Triterpene saponins from barrel medic (Medicago truncatula) aerial parts.
Triterpene saponins from Medicago truncatula aerial parts have been separated and their structures determined by the extensive use of 1D- and 2D-NMR experiments including 1H-1H (DQF-COSY, 1D-TOCSY) and 1H-13C (HSQC, HMBC) spectroscopy along with ESIMS. Fifteen individual compounds were isolated that included seven medicagenic acid and eight zanhic acid glycosides. Additionally, two soyasapogenol B and soyasapogenol E glycosides were identified by MS/MS and TLC. Four medicagenic acid glycosides (5, 11, 12, 14) and eight zanhic acid glycosides (1-4, 6-9) are reported here for the first time. The common feature of M. truncatula aerial part saponins is the (1-->3) linkage between the two glucose units at C-3 of medicagenic and zanhic acids, which is different from that found in alfalfa (Medicago sativa), where this linkage was always (1-->2). This may suggest differences in glucosyltransferases between these two Medicago species.
Kapusta
Ireneusz
I
Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland.
Stochmal
Anna
A
Perrone
Angela
A
Piacente
Sonia
S
Pizza
Cosimo
C
Oleszek
Wieslaw
W
D006027:Glycosides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D029902:Medicago / Q000737:chemistry*; D012503:Saponins / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D014315:Triterpenes / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*
D006027:Glycosides; D012503:Saponins; D014315:Triterpenes