Tetraprenol (BioDeep_00000007165)

 

Secondary id: BioDeep_00000175571, BioDeep_00000638555, BioDeep_00000872044

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


2,6,10,14-Hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-, (2E,6E,10E)- (9CI)

化学式: C20H34O (290.2609514)
中文名称: ALL TRANS-3,7,11-15-四甲基-2,6,10,14-十六烷四烯-1-醇, 香叶基香叶醇, 全氟聚醚基表面活性剂
谱图信息: 最多检出来源 Viridiplantae(plant) 2.63%

分子结构信息

SMILES: C/C(C)=C\CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CO
InChI: InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+

描述信息

Geranylgeraniol is an orally acitve vitamin K2 sub-type, an intermediate of the mevalonate pathway. Geranylgeraniol targets NF-kB signaling pathway and could alleviate LPS-induced microglial inflammation in animal model[1][2][3][4].
Geranylgeraniol is an orally acitve vitamin K2 sub-type, an intermediate of the mevalonate pathway. Geranylgeraniol targets NF-kB signaling pathway and could alleviate LPS-induced microglial inflammation in animal model[1][2][3][4].

同义名列表

29 个代谢物同义名

2,6,10,14-Hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-, (2E,6E,10E)- (9CI); 2,6,10,14-Hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-, (E,E,E)- (8CI); (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol; all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol; 2,6,10,14-Hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-; 3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol; trans,trans,trans-Geranylgeraniol; All-trans-Geranylgeraniol; (e,e,e)-geranylgeraniol; trans-Geranylgeraniol; Spectrum5_002040; NCGC00096069-01; SPECTRUM1505009; NCGC00096069-02; GERANYLGERANIOL; Gernaylgeraniol; FLUOROLINK(R) D; CHEBI:46762; Tetraprenol; CHEBI:24229; G3278_SIGMA; 24034-73-9; 7614-21-3; C09094; 3,7,11,15-tetramethylhexadeca-2E,6E,10E,14-tetraen-1-ol; (E,E,E)-Geranylgeranyl alcohol; Geranyl geraniol; Geranylgeraniol; Geranylgeraniol



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • plaunotol biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + geranylgeraniol ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + plaunotol

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • plaunotol biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + geranylgeraniol ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + plaunotol

