Mostafa Alilou

This study presents a phytochemical survey of two common intertidal red algal species, Bostrychia scorpioides and Catenella caespitosa, regarding their MAA (mycosporine-like amino acid) composition, which are known as biogenic sunscreen compounds. Six novel MAAs from Bostrychia scorpioides named bostrychines and two novel MAAs from Catenella caespitosa named catenellines were isolated using a protocol which included silica gel column chromatography, flash chromatography on reversed phase material and semipreparative HPLC (High-Performance Liquid Chromatography). The structure of the novel MAAs was elucidated using NMR (Nuclear Magnetic Resonance) and HR-MS (High-Resolution Mass Spectrometry), and their absolute configuration was confirmed by ECD (Electronic Circular Dichroism). All isolated MAAs possess a cyclohexenimine scaffold, and the metabolites from B. scorpioides are related to the known MAAs bostrychines A-F, which contain glutamine, glutamic acid and/or threonine in their side chains. The new MAAs from C. caespitosa contain taurine, an amino sulfonic acid that is also present in another MAA isolated from this species, namely, catenelline. Previous and new data confirm that intertidal red algae are chemically rich in MAAs, which explains their high tolerance against biologically harmful ultraviolet radiation.

We investigated the anticancer mechanism of a chloroform extract of marine sponge (Haliclona fascigera) (sample C) in human breast adenocarcinoma (MCF-7) cells. Viability analysis using MTT and neutral red uptake (NRU) assays showed that sample C exposure decreased the proliferation of cells. Flow cytometric data exhibited reactive oxygen species (ROS), nitric oxide (NO), dysfunction of mitochondrial potential, and apoptosis in sample C-treated MCF-7 cells. A qPCR array of sample C-treated MCF-7 cells showed crosstalk between different pathways of apoptosis, especially BIRC5, BCL2L2, and TNFRSF1A genes. Immunofluorescence analysis affirmed the localization of p53, bax, bcl2, MAPKPK2, PARP-1, and caspase-3 proteins in exposed cells. Bioassay-guided fractionation of sample C revealed Neviotin A as the most active compound triggering maximum cell death in MCF-7, indicating its pharmacological potency for the development of a drug for the treatment of human breast cancer.

Phytochemical investigation on the acetone extract of Salvia mirzayanii Rech. f. and Esfand. afforded seven new isoprenoids including six new sesterterpenoids salvimirzacolide A-F (1–6), and one new nor-diterpenoid (7). Their structures were established by comprehensive spectroscopic and spectrometric data analysis (1D and 2D NMR, HRMS) and DP4+ NMR chemical shift probability calculation technique. Moreover, the absolute configuration of compounds was determined by using electronic circular dichroism spectroscopy. Evaluation of antiproliferative properties of compounds isolated against four human melanoma cancer cells displayed no cytotoxic activity at the concentration range used.

The class of demosponges is the biggest and most diverse of all described sponge species and it is reported to produce a plethora of chemically different metabolites with interesting biological activities. The focus of the present study was to investigate the chemical composition of two Mediterranean demosponges, targeting their brominated compounds and prenylated hydroquinones, compounds with interesting cytotoxic and anti-microbial properties. In order to gain a deeper insight into the chemical diversity of their metabolites and their activities, 20 pure secondary metabolites including new natural products were isolated from two different species (Aplysina aerophoba and Spongia sp.) using various chromatographic techniques. Their structures were confirmed by NMR and HRMS, revealing molecules with various chemical scaffolds, mainly prenylated hydroquinones from Spongia sp. and halogenated compounds from Aplysina aerophoba, including 5 novel natural products. The isolated compounds were investigated for their cytotoxic properties using 9 different cell lines, and especially one compound, 2,6-dibromo-4-hydroxy-4-methoxycarbonylmethylcyclohexa-2,5-dien-1-one showed good activities in all tested models.