Steroids and Fatty Acid Esters from Cyperus sexangularis Leaf and Their Antioxidant, Anti-Inflammatory and Anti-Elastase Properties

Abstract

Cyperus sexangularis (CS) is a plant in the sedges family (Cyperaceae) that grows abundantly in swampy areas. The leaf sheath of plants in the Cyperus genus are mostly used domestically for mat making, while they are implicated for skin treatment in traditional medicine. The plant was investigated for its phytochemical contents as well as its antioxidant, anti-inflammatory and anti-elastase properties. The n-hexane and dichloromethane leaf extracts were chromatographed on a silica gel column to afford compounds 1–6. The compounds were characterized by nuclear magnetic resonance spectroscopy and mass spectrometry. The inhibitory effect of each compound against 2,2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO) and ferric ion radicals were determined by standard in vitro antioxidant methods. The in vitro anti-inflammatory response was measured using egg albumin denaturation (EAD) assay, while the anti-elastase activity of each compound in human keratinocyte (HaCaT) cells was also monitored. The compounds were characterized as three steroidal derivatives, stigmasterol (1), 17-(1-methyl-allyl)-hexadecahydro-cyclopenta[a]phenanthrene (2) and β-sitosterol (3), dodecanoic acid (4) and two fatty acid esters, ethyl nonadecanoate (5) and ethyl stearate (6). Stigmasterol (1) exhibited the best biological properties, with IC50 of 38.18 ± 2.30 µg/mL against DPPH, 68.56 ± 4.03 µg/mL against NO and 303.58 ± 10.33 µAAE/mg against Fe3+. At 6.25 µg/mL, stigmasterol inhibited EAD by 50%. This activity was lower when compared to diclofenac (standard), which demonstrated 75% inhibition of the protein at the same concentration. Compounds 1, 3, 4 and 5 showed comparable anti-elastase activity with an IC50 ≥ 50 µg/mL, whereas the activity of ursolic acid (standard) was double fold with an IC50 of 24.80 ± 2.60 µg/mL when compared to each of the compounds. In conclusion, this study has identified three steroids (1–3), one fatty acid (4), and two fatty acid esters (5 and 6) in C. sexangularis leaf for the first time. The compounds showed considerable antioxidant, anti-inflammatory and anti-elastase properties. Thus, the findings may serve as a justification for the folkloric use of the plant as a local skin ingredient. It may also serve to validate the biological role of steroids and fatty acid compounds in cosmeceutical formulations.

Secondary metabolites, spectra characterization, and antioxidant correlation analysis of the polar and nonpolar extracts of Bryophyllum pinnatum (Lam) Oken

“…Mbachu et al ( 2019 ) also identified 5-eicosene among the bioactive compounds in the essential oil of B. pinnatum . Fatty acid methyl esters (FAME) and fatty acids (FA) are known to possess low antioxidant activity (Pinto et al, 2017 ; Miya et al, 2023 ). However, a synergy in their antioxidant activity may explain the higher antioxidant activity of the PE compared to AA, as seen in Figure 2 , and the observed antioxidant activity of FA and FAME is evident in both the PE and NPE.…”

Preliminary Investigation of Astragalus arpilobus subsp. hauarensis: LC-MS/MS Chemical Profiling, In Vitro Evaluation of Antioxidant, Anti-Inflammatory Properties, Cytotoxicity, and In Silico Analysis against COX-2

“…However, it is important to note that while these identified compounds may contribute significantly to the anti-inflammatory and antioxidant effects observed, there could be other bioactive molecules present in the extract that were not detected via LC-MS analysis. These undetected molecules such as fatty acids, carotenoids, and steroids may also play a significant role in the observed anti-inflammatory capacity of the extract [ 52 ].…”

Comprehensive Phytochemical Analysis and Bioactivity Evaluation of Padina boergesenii: Unveiling Its Prospects as a Promising Cosmetic Component

“…Further compounds identified included fatty acyls, such as decane, 6-ethyl-2-methyl-and octadecane, 3-ethyl-5-(2-ethylbutyl)-, which may contribute as surfactants in skincare products [24,25]. Fatty acid derivatives, such as 2-monolinolenin, 2TMS derivatives, and benzyl (6Z,9Z,12Z)-6,9,12-octadecatrienoate hold potential for their ability to provide antioxidant and anti-inflammatory effects on the skin, contributing to overall skin health and anti-aging properties [26][27][28]. Hydrocarbon derivatives, including cyclopentanol, 2-methyl-, trans-, and cyclooctane acetic acid, 2-oxo-, may have unique properties that can contribute to the sensory aspects and formulation of cosmetic products [29,30].…”