CPC driven isolation and identification of Pistacia vera pericarp secondary metabolites: New source of rare and biologically active triterpenic acids

J Popp; E Petrakis; A Angelis; I Pisimisi; M Halabalaki; H Stuppner; AL Skaltsounis

doi:10.1055/s-0037-1608275

Planta Medica International Open, Table of Contents

Planta Medica International Open 2017; 4(S 01): S1-S202
DOI: 10.1055/s-0037-1608275

Poster Session

Georg Thieme Verlag KG Stuttgart · New York

CPC driven isolation and identification of Pistacia vera pericarp secondary metabolites: New source of rare and biologically active triterpenic acids

J Popp

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, Greece

²Institute of Pharmacy/Pharmacognosy, Center for Molecular Biosciences, University of Innsbruck, Innsbruck, Austria

,

E Petrakis

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, Greece

,

A Angelis

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, Greece

,

I Pisimisi

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, Greece

,

M Halabalaki

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, Greece

,

H Stuppner

²Institute of Pharmacy/Pharmacognosy, Center for Molecular Biosciences, University of Innsbruck, Innsbruck, Austria

,

AL Skaltsounis

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, Greece

› Author Affiliations

Abstract

Full Text

Pistacia vera L. is considered the only species in the genus Pistacia (family Anacardiaceae) that produces edible tree nuts, which are widely known as pistachios [1]. The sensory, nutritional, and health attributes of this popular snack food make it increasingly valued and of significant economic importance for several countries including Greece, the sixth largest producer worldwide. Thus, valorization of the main side product derived from pistachio processing, the pericarp or outer hull, is of great interest and can be determined by the content in valuable phytochemicals that merit utilization [2]. In this study, the ethyl acetate extract of pericarp, obtained by means of ultrasound-assisted extraction (UAE), was submitted to centrifugal partition chromatography (CPC) for the fractionation and separation of secondary metabolites. A step-gradient method was employed, in reversed-phase mode, using a series of four biphasic solvent systems consisted of n-hexane/EtOAc/EtOH/H₂O in order of decreasing polarity of the aqueous mobile phase (i.e. from 8:2:5:5 to 8:2:9:1 v/v/v/v). The separation was performed in preparative (1000 mL) CPC column, leading rapidly (< 5 hours) to the effective fractionation of 5 g of the initial extract. The comprehensive analysis of selected fractions by high resolution NMR and MS revealed that Greek pistachio pericarp comprises an excellent source of triterpenic acids, anacardic acids, and alkyl phenols. Interestingly, this process resulted in high amounts of 3a-(iso)masticadienolic and (iso)masticadienonic acids. The presence of 3a-(iso)masticadienolic acids in the Pistacia genus is reported herein for the first time, with the proposed CPC methodology enabling their efficient recovery.

Fig. 1

[1] Alasalvar C, Shahidi F. Tree nuts: composition, phytochemicals, and health effects. Boca Raton: CRC Press; 2008: 295 – 304.

[2] Erşan S, Güçlü Üstündağ Ö, Carle R, Schweiggert RM. J Agric Food Chem 2016; 64: 5334 – 5344.

Figures

Fig. 1