Elsevier

Phytochemistry

Volume 130, October 2016, Pages 262-272
Phytochemistry

Zebiriosides A-L, oleanane saponins from the roots of Dendrobangia boliviana

https://doi.org/10.1016/j.phytochem.2016.06.006Get rights and content

Highlights

  • Phytochemical study of Dendrobangia boliviana has been performed.

  • Fourteen oleanane saponins were determined by spectroscopic data.

  • Eleven saponins are serjanic acid glycosides.

  • Three saponins are phytolaccinic acid glycosides.

  • Two saponins showed cytotoxicity on fibroblasts.

Abstract

Twelve oleanane saponins, zebiriosides A-L, were isolated from the roots of Dendrobangia boliviana Rusby, together with two known saponins, talunùmoside I and 3-O-β-d-glucuronopyranosyl serjanic acid. These saponins are glycosides of serjanic or phytolaccinic acid. Their structures were established on two basis: first, their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C, DEPT) and 2D-NMR (1Hsingle bond1H COSY, TOCSY, HSQC, HMBC, and ROESY), and second by comparison with literature data. These compounds were evaluated for their cytotoxic, antileishmanial and hemolytic activities. No antileishmanial or hemolytic activities were revealed, however zebirioside C and zebirioside I showed cytotoxicity against fibroblasts with IC50 of 6.4 and 5.6 μM, respectively.

Graphical abstract

Twelve previously undescribed glycosides of phytolaccinic acid or serjanic acid were isolated from D. boliviana roots and their cytotoxic, antileishmanial and hemolytic activities were evaluated.

  1. Download : Download full-size image

Introduction

The genus Dendrobangia was at first classified in the family of Icacinaceae by Rusby in 1896. In 2001, Kârehed conducted a cladistic study based on morphological and biological characters (DNA sequences analysis) moving this very genus from Icacinaceae to Cardipteridaceae. He further divided the Icacinaceae “sensu lato” into four families and three orders: Icacinaceae « sensu stricto » (Garryales), Cardiopteridaceae and Stemonuraceae (Aquifoliales) and Pennantiaceae (Apiales) (Karehed, 2001). The Cardiopteridaceae, located in tropical zones, is composed of 43 species in 6 genera. The genus Dendrobangia is composed of three species: Dendrobangia multinerva Ducke, Dendrobangia tenuis Ducke and Dendrobangia boliviana Rusby. All of these large trees growing in the tropical areas. No phytochemical studies on this genus have been reported so far.

Dendrobangia boliviana Rusby is a tree widely distributed in the Neotropical region of Costa Rica and Panama, Brazil and Bolivia. It can be from 5 to 30 m high with 50 cm in diameter. It grows mainly in mountain forests and more rarely in floodplain forests, in an altitude of 100 and 1200 m. Ittolerates a wide range of soils. In Colombia, the community of the region Hibito consumes the fine fruits in their dried form. The wood of this tree is very strong and therefore used in construction, for furnitures, sporting goods, tool handles and interior coverings (De Stefano, 2007). In order to discover previously undescribed secondary metabolites of biological importance from Peru’s Amazon rainforest, we investigated the roots of D. boliviana. This paper examines the isolation and structure elucidation of twelve previously undescribed oleanane saponins (1–12) and two known compounds. The characterization of these 14 compounds, extractedfrom the roots of D. boliviana, were studied for the first time from both, chemical and biological point of view. We decided to, explore the cytotoxic, antileishmanial and hemolytic activities of the different molecules.

Section snippets

Results and discussion

The hydromethanolic extract of the roots of D. boliviana was purified by multiple chromatographic steps over silicagel and reversed phase C18 as well as by semi-preparative HPLC. This purification yielded, twelve previously undescribed saponins, zebiriosides A to L (1–12), together with two known compounds, 3-O-β-d-glucuronopyranosyl serjanic acid (13) (Jayasinghe et al., 1998) and talunùmoside I (14) (Kohda et al., 1992) (Fig. 1). Their structures were elucidated by a detailed analysis of

Conclusions

Phytochemical study of the roots of Dendrobangia boliviana, a Peruvian plant used mainly for the robustness of its wood, generate twelve previously undescribed saponins, zebirioside A to L (1–12), and two known saponins (13–14), which are glycosides of serjanic or phytolaccinic acid. Their chemical structures were determined by analyzing 1D and 2D NMR and MS data. This is the first report on the constituents of Dendrobangia species. All of these saponins were tested for their cytotoxic,

General experimental procedures

Optical rotations were measured in MeOH with a Perkin-Elmer 241 polarimeter. 1H and 13C NMR spectra were recorded in CD3OD on a Bruker Avance III-600 spectrometer equipped with a cryo platform (1H at 600 MHz and 13C at 151 MHz). 2D NMR experiments were performed using standard Bruker microprograms (TopSpin version 3.2 software). HR-ESI-MS and ESI-MS experiments were performed using a Micromass Q-TOF micro-instrument (Manchester, UK). The samples were introduced by direct infusion in a solution

Acknowledgment

Financial support by Ministry of Higher Education and Research (MESR), CNRS, Conseil Regional Champagne Ardenne, Conseil General de la Marne, and EU-programme FEDER to the PlAneT CPER project is gratefully acknowledged.

View full text