phytofluene (BioDeep_00000364621)

Main id: BioDeep_00000027847

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(12E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene

化学式: C40H62 (542.4851)
中文名称: 15-顺式-八氢番茄红素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(/C)(=C/C=C/C(/C)=C/C=C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/C)\CC/C=C(\C)/CC/C=C(\C)/C
InChI: InChI=1S/C40H62/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15,19-22,25,27-30H,13-14,16-18,23-24,26,31-32H2,1-10H3/b12-11+,25-15+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+

描述信息

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
Phytofluene is a carotenoid pigment with an orange color found naturally in tomatoes and other vegetables. It is the second product of carotenoid biosynthesis. It is formed from phytoene in a desaturation reaction leading to the formation of five conjugated double bonds. In the following step, addition of carbon-carbon conjugated double bonds leads to the formation of z-carotene and appearance of visible color.; Phytofluene is a carotenoid pigment with an orange color found naturally in tomatoes and other vegetables. It is the second product of carotenoid biosynthesis. Phytofluene is found in many foods, some of which are bitter gourd, yellow bell pepper, caraway, and pepper (c. annuum).

同义名列表

11 个代谢物同义名

phytofluene; 9-cis-phytofluene; (15Z)-7,8,11,12,7,8-Hexahydro-psi,psi-carotene; 15-cis-Phytofluene; (15Z)-Phytofluene; Hexahydrolycopene; (12E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene; 7,8,11,12,7,8-hexahydro-psi,psi-carotene; 7,7,8,8,11,12-hexahydro-psi,psi-carotene; all-trans-phytofluene; all-trans-Phytofluene



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(2)

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)

165 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。

亚细胞结构定位 关联基因列表
Cytoplasm 5 CD36, FABP1, HPGDS, LYPLAL1, SCARB1
Peripheral membrane protein 1 PLOD2
Endoplasmic reticulum membrane 4 ABCA1, ELOVL5, FADS3, PLOD2
Nucleus 4 FABP1, ISX, KLK3, SETD7
cytosol 4 FABP1, HPGDS, LYPLAL1, MB
dendrite 1 ELOVL5
phagocytic vesicle 3 ABCA1, CD36, STX8
trans-Golgi network 1 STX8
nucleoplasm 3 FABP1, HPGDS, SETD7
Cell membrane 4 ABCA1, CD36, NPC1L1, SCARB1
Multi-pass membrane protein 6 ABCA1, CD36, ELOVL5, FADS3, NPC1L1, SCARB1
cell surface 2 CD36, SCARB1
Golgi apparatus 2 ABCA1, CD36
Golgi membrane 1 INS
lysosomal membrane 1 SCARB1
neuronal cell body 1 ELOVL5
Lysosome 1 SCARB1
endosome 2 ABCA1, STX8
plasma membrane 6 ABCA1, CD36, KLK3, NPC1L1, SCARB1, STX8
Membrane 7 ABCA1, CD36, ELOVL5, FADS3, NPC1L1, SCARB1, STX8
apical plasma membrane 2 CD36, NPC1L1
basolateral plasma membrane 1 ABCA1
caveola 2 CD36, SCARB1
extracellular exosome 5 FABP1, KLK3, MB, PLOD2, SCARB1
Lumenal side 1 PLOD2
endoplasmic reticulum 4 APOC1, ELOVL5, PLOD2, STX8
extracellular space 6 CD36, CRP, IL6, INS, KLK3, LIPC
perinuclear region of cytoplasm 2 ABCA1, STX8
mitochondrion 1 LYPLAL1
protein-containing complex 2 FABP1, KLK3
intracellular membrane-bounded organelle 3 ABCA1, HPGDS, SCARB1
Secreted 5 APOC1, CRP, IL6, INS, LIPC
extracellular region 6 APOC1, CRP, IL6, INS, KLK3, LIPC
Single-pass membrane protein 1 STX8
external side of plasma membrane 2 ABCA1, CD36
chylomicron 1 APOC1
high-density lipoprotein particle 2 APOC1, LIPC
very-low-density lipoprotein particle 1 APOC1
nucleolus 1 SETD7
sarcoplasm 1 MB
Early endosome 1 STX8
recycling endosome 1 STX8
vesicle 1 STX8
Apical cell membrane 2 CD36, NPC1L1
Membrane raft 2 ABCA1, CD36
collagen trimer 1 CD36
intracellular vesicle 1 ABCA1
peroxisomal matrix 1 FABP1
secretory granule 1 KLK3
Late endosome 1 STX8
receptor complex 1 CD36
chromatin 1 ISX
cell periphery 1 CD36
Chromosome 1 SETD7
brush border membrane 2 CD36, NPC1L1
Endomembrane system 2 NPC1L1, STX8
endosome lumen 1 INS
Membrane, caveola 1 SCARB1
Cytoplasmic vesicle membrane 1 NPC1L1
Cell projection, dendrite 1 ELOVL5
specific granule membrane 1 CD36
[Isoform 2]: Cytoplasm, cytosol 1 LYPLAL1
SNARE complex 1 STX8
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, LIPC
endocytic vesicle membrane 2 CD36, SCARB1
endocytic vesicle 1 ABCA1
transport vesicle 1 INS
rough endoplasmic reticulum membrane 1 PLOD2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Single-pass type IV membrane protein 1 STX8
Rough endoplasmic reticulum 1 PLOD2
[Isoform 1]: Cytoplasm, cytosol 1 LYPLAL1
platelet alpha granule membrane 1 CD36
Cytoplasm, sarcoplasm 1 MB
interleukin-6 receptor complex 1 IL6
apical cortex 1 FABP1
dendritic tree 1 ELOVL5


