stigmast-7-enol and spinasterol

Phytosterols, which are produced in plants, are structurally similar to cholesterol. Their basic structures consist of a cyclo pentano-perhydrophenanthrene nucleus composed of 3 hexane rings and of a pentane ring with an alkyl side chain. There are around more than 250 phytosterols and related compounds that have been identified in natural resources. Among them, spinasterol and schottenol, its dihydro analog, are often found in seeds, and consequently in seed oils, and in other botanical parts of some plant families such as Sapotaceae, Cactaceae, and Cucurbitaceae. Spinasterol and/or schottenol has been identified in dietary and cosmetic argan oil, milk thistle seed oil, nigella seed oil, and pumkin seed oil. These phytosterols that have several bioactive properties make them potentially attractive molecules in pharmacology. Their chemical and biochemical features are summarized and the analytical methods used to characterize and analyze these compounds are presented.

Topics: Fatty Acids; Phytosterols; Plant Oils

Terpenoids from natural plant sources are valuable for their diverse biological activities that have important roles in the medical and agrochemical industries. In this study, we assessed the antioxidant, antifungal, and aphicidal activities of a mixture of spinasterol and 22,23-dihydrospinasterol from the leaves of Citrullus colocynthis. We used 1,1-diphenyl-2-picrylhydrazyl (DPPH) to assess antioxidant activity, and we measured antifungal activity using mycelium growth inhibition assays with three pathogenic fungi, Magnaporthe grisea, Rhizoctonia solani, and Phytophthora infestans. Aphicidal activity against adults of Myzus persicae was determined using in vitro and in vivo assays. Spinasterol and 22,23-dihydrospinasterol exhibited moderate antioxidant activity, even at lower concentrations: 19.98% at 0.78 µg mL

Topics: Antifungal Agents; Antioxidants; Citrullus colocynthis; Plant Leaves; Sitosterols; Stigmasterol; Triterpenes

Spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, were synthesized from commercially available stigmasterol by a four steps reactions. In addition, the effects of these phytosterols on cell growth and mitochondrial activity were evaluated on 158N murine oligodendrocytes, C6 rat glioma cells, and SK-N-BE human neuronal cells with the crystal violet test and the MTT test, respectively. The effects of spinasterol and schottenol were compared with 7-ketocholesterol (7KC) and ferulic acid, which is also present in argan and cactus pear seed oil. Whatever the cells considered, dose dependent cytotoxic effects of 7KC were observed whereas no or slight effects of ferulic acid were found. With spinasterol and schottenol, no or slight effects on cell growth were detected. With spinasterol, reduced mitochondrial activities (30-50%) were found on 158N and C6 cells; no effect was found on SK-N-BE. With schottenol, reduced mitochondrial activity were revealed on 158N (50%) and C6 (10-20%) cells; no effect was found on SK-N-BE. Altogether, these data suggest that spinasterol and schottenol can modulate mitochondrial activity and might therefore influence cell metabolism.

Topics: Animals; Cell Line; Cell Proliferation; Central Nervous System; Humans; Mice; Mitochondria; Phytosterols; Plant Oils; Pyrus; Rats; Seeds; Sitosterols; Stigmasterol

The objective of this study was to evaluate the biological activities of the major phytosterols present in argan oil (AO) and in cactus seed oil (CSO) in BV2 microglial cells. Accordingly, we first determined the sterol composition of AO and CSO, showing the presence of Schottenol and Spinasterol as major sterols in AO. While in CSO, in addition to these two sterols, we found mainly another sterol, the Sitosterol. The chemical synthesis of Schottenol and Spinasterol was performed. Our results showed that these two phytosterols, as well as sterol extracts from AO or CSO, are not toxic to microglial BV2 cells. However, treatments by these phytosterols impact the mitochondrial membrane potential. Furthermore, both Schottenol and Spinasterol can modulate the gene expression of two nuclear receptors, liver X receptor (LXR)-α and LXRβ, their target genes ABCA1 and ABCG1. Nonetheless, only Schottenol exhibited a differential activation vis-à-vis the nuclear receptor LXRβ. Thus Schottenol and Spinasterol can be considered as new LXR agonists, which may play protective roles by the modulation of cholesterol metabolism.

Topics: Animals; ATP Binding Cassette Transporter 1; ATP Binding Cassette Transporter, Subfamily G, Member 1; ATP-Binding Cassette Transporters; Cell Line; Gene Expression Regulation; Lipoproteins; Liver X Receptors; Membrane Potential, Mitochondrial; Mice; Microglia; Opuntia; Orphan Nuclear Receptors; Plant Oils; Seeds; Sitosterols; Sterols; Stigmasterol

Topics: Plant Extracts; Plants, Medicinal; Sitosterols; Stigmasterol