Lysophosphatidylcholines and Chlorophyll-Derived Molecules from the Diatom Cylindrotheca closterium with Anti-Inflammatory Activity

Abstract

Microalgae have been shown to be excellent producers of lipids, pigments, carbohydrates, and a plethora of secondary metabolites with possible applications in the pharmacological, nutraceutical, and cosmeceutical sectors. Recently, various microalgal raw extracts have been found to have anti-inflammatory properties. In this study, we performed the fractionation of raw extracts of the diatom Cylindrotheca closterium, previously shown to have anti-inflammatory properties, obtaining five fractions. Fractions C and D were found to significantly inhibit tumor necrosis factor alpha (TNF-⍺) release in LPS-stimulated human monocyte THP-1 cells. A dereplication analysis of these two fractions allowed the identification of their main components. Our data suggest that lysophosphatidylcholines and a breakdown product of chlorophyll, pheophorbide a, were probably responsible for the observed anti-inflammatory activity. Pheophorbide a is known to have anti-inflammatory properties. We tested and confirmed the anti-inflammatory activity of 1-palmitoyl-sn-glycero-3-phosphocholine, the most abundant lysophosphatidylcholine found in fraction C. This study demonstrated the importance of proper dereplication of bioactive extracts and fractions before isolation of compounds is commenced.

Pheophorbide a: State of the Art

“…This review also reports other important bioactivities shown for PPBa, such as antiviral [43], anti-inflammatory [6,[45][46][47], antioxidant [48][49][50][51], immunostimulatory [53] and anti-parasite activities [56]. These data show how this compound can have a plethora of applications for different human pathologies.…”

“…In recent years, many studies have investigated possible microalgae anti-inflammatory properties [6,45,46]. A recent study by Lauritano et al [47] investigated the capacity of extracts of the diatom Cylindrotheca closterium to inhibit the release of one of the main effectors of inflammation, Tumor Necrosis Factor α, in Lipopolysaccharide-stimulated human THP-1 monocytic leukemia cells (ATCC®TIB-202 TM ). They tested five fractions and identified Fraction C as the most active, able to inhibit 60% of Tumor Necrosis Factor α release at 100 µg/mL and 40% of Tumor Necrosis Factor α release at 50 µg/mL concentration.…”

In Silico Identification of Type III PKS Chalcone and Stilbene Synthase Homologs in Marine Photosynthetic Organisms

“…Microalgae are photosynthetic organisms adapted to live in several different environments, including marine, freshwater, polar, temperate and tropical. They are also known to produce a plethora of metabolites derived from primary and secondary metabolism, which have shown possible applications for human health (e.g., compounds with anti-cancer, anti-microbial, anti-diabetes, anti-epilepsy, anti-inflammatory, anti-atherosclerosis, anti-osteoporosis, immunomodulatory and antioxidant activities; [1][2][3][4][5][6][7][8][9][10]). Various studies have focused on the discovery of metabolic pathways involved in the synthesis of bioactive compounds [11][12][13][14].…”

Antiparasitic Potential of Chromatographic Fractions of Nephrolepis biserrata and Liquid Chromatography-Quadrupole Time-of-Flight-Mass Spectrometry Analysis

“…The LCMS analysis indicated the presence of various metabolites with antimicrobial, anti-inflammatory and antiparasitic potential [ 29 , 30 , 31 , 32 , 33 , 34 , 35 ]. Though there is a lack of information regarding the antiparasitic potential of these metabolites against marine parasites, their effectiveness against other parasites were widely reported [ 29 , 30 , 31 , 32 , 33 , 34 , 35 ]. Some of the important metabolites are phytosphingosine ( 6 ), a naturally occurring lipid which acts as antimicrobial (gram-positive bacteria, yeast and moulds) and anti-inflammatory [ 29 ].…”