7176-02-5
Chemical Structure
Fucoxanthinol
- CAS No.: 7176-02-5
- Formula:C40H56O5
- Molecular Weight:616.87
IUPAC Name: 1-(tert-butyl) 3-methyl 3-allylazetidine-1,3-dicarboxylate
InChIKey: NZEPSBGUXWWWSI-VOPPYBPXSA-N
SMILES: CC(C)(C[C@@H](C[C@]1(O)C)O)C1=[C@]=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C(C[C@]23[C@](O2)(C[C@H](CC3(C)C)O)C)=O
Biological Activity: Fucoxanthinol, a carotenoid, is a deacetylated Fucoxanthin (HY-N2302) metabolite with oral activity, and inhibits rat pancreatic lipase with an IC50 of 764 nM. Fucoxanthinol reduces expression of Bcl-2, Bcl-xL, survivin, XIAP, cIAP2, cyclin D1, cyclin D2, cyclin E, CDK4, CDK6, β-catenin, JunD, PPARγ, and induces GADD45α expression. Fucoxanthinol activates caspase-3, caspase-8, caspase-9, Nrf2/Keap1/ARE pathway, and inhibits activation of Akt, NF-κB, AP-1, PDPK1, GSK3β phosphorylation. Fucoxanthinol induces apoptosis, G0/G1 cell cycle arrest, inhibits cancer cell viability, proliferation, migration, invasiveness, tumour growth, adipocyte differentiation, oxidative stress, neurotoxicity, triglyceride absorption, angiogenesis, and obesity-induced inflammation. Fucoxanthinol can be used for the research of osteosarcoma, leukemia, lymphoma, adult T-cell leukemia, prostate cancer, colon cancer, breast cancer, hypertriglyceridaemia, Alzheimer’s disease, Parkinson’s disease, obesity, insulin resistance, malignant melanoma, and type II diabetes[1][7][9][10][13][16][17].
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Fucoxanthinol | Fucoxanthinol, a carotenoid, is a deacetylated Fucoxanthin (HY-N2302) metabolite with oral activity, and inhibits rat pancreatic lipase with an IC50 of 764 nM. Fucoxanthinol reduces expression of Bcl-2, Bcl-xL, survivin, XIAP, cIAP2, cyclin D1, cyclin D2, cyclin E, CDK4, CDK6, β-catenin, JunD, PPARγ, and induces GADD45α expression. Fucoxanthinol activates caspase-3, caspase-8, caspase-9, Nrf2/Keap1/ARE pathway, and inhibits activation of Akt, NF-κB, AP-1, PDPK1, GSK3β phosphorylation. Fucoxanthinol induces apoptosis, G0/G1 cell cycle arrest, inhibits cancer cell viability, proliferation, migration, invasiveness, tumour growth, adipocyte differentiation, oxidative stress, neurotoxicity, triglyceride absorption, angiogenesis, and obesity-induced inflammation. Fucoxanthinol can be used for the research of osteosarcoma, leukemia, lymphoma, adult T-cell leukemia, prostate cancer, colon cancer, breast cancer, hypertriglyceridaemia, Alzheimer’s disease, Parkinson’s disease, obesity, insulin resistance, malignant melanoma, and type II diabetes. | |||||||||||||||||||||
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- [1]. Martin LJ, et al. Fucoxanthin and Its Metabolite Fucoxanthinol in Cancer Prevention and Treatment. Marine drugs. 2015 Jul 31;13(8):4784-98. [Content Brief]
- [7]. Matsumoto M, et al. Suppressive effects of the marine carotenoids, fucoxanthin and fucoxanthinol on triglyceride absorption in lymph duct-cannulated rats. European journal of nutrition. 2010 Jun;49(4):243-9. [Content Brief]
- [9]. Pruccoli L, et al. Antioxidant and Neuroprotective Effects of Fucoxanthin and Its Metabolite Fucoxanthinol: A Comparative In Vitro Study. Current issues in molecular biology. 2024 Jun 14;46(6):5984-5998. [Content Brief]
- [10]. Maeda H, et al. Fucoxanthin and its metabolite, fucoxanthinol, suppress adipocyte differentiation in 3T3-L1 cells. Int J Mol Med. 2006 Jul;18(1):147-52. [Content Brief]
- [13]. Maeda H, et al. Fucoxanthinol, Metabolite of Fucoxanthin, Improves Obesity-Induced Inflammation in Adipocyte Cells. Marine drugs. 2015 Aug 04;13(8):4799-813. [Content Brief]
- [16]. Takahashi K, et al. Anticancer effects of fucoxanthin and fucoxanthinol on colorectal cancer cell lines and colorectal cancer tissues. Oncology letters. 2015 Sep;10(3):1463-1467. [Content Brief]
- [17]. Tsukui T, et al. Fucoxanthin and fucoxanthinol enhance the amount of docosahexaenoic acid in the liver of KKAy obese/diabetic mice. Journal of agricultural and food chemistry. 2007 Jun 27;55(13):5025-9. [Content Brief]
Keywords