phytol

Summary

Summary: Acyclic diterpene used in making synthetic forms of vitamin E and vitamin K1.

Top Publications

  1. Ischebeck T, Zbierzak A, Kanwischer M, Dormann P. A salvage pathway for phytol metabolism in Arabidopsis. J Biol Chem. 2006;281:2470-7 pubmed
    ..During senescence, chlorophyll is hydrolyzed, resulting in the release of free phytol and chlorophyllide...
  2. van den Brink D, Wanders R. Phytanic acid: production from phytol, its breakdown and role in human disease. Cell Mol Life Sci. 2006;63:1752-65 pubmed
    ..This review will centre on this research on phytanic acid: its origin, the mechanism by which its alpha-oxidation takes place, its role in human disease and the way it is produced from phytol.
  3. Ashibe B, Hirai T, Higashi K, Sekimizu K, Motojima K. Dual subcellular localization in the endoplasmic reticulum and peroxisomes and a vital role in protecting against oxidative stress of fatty aldehyde dehydrogenase are achieved by alternative splicing. J Biol Chem. 2007;282:20763-73 pubmed
    ..A gas chromatography-mass spectrometry-based analysis of metabolites in FALDH-expressing cells incubated with phytol or phytanic acid showed that FALDH-V, not FALDH-N, is the key aldehyde dehydrogenase in the degradation pathway ..
  4. Gloerich J, Ruiter J, van den Brink D, Ofman R, Ferdinandusse S, Wanders R. Peroxisomal trans-2-enoyl-CoA reductase is involved in phytol degradation. FEBS Lett. 2006;580:2092-6 pubmed
    b>Phytol is a naturally occurring precursor of phytanic acid. The last step in the conversion of phytol to phytanoyl-CoA is the reduction of phytenoyl-CoA mediated by an, as yet, unidentified enzyme...
  5. Gloerich J, van den Brink D, Ruiter J, van Vlies N, Vaz F, Wanders R, et al. Metabolism of phytol to phytanic acid in the mouse, and the role of PPARalpha in its regulation. J Lipid Res. 2007;48:77-85 pubmed
    b>Phytol, a branched-chain fatty alcohol, is the naturally occurring precursor of phytanic and pristanic acid, branched-chain fatty acids that are both ligands for the nuclear hormone receptor peroxisome proliferator-activated receptor ..
  6. Vavilin D, Vermaas W. Continuous chlorophyll degradation accompanied by chlorophyllide and phytol reutilization for chlorophyll synthesis in Synechocystis sp. PCC 6803. Biochim Biophys Acta. 2007;1767:920-9 pubmed
    ..pools were detected that differed markedly in the amount of 13C incorporated into the porphyrin (Por) and phytol (Phy) moieties of the molecule...
  7. van den Brink D, van Miert J, Dacremont G, Rontani J, Jansen G, Wanders R. Identification of fatty aldehyde dehydrogenase in the breakdown of phytol to phytanic acid. Mol Genet Metab. 2004;82:33-7 pubmed
    b>Phytol is a branched chain fatty alcohol, which is abundantly present in nature as part of the chlorophyll molecule...
  8. Bang M, Choi S, Jang T, Kim S, Kwon O, Kang T, et al. Phytol, SSADH inhibitory diterpenoid of Lactuca sativa. Arch Pharm Res. 2002;25:643-6 pubmed
    ..from the EtOAc fraction of Lactuca sativa through repeated column chromatography; then, it was identified as phytol, a diterpenoid, based on the interpretation of several spectral data...
  9. Schluter A, Giralt M, Iglesias R, Villarroya F. Phytanic acid, but not pristanic acid, mediates the positive effects of phytol derivatives on brown adipocyte differentiation. FEBS Lett. 2002;517:83-6 pubmed
    The phytol derivatives phytanic acid and pristanic acid may activate nuclear hormone receptors and influence gene expression and cell differentiation. Phytanic acid induces brown adipocyte differentiation...

More Information

Publications93

  1. McGinty D, Letizia C, Api A. Fragrance material review on phytol. Food Chem Toxicol. 2010;48 Suppl 3:S59-63 pubmed publisher
    A toxicological and dermatologic review of phytol when used as a fragrance ingredient is presented.
  2. Ryu K, Choi J, Chung S, Kim D. Anti-scratching behavioral effect of the essential oil and phytol isolated from Artemisia princeps Pamp. in mice. Planta Med. 2011;77:22-6 pubmed publisher
    The anti-scratching behavioral effect of the essential oil and phytol isolated from Artemisia princeps Pamp. (AP, family Asteraceae), which is widely used in traditional medicine for inflammatory diseases, was investigated IN VIVO...
  3. Gloerich J, van Vlies N, Jansen G, Denis S, Ruiter J, van Werkhoven M, et al. A phytol-enriched diet induces changes in fatty acid metabolism in mice both via PPARalpha-dependent and -independent pathways. J Lipid Res. 2005;46:716-26 pubmed
    ..effects of these physiological compounds in vivo, wild-type and PPARalpha-deficient (PPARalpha-/-) mice were fed a phytol-enriched diet...
