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 |
| Publication status | Published - 1997 May |
| Externally published | Yes |
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Keywords
- β-D- quinovoside
- β-D-xyloside
- C-NMR
- Acacia concinna
- Menthiafolic acid
- Monoterpene glycoside
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
- Drug Discovery
- Pharmacology
Cite this
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.
In: Chemical and Pharmaceutical Bulletin, Vol. 45, No. 5, 05.1997, p. 807-812.Research output: Contribution to journal › Article
}
TY - JOUR
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 - β-D- quinovoside
KW - β-D-xyloside
KW - C-NMR
KW - Acacia concinna
KW - Menthiafolic acid
KW - Monoterpene glycoside
UR - http://www.scopus.com/inward/record.url?scp=0031006226&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031006226&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0031006226
VL - 45
SP - 807
EP - 812
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 5
ER -