Anti-Inflammatory, Neurotrophic, and Cytotoxic Oxylipins Isolated from Chaenomeles sinensis Twigs

Abstract

Oxylipins are important biological molecules with diverse roles in human and plants such as pro-/anti-inflammatory, antimicrobial, and regulatory activity. Although there is an increasing number of plant-derived oxylipins, most of their physiological roles in humans remain unclear. Here, we describe the isolation, identification, and biological activities of four new oxylipins, chaenomesters A–D (1–4), along with a known compound (5), obtained from Chaenomeles sinensis twigs. Their chemical structures were determined by spectroscopic (i.e., NMR) and spectrometric (i.e., HRMS) data analysis including 1H NMR-based empirical rules and homonuclear-decoupled 1H NMR experiments. Chaenomester D (4), an omega-3 oxylipin, showed a potent inhibitory effect on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells (NO production, 8.46 ± 0.68 μM), neurotrophic activity in C6 cells through the induction of the secretion of nerve growth factor (NGF, 157.7 ± 2.4%), and cytotoxicity in A549 human cancer cell lines (IC50 = 27.4 μM).

Antioxidant and Cytotoxic Potential of Carlina vulgaris Extract and Bioactivity-Guided Isolation of Cytotoxic Components

“…The compounds belong to oxylipin family, which are products from the oxygenation of fatty acids accumulated in plants in response to stress conditions [ 20 , 21 ]. They exhibit interesting biological activities, including pro-/anti-inflammatory, antimicrobial, neuroprotective, and regulatory effects [ 22 , 23 ]. However, their actions depend on the chemical structure, and some opposite effects have been found for omega-3 and omega-6 oxylipins.…”

“…The current study revealed that pinellic acid did not demonstrate activity against HT-29, consistent with the existing literature indicating either its lack of activity or only mild cytotoxicity. Both PA and the other structurally similar omega-6 fatty acid showed no cytotoxicity against other types of cancer cell lines, such as lung adenocarcinoma, skin melanoma, adenosquamous carcinoma, and human glioblastoma [ 23 , 28 ]. Only moderate cytotoxic activity by PA was noted against hepatic cell carcinoma and prostate cancer [ 29 ].…”