Fucosterol | CAS#17605-67-3 | anti-inflammatory

MedKoo Cat#: 584404 | Name: Fucosterol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fucosterol has been reported to have antioxidant, antidiabetic, and anti-inflammatory effects. In one study, fucosterol exhibited a protective effect on LPS-induced acute lung injury with a possible mechanism inhibiting NF-κB activation, thereby inhibiting LPS-induced inflammatory response.

Chemical Structure

Fucosterol

CAS#17605-67-3

Theoretical Analysis

MedKoo Cat#: 584404

Name: Fucosterol

CAS#: 17605-67-3

Chemical Formula: C29H48O

Exact Mass: 412.3705

Molecular Weight: 412.70

Elemental Analysis: C, 84.40; H, 11.72; O, 3.88

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Related CAS #

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Synonym

Fucosterol; Fucosterin; (24E)-24-N-Propylidenecholesterol; trans-24-Ethylidenecholesterol; trans-24-ethylidene Cholesterol

IUPAC/Chemical Name

Stigmasta-5,24(28)-dien-3-ol, (3beta,24E)-

InChi Key

OSELKOCHBMDKEJ-JUGJNGJRSA-N

InChi Code

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

SMILES Code

C/C=C(C(C)C)\CC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities.

In vitro activity:

The protective effect of fucosterol (FST) on PM-induced macrophages are demonstrated in Figure 2. Cell viability, which was significantly affected by PM, recovered with FST exhibiting its cytoprotective effect. NO production, which was upregulated via PM, was significantly and dose-dependently downregulated through treatment with FST. Reference: Mar Drugs. 2020 Dec; 18(12): 628. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7763233/

In vivo activity:

Furthermore, this study examined vascular formation in transgenic zebrafish (fli1:EGFP) treated with fucosterol to examine the anti-angiogenic effects in vivo (Figure 8C). The vasculature of the dorsal longitudinal anastomotic vessel, intersegmental vessel, and parts of the dorsal aorta was interrupted in the fli1 transgenic zebrafish embryos following exposure to fucosterol. These results indicated that fucosterol inhibited tumorigenesis and angiogenesis without cytotoxicity in vivo. Reference: Mar Drugs. 2020 May; 18(5): 261. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7281529/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	2.42
	Ethanol	8.5	20.50

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 412.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jayawardena TU, Sanjeewa KKA, Lee HG, Nagahawatta DP, Yang HW, Kang MC, Jeon YJ. Particulate Matter-Induced Inflammation/Oxidative Stress in Macrophages: Fucosterol from Padina boryana as a Potent Protector, Activated via NF-κB/MAPK Pathways and Nrf2/HO-1 Involvement. Mar Drugs. 2020 Dec 9;18(12):628. doi: 10.3390/md18120628. PMID: 33317054; PMCID: PMC7763233. 2. Oh JH, Choi JS, Nam TJ. Fucosterol from an Edible Brown Alga Ecklonia stolonifera Prevents Soluble Amyloid Beta-Induced Cognitive Dysfunction in Aging Rats. Mar Drugs. 2018 Oct 5;16(10):368. doi: 10.3390/md16100368. PMID: 30301140; PMCID: PMC6213915. 3. Bae H, Lee JY, Song G, Lim W. Fucosterol Suppresses the Progression of Human Ovarian Cancer by Inducing Mitochondrial Dysfunction and Endoplasmic Reticulum Stress. Mar Drugs. 2020 May 16;18(5):261. doi: 10.3390/md18050261. PMID: 32429354; PMCID: PMC7281529. 4. Mao Z, Shen X, Dong P, Liu G, Pan S, Sun X, Hu H, Pan L, Huang J. Fucosterol exerts antiproliferative effects on human lung cancer cells by inducing apoptosis, cell cycle arrest and targeting of Raf/MEK/ERK signalling pathway. Phytomedicine. 2019 Aug;61:152809. doi: 10.1016/j.phymed.2018.12.032. Epub 2018 Dec 24. PMID: 31035050.