  4. Inoue Y, Hada T, Shiraishi A, Hirose K, Hamashima H, Kobayashi S. Biphasic effects of geranylgeraniol, teprenone, and phytol on the growth of Staphylococcus aureus. Antimicrob Agents Chemother. 2005;49:1770-4 pubmed
    ..activities against Staphylococcus aureus of three diterpenes, namely, geranylgeraniol, teprenone, and phytol, by using a broth dilution with shaking method to identify the effects of diterpenes with long aliphatic carbon ..
  5. Goto T, Takahashi N, Kato S, Egawa K, Ebisu S, Moriyama T, et al. Phytol directly activates peroxisome proliferator-activated receptor alpha (PPARalpha) and regulates gene expression involved in lipid metabolism in PPARalpha-expressing HepG2 hepatocytes. Biochem Biophys Res Commun. 2005;337:440-5 pubmed
    ..that activate PPAR using luciferase assays, a branched-carbon-chain alcohol (a component of chlorophylls), phytol, has been identified as a PPARalpha-specific activator...
  6. Elmazar M, El Abhar H, Schaalan M, Farag N. Phytol/Phytanic acid and insulin resistance: potential role of phytanic acid proven by docking simulation and modulation of biochemical alterations. PLoS ONE. 2013;8:e45638 pubmed publisher
    ..effect of TZDs, especially when it heterodimerizes with RXR, we aimed to test the potential antidiabetic effect of phytol (250 mg/kg), the natural precursor of phytanic acid, a RXR ligand and/or pioglitazone (5 mg/kg) to diabetic ..
  7. Valentin H, Lincoln K, Moshiri F, Jensen P, Qi Q, Venkatesh T, et al. The Arabidopsis vitamin E pathway gene5-1 mutant reveals a critical role for phytol kinase in seed tocopherol biosynthesis. Plant Cell. 2006;18:212-24 pubmed publisher
    ..Analysis of extracts from Arabidopsis and Synechocystis mutants revealed increased accumulation of free phytol. Heterologous expression of these genes in Escherichia coli supplemented with free phytol and in vitro assays of ..
  8. Ishizaki K, Larson T, Schauer N, Fernie A, Graham I, Leaver C. The critical role of Arabidopsis electron-transfer flavoprotein:ubiquinone oxidoreductase during dark-induced starvation. Plant Cell. 2005;17:2587-600 pubmed publisher
  9. Elmazar M, Nau H. Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands. Arch Toxicol. 2004;78:660-8 pubmed
    ..A non-teratogenic dose of the natural RXR agonist phytanic acid (100 mg/kg orally) or its precursor phytol (500 mg/kg orally) was coadministered with a synthetic RARalpha-agonist (Am580; 5 mg/kg orally) to NMRI mice on ..
  10. Hashimoto T, Shimizu N, Kimura T, Takahashi Y, Ide T. Polyunsaturated fats attenuate the dietary phytol-induced increase in hepatic fatty acid oxidation in mice. J Nutr. 2006;136:882-6 pubmed
    The effects of dietary phytol and the type of dietary fat on hepatic fatty acid oxidation were examined in male ICR mice. Mice were fed diets containing 0 or 5 g/kg phytol and 100 g/kg palm, safflower, or fish oil for 21 d...
  11. Hultqvist M, Olofsson P, Gelderman K, Holmberg J, Holmdahl R. A new arthritis therapy with oxidative burst inducers. PLoS Med. 2006;3:e348 pubmed
    ..Treatment of rats with phytol (3,7,11,15-tetramethyl-2-hexadecene-1-ol) increased oxidative burst in vivo and thereby corrected the effect of ..
  12. Mackie J, Atshaves B, Payne H, McIntosh A, Schroeder F, Kier A. Phytol-induced hepatotoxicity in mice. Toxicol Pathol. 2009;37:201-8 pubmed publisher
    ..Some other dietary fats contain lower levels of phytol, which is readily converted to phytanic acid after absorption...
  13. Hibasami H, Kyohkon M, Owaki S, Katsuzaki H, Imai K, Ohnishi K, et al. Diol- and triol-types of phytol induce apoptosis in lymphoid leukemia Molt 4B cells. Int J Mol Med. 2002;10:555-9 pubmed
    The exposure of human lymphoid leukemia Molt 4B cells to diol- and triol-types of phytol which were synthesized and identified by Mass, and 1H- and 13C-NMR, led to both growth inhibition and induction of programmed cell death (apoptosis)...
  14. Schelbert S, Aubry S, Burla B, Agne B, Kessler F, Krupinska K, et al. Pheophytin pheophorbide hydrolase (pheophytinase) is involved in chlorophyll breakdown during leaf senescence in Arabidopsis. Plant Cell. 2009;21:767-85 pubmed publisher
    ..Chlorophyllide, the last precursor of chlorophyll biosynthesis, is most likely not an intermediate of breakdown. Thus, chlorophyll anabolic and catabolic reactions are metabolically separated. ..
