24(S)-saringosterol from edible marine seaweed sargassum fusiforme is a novel selective LXRβ agonist

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 26, 2014, Pages 6130-6137

  Chen, Zhen ^a   Liu, Jiao ^b   Fu, Zhifei ^a   Ye, Cheng ^b   Zhang, Renshuai ^a   Song, Yiyun ^b   Zhang, Ying ^b   Li, Haihua ^a   Ying, Hao ^b   Liu, Hongbing ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

24(S) saringosterol; cholesterol metabolism; phytosterols; Sargassum fusiforme; selective LXR agonist

Indexed keywords

ALCOHOLS; CELL CULTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEAWEED; TRANSCRIPTION; CHOLESTEROL; GENE EXPRESSION; LIQUID CHROMATOGRAPHY; MEDICINE;

24(S)-SARINGOSTEROL; CHOLESTEROL METABOLISM; CHOLESTEROL TRANSPORT; PHYTOSTEROLS; SARGASSUM FUSIFORME; SEMI-PREPARATIVE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIES; TRADITIONAL CHINESE MEDICINE; TRANSCRIPTIONAL ACTIVITY; MEDIATED TRANSCRIPTION;

CHOLESTEROL; ALCOHOLS;

SARGASSUM FUSIFORME;

CHOLESTEROL; HYPOCHOLESTEROLEMIC AGENT; ISOPROTEIN; LIVER X RECEPTOR; ORPHAN NUCLEAR RECEPTOR; RECOMBINANT PROTEIN; SARINGOSTEROL; STIGMASTEROL;

AGONISTS; ANALOGS AND DERIVATIVES; ANALYSIS; CELL LINE; CHEMISTRY; CHINA; COMPARATIVE STUDY; CONFORMATION; DRUG EFFECTS; FUNCTIONAL FOOD; GENETICS; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR DOCKING; PACIFIC OCEAN; REPORTER GENE; SARGASSUM; SEAWEED; STEREOISOMERISM; TRANSPORT AT THE CELLULAR LEVEL;

ANTICHOLESTEREMIC AGENTS; BIOLOGICAL TRANSPORT; CELL LINE; CHINA; CHOLESTEROL; FUNCTIONAL FOOD; GENES, REPORTER; HUMANS; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; ORPHAN NUCLEAR RECEPTORS; PACIFIC OCEAN; PROTEIN ISOFORMS; RECOMBINANT PROTEINS; SARGASSUM; SEAWEED; STEREOISOMERISM; STIGMASTEROL;

EID: 84903781752     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf500083r     Document Type: Article

References (36)

