Natural Product (NP) Details

General Information of the NP (ID: NP9025)
Name
Fucoxanthin
Synonyms
all-trans-Fucoxanthin; (3'S,5'R,6'R)-3'-acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one; (3S,3'S,5R,5'R,6S,6'R)-3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-beta,beta-carotene; (3S,5R,6S,3'S,5'R,6'R)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,6-epoxy-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-3'-yl acetate; (1S,3R)-3-hydroxy-4-((3E,5E,7E,9E,11E,13E,15E)-18-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene)-3,5,5-trimethylcyclohexyl acetate; CCRIS 4055; BRN 0073179; Fucoxanthol; cis-Fucoxanthin; yl acetate; (3S,3'S,5R,5'R,6S,6'R,8'R)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,5',6,6',7,8-hexahydro-5,6-epoxy-beta,beta-caroten-3'-yl acetate; C42H58O6; Beta-sitosterol 45%; SCHEMBL37284; 5-18-04-00673 (Beilstein Handbook Reference); beta,beta-Carotene, 3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-, (3S,3'S,5R,5'R,6S,6'R)-; MLS000728353; Fucoxanthin, analytical standard; CHEMBL1575074; SJWWTRQNNRNTPU-ABBNZJFMSA-; Fucoxanthin carotenoid antioxidant; Fucoxanthin, carotenoid antioxidant; HMS2219K22; Fucoxanthin (from Wakame) (Brown Seaweed) (Undaria Pinnatifida); HY-N2302; ZINC8221218; 1772AH; LMPR01070300; MFCD01745140; AKOS037514648; CS-8167; NCGC00247434-01; AS-56344; SMR000453597; C08596; Q96385; 351F868; Fucoxanthin solution, 1 mg/L in ethanol, analytical standard; (1S,3R)-3-hydroxy-4-((3E,5E,7E,9E,11E,13E,15E)-18-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene)-3,5,5-trimethylcyclohexyl acetate; (3S,3'S,5R,5'R,6S)-3'-Acetoxy-5alpha,6alpha-epoxy-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,6,7,8-tetrahydro-beta,beta-carotene; (3S,3'S,5R,5'R,6S,6'R,8'R)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,5',6,6',7,8-hexahydro-5,6-epoxy-beta,beta-caroten-3'-
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Species Origin Saccharina japonica ...     Click to Show/Hide
Saccharina japonica
SuperKingdom: Eukaryota
Class: Phaeophyceae
Order: Laminariales
Family: Laminariaceae
Genus: Saccharina
Species: Saccharina japonica
Disease Metabolic disorder [ICD-11: 5C50-5D2Z] Phase 2 [1]
Structure
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2D MOL

3D MOL

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Formula
C42H58O6
PubChem CID
5281239
Canonical SMILES
CC(=CC=CC=C(C)C=CC=C(C)C(=O)CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=C=C3C(CC(CC3(C)O)OC(=O)C)(C)C
InChI
1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,40+,41+,42-/m0/s1
InChIKey
SJWWTRQNNRNTPU-ABBNZJFMSA-N
CAS Number
CAS 3351-86-8
Herb ID
HBIN026808
ETMC ID
7214
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation PIK3CB  Molecule Info 
Pathway MAP
                    In-vitro Model HeLa CVCL_0030 Endocervical adenocarcinoma Homo sapiens
SiHa CVCL_0032 Cervical squamous cell carcinoma Homo sapiens
Ca Ski CVCL_1100 Cervical squamous cell carcinoma Homo sapiens
                    In-vivo Model Five-week-old nude BALB/c mice were used for subcutaneous implantation of human cervical tumor cells HeLa (2*106 per site).
                    Experimental
                    Result(s)		 The combination of TRAIL with fucoxanthin showed synergistically inhibitory effects on cervical cancer cells.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction DNA damage
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
HT29 CVCL_A8EZ Colorectal adenocarcinoma Mus musculus
                    Experimental
                    Result(s)		 Since Phloroglucinol and Fucoxanthin alone reduced cancer cell line viability without an effect on normal cells and when in combination enhanced the cytotoxic effect of 5-Fu only in colon cancer cells.
