New septanoside and 20-hydroxyecdysone septanoside derivative from Atriplex portulacoides roots with preliminary biological activities Aymen Ben Nejma a , Asma Nguir a , Hichem Ben Jannet a,⇑ , M’hamed Ali Hamza a , Adam Daïch b , Mohamed Othman b , Ata Martin Lawson b,⇑ a Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11SE39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia b URCOM, EA 3221, INC3M CNRS FR-3038, UFR des Sciences et Techniques de l’Université du Havre, 25 Rue Philippe Lebon, B.P. 540, F-76058 Le Havre Cedex, France article info Article history: Received 26 January 2015 Accepted 11 March 2015 Available online xxxx Keywords: Atriplex portulacoides Chenopodiaceae 20-Hydroxyecdysone Portulasoid Septanoecdysone NMR Biological activities abstract The phytochemical investigation of a Tunisian plant Atriplex portulacoides (Chenopodiaceae) led to the isolation of two new compounds designated as portulasoid (2) and septanoecdysone (3) along with the known 20-hydroxyecdysone (20HE) (1). Their chemical structures were elucidated on the basis of extensive spectroscopic methods including ES-HRMS, 1D and 2D-NMR. The isolated compounds were finally tested for their antioxidant activity by using DPPH Å , ABTS +Å , Fe 3+ and catalase assays and also for their antibacterial and anticholinesterase activities. Ó 2015 Elsevier Ltd. All rights reserved. Atriplex portulacoides L. [Syn. Obione portulacoides (L.) Moq., Halimione portulacoides Aellen] is a perennial, shrubby halophytic plant. Widespreaded in salt marshes along the coasts of Europe, North Africa and South-West Asia, its belongs to Chenopodiaceae family (goosefoot family), that is largely distributed throughout the world especially in arid and saline regions. 1 This family is con- sisted of 104 genus and more than 1400 species, the majority growing naturally in saline soils. 2 Different species of Atriplex (A. hortensis, A. fruticosa, A. inflata, A. parvifolia, A. semibaccata, A. undulata, A. vestita) including A. portulacoides were reported as sources of interesting biological effects (antifungal, antiviral, antioxidant, cytotoxic, antimicrobial, etc.) through their extracts or their chemical constituents. 3–8 In a phytochemical point of view, previous investigations of some Atriplex species revealed the pres- ence of many classes of secondary metabolites such as tannins, fla- vonoids, alkaloids, proteins and amino acids as well as terpenoids, saponins and long chain alcohols. 7–11 Surprisingly and according to literature, only a few phytochemical study of Atriplex portulacoides was reported. 11 The present research work describes the isolation and the structural elucidation of the known 20-hydroxyecdysone (20HE) (1) from n-BuOH aerial parts extract of A. portulacoides, along with two new compounds: an O-butylated septanoside 2 and an O-ecdysone septanoside 3 from n-BuOH roots extract. 12 Compound 1 (m = 15 mg) (Fig. 1) was isolated as a white solid from the n-BuOH extract. Its UV spectrum exhibited a band at k max (MeOH): 243 nm. The 1 H NMR (300 MHz) spectrum recorded in CD 3 OD showed five methyl groups: d H 0.90 (H 18 ); d H 0.98 (H 19 ); d H 1.18 (H 21 and H 26 ) and d H 1.19 (H 27 ), a set of methylene group signals between d H 1.00 to d H 2.00, the ethylenic CH (d H 5.81; H 7 ), along with 3  CH-OH (d H 3.32; 3.83; 3.95) and 3  quaternary O-bonded carbons, that constitute a fingerprint of 20HE skeleton. This was corroborated by 13 C NMR spectrum which revealed, beside the three O-bonded quaternary carbons (d C 71.3; 77.9; 85.2), the presence of a,b-unsaturated ketone (d C 122.1; 168.0; 206.5). The spectral data using 1 H and 13 C NMR spectra were con- solidated through the 2D NMR spectroscopy examination such as: COSY, HMQC and HMBC (Table 1). Finally, the acquisition of the mass spectrum by using the ES-HRMS in a positive mode showed a peak at m/z 503.2986 that corresponds to a [M+Na] + pseudo- molecular ion. From the latter, a molecular formula of C 27 H 44 O 7 http://dx.doi.org/10.1016/j.bmcl.2015.03.028 0960-894X/Ó 2015 Elsevier Ltd. All rights reserved. ⇑ Corresponding authors. Tel.: +216 73500279; fax: +216 73500278 (H.B.J.); tel.: +33 02 32 74 44 00; fax: +33 02 32 74 43 91 (A.M.L.). E-mail addresses: hich.benjannet@yahoo.fr (H. Ben Jannet), lawsona@univ-le- havre.fr (A.M. Lawson). Bioorganic & Medicinal Chemistry Letters xxx (2015) xxx–xxx Contents lists available at ScienceDirect Bioorganic & Medicinal Chemistry Letters journal homepage: www.elsevier.com/locate/bmcl Please cite this article in press as: Ben Nejma, A.; et al. Bioorg. Med. Chem. Lett. (2015), http://dx.doi.org/10.1016/j.bmcl.2015.03.028