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

13 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Nemesio Villa-Ruano, Néstor Hernández-Silva, Jenaro Leocadio Varela-Caselis, Sergio Alberto-Ramirez-Garcia, Clemente Mosso-González. Controlled Production of Carnosic Acid and Carnosol in Cell Suspensions of Lepechinia meyenii Treated with Different Elicitors and Biosynthetic Precursors. Chemistry & biodiversity. 2023 Feb; 20(2):e202200733. doi: 10.1002/cbdv.202200733. [PMID: 36562957]
  • Mateus Alves Batista, Abrahão Victor Tavares de Lima Teixeira Dos Santos, Aline Lopes do Nascimento, Luiz Fernando Moreira, Indira Ramos Senna Souza, Heitor Ribeiro da Silva, Arlindo César Matias Pereira, Lorane Izabel da Silva Hage-Melim, José Carlos Tavares Carvalho. Potential of the Compounds from Bixa orellana Purified Annatto Oil and Its Granules (Chronic®) against Dyslipidemia and Inflammatory Diseases: In Silico Studies with Geranylgeraniol and Tocotrienols. Molecules (Basel, Switzerland). 2022 Feb; 27(5):. doi: 10.3390/molecules27051584. [PMID: 35268686]
  • Wahyu Dwi Saputra, Hiroki Shono, Yusuke Ohsaki, Halima Sultana, Michio Komai, Hitoshi Shirakawa. Geranylgeraniol Inhibits Lipopolysaccharide-Induced Inflammation in Mouse-Derived MG6 Microglial Cells via NF-κB Signaling Modulation. International journal of molecular sciences. 2021 Sep; 22(19):. doi: 10.3390/ijms221910543. [PMID: 34638882]
  • Eunhee Chung, Moamen M Elmassry, Jay J Cao, Gurvinder Kaur, Jannette M Dufour, Abdul N Hamood, Chwan-Li Shen. Beneficial effect of dietary geranylgeraniol on glucose homeostasis and bone microstructure in obese mice is associated with suppression of proinflammation and modification of gut microbiome. Nutrition research (New York, N.Y.). 2021 09; 93(?):27-37. doi: 10.1016/j.nutres.2021.07.001. [PMID: 34352722]
  • Gerda M Sanvee, Jamal Bouitbir, Stephan Krähenbühl. C2C12 myoblasts are more sensitive to the toxic effects of simvastatin than myotubes and show impaired proliferation and myotube formation. Biochemical pharmacology. 2021 08; 190(?):114649. doi: 10.1016/j.bcp.2021.114649. [PMID: 34111424]
  • Kayla Preece, Róbert Glávits, John R Foster, Timothy Murbach, John R Endres, Gábor Hirka, Adél Vértesi, Erzsébet Béres, Ilona Pasics Szakonyiné. A toxicological evaluation of geranylgeraniol. Regulatory toxicology and pharmacology : RTP. 2021 Aug; 124(?):104975. doi: 10.1016/j.yrtph.2021.104975. [PMID: 34144118]
  • Brad R Baker, Callum M Ives, Ashley Bray, Martin Caffrey, Stephen A Cochrane. Undecaprenol kinase: Function, mechanism and substrate specificity of a potential antibiotic target. European journal of medicinal chemistry. 2021 Jan; 210(?):113062. doi: 10.1016/j.ejmech.2020.113062. [PMID: 33310291]
  • Tianyuan Hu, Jiawei Zhou, Yuru Tong, Ping Su, Xinlin Li, Yuan Liu, Nan Liu, Xiaoyi Wu, Yifeng Zhang, Jiadian Wang, Linhui Gao, Lichan Tu, Yun Lu, Zhouqian Jiang, Yongjin J Zhou, Wei Gao, Luqi Huang. Engineering chimeric diterpene synthases and isoprenoid biosynthetic pathways enables high-level production of miltiradiene in yeast. Metabolic engineering. 2020 07; 60(?):87-96. doi: 10.1016/j.ymben.2020.03.011. [PMID: 32268192]
  • Takuma Matsubara, Nana Takakura, Mariko Urata, Yuya Muramatsu, Makoto Tsuboi, Kazuma Yasuda, William N Addison, Min Zhang, Kou Matsuo, Chihiro Nakatomi, Yukiyo Shigeyama-Tada, Takeshi Kaneuji, Atsuko Nakamichi, Shoichiro Kokabu. Geranylgeraniol Induces PPARγ Expression and Enhances the Biological Effects of a PPARγ Agonist in Adipocyte Lineage Cells. In vivo (Athens, Greece). 2018 Nov; 32(6):1339-1344. doi: 10.21873/invivo.11384. [PMID: 30348686]
  • Antônio P R Bitencourt, Jonatas L Duarte, Anna E M F M Oliveira, Rodrigo A S Cruz, José C T Carvalho, Antônio T A Gomes, Irlon M Ferreira, Roseane M Ribeiro-Costa, José O C Silva-Júnior, Caio P Fernandes. Preparation of aqueous nanodispersions with annatto (Bixa orellana L.) extract using an organic solvent-free and low energy method. Food chemistry. 2018 Aug; 257(?):196-205. doi: 10.1016/j.foodchem.2018.02.067. [PMID: 29622198]
  • Anna Jaśkiewicz, Beata Pająk, Anna Litwiniuk, Kaja Urbańska, Arkadiusz Orzechowski. Geranylgeraniol Prevents Statin-Dependent Myotoxicity in C2C12 Muscle Cells through RAP1 GTPase Prenylation and Cytoprotective Autophagy. Oxidative medicine and cellular longevity. 2018; 2018(?):6463807. doi: 10.1155/2018/6463807. [PMID: 29951166]
  • Jesús Casas, Maitane Ibarguren, Rafael Álvarez, Silvia Terés, Victoria Lladó, Stefano P Piotto, Simona Concilio, Xavier Busquets, David J López, Pablo V Escribá. G protein-membrane interactions II: Effect of G protein-linked lipids on membrane structure and G protein-membrane interactions. Biochimica et biophysica acta. Biomembranes. 2017 Sep; 1859(9 Pt B):1526-1535. doi: 10.1016/j.bbamem.2017.04.005. [PMID: 28411171]