In vitro protocol:

In vivo protocol:

1. Bae H, Lee JY, Song G, Lim W. Fucosterol Suppresses the Progression of Human Ovarian Cancer by Inducing Mitochondrial Dysfunction and Endoplasmic Reticulum Stress. Mar Drugs. 2020 May 16;18(5):261. doi: 10.3390/md18050261. PMID: 32429354; PMCID: PMC7281529. 2. Mao Z, Shen X, Dong P, Liu G, Pan S, Sun X, Hu H, Pan L, Huang J. Fucosterol exerts antiproliferative effects on human lung cancer cells by inducing apoptosis, cell cycle arrest and targeting of Raf/MEK/ERK signalling pathway. Phytomedicine. 2019 Aug;61:152809. doi: 10.1016/j.phymed.2018.12.032. Epub 2018 Dec 24. PMID: 31035050.

1: Li Y, Li X, Liu G, Sun R, Wang L, Wang J, Wang H. Fucosterol attenuates lipopolysaccharide-induced acute lung injury in mice. J Surg Res. 2015 May 15;195(2):515-21. doi: 10.1016/j.jss.2014.12.054. Epub 2015 Jan 10. PubMed PMID: 25818525. 2: Hoang MH, Jia Y, Jun HJ, Lee JH, Lee BY, Lee SJ. 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 Nov 21;60(46):11567-75. doi: 10.1021/jf3019084. Epub 2012 Nov 8. PubMed PMID: 23116181. 3: Ji YB, Ji CF, Yue L. Study on human promyelocytic leukemia HL-60 cells apoptosis induced by fucosterol. Biomed Mater Eng. 2014;24(1):845-51. doi: 10.3233/BME-130876. PubMed PMID: 24211971. 4: Choi JS, Han YR, Byeon JS, Choung SY, Sohn HS, Jung HA. Protective effect of fucosterol isolated from the edible brown algae, Ecklonia stolonifera and Eisenia bicyclis, on tert-butyl hydroperoxide- and tacrine-induced HepG2 cell injury. J Pharm Pharmacol. 2015 Aug;67(8):1170-8. doi: 10.1111/jphp.12404. Epub 2015 Mar 13. PubMed PMID: 25773602. 5: Sun Z, Mohamed MAA, Park SY, Yi TH. Fucosterol protects cobalt chloride induced inflammation by the inhibition of hypoxia-inducible factor through PI3K/Akt pathway. Int Immunopharmacol. 2015 Dec;29(2):642-647. doi: 10.1016/j.intimp.2015.09.016. Epub 2015 Sep 26. PubMed PMID: 26395918. 6: Yoo MS, Shin JS, Choi HE, Cho YW, Bang MH, Baek NI, Lee KT. Fucosterol isolated from Undaria pinnatifida inhibits lipopolysaccharide-induced production of nitric oxide and pro-inflammatory cytokines via the inactivation of nuclear factor-κB and p38 mitogen-activated protein kinase in RAW264.7 macrophages. Food Chem. 2012 Dec 1;135(3):967-75. doi: 10.1016/j.foodchem.2012.05.039. Epub 2012 May 11. PubMed PMID: 22953812. 7: Zhen XH, Quan YC, Jiang HY, Wen ZS, Qu YL, Guan LP. Fucosterol, a sterol extracted from Sargassum fusiforme, shows antidepressant and anticonvulsant effects. Eur J Pharmacol. 2015 Dec 5;768:131-8. doi: 10.1016/j.ejphar.2015.10.041. Epub 2015 Oct 26. PubMed PMID: 26515446. 8: Jung HA, Bhakta HK, Min BS, Choi JS. Fucosterol activates the insulin signaling pathway in insulin resistant HepG2 cells via inhibiting PTP1B. Arch Pharm Res. 2016 Oct;39(10):1454-1464. Epub 2016 Aug 20. PubMed PMID: 27544192. 9: Kim MS, Oh GH, Kim MJ, Hwang JK. Fucosterol inhibits matrix metalloproteinase expression and promotes type-1 procollagen production in UVB-induced HaCaT cells. Photochem Photobiol. 2013 Jul-Aug;89(4):911-8. doi: 10.1111/php.12061. Epub 2013 Mar 18. PubMed PMID: 23418792. 