Target and Pathway
Target(s) DNA-binding factor KBF1 (p105)  Molecule Info  [4]
Integrin beta-1 (ITGB1)  Molecule Info  [5]
Protein kinase B alpha (AKT1)  Molecule Info  [4]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 ErbB signaling pathway
3 Ras signaling pathway
4 Rap1 signaling pathway
5 cGMP-PKG signaling pathway
6 cAMP signaling pathway
7 Chemokine signaling pathway
8 HIF-1 signaling pathway
9 FoxO signaling pathway
10 Sphingolipid signaling pathway
11 mTOR signaling pathway
12 PI3K-Akt signaling pathway
13 AMPK signaling pathway
14 Apoptosis
15 Adrenergic signaling in cardiomyocytes
16 VEGF signaling pathway
17 Osteoclast differentiation
18 Focal adhesion
19 Tight junction
20 Signaling pathways regulating pluripotency of stem cells
21 Platelet activation
22 Toll-like receptor signaling pathway
23 Jak-STAT signaling pathway
24 T cell receptor signaling pathway
25 B cell receptor signaling pathway
26 Fc epsilon RI signaling pathway
27 Fc gamma R-mediated phagocytosis
28 TNF signaling pathway
29 Neurotrophin signaling pathway
30 Cholinergic synapse
31 Dopaminergic synapse
32 Insulin signaling pathway
33 Progesterone-mediated oocyte maturation
34 Estrogen signaling pathway
35 Prolactin signaling pathway
36 Thyroid hormone signaling pathway
37 Adipocytokine signaling pathway
38 Glucagon signaling pathway
39 Regulation of lipolysis in adipocytes
40 Non-alcoholic fatty liver disease (NAFLD)
41 Carbohydrate digestion and absorption
42 Chagas disease (American trypanosomiasis)
43 Toxoplasmosis
44 Tuberculosis
45 Hepatitis C
46 Hepatitis B
47 Measles
48 Influenza A
49 HTLV-I infection
50 Epstein-Barr virus infection
51 Pathways in cancer
52 Proteoglycans in cancer
53 Colorectal cancer
54 Renal cell carcinoma
55 Pancreatic cancer
56 Endometrial cancer
57 Glioma
58 Prostate cancer
59 Melanoma
60 Chronic myeloid leukemia
61 Acute myeloid leukemia
62 Small cell lung cancer
63 Non-small cell lung cancer
64 Central carbon metabolism in cancer
65 Choline metabolism in cancer
66 Phagosome
67 Axon guidance
68 ECM-receptor interaction
69 Cell adhesion molecules (CAMs)
70 Leukocyte transendothelial migration
71 Regulation of actin cytoskeleton
72 Bacterial invasion of epithelial cells
73 Pathogenic Escherichia coli infection
74 Shigellosis
75 Pertussis
76 Leishmaniasis
77 Hypertrophic cardiomyopathy (HCM)
78 Arrhythmogenic right ventricular cardiomyopathy (ARVC)
79 Dilated cardiomyopathy
80 NF-kappa B signaling pathway
81 NOD-like receptor signaling pathway
82 RIG-I-like receptor signaling pathway
83 Cytosolic DNA-sensing pathway
84 Cocaine addiction
85 Epithelial cell signaling in Helicobacter pylori infection
86 Salmonella infection
87 Legionellosis
88 Amoebiasis
89 Herpes simplex infection
90 Transcriptional misregulation in cancer
91 Viral carcinogenesis
92 MicroRNAs in cancer
93 Inflammatory bowel disease (IBD)
NetPath Pathway TSH Signaling Pathway Click to Show/Hide
2 IL5 Signaling Pathway
3 IL1 Signaling Pathway
4 TCR Signaling Pathway
5 IL2 Signaling Pathway
6 TNFalpha Signaling Pathway
7 Leptin Signaling Pathway
Panther Pathway Angiogenesis Click to Show/Hide
2 Apoptosis signaling pathway
3 EGF receptor signaling pathway
4 Endothelin signaling pathway
5 FGF signaling pathway
6 Huntington disease
7 Hypoxia response via HIF activation
8 Inflammation mediated by chemokine and cytokine signaling pathway
9 Insulin/IGF pathway-protein kinase B signaling cascade
10 Interleukin signaling pathway