  • Nicola Ferri, Silvia Marchianò, Maria Giovanna Lupo, Annalisa Trenti, Giuseppe Biondo, Paola Castaldello, Alberto Corsini. Geranylgeraniol prevents the simvastatin-induced PCSK9 expression: Role of the small G protein Rac1. Pharmacological research. 2017 Aug; 122(?):96-104. doi: 10.1016/j.phrs.2017.05.021. [PMID: 28554582]
  • Elizabeth de Wolf, Marwan Ibrahim Abdullah, Stefanie M Jones, Karen Menezes, Darren M Moss, Falko P Drijfhout, Sarah R Hart, Clare Hoskins, Euan A Stronach, Alan Richardson. Dietary geranylgeraniol can limit the activity of pitavastatin as a potential treatment for drug-resistant ovarian cancer. Scientific reports. 2017 07; 7(1):5410. doi: 10.1038/s41598-017-05595-4. [PMID: 28710496]
  • Colin S Brent, John A Byers, Anat Levi-Zada. An insect anti-antiaphrodisiac. eLife. 2017 07; 6(?):. doi: 10.7554/elife.24063. [PMID: 28695826]
  • Hoda Yeganehjoo, Russell DeBose-Boyd, Brian K McFarlin, Huanbiao Mo. Synergistic Impact of d-δ-Tocotrienol and Geranylgeraniol on the Growth and HMG CoA Reductase of Human DU145 Prostate Carcinoma Cells. Nutrition and cancer. 2017 May; 69(4):682-691. doi: 10.1080/01635581.2017.1299876. [PMID: 28362175]
  • Vijay P Sonar, Angela Corona, Simona Distinto, Elias Maccioni, Rita Meleddu, Benedetta Fois, Costantino Floris, Nilesh V Malpure, Stefano Alcaro, Enzo Tramontano, Filippo Cottiglia. Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase. European journal of medicinal chemistry. 2017 Apr; 130(?):248-260. doi: 10.1016/j.ejmech.2017.02.054. [PMID: 28254698]
  • Eric Keven Silva, Giovani L Zabot, Cinthia B B Cazarin, Mário R Maróstica, M Angela A Meireles. Biopolymer-prebiotic carbohydrate blends and their effects on the retention of bioactive compounds and maintenance of antioxidant activity. Carbohydrate polymers. 2016 Jun; 144(?):149-58. doi: 10.1016/j.carbpol.2016.02.045. [PMID: 27083804]
  • S Zafar, D E Coates, M P Cullinan, B K Drummond, T Milne, G J Seymour. Zoledronic acid and geranylgeraniol regulate cellular behaviour and angiogenic gene expression in human gingival fibroblasts. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 2014 Oct; 43(9):711-21. doi: 10.1111/jop.12181. [PMID: 24762323]
  • René F Ramos Alvarenga, Baojie Wan, Taichi Inui, Scott G Franzblau, Guido F Pauli, Birgit U Jaki. Airborne antituberculosis activity of Eucalyptus citriodora essential oil. Journal of natural products. 2014 Mar; 77(3):603-10. doi: 10.1021/np400872m. [PMID: 24641242]
  • Jinyong Kim, Joon No Lee, James Ye, Rosy Hao, Russell Debose-Boyd, Jin Ye. Sufficient production of geranylgeraniol is required to maintain endotoxin tolerance in macrophages. Journal of lipid research. 2013 Dec; 54(12):3430-7. doi: 10.1194/jlr.m042549. [PMID: 24062519]
  • Puspo E Giriwono, Hitoshi Shirakawa, Yusuke Ohsaki, Shuichi Hata, Hiroki Kuriyama, Shoko Sato, Tomoko Goto, Michio Komai. Dietary supplementation with geranylgeraniol suppresses lipopolysaccharide-induced inflammation via inhibition of nuclear factor-κB activation in rats. European journal of nutrition. 2013 Apr; 52(3):1191-9. doi: 10.1007/s00394-012-0429-y. [PMID: 22847643]
  • Markus Schröder, Walter Vetter. Investigation of unsaponifiable matter of plant oils and isolation of eight phytosterols by means of high-speed counter-current chromatography. Journal of chromatography. A. 2012 May; 1237(?):96-105. doi: 10.1016/j.chroma.2012.03.033. [PMID: 22481107]
  • Megumi Fujita, Makiko Tohi, Kyoko Sawada, Yasuhiro Yamamoto, Tsutomu Nakamura, Tatsurou Yagami, Motohiro Yamamori, Noboru Okamura. Involvement of the mevalonate pathway in the antiproliferative effect of zoledronate on ACHN renal cell carcinoma cells. Oncology reports. 2012 May; 27(5):1371-6. doi: 10.3892/or.2012.1683. [PMID: 22322451]
  • Sol A Green, Xiuyin Chen, Niels J Nieuwenhuizen, Adam J Matich, Mindy Y Wang, Barry J Bunn, Yar-Khing Yauk, Ross G Atkinson. Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis). Journal of experimental botany. 2012 Mar; 63(5):1951-67. doi: 10.1093/jxb/err393. [PMID: 22162874]
  • Tomoko Toyama, Michiru Tahara, Kisaburo Nagamune, Kenji Arimitsu, Yoshio Hamashima, Nirianne M Q Palacpac, Hiroshi Kawaide, Toshihiro Horii, Kazuyuki Tanabe. Gibberellin biosynthetic inhibitors make human malaria parasite Plasmodium falciparum cells swell and rupture to death. PloS one. 2012; 7(3):e32246. doi: 10.1371/journal.pone.0032246. [PMID: 22412858]