  15. Saikia D, Parihar S, Chanda D, Ojha S, Kumar J, Chanotiya C, et al. Antitubercular potential of some semisynthetic analogues of phytol. Bioorg Med Chem Lett. 2010;20:508-12 pubmed publisher
    b>Phytol, a diterpene alcohol was modified to several semisynthetic analogues. Some of the modifications were done logically to enhance lipophilicity of the molecule. Analogues 14, 16 and 18 exhibited antitubercular activity (MIC 15...
  16. Aachoui Y, Chowdhury R, Fitch R, Ghosh S. Molecular signatures of phytol-derived immunostimulants in the context of chemokine-cytokine microenvironment and enhanced immune response. Cell Immunol. 2011;271:227-38 pubmed publisher
    In a previous report, we observed that the phytol-derived immunostimulant, PHIS-01 (phytanol), is a nontoxic oil-in-water adjuvant which is superior to most commercial adjuvants...
  17. Aachoui Y, Schulte M, Fitch R, Ghosh S. Synthetic adjuvants for vaccine formulations: evaluation of new phytol derivatives in induction and persistence of specific immune response. Cell Immunol. 2011;271:308-18 pubmed publisher
    ..of the structural features important for adjuvanticity, we studied compounds derived from a diterpene phytol and assessed their efficacy...
  18. Kagoura M, Matsui C, Morohashi M. Phytol is a novel tumor promoter on ICR mouse skin. Jpn J Cancer Res. 1999;90:377-84 pubmed
    b>Phytol is a branched, long-chain aliphatic alcohol which has various biological effects...
  19. Vetter W, Schröder M, Lehnert K. Differentiation of refined and virgin edible oils by means of the trans- and cis-phytol isomer distribution. J Agric Food Chem. 2012;60:6103-7 pubmed publisher
    ..Here, we explored the suitability of the relative abundance of cis-phytol as a marker for authentication of nonrefined edible oils...
  20. Hassan E, Matloub A, Aboutabl M, Ibrahim N, Mohamed S. Assessment of anti-inflammatory, antinociceptive, immunomodulatory, and antioxidant activities of Cajanus cajan L. seeds cultivated in Egypt and its phytochemical composition. Pharm Biol. 2016;54:1380-91 pubmed publisher
    ..Twenty-one unsaponifiable compounds (mainly phytol, 2,6-di-(t-butyl)-4-hydroxy-4-methyl-2,5-cyclohexadiene-1-one, β-sitosterol, stigmasterol, and campesterol), as ..
  21. Daudin J, Monnet D, Kavian N, Espy C, Wang A, Chereau C, et al. Protective effect of pristane on experimental autoimmune uveitis. Immunol Lett. 2011;141:83-93 pubmed publisher
    This study evaluates the effects of pristane and phytol, two mineral oils with pro-oxidative effects, on the course of experimental autoimmune uveitis...
  22. Zhang F, Ai W, Hu X, Meng Y, Yuan C, Su H, et al. Phytol stimulates the browning of white adipocytes through the activation of AMP-activated protein kinase (AMPK) α in mice fed high-fat diet. Food Funct. 2018;9:2043-2050 pubmed publisher
    ..This study aimed to investigate the browning effects of phytol on mice inguinal subcutaneous white adipose tissue (iWAT) and explore the underlying mechanisms...
  23. Soares J, Rodrigues D, Gonçalves M, Lemos M, Gallarreta M, Bianchini M, et al. Paraquat exposure-induced Parkinson's disease-like symptoms and oxidative stress in Drosophila melanogaster: Neuroprotective effect of Bougainvillea glabra Choisy. Biomed Pharmacother. 2017;95:245-251 pubmed publisher
    ..GC-MS and HPLC analyses of BG extract revealed the presence of many antioxidant compounds such as phytol, ?,?-tocopherol, squalene, stigmasterol, geranylgeraniol, quercetin, and caffeic, vanillic, coumaric, ferulic ..
  24. Wang H, Olmstead A, Li H, LeBlanc G. The screening of chemicals for juvenoid-related endocrine activity using the water flea Daphnia magna. Aquat Toxicol. 2005;74:193-204 pubmed
    ..All registered positive. Results demonstrate that an in vivo assay with a crustacean species customarily employed in toxicity testing can be used to effectively screen chemicals for juvenoid-modulating activity. ..
  25. Jorge L, Meniqueti A, Silva R, Santos K, Da Silva E, Gonçalves J, et al. Antioxidant activity and chemical composition of oleoresin from leaves and flowers of Brunfelsia uniflora. Genet Mol Res. 2017;16: pubmed publisher
    ..03% at 60°C and 200 bar for the flowers. The main extracted compounds from leaves were phytol varying from 11.95 to 36.42% and ?-tocopherol from 15.53 to 43.10%, and from flowers were geranyl linalool from 11...
  26. Guyer L, Salinger K, Krügel U, Hortensteiner S. Catalytic and structural properties of pheophytinase, the phytol esterase involved in chlorophyll breakdown. J Exp Bot. 2017;: pubmed publisher
    ..A key feature of chlorophyll breakdown is the removal of the hydrophobic phytol chain that renders phyllobilins water soluble, an important prerequisite for their ultimate storage in the vacuole ..