11 PI3 kinase pathway
12 T cell activation
13 VEGF signaling pathway
14 p53 pathway
15 Ras Pathway
16 p53 pathway by glucose deprivation
17 p53 pathway feedback loops 2
18 CCKR signaling map ST
19 Integrin signalling pathway
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
2 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
3 Fc Epsilon Receptor I Signaling in Mast Cells
4 Insulin Signalling
5 Leucine Stimulation on Insulin Signaling
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Fc-epsilon receptor I signaling in mast cells
3 Endothelins
4 BCR signaling pathway
5 LPA receptor mediated events
6 Insulin Pathway
7 IL4-mediated signaling events
8 TCR signaling in na&#xef
9
10 Plasma membrane estrogen receptor signaling
11 CD40/CD40L signaling
12 Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met)
13 Signaling events mediated by PTP1B
14 S1P3 pathway
15 Coregulation of Androgen receptor activity
16 Reelin signaling pathway
17 Integrin-linked kinase signaling
18 TCR signaling in na&#xef
19
20 Angiopoietin receptor Tie2-mediated signaling
21 FAS (CD95) signaling pathway
22 Thromboxane A2 receptor signaling
23 Regulation of Telomerase
24 FOXA2 and FOXA3 transcription factor networks
25 Glucocorticoid receptor regulatory network
26 mTOR signaling pathway
27 CXCR4-mediated signaling events
28 IGF1 pathway
29 FoxO family signaling
30 IL2 signaling events mediated by PI3K
31 Ceramide signaling pathway
32 p75(NTR)-mediated signaling
33 E-cadherin signaling in the nascent adherens junction
34 amb2 Integrin signaling
35 Integrins in angiogenesis
36 IFN-gamma pathway
37 ErbB1 downstream signaling
38 ErbB2/ErbB3 signaling events
39 IL6-mediated signaling events
40 E-cadherin signaling in keratinocytes
41 Nephrin/Neph1 signaling in the kidney podocyte
42 Retinoic acid receptors-mediated signaling
43 IL8- and CXCR2-mediated signaling events
44 Signaling events mediated by the Hedgehog family
45 Nongenotropic Androgen signaling
46 Hedgehog signaling events mediated by Gli proteins
47 Caspase Cascade in Apoptosis
48 CXCR3-mediated signaling events
49 VEGFR1 specific signals
50 Signaling events mediated by Stem cell factor receptor (c-Kit)
51 Signaling events mediated by VEGFR1 and VEGFR2
52 a6b1 and a6b4 Integrin signaling
53 Aurora A signaling
54 Insulin-mediated glucose transport
55 Class I PI3K signaling events mediated by Akt
56 IL8- and CXCR1-mediated signaling events
57 HIF-1-alpha transcription factor network
58 p53 pathway
59 Trk receptor signaling mediated by PI3K and PLC-gamma
60 VEGFR3 signaling in lymphatic endothelium
61 FGF signaling pathway
62 Signaling events mediated by PRL
63 RhoA signaling pathway
64 Beta1 integrin cell surface interactions
65 Integrin family cell surface interactions
66 Arf6 trafficking events
67 Signaling events mediated by TCPTP
68 Alpha9 beta1 integrin signaling events
69 Plexin-D1 Signaling
70 Syndecan-4-mediated signaling events
71 Urokinase-type plasminogen activator (uPA) and uPAR-mediated signaling
72 a4b7 Integrin signaling
73 Syndecan-2-mediated signaling events
74 Validated targets of C-MYC transcriptional repression
75 Alpha4 beta1 integrin signaling events
76 Signaling events mediated by focal adhesion kinase
77 Atypical NF-kappaB pathway
78 Canonical NF-kappaB pathway
79 IL12-mediated signaling events
80 Alternative NF-kappaB pathway
81 Osteopontin-mediated events
82 Signaling events mediated by HDAC Class I