  • Takeru Yokoi, Keisuke Isobe, Tohru Yoshimura, Hisashi Hemmi. Archaeal phospholipid biosynthetic pathway reconstructed in Escherichia coli. Archaea (Vancouver, B.C.). 2012; 2012(?):438931. doi: 10.1155/2012/438931. [PMID: 22645416]
  • Asagi Ito, Hitoshi Shirakawa, Naofumi Takumi, Yoshihiko Minegishi, Ai Ohashi, Zakir H Howlader, Yusuke Ohsaki, Toshiro Sato, Tomoko Goto, Michio Komai. Menaquinone-4 enhances testosterone production in rats and testis-derived tumor cells. Lipids in health and disease. 2011 Sep; 10(?):158. doi: 10.1186/1476-511x-10-158. [PMID: 21914161]
  • K Patel, R Jhaveri, J George, G Qiang, C Kenedi, K Brown, C Cates, A Zekry, H L Tillmann, L Elliott, R Kilaru, J Albrecht, A Conrad, J G McHutchison. Open-label, ascending dose, prospective cohort study evaluating the antiviral efficacy of Rosuvastatin therapy in serum and lipid fractions in patients with chronic hepatitis C. Journal of viral hepatitis. 2011 May; 18(5):331-7. doi: 10.1111/j.1365-2893.2010.01310.x. [PMID: 20367801]
  • William B Rizzo. The role of fatty aldehyde dehydrogenase in epidermal structure and function. Dermato-endocrinology. 2011 Apr; 3(2):91-9. doi: 10.4161/derm.3.2.14619. [PMID: 21695018]
  • Mathieu Blanc, Wei Yuan Hsieh, Kevin A Robertson, Steven Watterson, Guanghou Shui, Paul Lacaze, Mizanur Khondoker, Paul Dickinson, Garwin Sing, Sara Rodríguez-Martín, Peter Phelan, Thorsten Forster, Birgit Strobl, Matthias Müller, Rudolph Riemersma, Timothy Osborne, Markus R Wenk, Ana Angulo, Peter Ghazal. Host defense against viral infection involves interferon mediated down-regulation of sterol biosynthesis. PLoS biology. 2011 Mar; 9(3):e1000598. doi: 10.1371/journal.pbio.1000598. [PMID: 21408089]
  • Angelo Aquino, Grazia Graziani, Ornella Franzese, Salvatore P Prete, Enzo Bonmassar, Laura Bonmassar, Stefania D'Atri. Exogenous control of the expression of Group I CD1 molecules competent for presentation of microbial nonpeptide antigens to human T lymphocytes. Clinical & developmental immunology. 2011; 2011(?):790460. doi: 10.1155/2011/790460. [PMID: 21603161]
  • Agata Bielecka-Dąbrowa, Simon Hannam, Jacek Rysz, Maciej Banach. Malignancy-associated dyslipidemia. The open cardiovascular medicine journal. 2011; 5(?):35-40. doi: 10.2174/1874192401105010035. [PMID: 21660223]
  • Elsa Youngsteadt, Patricia Guerra Bustios, Coby Schal. Divergent chemical cues elicit seed collecting by ants in an obligate multi-species mutualism in lowland Amazonia. PloS one. 2010 Dec; 5(12):e15822. doi: 10.1371/journal.pone.0015822. [PMID: 21209898]
  • Stanimir S Ivanov, Guillaume Charron, Howard C Hang, Craig R Roy. Lipidation by the host prenyltransferase machinery facilitates membrane localization of Legionella pneumophila effector proteins. The Journal of biological chemistry. 2010 Nov; 285(45):34686-98. doi: 10.1074/jbc.m110.170746. [PMID: 20813839]
  • Jayaram Bhandari, A Heather Fitzpatrick, Dring N Crowell. Identification of a novel abscisic acid-regulated farnesol dehydrogenase from Arabidopsis. Plant physiology. 2010 Nov; 154(3):1116-27. doi: 10.1104/pp.110.157784. [PMID: 20807998]
  • Ryouichi Tanaka, Maxi Rothbart, Seiko Oka, Atsushi Takabayashi, Kaori Takahashi, Masaru Shibata, Fumiyoshi Myouga, Reiko Motohashi, Kazuo Shinozaki, Bernhard Grimm, Ayumi Tanaka. LIL3, a light-harvesting-like protein, plays an essential role in chlorophyll and tocopherol biosynthesis. Proceedings of the National Academy of Sciences of the United States of America. 2010 Sep; 107(38):16721-5. doi: 10.1073/pnas.1004699107. [PMID: 20823244]
  • Vasiliki Falara, Eran Pichersky, Angelos K Kanellis. A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes. Plant physiology. 2010 Sep; 154(1):301-10. doi: 10.1104/pp.110.159566. [PMID: 20595348]
  • Maiko Mitake, Hiroko Ogawa, Kazuo Uebaba, Yoshihiro Shidoji. Increase in plasma concentrations of geranylgeranoic Acid after turmeric tablet intake by healthy volunteers. Journal of clinical biochemistry and nutrition. 2010 May; 46(3):252-8. doi: 10.3164/jcbn.09-109. [PMID: 20490321]
  • Paul Targett-Adams, Steeve Boulant, Mark W Douglas, John McLauchlan. Lipid metabolism and HCV infection. Viruses. 2010 May; 2(5):1195-1217. doi: 10.3390/v2051195. [PMID: 21994676]
  • Kathryn M Castorena, Kenneth A Stapleford, David J Miller. Complementary transcriptomic, lipidomic, and targeted functional genetic analyses in cultured Drosophila cells highlight the role of glycerophospholipid metabolism in Flock House virus RNA replication. BMC genomics. 2010 Mar; 11(?):183. doi: 10.1186/1471-2164-11-183. [PMID: 20236518]
