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Highly Polar Triterpenoid Saponins from the Roots of Saponaria officinalis L.
Author(s) -
MoniuszkoSzajwaj Barbara,
Masullo Milena,
Kowalczyk Mariusz,
Pecio Łukasz,
SzumacherStrabel Małgorzata,
Cieślak Adam,
Piacente Sonia,
Oleszek Wiesław,
Stochmal Anna
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500224
Subject(s) - chemistry , saponin , stereochemistry , triterpenoid saponin , triterpenoid , glycoside , medicine , alternative medicine , pathology
Five new triterpenoid saponins, including 3‐ O ‐ β ‐ d ‐galactopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)]‐ β ‐ d ‐glucuronopyranosyl quillaic acid 28‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→3)‐ β ‐ d ‐xylopyranosyl‐(1→4)‐ α ‐ l ‐rhamnopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)‐(4‐ O ‐acetyl)‐ β ‐ d ‐quinovopyranosyl‐(1→4)]‐ β ‐ d ‐fucopyranoside ( 1 ), 3‐ O ‐ β ‐ d ‐galactopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)]‐ β ‐ d ‐glucuronopyranosyl quillaic acid 28‐ O ‐(6‐ O ‐acetyl)‐ β ‐ d ‐glucopyranosyl‐(1→3)‐[ β ‐ d ‐xylopyranosyl‐(1→4)]‐ α ‐ l ‐rhamnopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)‐(4‐ O ‐acetyl)‐ β ‐ d ‐quinovopyranosyl‐(1→4)]‐ β ‐ d ‐fucopyranoside ( 2 ), 3‐ O ‐ β ‐ d ‐galactopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)]‐ β ‐ d ‐glucuronopyranosyl quillaic acid 28‐ O ‐ β ‐ d ‐xylopyranosyl‐(1→4)‐ α ‐ l ‐rhamnopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)‐(4‐ O ‐acetyl)‐ β ‐ d ‐quinovopyranosyl‐(1→4)]‐ β ‐ d ‐fucopyranoside ( 3 ), 3‐ O ‐ β ‐ d ‐galactopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)]‐ β ‐ d ‐glucuronopyranosyl quillaic acid 28‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→3)‐ β ‐ d ‐xylopyranosyl‐(1→4)‐ α ‐ l ‐rhamnopyranosyl‐(1→2)‐[(4‐ O ‐acetyl)‐ β ‐ d ‐quinovopyranosyl‐(1→4)]‐ β ‐ d ‐fucopyranoside ( 4 ), 3‐ O ‐ β ‐ d ‐galactopyranosyl‐(1→2)‐[ β ‐ d ‐xylopyranosyl‐(1→3)]‐ β ‐ d ‐glucuronopyranosyl quillaic acid 28‐ O ‐(6‐ O ‐acetyl)‐ β ‐ d ‐glucopyranosyl‐(1→3)‐[ β ‐ d ‐xylopyranosyl‐(1→4)]‐ α ‐ l ‐rhamnopyranosyl‐(1→2)‐[(4‐ O ‐acetyl)‐ β ‐ d ‐quinovopyranosyl‐(1→4)]‐ β ‐ d ‐fucopyranoside ( 5 ) together with two known congeners, saponariosides A ( 6 ) and B ( 7 ) were isolated from the roots of Saponaria officinalis L. Their structures were elucidated by extensive spectroscopic methods, including 1D‐ ( 1 H, 13 C) and 2D‐ NMR ( DQF ‐ COSY , TOCSY , HSQC , and HMBC ) experiments, HR ‐ ESI ‐ MS , and acid hydrolysis.
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