  27. Arnhold T, Elmazar M, Nau H. Prevention of vitamin A teratogenesis by phytol or phytanic acid results from reduced metabolism of retinol to the teratogenic metabolite, all-trans-retinoic acid. Toxicol Sci. 2002;66:274-82 pubmed
    ..M. Elmazar et al., 2001, TOXICOL: Appl. Pharmacol. 170, 2-9). In the present study the influence of phytol and phytanic acid (a RXR-selective ligand) on the teratogenicity of retinol and the RAR-selective ligand all-trans-..
  28. Gutiérrez Nava Z, Jiménez Aparicio A, Herrera Ruiz M, Jimenez Ferrer E. Immunomodulatory Effect of Agave tequilana Evaluated on an Autoimmunity Like-SLE Model Induced in Balb/c Mice with Pristane. Molecules. 2017;22: pubmed publisher
    ..the presence of the following compounds: β-sitosterol glycoside; 3,7,11,15-tetramethyl-2-hexadecen-1-ol (phytol); octadecadienoic acid-2,3-dihydroxypropyl ester; stigmasta-3,5-dien-7-one; cycloartenone and cycloartenol...
  29. Ruiz Aracama A, Goicoechea E, Guillén M. Direct study of minor extra-virgin olive oil components without any sample modification. 1H NMR multisupression experiment: A powerful tool. Food Chem. 2017;228:301-314 pubmed publisher
    ..deuterated chloroform) are thoroughly described, identifying for the first time those of the protons of esters of phytol and of geranylgeraniol...
  30. Costa J, Ferreira P, De Sousa D, Jordan J, Freitas R. Anticonvulsant effect of phytol in a pilocarpine model in mice. Neurosci Lett. 2012;523:115-8 pubmed publisher
    The present study investigated the effects of phytol in pilocarpine-induced seizures. The latency for development of convulsions and mortality rate was recorded in this model using mice...
  31. Storey S, Huang H, McIntosh A, Martin G, Kier A, Schroeder F. Impact of Fabp1/Scp-2/Scp-x gene ablation (TKO) on hepatic phytol metabolism in mice. J Lipid Res. 2017;58:1153-1165 pubmed publisher
    ..protein [Fabp1 (L-FABP)] gene products facilitate hepatic uptake and metabolism of lipotoxic dietary phytol. However, interpretation of physiological function in mice singly gene ablated in the Scp-2/Scp-x has been ..
  32. Landrock D, Milligan S, Martin G, McIntosh A, Landrock K, Schroeder F, et al. Effect of Fabp1/Scp-2/Scp-x Ablation on Whole Body and Hepatic Phenotype of Phytol-Fed Male Mice. Lipids. 2017;52:385-397 pubmed publisher
    ..uptake, cytosolic transport, and peroxisomal oxidation of toxic branched-chain fatty acids derived from dietary phytol. Since male wild-type (WT) mice express markedly higher levels of these proteins than females, the impact of ..
  33. Malecki E, Knies C, Werz E, Rosemeyer H. Mitsunobu reactions of 5-fluorouridine with the terpenols phytol and nerol: DNA building blocks for a biomimetic lipophilization of nucleic acids. Chem Biodivers. 2013;10:2209-20 pubmed publisher
    ..This fully protected derivative was submitted to Mitsunobu reactions with either phytol ((Z and E)-isomer) or nerol ((Z)-isomer) to yield the nucleoterpenes 4a and 4b...
  34. Johannsen M, Peper S, Depta A. Simulated moving bed chromatography with supercritical fluids for the resolution of bi-naphthol enantiomers and phytol isomers. J Biochem Biophys Methods. 2002;54:85-102 pubmed
    ..steps of process development for SMB SFC are presented using the separations of the bi-naphthol enantiomers and phytol isomers as examples...
  35. Roca Saavedra P, Mariño Lorenzo P, Miranda J, Porto Arias J, Lamas A, Vazquez B, et al. Phytanic acid consumption and human health, risks, benefits and future trends: A review. Food Chem. 2017;221:237-247 pubmed publisher
    Phytanic acid is a methyl-branched fatty acid present in the human diet, derived from the enzymatic degradation of phytol and subsequently oxidized by the rumenal microbiota and certain marine organisms...
  36. Zeb A, Ullah F, Ayaz M, Ahmad S, Sadiq A. Demonstration of biological activities of extracts from Isodon rugosus Wall. Ex Benth: Separation and identification of bioactive phytoconstituents by GC-MS analysis in the ethyl acetate extract. BMC Complement Altern Med. 2017;17:284 pubmed publisher
    ..Some of the bioactive compounds identified in GC-MS analysis are palmitic acid, hinokiol, ?-amyrin, phytol, ethyl linolate, cyclohexanone, hinokione, methyl palmitate, ethyl palmitate and stigmasterol acetate...