  • Humberto M Spindola, Leila Servat, Carina Denny, Rodney A F Rodrigues, Marcos N Eberlin, Elaine Cabral, Ilza M O Sousa, Jorge Y Tamashiro, João E Carvalho, Mary A Foglio. Antinociceptive effect of geranylgeraniol and 6alpha,7beta-dihydroxyvouacapan-17beta-oate methyl ester isolated from Pterodon pubescens Benth. BMC pharmacology. 2010 Jan; 10(?):1. doi: 10.1186/1471-2210-10-1. [PMID: 20055987]
  • Tsuyoshi Goto, Nobuyuki Takahashi, Shizuka Hirai, Teruo Kawada. Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism. PPAR research. 2010; 2010(?):483958. doi: 10.1155/2010/483958. [PMID: 20613991]
  • Keisuke Oda, Satoshi Makino, Chiaki Masuda, Tatsuhiro Yoshiki, Yoshihisa Kitamura, Kazuyuki Takata, Daijiro Yanagisawa, Takashi Taniguchi, Ikuo Tooyama. The mRNA distribution of C7orf24, a gamma-glutamyl cyclotransferase, in rat tissues. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society. 2009 Dec; 57(12):1121-6. doi: 10.1369/jhc.2009.953976. [PMID: 19687470]
  • Michel Havaux, Brigitte Ksas, Agnieszka Szewczyk, Dominique Rumeau, Fabrice Franck, Stefano Caffarri, Christian Triantaphylidès. Vitamin B6 deficient plants display increased sensitivity to high light and photo-oxidative stress. BMC plant biology. 2009 Nov; 9(?):130. doi: 10.1186/1471-2229-9-130. [PMID: 19903353]
  • Marcelo Bertalan, Rodolpho Albano, Vânia de Pádua, Luc Rouws, Cristian Rojas, Adriana Hemerly, Kátia Teixeira, Stefan Schwab, Jean Araujo, André Oliveira, Leonardo França, Viviane Magalhães, Sylvia Alquéres, Alexander Cardoso, Wellington Almeida, Marcio Martins Loureiro, Eduardo Nogueira, Daniela Cidade, Denise Oliveira, Tatiana Simão, Jacyara Macedo, Ana Valadão, Marcela Dreschsel, Flávia Freitas, Marcia Vidal, Helma Guedes, Elisete Rodrigues, Carlos Meneses, Paulo Brioso, Luciana Pozzer, Daniel Figueiredo, Helena Montano, Jadier Junior, Gonçalo de Souza Filho, Victor Martin Quintana Flores, Beatriz Ferreira, Alan Branco, Paula Gonzalez, Heloisa Guillobel, Melissa Lemos, Luiz Seibel, José Macedo, Marcio Alves-Ferreira, Gilberto Sachetto-Martins, Ana Coelho, Eidy Santos, Gilda Amaral, Anna Neves, Ana Beatriz Pacheco, Daniela Carvalho, Letícia Lery, Paulo Bisch, Shaila C Rössle, Turán Urményi, Alessandra Rael Pereira, Rosane Silva, Edson Rondinelli, Wanda von Krüger, Orlando Martins, José Ivo Baldani, Paulo C G Ferreira. Complete genome sequence of the sugarcane nitrogen-fixing endophyte Gluconacetobacter diazotrophicus Pal5. BMC genomics. 2009 Sep; 10(?):450. doi: 10.1186/1471-2164-10-450. [PMID: 19775431]
  • Cristina Rodríguez, Javier F Alcudia, José Martínez-González, Anna Guadall, Berta Raposo, Sonia Sánchez-Gómez, Lina Badimon. Statins normalize vascular lysyl oxidase down-regulation induced by proatherogenic risk factors. Cardiovascular research. 2009 Aug; 83(3):595-603. doi: 10.1093/cvr/cvp136. [PMID: 19406911]
  • Nikolas H Kazmers, Sophia A Ma, Tomohiko Yoshida, Paula H Stern. Rho GTPase signaling and PTH 3-34, but not PTH 1-34, maintain the actin cytoskeleton and antagonize bisphosphonate effects in mouse osteoblastic MC3T3-E1 cells. Bone. 2009 Jul; 45(1):52-60. doi: 10.1016/j.bone.2009.03.675. [PMID: 19361585]
  • Xilin Yang, Hailu Zhao, Yi Sui, Ronald C W Ma, Wing Yee So, Gary T C Ko, Alice P S Kong, Risa Ozaki, Chun Yip Yeung, Gang Xu, Peter C Y Tong, Juliana C N Chan. Additive interaction between the renin-angiotensin system and lipid metabolism for cancer in type 2 diabetes. Diabetes. 2009 Jul; 58(7):1518-25. doi: 10.2337/db09-0105. [PMID: 19401427]
  • Qi Zhou, Yi Zhou, Fred A Kummerow. High-dose lovastatin decreased basal prostacyclin production in cultured endothelial cells. Prostaglandins & other lipid mediators. 2009 Jun; 89(1-2):1-7. doi: 10.1016/j.prostaglandins.2008.12.005. [PMID: 19135546]
  • Naoyuki Yoshikawa, Jun Yamada, Nelson H Tsuno, Yurai Okaji, Kazushige Kawai, Takeshi Tsuchiya, Satomi Yoneyama, Junichiro Tanaka, Yasutaka Shuno, Takeshi Nishikawa, Hirokazu Nagawa, Noriko Oshima, Koki Takahashi. Plaunotol and geranylgeraniol induce caspase-mediated apoptosis in colon cancer. The Journal of surgical research. 2009 May; 153(2):246-53. doi: 10.1016/j.jss.2008.04.021. [PMID: 18805546]
  • Tomohiko Yoshida, Mary F Clark, Paula H Stern. The small GTPase RhoA is crucial for MC3T3-E1 osteoblastic cell survival. Journal of cellular biochemistry. 2009 Apr; 106(5):896-902. doi: 10.1002/jcb.22059. [PMID: 19184980]
  • Beata Myśliwa-Kurdziel, Katalin Solymosi, Jerzy Kruk, Béla Böddi, Kazimierz Strzałka. Solvent effects on fluorescence properties of protochlorophyll and its derivatives with various porphyrin side chains. European biophysics journal : EBJ. 2008 Sep; 37(7):1185-93. doi: 10.1007/s00249-008-0288-x. [PMID: 18340441]
