Phytoceramides from the Marine Sponge Monanchora clathrata: Structural Analysis and Cytoprotective Effects

Abstract

In our research on sphingolipids from marine invertebrates, a mixture of phytoceramides was isolated from the sponge Monanchora clathrata (Western Australia). Total ceramide, ceramide molecular species (obtained by RP-HPLC, high-performance liquid chromatography on reversed-phase column) and their sphingoid/fatty acid components were analyzed by NMR (nuclear magnetic resonance) spectroscopy and mass spectrometry. Sixteen new (1b, 3a, 3c, 3d, 3f, 3g, 5c, 5d, 5f, 5g, 6b–g) and twelve known (2b, 2e, 2f, 3b, 3e, 4a–c, 4e, 4f, 5b, 5e) compounds were shown to contain phytosphingosine-type backbones i-t17:0 (1), n-t17:0 (2), i-t18:0 (3), n-t18:0 (4), i-t19:0 (5), or ai-t19:0 (6), N-acylated with saturated (2R)-2-hydroxy C21 (a), C22 (b), C23 (c), i-C23 (d), C24 (e), C25 (f), or C26 (g) acids. The used combination of the instrumental and chemical methods permitted the more detailed investigation of the sponge ceramides than previously reported. It was found that the cytotoxic effect of crambescidin 359 (alkaloid from M. clathrata) and cisplatin decreased after pre-incubation of MDA-MB-231 and HL-60 cells with the investigated phytoceramides. In an in vitro paraquat model of Parkinson’s disease, the phytoceramides decreased the neurodegenerative effect and ROS (reactive oxygen species) formation induced by paraquat in neuroblastoma cells. In general, the preliminary treatment (for 24 or 48 h) of the cells with the phytoceramides of M. clathrata was necessary for their cytoprotective functions, otherwise the additive damaging effect of these sphingolipids and cytotoxic compounds (crambescidin 359, cisplatin or paraquat) was observed.

Metabolic Comparison and Molecular Networking of Antimicrobials in Streptomyces Species

“…Phytoceramide is reported to promote hydration and enhance the healing process of damaged human stratum corneum in human skin and can be used in the cosmetic industry for creating skin barrier moisturizers [102]. Moreover, phytoceramides were found to be cytotoxic to the MES-SA, MCF-7, and HK-2 cell lines in the previous study of Monanchora clathrata, and have further proven to be used in the prevention of neurodegeneration in both in vivo and in vitro [103]. The ability of cyclo-(Pro-Gly) to decrease motor neuronal death demonstrates the neuroprotective function after brain injury and this compound also shows anxiolytic activity [104,105].…”