Natural Product (NP) Details

General Information of the NP (ID: NP8625)
Name
Gamma tocotrienol
Synonyms
gamma-Tocotrienol; 14101-61-2; Gama-Tocotrienol; Plastochromanol 3; UNII-185QAE24TR; D-gamma-Tocotrienol; 7,8-Dimethyltocotrienol; 185QAE24TR; CHEBI:33277; (2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol; (R-(E,E))-3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol; .gamma.-Tocotrienol; (R)-2,7,8-Trimethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)chroman-6-ol; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, (R-(E,E))-; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-; 2H-1-benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-; 2R,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol; Plastochromanol; 2R-gamma-tocotrienol; (R)-gamma-Tocotrienol; D-.gamma.-Tocotrienol; (R)-.gamma.-Tocotrienol; BIDD:PXR0016; CHEMBL120697; SCHEMBL3272929; SCHEMBL16430897; DTXSID101019984; HMS3650C14; ZINC3791929; 1715AH; LMPR02020057; gamma-Tocotrienol, analytical standard; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-tr imethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI); HY-108694; CS-0029988; C14155; D-gamma-Tocotrienol, analytical reference material; SR-01000946268; SR-01000946268-1; Q15633932; UNII-KP2MW85SSQ component OTXNTMVVOOBZCV-WAZJVIJMSA-N; (R)-2,7,8-trimethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-ol; 6-Chromanol, 2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-; 6-Chromanol, 2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)- (7CI,8CI); (2R)-2,7,8-trimethyl-2-(4',8',12'-trimethyl-trideca-3',7',11'-trienyl)-6-hydroxychroman; (2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol; 153831-49-3; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-, (2R)-; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)
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Species Origin Bixa orellana ...     Click to Show/Hide
Bixa orellana
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malvales
Family: Bixaceae
Genus: Bixa
Species: Bixa orellana
Disease Prostate cancer [ICD-11: 2C82] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C28H42O2
PubChem CID
5282349
Canonical SMILES
CC1=C(C=C2CCC(OC2=C1C)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)O
InChI
1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1
InChIKey
OTXNTMVVOOBZCV-WAZJVIJMSA-N
CAS Number
CAS 14101-61-2
ChEBI ID
CHEBI:33277
TTD Drug ID
D09YBF
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          GW9662      Breast 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 Expression CCND1  Molecule Info 
Pathway MAP
Down-regulation Expression CDK4  Molecule Info 
Pathway MAP
Down-regulation Expression CDK6  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression HPGDS  Molecule Info 
Pathway MAP
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
MDA-231 Breast cancer Homo sapiens
Neoplastic +SA cells derived from a mammary adenocarcinoma Mammary Adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combined Gamma -tocotrienol and PPAR Gamma antagonists treatment in PPAR Gamma negative/silenced breast cancer cells are mediated through PPAR Gamma -independent mechanisms that are associated with a downregulation in COX-2, PGDS, and PGD2 synthesis.
          Pravastatin      Hyper-lipoproteinaemia     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
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation JNK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation p38 beta  Molecule Info 
Pathway MAP
                    In-vitro Model Neoplastic mouse +SA mammary epithelial cells Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Treatment with subeffective doses of pravastatin or gamma-tocotrienol alone had no effect, whereas combined treatment of these compounds resulted in a relatively large decrease in intracellular levels of phosphorylated (activated) MAPK, JNK, p38, and Akt.
          Simvastatin      Hyper-lipoproteinaemia     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
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation JNK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation p38 beta  Molecule Info 
Pathway MAP
                    In-vitro Model Neoplastic mouse +SA mammary epithelial cells Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Treatment with subeffective doses of simvastatin or gamma-tocotrienol alone had no effect, whereas combined treatment of these compounds resulted in a relatively large decrease in intracellular levels of phosphorylated (activated) MAPK, JNK, p38, and Akt.
          Celecoxib      Rheumatoid arthritis     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
                    In-vitro Model +SA mammary epithelial cells' Healthy Homo sapiens
                    Experimental
                    Result(s)		 Combined low dose treatment of Gamma-tocotrienol and celecoxibthe showed synergistic antiproliferative effects of against +SA mammary tumor cells in culture.
          Atorvastatin      Cardiovascular disease     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Inhibition Mevalonate pathway
                    In-vitro Model NCI-H2052 CVCL_1518 Pleural sarcomatoid mesothelioma Homo sapiens
NCI-H28 CVCL_1555 Pleural sarcomatoid mesothelioma Homo sapiens
NCI-H2452 CVCL_1553 Pleural biphasic mesothelioma Homo sapiens
MSTO-211H CVCL_1430 Pleural biphasic mesothelioma Homo sapiens
                    Experimental
                    Result(s)		 Statin + Gamma-T3 combinations induced greater cell growth inhibition more than each single treatment via inhibition of mevalonate pathway, a well-known target of both Gamma-T3 and statins.
          Mevastatin      Diabetic foot ulcer     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
                    In-vitro Model Neoplastic mouse +SA mammary epithelial cells Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Treatment with subeffective doses of mevastatin or gamma-tocotrienol alone had no effect, whereas combined treatment of these compounds resulted in a relatively large decrease in intracellular levels of phosphorylated (activated) MAPK, JNK, p38, and Akt.
          Lovastatin      Hyper-lipoproteinaemia     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
                    In-vitro Model Neoplastic mouse +SA mammary epithelial cells Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Treatment with subeffective doses of Lovastatin or gamma-tocotrienol alone had no effect, whereas combined treatment of these compounds resulted in a relatively large decrease in intracellular levels of phosphorylated (activated) MAPK, JNK, p38, and Akt.
          Atorvastatin + Celecoxib     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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Induction Cell cycle arrest in G0/G1 phase
Increase DNA fragmentation
                    In-vitro Model HT29 CVCL_A8EZ Colorectal adenocarcinoma Mus musculus
HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Atorvastatin with gamma-tocotrienol and celecoxib exhibited a strong synergy against human colon cancer cells in causing cell cycle arrest and apoptosis.
References
Reference 1 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
Reference 2 Synergistic Antiproliferative Effects of Combined Gamma -Tocotrienol and PPAR Gamma Antagonist Treatment Are Mediated through PPAR Gamma -Independent Mechanisms in Breast Cancer Cells. PPAR Res. 2014;2014:439146.
Reference 3 Synergistic antiproliferative effects of gamma-tocotrienol and statin treatment on mammary tumor cells. Lipids. 2007 Dec;42(12):1113-23.
Reference 4 Synergistic anticancer effects of combined gamma-tocotrienol and celecoxib treatment are associated with suppression in Akt and NFkappaB signaling. Biomed Pharmacother. 2010 May;64(5):327-32.
Reference 5 Synergistic effect of combined treatment with gamma-tocotrienol and statin on human malignant mesothelioma cells. Cancer Lett. 2013 Oct 1;339(1):116-27.
Reference 6 Synergistic actions of atorvastatin with gamma-tocotrienol and celecoxib against human colon cancer HT29 and HCT116 cells. Int J Cancer. 2010 Feb 15;126(4):852-63.
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