New Acylated Saponins from Polygala myrtifolia

✍ Scribed by Mohamed Haddad; Tomofumi Miyamoto; Clément Delaude; Marie-Aleth Lacaille-Dubois

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 127 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390247

✦ Synopsis

Abstract

The ten new acylated presenegenin (=(2__β__,3__β__,4__α__)‐2,3,27‐trihydroxyolean‐12‐ene‐23,28‐dioic acid) glycosides 1–10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans‐ and __cis‐__4‐methoxycinnamoyl derivatives, i.e., myrtifoliosides A~1~/A~2~ (1/2), B~1~/B~2~ (3/4), C~1~/C~2~ (5/6), D~1~/D~2~ (7/8), and E~1~/E~2~ (9/10). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐{O‐β‐D‐galactopyranosyl‐(1→3)‐O‐β‐D‐xylopyranosyl‐(1→4)‐O‐[D‐apio‐β‐D‐furanosyl‐(1→3)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐O‐[α‐L‐arabinopyranosyl‐(1→3)]‐4‐O‐(__trans‐4‐methoxycinnamoyl)‐β‐D‐fucopyranosyl} ester (1) and its cis‐isomer 2, 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐{O‐β‐D‐galactopyranosyl‐(1→3)‐O‐β‐D‐xylopyranosyl‐(1→4)‐O‐[D‐apio‐β‐D‐furanosyl‐(1→3)]‐α‐L‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D‐fucopyranosyl} ester (3) and its cis‐isomer 4, 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐{O‐β‐D‐galactopyranosyl‐(1→3)‐O‐β‐D‐xylopyranosyl‐(1→4)‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D‐fucopyranosyl} ester (5) and its cis‐isomer 6, 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐{O‐D‐apio‐β‐D‐furanosyl‐(1→3)‐O‐[β‐D‐xylopyranosyl‐(1→4)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐__methoxycinnamoyl)‐β‐D‐fucopyranosyl} ester (7) and its cis‐isomer 8, and 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐{O‐α‐L‐arabinopyranosyl‐(1→3)‐O‐[β‐D‐xylopyranosyl‐(1→4)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐4‐O‐(trans‐4‐ methoxycinnamoyl)‐β‐D‐fucopyranosyl} ester (9) and its cis‐isomer 10.