Elsevier

Phytochemistry

Volume 54, Issue 8, August 2000, Pages 853-859
Phytochemistry

Triterpenoid saponins from Fagonia cretica

https://doi.org/10.1016/S0031-9422(00)00168-0Get rights and content

Abstract

Four new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia cretica. They were characterized as 3-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] hederagenin 28-O-β-D-glucopyranosyl ester, 3-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] oleanolic acid 28-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] ester, 3-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] 27-hydroxy oleanolic acid 28-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] ester and 3β-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] ester. The structures of the saponins were assigned by spectral analyses (FABMS, 1H, 13C NMR, 1H–1H COSY, TOCSY, HMQC and HMBC spectra) and NOE experiments. To the best of our knowledge the genin 3β hydroxy olean-12-en-27-al-28-oic acid is new.

Introduction

The genus Fagonia is represented by 18 species in the flora of Egypt (Tackholm, 1974). In an earlier study, flavonoids were identified from some Fagonia species (Saleh et al., 1990). The saponin-containing fraction from Fagonia cretica showed significant anti-inflammatory activity and considerable analgesic and antipyretic effects (El-Shabrawy et al., 1997).

Section snippets

Results and discussion

Fagonia cretica was previously studied by us for its saponin content and three bisdesmosides of hederagenin and oleanolic acid were isolated and identified (Melek et al., 1994). Further examination of this plant led to the isolation of four additional new saponins 14. Their structures were determined using mass spectrometry, 1D and 2D NMR spectroscopy as well as NOE experiments. The NMR data are presented in Table 1, Table 2.

On acid hydrolysis, saponin 1 afforded an aglycone that was

Experimental

Optical rotations were measured with JASCO DIP 1000 digital polarimeter. MS were measured on a JEOL JMX-SX 102 mass spectrometer. NMR spectra were obtained with JEOL GSX-500 FT NMR spectrometer and chemical shifts were given in ppm with TMS as international standard. HPLC was carried out on a JASCO system 800 instrument.

For plant material extraction, refer to our earlier paper (Melek et al., 1994). The fraction eluted with CHCl3:MeOH:H2O (67:30:3) yielded saponin mixture. The mixture was

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