10: Terasaki M, Hirose A, Narayan B, Baba Y, Kawagoe C, Yasui H, Saga N, Hosokawa M, Miyashita K. EVALUATION OF RECOVERABLE FUNCTIONAL LIPID COMPONENTS OF SEVERAL BROWN SEAWEEDS (PHAEOPHYTA) FROM JAPAN WITH SPECIAL REFERENCE TO FUCOXANTHIN AND FUCOSTEROL CONTENTS(1). J Phycol. 2009 Aug;45(4):974-80. doi: 10.1111/j.1529-8817.2009.00706.x. Epub 2009 Jul 28. PubMed PMID: 27034228. 11: Hwang E, Park SY, Sun ZW, Shin HS, Lee DG, Yi TH. The protective effects of fucosterol against skin damage in UVB-irradiated human dermal fibroblasts. Mar Biotechnol (NY). 2014 Jun;16(3):361-70. doi: 10.1007/s10126-013-9554-8. Epub 2013 Oct 20. PubMed PMID: 24142195. 12: Lee S, Lee YS, Jung SH, Kang SS, Shin KH. Anti-oxidant activities of fucosterol from the marine algae Pelvetia siliquosa. Arch Pharm Res. 2003 Sep;26(9):719-22. PubMed PMID: 14560919. 13: Jung HA, Islam MN, Lee CM, Oh SH, Lee S, Jung JH, Choi JS. Kinetics and molecular docking studies of an anti-diabetic complication inhibitor fucosterol from edible brown algae Eisenia bicyclis and Ecklonia stolonifera. Chem Biol Interact. 2013 Oct 25;206(1):55-62. doi: 10.1016/j.cbi.2013.08.013. Epub 2013 Aug 29. PubMed PMID: 23994501. 14: Fujimoto Y, Morisaki M, Ikekawa N. Stereochemical importance of fucosterol epoxide in the conversion of sitosterol into cholesterol in the silkworm Bombyx mori. Biochemistry. 1980 Mar 18;19(6):1065-9. PubMed PMID: 7370223. 15: Hagiwara H, Wakita K, Inada Y, Hirose S. Fucosterol decreases angiotensin converting enzyme levels with reduction of glucocorticoid receptors in endothelial cells. Biochem Biophys Res Commun. 1986 Aug 29;139(1):348-52. PubMed PMID: 3021129. 16: Mansour MP, Shrestha P, Belide S, Petrie JR, Nichols PD, Singh SP. Characterization of oilseed lipids from "DHA-producing Camelina sativa": a new transformed land plant containing long-chain omega-3 oils. Nutrients. 2014 Feb 21;6(2):776-89. doi: 10.3390/nu6020776. PubMed PMID: 24566436; PubMed Central PMCID: PMC3942731. 17: Acartürk F, Imai T, Saito H, Ishikawa M, Otagiri M. Comparative study on inclusion complexation of maltosyl-beta-cyclodextrin, heptakis(2,6-di-O-methyl)-beta-cyclodextrin and beta-cyclodextrin with fucosterol in aqueous and solid state. J Pharm Pharmacol. 1993 Dec;45(12):1028-32. PubMed PMID: 7908969. 18: Lee DG, Park SY, Chung WS, Park JH, Shin HS, Hwang E, Kim IH, Yi TH. The bone regenerative effects of fucosterol in in vitro and in vivo models of postmenopausal osteoporosis. Mol Nutr Food Res. 2014 Jun;58(6):1249-57. doi: 10.1002/mnfr.201300319. Epub 2014 Mar 7. PubMed PMID: 24604889. 19: Khanavi M, Gheidarloo R, Sadati N, Ardekani MR, Nabavi SM, Tavajohi S, Ostad SN. Cytotoxicity of fucosterol containing fraction of marine algae against breast and colon carcinoma cell line. Pharmacogn Mag. 2012 Jan;8(29):60-4. doi: 10.4103/0973-1296.93327. PubMed PMID: 22438665; PubMed Central PMCID: PMC3307205. 20: Jung HA, Jung HJ, Jeong HY, Kwon HJ, Kim MS, Choi JS. Anti-adipogenic activity of the edible brown alga Ecklonia stolonifera and its constituent fucosterol in 3T3-L1 adipocytes. Arch Pharm Res. 2014 Jun;37(6):713-20. doi: 10.1007/s12272-013-0237-9. Epub 2013 Sep 8. PubMed PMID: 24014306.