The Role of Sargahydroquinoic Acid and Sargachromenol in the Anti-Inflammatory Effect of

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2024 Mar 27

PMID 38535449

Authors

Yena Park

Lei Cao

Suhyeon Baek

Seungjin Jeong

Hyun Jung Yun

Mi-Bo Kim

Sang Gil Lee

Affiliations

Soon will be listed here.

Abstract

The anti-inflammatory effect of the ethanol extract of and its fractions were investigated in this study. The ethanol extract exhibited a strong anti-inflammatory effect on lipopolysaccharide-stimulated RAW 264.7 macrophages and effectively suppressed the M1 polarization of murine bone-marrow-derived macrophages stimulated by lipopolysaccharides and IFN-γ (interferon-gamma). Through a liquid-liquid extraction process, five fractions (n-hexane, chloroform, ethyl acetate, butanol, and aqueous) were acquired. Among these fractions, the chloroform fraction (SYCF) was found to contain the highest concentration of phenolic compounds, along with two primary meroterpenoids, sargahydroquinoic acid (SHQA) and sargachromenol (SCM), and exhibit significant antioxidant capacity. It also demonstrated a robust anti-inflammatory effect. A direct comparison was conducted to assess the relative contribution of SHQA and SCM to the anti-inflammatory properties of SYCF. The concentrations of SHQA and SCM tested were determined based on their relative abundance in SYCF. SHQA contributed to a significant portion of the anti-inflammatory property of SYCF, while SCM played a limited role. These findings not only highlight the potential of the chloroform-ethanol fractionation approach for concentrating meroterpenoids in but also demonstrate that SHQA and other bioactive compounds work additively or synergistically to produce the potent anti-inflammatory effect of SYCF.

Citing Articles

Optimized Extraction of Sargahydroquinoic Acid, Major Bioactive Substance, from Using Response Surface Methodology.

Baek S, Bae J, Miao Y, Kim G, Ryu B, Lee B Mar Drugs. 2024; 22(12).

PMID: 39728118 PMC: 11676218. DOI: 10.3390/md22120543.

References

Jeong S, Kim M, Baek S, Lee J, Lee H, Cao B . Suppression of Pro-Inflammatory M1 Polarization of LPS-Stimulated RAW 264.7 Macrophage Cells by Fucoxanthin-Rich . Mar Drugs. 2023; 21(10). PMC: 10608208. DOI: 10.3390/md21100533. View

Liu J, Luthuli S, Yang Y, Cheng Y, Zhang Y, Wu M . Therapeutic and nutraceutical potentials of a brown seaweed . Food Sci Nutr. 2020; 8(10):5195-5205. PMC: 7590327. DOI: 10.1002/fsn3.1835. View

Ogier-Denis E, Ben Mkaddem S, Vandewalle A . NOX enzymes and Toll-like receptor signaling. Semin Immunopathol. 2008; 30(3):291-300. DOI: 10.1007/s00281-008-0120-9. View

Generalic Mekinic I, Skroza D, Simat V, Hamed I, cagalj M, Popovic Perkovic Z . Phenolic Content of Brown Algae (Pheophyceae) Species: Extraction, Identification, and Quantification. Biomolecules. 2019; 9(6). PMC: 6628088. DOI: 10.3390/biom9060244. View

Jose S, Tan S, Ooi Y, Ramasamy R, Vidyadaran S . Mesenchymal stem cells exert anti-proliferative effect on lipopolysaccharide-stimulated BV2 microglia by reducing tumour necrosis factor-α levels. J Neuroinflammation. 2014; 11:149. PMC: 4156657. DOI: 10.1186/s12974-014-0149-8. View

Khatibi S, Hamidi S, Siahi-Shadbad M . Application of Liquid-Liquid Extraction for the Determination of Antibiotics in the Foodstuff: Recent Trends and Developments. Crit Rev Anal Chem. 2020; 52(2):327-342. DOI: 10.1080/10408347.2020.1798211. View

Claria J . Cyclooxygenase-2 biology. Curr Pharm Des. 2003; 9(27):2177-90. DOI: 10.2174/1381612033454054. View

Lim S, Choi A, Kwon M, Joung E, Shin T, Lee S . Evaluation of antioxidant activities of various solvent extract from Sargassum serratifolium and its major antioxidant components. Food Chem. 2018; 278:178-184. DOI: 10.1016/j.foodchem.2018.11.058. View

Wu Y, Gao H, Wang Y, Peng Z, Guo Z, Ma Y . Effects of different extraction methods on contents, profiles, and antioxidant abilities of free and bound phenolics of Sargassum polycystum from the South China Sea. J Food Sci. 2022; 87(3):968-981. PMC: 9304242. DOI: 10.1111/1750-3841.16051. View

10.

Benzie I, Strain J . The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay. Anal Biochem. 1996; 239(1):70-6. DOI: 10.1006/abio.1996.0292. View

11.

Liu L, Heinrich M, Myers S, Dworjanyn S . Towards a better understanding of medicinal uses of the brown seaweed Sargassum in Traditional Chinese Medicine: a phytochemical and pharmacological review. J Ethnopharmacol. 2012; 142(3):591-619. DOI: 10.1016/j.jep.2012.05.046. View

12.

Xu Q, Choksi S, Qu J, Jang J, Choe M, Banfi B . NADPH Oxidases Are Essential for Macrophage Differentiation. J Biol Chem. 2016; 291(38):20030-41. PMC: 5025689. DOI: 10.1074/jbc.M116.731216. View

13.

Li H, Sun W, Deng M, Qi C, Chen C, Zhu H . Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus . Mar Drugs. 2018; 16(6). PMC: 6025407. DOI: 10.3390/md16060177. View

14.

Gwon W, Joung E, Kwon M, Lim S, Utsuki T, Kim H . Sargachromenol protects against vascular inflammation by preventing TNF-α-induced monocyte adhesion to primary endothelial cells via inhibition of NF-κB activation. Int Immunopharmacol. 2016; 42:81-89. DOI: 10.1016/j.intimp.2016.11.014. View

15.

Fuloria N, Raheja R, Shah K, Oza M, Kulkarni Y, Subramaniyan V . Biological activities of meroterpenoids isolated from different sources. Front Pharmacol. 2022; 13:830103. PMC: 9527340. DOI: 10.3389/fphar.2022.830103. View

16.

Donaldson J . Immunofluorescence Staining. Curr Protoc Cell Biol. 2015; 69:4.3.1-4.3.7. DOI: 10.1002/0471143030.cb0403s69. View

17.

Ainsworth E, Gillespie K . Estimation of total phenolic content and other oxidation substrates in plant tissues using Folin-Ciocalteu reagent. Nat Protoc. 2007; 2(4):875-7. DOI: 10.1038/nprot.2007.102. View

18.

Murray P . Macrophage Polarization. Annu Rev Physiol. 2016; 79:541-566. DOI: 10.1146/annurev-physiol-022516-034339. View

19.

Catarino M, Silva-Reis R, Chouh A, Silva S, Braga S, Silva A . Applications of Antioxidant Secondary Metabolites of spp. Mar Drugs. 2023; 21(3). PMC: 10052768. DOI: 10.3390/md21030172. View

20.

Kim S, Choi H, Lee W, Park G, Shin W, Kim Y . Sargaquinoic acid and sargahydroquinoic acid from Sargassum yezoense stimulate adipocyte differentiation through PPARalpha/gamma activation in 3T3-L1 cells. FEBS Lett. 2008; 582(23-24):3465-72. DOI: 10.1016/j.febslet.2008.09.011. View