Elsevier

Phytochemistry Letters

Volume 10, December 2014, Pages 160-163
Phytochemistry Letters

Isolation of diterpenes and flavonoids from a new type of propolis from Saudi Arabia

https://doi.org/10.1016/j.phytol.2014.08.022Get rights and content

Highlights

  • A new type of propolis from Saudi Arabia has been partially characterised.

  • A new kaurane diterpene was fully characterised.

  • Three of the compounds isolated had anti-trypanosomal properties.

Abstract

The chemical composition and biological activity of a sample of Saudi Arabian propolis were investigated. A new diterpene propsiadin ((ent)-2-oxo-kaur-16-en-6,18-diol) (3) along with the flavonoids 3,4-dihydro-2-(3,4-dihydroxyphenyl)-2H-chromene-3,7-diol (1), psiadiarabin (2) and the diterpene psiadin (4) were isolated from a Saudi Arabian propolis. Their structures were determined by HR-ESI-MS, 1D and 2D NMR. Compound 1 was inactive against Trypanosoma brucei and Mycobacterium marinum while compounds 24 had MICs of 30.9, 78.1 and 78.1 μM against T. brucei respectively and 312.1, 312.1 and 69.1 μM against M. marinum. The likely sources of the propolis are Psiadia arabica and Psiadia punctulata and it represents a new type of propolis not described before.

Introduction

Propolis is used in traditional medicine in many countries (Popova et al., 2010). Recently it has become popular as a component of health food and an alternative medicine (da Silva Frozza et al., 1997, Petrova et al., 2010). Honey bees (Apis mellifera) collect exudates from various buds and flora in order to seal the walls of the hive and protect it from micro-organisms (Piccinelli et al., 2011). Propolis composition varies according to geographic region (Bertelli et al., 2012, Salatino et al., 2011, Watson et al., 2006). Propolis has antimicrobial, antimycotic, anti-inflammatory, antioxidant, antitumor, anti-neurodegenerative, antituberculosis, antiviral, cytotoxic, anti-inflammatory, and immunomodulatory activities (Falcao et al., 2010, Yildirim et al., 2004). It contains many chemical constituents and to date more than 300 compounds have been identified as constituents including polyphenols, flavanones, flavonols, flavones, dihydroflavonols, chalcones, phenolic acids and their esters, monoterpenes, sesquiterpenes, diterpenes and triterpenes, steroids, aromatic aldehydes, alcohols, naphthalene and stilbene derivatives (Abu-Mellal et al., 2012, da Silva Frozza et al., 1997). This study reports the characterisation of a new type of propolis from Saudi Arabia and its activity on Trypanosoma brucei brucei the causative organism of African sleeping sickness. A new diterpene propsiadin ((ent)-2-oxo-kaur-16-en-6,18-diol) (3) along with the flavonoids 3,4-dihydro-2-(3,4-dihydroxyphenyl)-2H-chromene-3,7-diol (1), psiadiarabin (2) and the diterpene psiadin (4). The likely sources of the propolis are Psiadia arabica and Psiadia punctulata and it represents a new type of propolis not described before.

Section snippets

Results and discussion

The isolated compounds (Fig. 1) were obtained from an ethanol extract of the Saudi Arabian propolis. Compounds 3 and 4 were obtained by column chromatography followed by medium pressure flash chromatography on silica gel. The elemental compositions for the compounds were obtained from LC–MS analysis using an Orbitrap mass spectrometer. The structures were identified by 1D and 2D NMR analysis as summarised in Table 1, Table 2.

Compound 1 gave a molecular ion [M+H]+ at m/z 275.0910 HR-ESIMS

General methods

Optical rotation: optical rotations were measured on a Perkin–Elmer 431 polarimeter at 20 °C.

The NMR spectra [1H and 13C NMR, DEPT 135; 2D H, H-COSY, heteronuclear single quantum correlation (HSQC, HMBC, NOESY)] were obtained using Bruker Avance 600 and JEOL-LA 400 FT-NMR spectrometer systems with CDCl3 and d6-DMSO as solvents and referencing to the signal for the residual protons. Chemical shifts are given in ppm, and coupling constants are in Hz. MestReNova 8.1.2 was used for processing the

Acknowledgement

S. Almutairi is grateful to the Saudi government for a Ph.D. scholarship.

References (19)

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