New Triterpenoidal Saponins Acylated with Monoterpenic Acid from Albizia adianthifolia

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

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: German
• Weight: 133 KB
• Volume: 87
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200490112

✦ Synopsis

Abstract

Four new triterpenoidal saponins acylated with monoterpenic acid, i.e., adianthifoliosides C, D, E, and F (1–4), besides the two known julibroside III and the monodesmonoterpenyl elliptoside A, were isolated from the roots of Albizia adianthifolia. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR studies and mass spectrometry as 3‐O‐{O‐α‐L‐arabinopyranosyl‐(1→2)‐O‐β‐d‐fucopyranosyl‐(1→6)‐O‐[β‐d‐glucopyranosyl‐(1→2)]‐β‐d‐glucopyranosyl}‐21‐O‐{(2__E__,6__S__)‐6‐{{4‐O‐[(2__E__,6__S__)‐2,6‐dimethyl‐6‐(β‐D‐quinovopyranosyloxy)octa‐2,7‐dienoyl]‐β‐d‐quinovopyranosyl}oxy}‐2‐(hydroxymethyl)‐6‐methylocta‐2,7‐dienoyl}acacic acid 28‐{O‐α‐L‐arabinofuranosyl‐(1→4)‐O‐[β‐d‐glucopyranosyl‐(1→3)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐β‐d‐glucopyranosyl} ester (1), 21‐O‐{(2__E__,6__S__)‐6‐{{4‐O‐[(2__E__,6__S__)‐2,6‐dimethyl‐6‐(β‐d‐quinovopyranosyloxy)octa‐2,7‐dienoyl]‐β‐d‐quinovopyranosyl}oxy}‐2‐(hydroxymethyl)‐6‐methylocta‐2,7‐dienoyl}‐3‐O‐{O‐β‐D‐xylopyranosyl‐(1→2)‐O‐β‐d‐fucopyranosyl‐(1→6)‐2‐(acetylamino)‐2‐deoxy‐β‐d‐glucopyranosyl}acacic acid 28‐{O‐α‐L‐arabinofuranosyl‐(1→4)‐O‐[β‐d‐glucopyranosyl‐(1→3)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐β‐d‐glucopyranosyl} ester (2), 21‐O‐{(2__E__,6__S__)‐6‐{{3‐O‐[(2__E__,6__S__)‐2,6‐dimethyl‐6‐(β‐d‐quinovopyranosyloxy)octa‐2,7‐dienoyl]‐β‐d‐quinovopyranosyl}oxy}‐2,6‐dimethylocta‐2,7‐dienoyl}‐3‐O‐{O‐β‐D‐xylopyranosyl‐(1→2)‐O‐β‐d‐fucopyranosyl‐(1→6)‐2‐(acetylamino)‐2‐deoxy‐β‐d‐glucopyranosyl}acacic acid 28‐{O‐α‐L‐arabinofuranosyl‐(1→4)‐O‐[β‐d‐glucopyranosyl‐(1→3)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐β‐d‐glucopyranosyl} ester (3), and 3‐O‐{O‐α‐L‐arabinopyranosyl‐(1→2)‐O‐β‐d‐fucopyranosyl‐(1→6)‐O‐[β‐d‐glucopyranosyl‐(1→2)]‐β‐d‐glucopyranosyl}‐21‐O‐{(2__E__,6__S__)‐2,6‐dimethyl‐6‐(β‐d‐quinovopyranosyloxy)octa‐2,7‐dienoyl}acacic acid 28‐{O‐α‐L‐arabinofuranosyl‐(1→4)‐O‐[β‐d‐glucopyranosyl‐(1→3)]‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐β‐d‐glucopyranosyl} ester (4).