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

doi:10.1248/cpb.45.807

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

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

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.

Original language	English
Pages (from-to)	807-812
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	45
Issue number	5
DOIs	https://doi.org/10.1248/cpb.45.807
Publication status	Published - 1997 May
Externally published	Yes

Keywords

Acacia concinna
C-NMR
Menthiafolic acid
Monoterpene glycoside
β-D- quinovoside
β-D-xyloside

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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title = "Acacia concinna Saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction",

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.",

keywords = "Acacia concinna, C-NMR, Menthiafolic acid, Monoterpene glycoside, β-D- quinovoside, β-D-xyloside",

author = "Fumiyuki Kiuchi and Abdul Gafur and Tohoru Obata and Akiko Tachibana and Yoshisuke Tsuda",

year = "1997",

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T1 - Acacia concinna Saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction

AU - Kiuchi, Fumiyuki

AU - Gafur, Abdul

AU - Obata, Tohoru

AU - Tachibana, Akiko

AU - Tsuda, Yoshisuke

PY - 1997/5

Y1 - 1997/5

N2 - 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.

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.

KW - Acacia concinna

KW - C-NMR

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KW - Monoterpene glycoside

KW - β-D- quinovoside

KW - β-D-xyloside

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