1. 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, 591-619
2. Nisizawa, K.; Noda, H.; Kikuchi, R.; Watanabe, T. The main seaweed foods in Japan Hydrobiologia 1987, 151-152, 5-29
3. Chen, Z.; Liu, H. B. Research progress in chemical components and biological activity of Sargassum Chin. J. Mar. Drugs 2012, 31, 41-51
4. Fitzgerald, C.; Gallagher, E.; Tasdemir, D.; Hayes, M. Heart health peptides from macroalgae and their potential use in functional foods J. Agric. Food Chem. 2011, 59, 6829-6836
5. Wang, W.; Li, H.; Wang, Y.; Xia, X. Chemical constituents from brown alga Sargassum fusiforme Chinese Tradit. Herb. Drugs 2008, 39, 657-661
6. Yu, Z.; Shuai, L.; Li, X.; Duan, D.; Guo, Y. Regulating effect of Sargassum fusiforme (Harv.) Setch. on the level of blood lipid in experimental rats with hyperlipidemia Med. Plant 2013, 4, 54-56
7. Mao, W.; Li, B.; Gu, Q.; Fang, Y.; Xing, H. Preliminary studies on the chemical characterization and antihyperlipidemic activity of polysaccharide from the brown alga Sargassum fusiforme Hydrobiologia 2004, 512, 263-266
8. Kritchevsky, D.; Chen, S. C. Phytosterols-health benefits and potential concerns: a review Nutr. Res. (N.Y.) 2005, 25, 413-428
9. Marangoni, F.; Poli, A. Phytosterols and cardiovascular health Pharmacol. Res. 2010, 61, 193-199
10. He, W.-S.; Jia, C.-S.; Yang, Y.-B.; Ma, Y.; Zhang, X.-M.; Feng, B.; Jin, J. Cholesterol-lowering effects of plant steryl and stanyl laurate by oral administration in mice J. Agric. Food Chem. 2011, 59, 5093-5099
11. Moran-Valero, M. I.; Martin, D.; Torrelo, G.; Reglero, G.; Torres, C. F. Phytosterols esterified with conjugated linoleic acid. In vitro intestinal digestion and interaction on cholesterol bioaccessibility J. Agric. Food Chem. 2012, 60, 11323-11330
12. Eilat-Adar, S.; Sinai, T.; Yosefy, C.; Henkin, Y. Nutritional recommendations for cardiovascular disease prevention Nutrients 2013, 5, 3646-3683
13. Silbernagel, G.; Genser, B.; Nestel, P.; März, W. Plant sterols and atherosclerosis Curr. Opin. Lipidol. 2013, 24, 12-17
14. Calpe-Berdiel, L.; Escolà-Gil, J. C.; Blanco-Vaca, F. New insights into the molecular actions of plant sterols and stanols in cholesterol metabolism Atherosclerosis 2009, 203, 18-31
15. Plat, J.; Nichols, J. A.; Mensink, R. P. Plant sterols and stanols: effects on mixed micellar composition and LXR (target gene) activation J. Lipid Res. 2005, 46, 2468-2476
16. Repa, J. J.; Mangelsdorf, D. J. The liver X receptor gene team: potential new players in atherosclerosis Nat. Med. 2002, 8, 1243-1248
17. Viennois, E.; Mouzat, K.; Dufour, J.; Morel, L.; Lobaccaro, J.; Baron, S. Selective liver X receptor modulators (SLiMs): what use in human health? Mol. Cell. Endocrinol. 2012, 351, 129-141
18. Bonamassa, B.; Moschetta, A. Atherosclerosis: lessons from LXR and the intestine Trends Endocrinol. Metab. 2013, 24, 120-128
19. Calkin, A. C.; Tontonoz, P. Liver X receptor signaling pathways and atherosclerosis Arterioscler. Thromb. Vasc. Biol. 2010, 30, 1513-1518
20. Hovenkamp, E.; Demonty, I.; Plat, J.; Lütjohann, D.; Mensink, R. P.; Trautwein, E. A. Biological effects of oxidized phytosterols: a review of the current knowledge Prog. Lipid Res. 2008, 47, 37-49
21. Ikeda, I.; Tanaka, K.; Sugano, M.; Vahouny, G. V; Gallo, L. L. Inhibition of cholesterol absorption in rats by plant sterols J. Lipid Res. 1988, 29, 1573-1582
22. Song, Y.; Shan, S.; Zhang, Y.; Liu, W.; Ding, W.; Ren, W.; Xia, H.; Li, X.; Zhang, Q.; Zhao, L.; Li, X.; Yan, J.; Ying, H. Ligand-dependent corepressor acts as a novel corepressor of thyroid hormone receptor and represses hepatic lipogenesis in mice J. Hepatol. 2012, 56, 248-254
23. Williams, S.; Bledsoe, R. K.; Collins, J. L.; Boggs, S.; Lambert, M. H.; Miller, A. B.; Moore, J.; McKee, D. D.; Moore, L.; Nichols, J.; Parks, D.; Watson, M.; Wisely, B.; Willson, T. M. X-Ray crystal structure of the liver X receptor β ligand binding domain: regulation by a histidine-tryptophan switch J. Biol. Chem. 2003, 278, 27138-27143
24. Wu, Z. H.; Liu, T.; Gu, C. X.; Shao, C. L.; Zhou, J.; Wang, C. Y. Steroids and triterpenoids from the brown alga Kjellmaniella crassifolia Chem. Nat. Compd. 2012, 48, 158-160
25. Permeh, P.; Saeidnia, S.; Mashinchian-Moradi, A.; Gohari, A. R. Sterols from Sargassum oligocystum, a brown algae from the Persian Gulf, and their bioactivity Nat. Prod. Res. 2012, 26, 774-777
26. Cui, J. G.; Lin, C. W.; Zeng, L. M.; Su, J. Y. Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol Steroids 2002, 67, 1015-1019
27. Yue, J. M.; Chen, S. N.; Lin, Z. W.; Sun, H. D. Sterols from the fungus Lactarium volemus Phytochemistry 2001, 56, 801-806
28. Catalan, C. A. N.; Kokke, W. C. M. C.; Duque, C.; Djerassi, C. Synthesis of (24 R)- and (24 S)-5,28-stigmastadien-3β-ol and determination of the stereochemistry of their 24-hydroxy analogs, the saringosterols J. Org. Chem. 1983, 48, 5207-5214
29. Hoang, M. H.; Jia, Y.; Jun, H. J.; Lee, J. H.; Lee, B. Y.; Lee, S. J. Fucosterol is a selective liver X receptor modulator that regulates the expression of key genes in cholesterol homeostasis in macrophages, hepatocytes, and intestinal cells J. Agric. Food Chem. 2012, 60, 11567-11575
30. Degirolamo, C.; Moschetta, A. Casting a shadow on liver X receptor-mediated atheroprotection: is LXRβ to blame? J. Intern. Med. 2012, 272, 449-451
31. Schultz, J. R.; Tu, H.; Luk, A.; Repa, J. J.; Medina, J. C.; Li, L.; Schwendner, S.; Wang, S.; Thoolen, M.; Mangelsdorf, D. J.; Lustig, K. D.; Shan, B. Role of LXRs in control of lipogenesis Genes Dev. 2000, 14, 2831-2838
32. García-Mediavilla, M. V.; Pisonero-Vaquero, S.; Lima-Cabello, E.; Benedicto, I.; Majano, P. L.; Jorquera, F.; González-Gallego, J.; Sánchez-Campos, S. Liver X receptor α-mediated regulation of lipogenesis by core and NS5A proteins contributes to HCV-induced liver steatosis and HCV replication Lab. Invest. 2012, 92, 1191-1202
33. Hu, X.; Steffensen, K. R.; Jiang, Z.-Y.; Parini, P.; Gustafsson, J.-Å.; Gåfvels, M.; Eggertsen, G. LXRβ activation increases intestinal cholesterol absorption, leading to an atherogenic lipoprotein profile J. Intern. Med. 2012, 272, 452-464
34. Fitzgerald, M. L.; Mujawar, Z.; Tamehiro, N. ABC transporters, atherosclerosis and inflammation Atherosclerosis 2010, 211, 361-370
35. Jeon, T.-I.; Osborne, T. F. SREBPs: metabolic integrators in physiology and metabolism Trends Endocrinol. Metab. 2012, 23, 65-72
36. Ye, D.; Lammers, B.; Zhao, Y.; Meurs, I.; Van Berkel, T. J.; Van Eck, M. ATP-binding cassette transporters A1 and G1, HDL metabolism, cholesterol efflux, and inflammation: important targets for the treatment of atherosclerosis Curr. Drug Targets 2011, 12, 647-660