83 IL1-mediated signaling events
84 TNF receptor signaling pathway
85 IL23-mediated signaling events
86 HIV-1 Nef: Negative effector of Fas and TNF-alpha
87 EPO signaling pathway
Reactome Activation of BAD and translocation to mitochondria Click to Show/Hide
2 GPVI-mediated activation cascade
3 PIP3 activates AKT signaling
4 Translocation of GLUT4 to the plasma membrane
5 Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
6 AKT phosphorylates targets in the cytosol
7 AKT phosphorylates targets in the nucleus
8 Negative regulation of the PI3K/AKT network
9 eNOS activation
10 AKT-mediated inactivation of FOXO1A
11 Integrin alphaIIb beta3 signaling
12 Deactivation of the beta-catenin transactivating complex
13 CD28 dependent PI3K/Akt signaling
14 CTLA4 inhibitory signaling
15 G beta:gamma signalling through PI3Kgamma
16 KSRP (KHSRP) binds and destabilizes mRNA
17 VEGFR2 mediated vascular permeability
18 TP53 Regulates Metabolic Genes
19 Constitutive Signaling by AKT1 E17K in Cancer
20 Elastic fibre formation
21 Fibronectin matrix formation
22 Immunoregulatory interactions between a Lymphoid and a non-Lymphoid cell
23 Cell surface interactions at the vascular wall
24 Basigin interactions
25 Molecules associated with elastic fibres
26 Integrin cell surface interactions
27 Laminin interactions
28 Syndecan interactions
29 ECM proteoglycans
30 Other semaphorin interactions
31 Localization of the PINCH-ILK-PARVIN complex to focal adhesions
32 CHL1 interactions
33 RHO GTPases Activate Formins
34 Platelet Adhesion to exposed collagen
35 Activation of NF-kappaB in B cells
36 RIP-mediated NFkB activation via ZBP1
37 Regulated proteolysis of p75NTR
38 NF-kB is activated and signals survival
39 Senescence-Associated Secretory Phenotype (SASP)
40 FCERI mediated NF-kB activation
41 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
42 Transcriptional regulation of white adipocyte differentiation
43 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
44 Interleukin-1 processing
45 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
46 IkBA variant leads to EDA-ID
47 CLEC7A (Dectin-1) signaling
48 CD209 (DC-SIGN) signaling
49 CLEC7A/inflammasome pathway
50 MAP3K8 (TPL2)-dependent MAPK1/3 activation
51 TRAF6 mediated NF-kB activation
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 DNA Damage Response (only ATM dependent)
3 TCR Signaling Pathway
4 Notch Signaling Pathway
5 EPO Receptor Signaling
6 IL-2 Signaling Pathway
7 Insulin Signaling
8 Endochondral Ossification
9 EGF/EGFR Signaling Pathway
10 IL-4 Signaling Pathway
11 TGF beta Signaling Pathway
12 IL-6 signaling pathway
13 Wnt Signaling Pathway Netpath
14 Copper homeostasis
15 Extracellular vesicle-mediated signaling in recipient cells
16 Apoptosis-related network due to altered Notch3 in ovarian cancer
17 IL-3 Signaling Pathway
18 Cardiac Hypertrophic Response
19 Translocation of GLUT4 to the Plasma Membrane
20 Regulation of mRNA Stability by Proteins that Bind AU-rich Elements
21 PIP3 activates AKT signaling
22 Signal Transduction of S1P Receptor
23 T-Cell Receptor and Co-stimulatory Signaling
24 Primary Focal Segmental Glomerulosclerosis FSGS
25 Apoptosis
26 Alpha 6 Beta 4 signaling pathway
27 BDNF signaling pathway
28 Integrated Pancreatic Cancer Pathway
29 Oncostatin M Signaling Pathway
30 Corticotropin-releasing hormone
31 Interleukin-11 Signaling Pathway
32 AGE/RAGE pathway
33 TNF alpha Signaling Pathway
34 B Cell Receptor Signaling Pathway
