FLUOROLINK(R) D (BioDeep_00000872044)

Main id: BioDeep_00000007165

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


(e,e,e)-geranylgeraniol

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, 全氟聚醚基表面活性剂, 香叶基香叶醇
谱图信息: 最多检出来源 () 0%

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

描述信息

A diterpenoid that is hexadeca-2,6,10,14-tetraene substituted by methyl groups at positions 3, 7, 11 and 15 and a hydroxy group at position 1.
A geranylgeraniol in which all four double bonds have E- (trans-) geometry.
Geranylgeraniol, also known as tetraprenol or (2e,6e,10e)-geranylgeraniol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeraniol is considered to be an isoprenoid lipid molecule. Geranylgeraniol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Geranylgeraniol can be found in flaxseed, which makes geranylgeraniol a potential biomarker for the consumption of this food product. Geranylgeraniol is a diterpene alcohol which plays a role in several important biological processes. It is an intermediate in the biosynthesis of other diterpenes and of vitamins E and K. It also used in the post-translational modification known as geranylgeranylation. Geranylgeraniol is a pheromone for bumblebees and a variety of other insects .
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

5 个代谢物同义名

GERANYLGERANIOL; (e,e,e)-geranylgeraniol; FLUOROLINK(R) D; Geranylgeraniol; Geranylgeraniol



数据库引用编号

21 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
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