  37. Ahmad S, Ullah F, Zeb A, Ayaz M, Ullah F, Sadiq A. Evaluation of Rumex hastatus D. Don for cytotoxic potential against HeLa and NIH/3T3 cell lines: chemical characterization of chloroform fraction and identification of bioactive compounds. BMC Complement Altern Med. 2016;16:308 pubmed publisher
    ..fraction revealed the identification of 78 compounds with the identification of bioactive ones like ar-tumerone, phytol, dihydrojasmone, sitostenone etc. It can be concluded from our results that Rumex hastatus D...
  38. Huang Y, Zhang D, Xue S, Wang M, Cong W. The Potential of Microalgae Lipids for Edible Oil Production. Appl Biochem Biotechnol. 2016;180:438-451 pubmed
    ..oceanica, but the content of which was lower in neutral lipids. Phytol was identified as the major unsaponifiable component in lipids of the three algae...
  39. Hammami S, Snène A, El Mokni R, Faidi K, Falconieri D, Dhaouadi H, et al. Essential Oil Constituents and Antioxidant Activity of Asplenium Ferns. J Chromatogr Sci. 2016;54:1341-5 pubmed publisher
    ..5%); however, only 29 volatiles were identified in A. trichomanes showing a high amount of phytol, an odorous diterpene alcohol, representing 14.4% of the total oil contents...
  40. Wanders R, Komen J, Ferdinandusse S. Phytanic acid metabolism in health and disease. Biochim Biophys Acta. 2011;1811:498-507 pubmed publisher
    ..Finally, we present new data on the omega-oxidation of phytanic acid making use of a recently generated mouse model for Refsum disease in which the gene encoding phytanoyl-CoA 2-hydroxylase has been disrupted. ..
  41. Vom Dorp K, Hölzl G, Plohmann C, Eisenhut M, Abraham M, Weber A, et al. Remobilization of Phytol from Chlorophyll Degradation Is Essential for Tocopherol Synthesis and Growth of Arabidopsis. Plant Cell. 2015;27:2846-59 pubmed publisher
    b>Phytol from chlorophyll degradation can be phosphorylated to phytyl-phosphate and phytyl-diphosphate, the substrate for tocopherol (vitamin E) synthesis...
  42. Almeida J, Azevedo M, Spicher L, Glauser G, Vom Dorp K, Guyer L, et al. Down-regulation of tomato PHYTOL KINASE strongly impairs tocopherol biosynthesis and affects prenyllipid metabolism in an organ-specific manner. J Exp Bot. 2016;67:919-34 pubmed publisher
    ..The latter, phytyl diphosphate, can be derived from chlorophyll phytol tail recycling, which depends on phytol kinase (VTE5) activity...
  43. Schwender J, Gemünden C, Lichtenthaler H. Chlorophyta exclusively use the 1-deoxyxylulose 5-phosphate/2-C-methylerythritol 4-phosphate pathway for the biosynthesis of isoprenoids. Planta. 2001;212:416-23 pubmed
    ..Mesostignma virilde the same IPP biosynthesis pattern as in higher plants: sterols are formed via MVA, and the phytol-moiety of chlorophylls via the DOXP/MEP pathway...
  44. Savolainen K, Kotti T, Schmitz W, Savolainen T, Sormunen R, Ilves M, et al. A mouse model for alpha-methylacyl-CoA racemase deficiency: adjustment of bile acid synthesis and intolerance to dietary methyl-branched lipids. Hum Mol Genet. 2004;13:955-65 pubmed
    ..Exposure of Amacr(-/-) mice to a diet supplemented with phytol, a source for branched-chain fatty acids, triggered the development of a disease state with liver manifestations, ..
  45. Aparicio Ruiz R, Riedl K, Schwartz S. Identification and quantification of metallo-chlorophyll complexes in bright green table olives by high-performance liquid chromatrography-mass spectrometry quadrupole/time-of-flight. J Agric Food Chem. 2011;59:11100-8 pubmed publisher
    ..g., pheophytin a/b and 15(2)-Me-phytol-chlorin e(6))...
  46. da Silva J, Antinarelli L, Ribeiro A, Coimbra E, Scio E. The effect of the phytol-rich fraction from Lacistema pubescens against Leishmania amazonensis is mediated by mitochondrial dysfunction. Exp Parasitol. 2015;159:143-50 pubmed publisher
    ..In this work the phytol-rich hexane fraction (PRF) from the leaves of Lacistema pubescens was obtained and identified by GC-MS analysis...
  47. Seedorf U, Raabe M, Ellinghaus P, Kannenberg F, Fobker M, Engel T, et al. Defective peroxisomal catabolism of branched fatty acyl coenzyme A in mice lacking the sterol carrier protein-2/sterol carrier protein-x gene function. Genes Dev. 1998;12:1189-201 pubmed
    ..These results corresponded to high-affinity binding of phytanoyl-CoA to the recombinant rat SCP2 protein, as well as high 3-ketopristanoyl-CoA thiolase activity of the recombinant rat SCPx protein. ..
