpenes
Saponins
Glycosides
Acids
Diazomethane
Methylation
Esters

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

これを引用

Acacia concinna Saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction. / Kiuchi, Fumiyuki; Gafur, Abdul; Obata, Tohoru; Tachibana, Akiko; Tsuda, Yoshisuke.

:: Chemical and Pharmaceutical Bulletin, 巻 45, 番号 5, 05.1997, p. 807-812.

研究成果: Article

Kiuchi, Fumiyuki ; Gafur, Abdul ; Obata, Tohoru ; Tachibana, Akiko ; Tsuda, Yoshisuke. / Acacia concinna Saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction. :: Chemical and Pharmaceutical Bulletin. 1997 ; 巻 45, 番号 5. pp. 807-812.
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abstract = "From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid- 6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.",
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AU - Tsuda, Yoshisuke

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AB - From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid- 6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.

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