  • Oliver Vögler, Juana M Barceló, Catalina Ribas, Pablo V Escribá. Membrane interactions of G proteins and other related proteins. Biochimica et biophysica acta. 2008 Jul; 1778(7-8):1640-52. doi: 10.1016/j.bbamem.2008.03.008. [PMID: 18402765]
  • R F S Menna-Barreto, G A T Laranja, M C C Silva, M G P Coelho, M C Paes, M M Oliveira, S L de Castro. Anti-Trypanosoma cruzi activity of Pterodon pubescens seed oil: geranylgeraniol as the major bioactive component. Parasitology research. 2008 Jun; 103(1):111-7. doi: 10.1007/s00436-008-0937-0. [PMID: 18343952]
  • J C H van der Hilst, B Kluve-Beckerman, E J Bodar, J W M van der Meer, J P H Drenth, A Simon. Lovastatin inhibits formation of AA amyloid. Journal of leukocyte biology. 2008 May; 83(5):1295-9. doi: 10.1189/jlb.1107723. [PMID: 18285405]
  • Anders Vik, Anthony James, Lise-Lotte Gundersen. Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro. Planta medica. 2007 Oct; 73(13):1410-2. doi: 10.1055/s-2007-990238. [PMID: 17924309]
  • Jun Yamada, Kazushige Kawai, Nelson H Tsuno, Joji Kitayama, Takeshi Tsuchiya, Satomi Yoneyama, Masahiro Asakage, Yurai Okaji, Koki Takahashi, Hirokazu Nagawa. Plaunotol induces apoptosis of gastric cancer cells. Planta medica. 2007 Aug; 73(10):1068-73. doi: 10.1055/s-2007-981578. [PMID: 17691055]
  • Juraithip Wungsintaweekul, Chutima Sriyapai, Sanlaya Kaewkerd, Supinya Tewtrakul, Damrong Kongduang, Wanchai De-Eknamkul. Establishment of Croton stellatopilosus suspension culture for geranylgeraniol production and diterpenoid biosynthesis. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 May; 62(5-6):389-96. doi: 10.1515/znc-2007-5-612. [PMID: 17708445]
  • Nivea Oliveira Calixto, Maria Cristina da Costa e Silva, Carlos Roberto Machado Gayer, Marsen Garcia Pinto Coelho, Márcia Cristina Paes, Adriane Regina Todeschini. Antiplatelet activity of geranylgeraniol isolated from Pterodon pubescens fruit oil is mediated by inhibition of cyclooxygenase-1. Planta medica. 2007 May; 73(5):480-3. doi: 10.1055/s-2007-967177. [PMID: 17443436]
  • Natsajee Nualkaew, Wanchai De-Eknamkul, Toni M Kutchan, Meinhart H Zenk. Membrane-bound geranylgeranyl diphosphate phosphatases: purification and characterization from Croton stellatopilosus leaves. Phytochemistry. 2006 Aug; 67(15):1613-20. doi: 10.1016/j.phytochem.2005.12.014. [PMID: 16445953]
  • Ilaria Zanotti, Francesco Potì, Elda Favari, Knut R Steffensen, Jan-Ake Gustafsson, Franco Bernini. Pitavastatin effect on ATP binding cassette A1-mediated lipid efflux from macrophages: evidence for liver X receptor (LXR)-dependent and LXR-independent mechanisms of activation by cAMP. The Journal of pharmacology and experimental therapeutics. 2006 Apr; 317(1):395-401. doi: 10.1124/jpet.105.093930. [PMID: 16415093]
  • Anne R Kinderlerer, Rivka Steinberg, Michael Johns, Sarah K Harten, Elaine A Lidington, Dorian O Haskard, Patrick H Maxwell, Justin C Mason. Statin-induced expression of CD59 on vascular endothelium in hypoxia: a potential mechanism for the anti-inflammatory actions of statins in rheumatoid arthritis. Arthritis research & therapy. 2006; 8(4):R130. doi: 10.1186/ar2019. [PMID: 16859540]
  • Ryosuke Inoue, Nori-aki Matsuki, Gao Jing, Takashi Kanematsu, Kihachiro Abe, Masato Hirata. The inhibitory effect of alendronate, a nitrogen-containing bisphosphonate on the PI3K-Akt-NFkappaB pathway in osteosarcoma cells. British journal of pharmacology. 2005 Nov; 146(5):633-41. doi: 10.1038/sj.bjp.0706373. [PMID: 16100524]
  • Timothy E Johnson, Xiaohua Zhang, Shu Shi, Diane R Umbenhauer. Statins and PPARalpha agonists induce myotoxicity in differentiated rat skeletal muscle cultures but do not exhibit synergy with co-treatment. Toxicology and applied pharmacology. 2005 Nov; 208(3):210-21. doi: 10.1016/j.taap.2005.03.004. [PMID: 16239165]
  • Carlos Fernández-Hernando, Yajaira Suárez, Miguel A Lasunción. Lovastatin-induced PC-12 cell differentiation is associated with RhoA/RhoA kinase pathway inactivation. Molecular and cellular neurosciences. 2005 Aug; 29(4):591-602. doi: 10.1016/j.mcn.2005.04.012. [PMID: 15951198]
  • N Ferri, R Paoletti, A Corsini. Lipid-modified proteins as biomarkers for cardiovascular disease: a review. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2005 Jul; 10(4):219-37. doi: 10.1080/13547500500216660. [PMID: 16191483]
  • Sérgio S Funari, Jesús Prades, Pablo V Escribá, Francisca Barceló. Farnesol and geranylgeraniol modulate the structural properties of phosphatidylethanolamine model membranes. Molecular membrane biology. 2005 Jul; 22(4):303-11. doi: 10.1080/09687860500135411. [PMID: 16154902]