  48. van den Brink D, van Miert J, Wanders R. Assay for Sjögren-Larsson syndrome based on a deficiency of phytol degradation. Clin Chem. 2005;51:240-2 pubmed
  49. Selkälä E, Nair R, Schmitz W, Kvist A, Baes M, Hiltunen J, et al. Phytol is lethal for Amacr-deficient mice. Biochim Biophys Acta. 2015;1851:1394-405 pubmed publisher
    ..in bile acid synthesis and in methyl-branched fatty acids such as pristanic acid, a metabolite derived from phytol. Consequently, patients with Amacr deficiency accumulate C27-bile acid intermediates, pristanic and phytanic acid ..
  50. Glabonjat R, Ehgartner J, Duncan E, Raber G, Jensen K, Krikowa F, et al. Arsenolipid biosynthesis by the unicellular alga Dunaliella tertiolecta is influenced by As/P ratio in culture experiments. Metallomics. 2018;10:145-153 pubmed publisher
    ..35-65% of total arsenolipids. The new compound contains a phytol aglycone and a methoxy group replacing a sugar hydroxyl - two structural features not previously observed for ..
  51. Xin H, Guo R, Liu F, Cheng R, Zhou J. [Study on the volatile oil of leaf of red gland Lonicera in guangxi]. Zhong Yao Cai. 2011;34:1379-83 pubmed
    ..The main components of fresh leaves of red gland Lonicera were n-Hexadecanoic acid (11.90%), Phytol (11.79) and 9,12,15-Octadecatrienoic acid, methyl ester, (Z, Z, Z)(7...
  52. Qiu Q, Zhen H, Huang P. [Study on volatile components from flowers of Gymnema sylvestre]. Zhong Yao Cai. 2013;36:575-7 pubmed
    ..73% of all quantity. The principal volatile components are Phytol, Pentacosane, 10-Heneicosene (c, t), 3-Eicosene, (E) -and 2-Methyl-Z-2-docosane...
  53. Baqueiro Peña I, Guerrero Beltrán J. Physicochemical and antioxidant characterization of Justicia spicigera. Food Chem. 2017;218:305-312 pubmed publisher
    ..33, 1.23±0.87, and 0.88±0.94g with the DPPH method for F, JD and DS J. spicigera, respectively. Eucalyptol, phytol, and azulene were identified as the main compounds. J...
  54. Adam K, Thiel R, Zapp J, Becker H. Involvement of the mevalonic acid pathway and the glyceraldehyde-pyruvate pathway in terpenoid biosynthesis of the liverworts Ricciocarpos natans and Conocephalum conicum. Arch Biochem Biophys. 1998;354:181-7 pubmed
    ..of 13C-labeled glucose into borneol, bornyl acetate, the sesquiterpenes cubebanol and ricciocarpin A, phytol, and stigmasterol has been studied in axenic cultures of the liverworts Ricciocarpos natans and Conocephalum ..
  55. Itoh D, Kawano K, Nabeta K. Biosynthesis of chloroplastidic and extrachloroplastidic terpenoids in liverwort cultured cells: 13C serine as a probe of terpene biosynthesis via mevalonate and non-mevalonate pathways. J Nat Prod. 2003;66:332-6 pubmed
    ..Thus, serine is a potential probe to determine the origin of terpenoid biosynthesis, in either the mevalonate or non-mevalonate pathway. ..
  56. Yuan Z, Han L, Fan X, Li S, Shi D, Sun J, et al. [Chemical constituents from red alga Corallina pilulifera]. Zhongguo Zhong Yao Za Zhi. 2006;31:1787-90 pubmed
    ..Seven compounds were isolated from red alga C. pilulifera, their structures were identified as (E) -phytol epoxide (1), phytenal (2), phytol (3), dehydrovomifoliol (4), loliolide (5), 3beta-hydroxy-5alpha, 6alpha-epoxy-7-..
  57. Wierzbicki A. Clinical significance of oxidation from phytol to phytanic acid in man. Mol Genet Metab. 2004;83:347 pubmed
  58. Tao R, Wang C, Kong Z. Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo biloba L. leaves. Molecules. 2013;18:2166-82 pubmed publisher
    ..A proportion of isophytol and GBP of 38.19%:61.81% (wt/wt) was determined by mixture design as the optimal proportion for the synergistic effect of GBP with isophytol against Salmonella enterica...
  59. Roy Chowdhury R, Fitch R, Ghosh S. Efficacy of phytol-derived diterpenoid immunoadjuvants over alum in shaping the murine host's immune response to Staphylococcus aureus. Vaccine. 2013;31:1178-86 pubmed publisher
    ..The objective of this study was to understand the mechanisms by which alum and two phytol-derived immunoadjuvants, phytanol (PHIS-01)(1) and phytanyl chloride (PCl)(2) shape the interaction between S...
  60. Elusiyan C, Ani N, Adewunmi C, Olugbade T. Distribution of iridiod glucosides and anti-oxidant compounds in Spathodea campanulata parts. Afr J Tradit Complement Altern Med. 2011;8:27-33 pubmed
    ..44 µg/ml), Kampeferol diglucoside (leaf; EC(50) = 8.87 µg/ml) and Caffeic acid (leaf and fruits). The non anti-oxidant components isolated in the study include ajugol (stem bark and fruits) and phytol (leaf).