35 Prostate Cancer
36 Signaling Pathways in Glioblastoma
37 TSLP Signaling Pathway
38 IL17 signaling pathway
39 IL-7 Signaling Pathway
40 Regulation of Microtubule Cytoskeleton
41 TWEAK Signaling Pathway
42 FSH signaling pathway
43 Leptin signaling pathway
44 TSH signaling pathway
45 RANKL/RANK Signaling Pathway
46 Integrated Breast Cancer Pathway
47 SREBP signalling
48 Integrated Cancer pathway
49 IL-1 signaling pathway
50 Metabolism of nitric oxide
51 Integrin-mediated Cell Adhesion
52 TFs Regulate miRNAs related to cardiac hypertrophy
53 MicroRNAs in cardiomyocyte hypertrophy
54 Angiogenesis
55 TOR Signaling
56 Regulation of toll-like receptor signaling pathway
57 AMPK Signaling
58 Androgen receptor signaling pathway
59 IL-5 Signaling Pathway
60 Signaling of Hepatocyte Growth Factor Receptor
61 Focal Adhesion
62 Hair Follicle Development: Organogenesis (Part 2 of 3)
63 Extracellular matrix organization
64 Elastic fibre formation
65 Nanoparticle-mediated activation of receptor signaling
66 JAK/STAT
67 Pathogenic Escherichia coli infection
68 Arrhythmogenic Right Ventricular Cardiomyopathy
69 Neural Crest Differentiation
70 Semaphorin interactions
71 Platelet Adhesion to exposed collagen
72 L1CAM interactions
73 Integrin cell surface interactions
74 Immunoregulatory interactions between a Lymphoid and a non-Lymphoid cell
75 Cell surface interactions at the vascular wall
76 Cell junction organization
77 SIDS Susceptibility Pathways
78 TGF Beta Signaling Pathway
79 Oxidative Stress
80 Apoptosis Modulation by HSP70
81 MAPK Signaling Pathway
82 Myometrial Relaxation and Contraction Pathways
83 IL1 and megakaryotyces in obesity
84 Hair Follicle Development: Cytodifferentiation (Part 3 of 3)
85 Hair Follicle Development: Induction (Part 1 of 3)
86 Selenium Metabolism and Selenoproteins
87 Cytosolic sensors of pathogen-associated DNA
88 Fc epsilon receptor (FCERI) signaling
89 Transcriptional Regulation of White Adipocyte Differentiation
90 Signaling by the B Cell Receptor (BCR)
91 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
92 Structural Pathway of Interleukin 1 (IL-1)
93 EBV LMP1 signaling
94 Aryl Hydrocarbon Receptor
95 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
96 Signalling by NGF
97 TCR signaling
98 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
99 Interleukin-1 signaling
100 Interleukin-1 processing
101 Apoptosis Modulation and Signaling
102 Folate Metabolism
103 Vitamin B12 Metabolism
104 Selenium Micronutrient Network
105 Osteopontin Signaling
References
Reference 1 ClinicalTrials.gov (NCT03613740) Effect of Fucoxanthin on the Metabolic Syndrome, Insulin Sensitivity and Insulin Secretion
Reference 2 Sensitization of TRAIL-resistant cervical cancer cells through combination of TRAIL and fucoxanthin treatments. Eur Rev Med Pharmacol Sci. 2017 Dec;21(24):5594-5601.
Reference 3 Anticancer effects of seaweed compounds fucoxanthin and phloroglucinol, alone and in combination with 5-fluorouracil in colon cells. J Toxicol Environ Health A. 2017;80(13-15):776-787.
Reference 4 Fucoxanthin and its deacetylated product, fucoxanthinol, induce apoptosis of primary effusion lymphomas. Cancer Lett. 2011 Jan 28;300(2):225-34.
Reference 5 Dietary Fucoxanthin Induces Anoikis in Colorectal Adenocarcinoma by Suppressing Integrin Signaling in a Murine Colorectal Cancer Model. J Clin Med. 2019 Dec 29;9(1):90.
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