Abstract
Two new spirostanol sapogenins (5β-spirost-25(27)-en-1β,2β,3β,5β-tetrol 3 and its 25,27-dihydro derivative, (25S)-spirostan-1β,2β,3β,5β-tetrol 4) and four new saponins were isolated from the roots and rhizomes of Convallaria majalis L. together with known sapogenins (isolated from Liliaceae): 5β-spirost-25(27)-en-1β,3β-diol 1, (25S)-spirostan-1β,3β-diol 2, 5β-spirost-25(27)-en-1β,3β,4β,5β-tetrol 5, (25S)-spirostan-1β,3β,4β,5β-tetrol 6, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 7 and (25S)-spirostan-1β,2β,3β,4β,5β-pentol 8. New steroidal saponins were found to be pentahydroxy 5-O-glycosides; 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-β-galactopyranoside 9, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-β-arabinonoside 11, 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-O-galactoside 10 and 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-O-arabinoside 12 were isolated for the first time. The structures of those compounds were determined by NMR spectroscopy, including 2D COSY, HMBC, HSQC, NOESY, ROESY experiments, theoretical calculations of shielding constants by GIAO DFT, and mass spectrometry (FAB/LSI HR MS). An attempt was made to test biological activity, particularly as potential chemotherapeutic agents, using in silico methods. A set of 12 compounds was docked to the PDB structures of HER2 receptor and tubulin. The results indicated that diols have a higher affinity to the analyzed targets than tetrols and pentols. Two compounds (25S)-spirosten-1β,3β-diol 1 and 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-galactoside 9 were selected for further evaluation of biological activity.
Highlights
Convallaria majalis from the family Liliaceae is widely distributed in Europe whereas Convallaria keisukei grows in East Asia
As a continuation of our studies on the structure and biological properties of the constituents of C. majalis we presently report the isolation of eight sapogenins (1–8) and four saponins (9–12) (Figure 1) and their characterization by NMR spectroscopy supported by theoretical calculations (GIAO DFT)
Steroidal saponins with sugar moiety attached to the angular position of C5 were first found in C. keisukei by Kimura et al in 1968
Summary
Convallaria majalis from the family Liliaceae (lily of the valley) is widely distributed in Europe whereas Convallaria keisukei grows in East Asia. C. majalis is a known source of cardiac glycosides. Non-cardiac substances, such as steroidal saponins, are of pharmaceutical interest [1]. Insecticidal, antiparasitic, antifungal, antibacterial, antiviral, anti-inflammatory, antihyperlipidemic, antidiabetic and antitumor properties, among others [2]. Steroidal glycosides have a wide variety of commercial uses such as surfactants, foaming agents and precursors for the industrial production of pharmaceutical drugs [3]. Convallasaponins were isolated from the flowers of C. keisukei [4,5,6,7,8,9] and from the roots of
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