  61. Rontani J, Bonin P, Volkman J. Biodegradation of free phytol by bacterial communities isolated from marine sediments under aerobic and denitrifying conditions. Appl Environ Microbiol. 1999;65:5484-92 pubmed
    Biodegradation of (E)-phytol [3,7,11, 15-tetramethylhexadec-2(E)-en-1-ol] by two bacterial communities isolated from recent marine sediments under aerobic and denitrifying conditions was studied at 20 degrees C...
  62. Baes M, Huyghe S, Carmeliet P, Declercq P, Collen D, Mannaerts G, et al. Inactivation of the peroxisomal multifunctional protein-2 in mice impedes the degradation of not only 2-methyl-branched fatty acids and bile acid intermediates but also of very long chain fatty acids. J Biol Chem. 2000;275:16329-36 pubmed
    ..VLCFA in brain and liver phospholipids, immature C(27) bile acids in bile, and, after supplementation with phytol, pristanic and phytanic acid in liver triacylglycerols...
  63. Huo S, Negishi E. A convenient and asymmetric protocol for the synthesis of natural products containing chiral alkyl chains via Zr-catalyzed asymmetric carboalumination of alkenes. Synthesis of phytol and vitamins E and K. Org Lett. 2001;3:3253-6 pubmed
    ..In addition, phytol and vitamin K were synthesized in 21% and 28% overall yields, respectively, over five steps from 1.
  64. Couladis M, Chinou I, Tzakou O, Loukis A. Composition and antimicrobial activity of the essential oil of Ballota pseudodictamnus L. Bentham. Phytother Res. 2002;16:723-6 pubmed
    ..From the 52 identified constituents of the oil, caryophyllene oxide, phytol and gamma-muurolene were the major components...
  65. Kim D, Filtz M, Proteau P. The methylerythritol phosphate pathway contributes to carotenoid but not phytol biosynthesis in Euglena gracilis. J Nat Prod. 2004;67:1067-9 pubmed
    ..Interestingly, the MEP pathway is not involved in the biosynthesis of phytol, a result not previously observed for other chloroplast-containing organisms.
  66. Atshaves B, McIntosh A, Payne H, Mackie J, Kier A, Schroeder F. Effect of branched-chain fatty acid on lipid dynamics in mice lacking liver fatty acid binding protein gene. Am J Physiol Cell Physiol. 2005;288:C543-58 pubmed
    ..acid, a branched-chain fatty acid, were determined in L-FABP gene-ablated mice fed a diet with and without 1% phytol (a metabolic precursor to phytanic acid)...
  67. Atanasov V, Knorr N, Duran R, Ingebrandt S, Offenhäusser A, Knoll W, et al. Membrane on a chip: a functional tethered lipid bilayer membrane on silicon oxide surfaces. Biophys J. 2005;89:1780-8 pubmed
    ..We demonstrate the functional incorporation of the ion carrier valinomycin and of the ion channel gramicidin. ..
  68. Itoh T, Yano K, Kajino T, Inada Y, Fukushima Y. Phytol-modified heme in mesoporous silica: conjugates as models of hemoproteins. Biotechnol Bioeng. 2006;93:476-84 pubmed
    A ferriprotoporphyrin, hemin (Fe(3+)), modified with 3,7,11,15-tetramethyl-2-hexadecen-1-ol, phytol, was adsorbed in nano-spaces of about 4 nm in diameter in mesoporous silica (FSM; folded-sheet mesoporous material) forming a phytol-..
  69. Na Z. [Study on the chemical constituents of the volatile oil from aerial parts of Isodon eriocalyx var. laxiflora]. Zhongguo Zhong Yao Za Zhi. 2005;30:1268-70 pubmed
    ..To study the chemical constituents of the volatile oil from the aerial parts of Isodon eriocalyx var. laxiflora...
  70. Atshaves B, McIntosh A, Landrock D, Payne H, Mackie J, Maeda N, et al. Effect of SCP-x gene ablation on branched-chain fatty acid metabolism. Am J Physiol Gastrointest Liver Physiol. 2007;292:G939-51 pubmed
    Despite the importance of peroxisomal oxidation in branched-chain lipid (phytol, cholesterol) detoxification, little is known regarding the factors regulating the peroxisomal uptake, targeting, and metabolism of these lipids...
  71. Addlesee H, Gibson L, Jensen P, Hunter C. Cloning, sequencing and functional assignment of the chlorophyll biosynthesis gene, chlP, of Synechocystis sp. PCC 6803. FEBS Lett. 1996;389:126-30 pubmed
    ..We conclude that this gene, which we term chlP, encodes the enzyme catalysing the stepwise hydrogenation of geranylgeraniol to phytol during chla biosynthesis.
  72. Sun J, Han L, Yang R, Shi D, Uan Z, Shi J. [Studies on chemical constituents of Laurencia tristicha ( II )]. Zhongguo Zhong Yao Za Zhi. 2007;32:2610-2 pubmed
    ..To search for chemical constituents with structural diversity from Laurencia tristicha to supply for biological assay...
