Lanostane-Type Saponins from Vitaliana primuliflora.

Włodarczyk Włodarczyk,Szumny Szumny,Gleńsk Gleńsk

doi:10.3390/molecules24081606

Abstract

The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor-triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-d-glucopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.

Highlights

Some plants are rich in secondary metabolites of a specific class, e.g., saponins
Steroidal saponins are abundant in monocotyledons, while triterpenoid saponins are abundant in eudicotyledons, with several exceptions
The 27-nor-lanostane glycosides 12 and 13 were dominant among saponins detected by ESI-MS in the negative mode in all Vitaliana plants

Summary

Introduction

Some plants are rich in secondary metabolites of a specific class, e.g., saponins. They can reach up to 10% of dry mass and, are attractive for industrial usage. Steroidal saponins are abundant in monocotyledons, while triterpenoid saponins are abundant in eudicotyledons, with several exceptions. Among a few cases of medicinally valuable steroidal glycosides present in angiosperms, cardiac glycosides and their open-lactone analogs should be mentioned [1]. Other economically important compounds are appetite suppressants from the South. African Hoodia sp., Euphorbiaceae [2] or male hormone imitators from Tribulus sp., Zygophyllaceae [3]. Typical triterpenoids (C30 ) are rare in monocotyledons [4]

Methods

Results

Conclusion