  • Roseli de Moura Espíndola, Rogério Pietro Mazzantini, Thomas Prates Ong, Aline de Conti, Renato Heidor, Fernando Salvador Moreno. Geranylgeraniol and beta-ionone inhibit hepatic preneoplastic lesions, cell proliferation, total plasma cholesterol and DNA damage during the initial phases of hepatocarcinogenesis, but only the former inhibits NF-kappaB activation. Carcinogenesis. 2005 Jun; 26(6):1091-9. doi: 10.1093/carcin/bgi047. [PMID: 15718255]
  • Yasuomi Urano, Ikuo Hayashi, Noriko Isoo, Patrick C Reid, Yoshikazu Shibasaki, Noriko Noguchi, Taisuke Tomita, Takeshi Iwatsubo, Takao Hamakubo, Tatsuhiko Kodama. Association of active gamma-secretase complex with lipid rafts. Journal of lipid research. 2005 May; 46(5):904-12. doi: 10.1194/jlr.m400333-jlr200. [PMID: 15716592]
  • Timothy S Mulligan, Steven A Farber. A 'block and rescue' pharmacogenetic approach to dissecting a biochemical pathway controlling germ cell migration. Zebrafish. 2005; 1(4):343-7. doi: 10.1089/zeb.2005.1.343. [PMID: 18248212]
  • Timothy E Johnson, Xiaohua Zhang, Kimberly B Bleicher, Gary Dysart, Amy F Loughlin, William H Schaefer, Diane R Umbenhauer. Statins induce apoptosis in rat and human myotube cultures by inhibiting protein geranylgeranylation but not ubiquinone. Toxicology and applied pharmacology. 2004 Nov; 200(3):237-50. doi: 10.1016/j.taap.2004.04.010. [PMID: 15504460]
  • Gemma Llaverias, Manuel Vázquez-Carrera, Rosa M Sánchez, Véronique Noé, Carlos J Ciudad, Juan C Laguna, Marta Alegret. Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism. Journal of lipid research. 2004 Nov; 45(11):2015-24. doi: 10.1194/jlr.m400049-jlr200. [PMID: 15314095]
  • Carlos Fernández, María del Val T Lobo Md, Diego Gómez-Coronado, Miguel A Lasunción. Cholesterol is essential for mitosis progression and its deficiency induces polyploid cell formation. Experimental cell research. 2004 Oct; 300(1):109-20. doi: 10.1016/j.yexcr.2004.06.029. [PMID: 15383319]
  • Masaru Shibata, Michito Tsuyama, Tsuneaki Takami, Hideyuki Shimizu, Yoshichika Kobayashi. Accumulation of menaquinones with incompletely reduced side chains and loss of alpha-tocopherol in rice mutants with alternations in the chlorophyll moiety. Journal of experimental botany. 2004 Sep; 55(405):1989-96. doi: 10.1093/jxb/erh218. [PMID: 15286146]
  • Ilaria Zanotti, Elda Favari, Andrei C Sposito, George H Rothblat, Franco Bernini. Pitavastatin increases ABCA1-mediated lipid efflux from Fu5AH rat hepatoma cells. Biochemical and biophysical research communications. 2004 Aug; 321(3):670-4. doi: 10.1016/j.bbrc.2004.07.020. [PMID: 15358158]
  • Heather L Hartman, Katherine E Bowers, Carol A Fierke. Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium. The Journal of biological chemistry. 2004 Jul; 279(29):30546-53. doi: 10.1074/jbc.m403469200. [PMID: 15131129]
  • Jonathan P Coxon, Grenville M Oades, Roger S Kirby, Kay W Colston. Zoledronic acid induces apoptosis and inhibits adhesion to mineralized matrix in prostate cancer cells via inhibition of protein prenylation. BJU international. 2004 Jul; 94(1):164-70. doi: 10.1111/j.1464-4096.2004.04831.x. [PMID: 15217454]
  • Yoshihiro Shidoji, Hiroko Ogawa. Natural occurrence of cancer-preventive geranylgeranoic acid in medicinal herbs. Journal of lipid research. 2004 Jun; 45(6):1092-103. doi: 10.1194/jlr.m300502-jlr200. [PMID: 15060084]
  • Natividad Ruiz-Velasco, Angeles Domínguez, Miguel A Vega. Statins upregulate CD36 expression in human monocytes, an effect strengthened when combined with PPAR-gamma ligands Putative contribution of Rho GTPases in statin-induced CD36 expression. Biochemical pharmacology. 2004 Jan; 67(2):303-13. doi: 10.1016/j.bcp.2003.09.006. [PMID: 14698043]
  • M C C Silva, C R M Gayer, C S Lopes, N O Calixto, P A Reis, C P B Passaes, M C Paes, S R Dalmau, K C C Sabino, A R Todeschini, M G P Coelho. Acute and topic anti-edematogenic fractions isolated from the seeds of Pterodon pubescens. The Journal of pharmacy and pharmacology. 2004 Jan; 56(1):135-41. doi: 10.1211/0022357022485. [PMID: 14980011]
  • Shiu-Ying Ho, Juanita L Thorpe, Yun Deng, Evelyn Santana, Robert A DeRose, Steven A Farber. Lipid metabolism in zebrafish. Methods in cell biology. 2004; 76(?):87-108. doi: 10.1016/s0091-679x(04)76006-9. [PMID: 15602873]
  • Niels W C J van de Donk, Marloes M J Kamphuis, Berris van Kessel, Henk M Lokhorst, Andries C Bloem. Inhibition of protein geranylgeranylation induces apoptosis in myeloma plasma cells by reducing Mcl-1 protein levels. Blood. 2003 Nov; 102(9):3354-62. doi: 10.1182/blood-2003-03-0970. [PMID: 12855556]
  • C Daniel Meyers, Lisa R Tannock, Thomas N Wight, Alan Chait. Statin-exposed vascular smooth muscle cells secrete proteoglycans with decreased binding affinity for LDL. Journal of lipid research. 2003 Nov; 44(11):2152-60. doi: 10.1194/jlr.m300252-jlr200. [PMID: 12923222]