  73. Myśliwa Kurdziel B, Solymosi K, Kruk J, Böddi B, Strzałka K. Solvent effects on fluorescence properties of protochlorophyll and its derivatives with various porphyrin side chains. Eur Biophys J. 2008;37:1185-93 pubmed publisher
    ..in Photochem Photobiol 79:62-67, 2004), and they indicate that the presence of phytol chain in the porphyrin ring influences the spectral properties of the whole chromophore...
  74. Jia X, Zhang Y, Yang Y, Wang J. [Extraction and GC-MS analysis of essential oil from leaves of Discocleidion rufescens]. Zhong Yao Cai. 2008;31:845-7 pubmed
    ..37 compounds, representing 92.25% of total oil were indentified and their relative amount was determined. The oil is rich in Phytol (39.30%, n-Hexadecanoic acid (11.72%), (Z) -3-Teoadecen-5-yne (5.78%) and beta-Pinene (3.63%).
  75. Pu L, Yuan X, Tang T. [Analysis of volatile oil from Ardisia brevicaulis]. Zhong Yao Cai. 2009;32:1694-7 pubmed
    ..To analyze and compare the compounds in the essential oil from the leaves and roots of Ardisia brevicaulis...
  76. Aachoui Y, Ghosh S. Immune enhancement by novel vaccine adjuvants in autoimmune-prone NZB/W F1 mice: relative efficacy and safety. BMC Immunol. 2011;12:61 pubmed publisher
    ..The objective here was to assess the effectiveness of experimental adjuvants: two phytol-derived immunostimulants PHIS-01 (phytanol) and PHIS-03 (phytanyl mannose), and a new commercial adjuvant from ..
  77. Grace M, Lategan C, Graziose R, Smith P, Raskin I, Lila M. Antiplasmodial activity of the ethnobotanical plant Cassia fistula. Nat Prod Commun. 2012;7:1263-6 pubmed
    ..Three main antiplasmodial principles, phytol (1) (IC50 18.9 +/- 0.60 microM), lutein (2) (IC50 12.5 +/- 0...
  78. Kelly M, Mathie A, Vallance C. A pharmacological action of vitamin E unrelated to its antioxidant capacity. Methods Find Exp Clin Pharmacol. 2006;28:499-505 pubmed
    ..with structural similarities to the side chain of vitamin E produced similar stimulatory responses and some, like phytol, were more potent than the vitamin (EC(50): 1.0 +/- 0...
  79. van den Brink D, van Miert J, Dacremont G, Rontani J, Wanders R. Characterization of the final step in the conversion of phytol into phytanic acid. J Biol Chem. 2005;280:26838-44 pubmed
    b>Phytol is a branched-chain fatty alcohol that is a naturally occurring precursor of phytanic acid, a fatty acid involved in the pathogenesis of Refsum disease...
  80. Arai Y, Hattori T, Hamaguchi N, Masuda K, Takano A, Shiojima K. Fern constituents: dryocrassy formate, sitostanyl formate and 12alpha-hydroxyfern-9(11)-ene from Cyathea podophylla. Chem Pharm Bull (Tokyo). 2003;51:1311-3 pubmed
    ..Their structures were elucidated by spectroscopic techniques and synthesis. Ten known triterpenoids, three derivatives of phytol, a stanol, and beta-tocopherol were also identified from this fern.
  81. Brites P, Motley A, Gressens P, Mooyer P, Ploegaert I, Everts V, et al. Impaired neuronal migration and endochondral ossification in Pex7 knockout mice: a model for rhizomelic chondrodysplasia punctata. Hum Mol Genet. 2003;12:2255-67 pubmed
    ..These findings demonstrate that Pex7 knockout mice provide an important model to study the role of peroxisomal functioning in the pathogenesis of the human disorder...
  82. Mezzar S, De Schryver E, Asselberghs S, Meyhi E, Morvay P, Baes M, et al. Phytol-induced pathology in 2-hydroxyacyl-CoA lyase (HACL1) deficient mice. Evidence for a second non-HACL1-related lyase. Biochim Biophys Acta Mol Cell Biol Lipids. 2017;1862:972-990 pubmed publisher
    ..However, upon dietary administration of phytol, phytanic acid accumulated in tissues, mainly in liver and serum of KO mice...
  83. Depta A, Giese T, Johannsen M, Brunner G. Separation of stereoisomers in a simulated moving bed-supercritical fluid chromatography plant. J Chromatogr A. 1999;865:175-86 pubmed
    ..Therefore, isotherms for two phytol isomers are measured and correlated...
  84. Takaichi S, Inoue K, Akaike M, Kobayashi M, Oh oka H, Madigan M. The major carotenoid in all known species of heliobacteria is the C30 carotenoid 4,4'-diaponeurosporene, not neurosporene. Arch Microbiol. 1997;168:277-81 pubmed
    ..Furthermore, the esterifying alcohol of bacteriochlorophyll g from all known species of heliobacteria was determined to be farnesol (C15) instead of the usual phytol (C20). Heliobacteria may be unable to produce geranylgeranyol (C20).