  • O Fromigue, N Kheddoumi, J-J Body. Bisphosphonates antagonise bone growth factors' effects on human breast cancer cells survival. British journal of cancer. 2003 Jul; 89(1):178-84. doi: 10.1038/sj.bjc.6601009. [PMID: 12838321]
  • Bettina Haslinger, Robert Kleemann, Karin H Toet, Teake Kooistra. Simvastatin suppresses tissue factor expression and increases fibrinolytic activity in tumor necrosis factor-alpha-activated human peritoneal mesothelial cells. Kidney international. 2003 Jun; 63(6):2065-74. doi: 10.1046/j.1523-1755.2003.t01-2-00004.x. [PMID: 12753293]
  • Nicola Ferri, Kohei Yokoyama, Martin Sadilek, Rodolfo Paoletti, Rafael Apitz-Castro, Michael H Gelb, Alberto Corsini. Ajoene, a garlic compound, inhibits protein prenylation and arterial smooth muscle cell proliferation. British journal of pharmacology. 2003 Mar; 138(5):811-8. doi: 10.1038/sj.bjp.0705126. [PMID: 12642382]
  • W A Grasser, A P Baumann, S F Petras, H J Harwood, R Devalaraja, R Renkiewicz, V Baragi, D D Thompson, V M Paraklar. Regulation of osteoclast differentiation by statins. Journal of musculoskeletal & neuronal interactions. 2003 Mar; 3(1):53-62. doi: NULL. [PMID: 15758366]
  • Toshiko Shibayama-Imazu, Shizuka Sakairi, Akiko Watanabe, Toshihiro Aiuchi, Shigeo Nakajo, Kazuyasu Nakaya. Vitamin K(2) selectively induced apoptosis in ovarian TYK-nu and pancreatic MIA PaCa-2 cells out of eight solid tumor cell lines through a mechanism different from geranylgeraniol. Journal of cancer research and clinical oncology. 2003 Jan; 129(1):1-11. doi: 10.1007/s00432-002-0393-7. [PMID: 12618894]
  • Bettina Haslinger, Martin F Goedde, Karin H Toet, Teake Kooistra. Simvastatin increases fibrinolytic activity in human peritoneal mesothelial cells independent of cholesterol lowering. Kidney international. 2002 Nov; 62(5):1611-9. doi: 10.1046/j.1523-1755.2002.00601.x. [PMID: 12371961]
  • Justin C Mason, Zahra Ahmed, Rivka Mankoff, Elaine A Lidington, Saifur Ahmad, Vinay Bhatia, Anne Kinderlerer, Anna M Randi, Dorian O Haskard. Statin-induced expression of decay-accelerating factor protects vascular endothelium against complement-mediated injury. Circulation research. 2002 Oct; 91(8):696-703. doi: 10.1161/01.res.0000038151.57577.19. [PMID: 12386146]
  • Björn Ludolph, Frank Eisele, Herbert Waldmann. Solution- and solid-phase synthesis of the polybasic lipid-modified C termini of Rho A and K-Ras 4B. Chembiochem : a European journal of chemical biology. 2002 Sep; 3(9):901-4. doi: 10.1002/1439-7633(20020902)3:9<901::aid-cbic901>3.0.co;2-u. [PMID: 12210992]
  • Yuichi Kodaira, Kiyotaka Usui, Itaru Kon, Hiroshi Sagami. Formation of (R)-2,3-dihydrogeranylgeranoic acid from geranylgeraniol in rat thymocytes. Journal of biochemistry. 2002 Aug; 132(2):327-34. doi: 10.1093/oxfordjournals.jbchem.a003227. [PMID: 12153732]
  • Nobuyuki Takahashi, Teruo Kawada, Tsuyoshi Goto, Takayuki Yamamoto, Aki Taimatsu, Naoko Matsui, Kazuhiro Kimura, Masayuki Saito, Masashi Hosokawa, Kazuo Miyashita, Tohru Fushiki. Dual action of isoprenols from herbal medicines on both PPARgamma and PPARalpha in 3T3-L1 adipocytes and HepG2 hepatocytes. FEBS letters. 2002 Mar; 514(2-3):315-22. doi: 10.1016/s0014-5793(02)02390-6. [PMID: 11943173]
  • Christopher J Edwards, Tim D Spector. Statins as modulators of bone formation. Arthritis research. 2002; 4(3):151-3. doi: 10.1186/ar399. [PMID: 12010563]
  • S Takaichi, T Maoka, M Yamada, K Matsuura, Y Haikawa, S Hanada. Absence of carotenes and presence of a tertiary methoxy group in a carotenoid from a thermophilic filamentous photosynthetic bacterium Roseiflexus castenholzii. Plant & cell physiology. 2001 Dec; 42(12):1355-62. doi: 10.1093/pcp/pce172. [PMID: 11773528]
  • J Nah, S J Song, K Back. Partial characterization of farnesyl and geranylgeranyl diphosphatases induced in rice seedlings by UV-C irradiation. Plant & cell physiology. 2001 Aug; 42(8):864-7. doi: 10.1093/pcp/pce102. [PMID: 11522913]
  • K Yasunari, K Maeda, M Minami, J Yoshikawa. HMG-CoA reductase inhibitors prevent migration of human coronary smooth muscle cells through suppression of increase in oxidative stress. Arteriosclerosis, thrombosis, and vascular biology. 2001 Jun; 21(6):937-42. doi: 10.1161/01.atv.21.6.937. [PMID: 11397700]
  • I Rajbhandari, S Takamatsu, D G Nagle. A new dehydrogeranylgeraniol antioxidant from Saururus cernuus that inhibits intracellular reactive oxygen species (ROS)-catalyzed oxidation within HL-60 cells. Journal of natural products. 2001 Jun; 64(6):693-5. doi: 10.1021/np0101346. [PMID: 11421725]