文献列表

  • Pedro Brivaldo Viana da Silva, Lívia Beatriz Brenelli, Lilian Regina Barros Mariutti. Waste and by-products as sources of lycopene, phytoene, and phytofluene - Integrative review with bibliometric analysis. Food research international (Ottawa, Ont.). 2023 07; 169(?):112838. doi: 10.1016/j.foodres.2023.112838. [PMID: 37254412]
  • Aleksandr A Ashikhmin, Anton S Benditkis, Andrey A Moskalenko, Alexander A Krasnovsky. ζ-Carotene: Generation and Quenching of Singlet Oxygen, Comparison with Phytofluene. Biochemistry. Biokhimiia. 2022 Oct; 87(10):1169-1178. doi: 10.1134/s0006297922100108. [PMID: 36273885]
  • Karolina Tkacz, Ángel Gil-Izquierdo, Sonia Medina, Igor Piotr Turkiewicz, Raúl Domínguez-Perles, Paulina Nowicka, Aneta Wojdyło. Phytoprostanes, phytofurans, tocopherols, tocotrienols, carotenoids and free amino acids and biological potential of sea buckthorn juices. Journal of the science of food and agriculture. 2022 Jan; 102(1):185-197. doi: 10.1002/jsfa.11345. [PMID: 34061348]
  • Nancy E Moran, Jennifer M Thomas-Ahner, Jessica L Fleming, Joseph P McElroy, Rebecca Mehl, Elizabeth M Grainger, Ken M Riedl, Amanda E Toland, Steven J Schwartz, Steven K Clinton. Single Nucleotide Polymorphisms in β-Carotene Oxygenase 1 are Associated with Plasma Lycopene Responses to a Tomato-Soy Juice Intervention in Men with Prostate Cancer. The Journal of nutrition. 2019 03; 149(3):381-397. doi: 10.1093/jn/nxy304. [PMID: 30801647]
  • Paula Mapelli-Brahm, Charles Desmarchelier, Marielle Margier, Emmanuelle Reboul, Antonio J Meléndez Martínez, Patrick Borel. Phytoene and Phytofluene Isolated from a Tomato Extract are Readily Incorporated in Mixed Micelles and Absorbed by Caco-2 Cells, as Compared to Lycopene, and SR-BI is Involved in their Cellular Uptake. Molecular nutrition & food research. 2018 11; 62(22):e1800703. doi: 10.1002/mnfr.201800703. [PMID: 30192047]
  • David C Nieman, Courtney L Capps, Christopher R Capps, Zack L Shue, Jennifer E McBride. Effect of 4-Week Ingestion of Tomato-Based Carotenoids on Exercise-Induced Inflammation, Muscle Damage, and Oxidative Stress in Endurance Runners. International journal of sport nutrition and exercise metabolism. 2018 May; 28(3):266-273. doi: 10.1123/ijsnem.2017-0272. [PMID: 29091464]
  • Paula Mapelli-Brahm, Joana Corte-Real, Antonio J Meléndez-Martínez, Torsten Bohn. Bioaccessibility of phytoene and phytofluene is superior to other carotenoids from selected fruit and vegetable juices. Food chemistry. 2017 Aug; 229(?):304-311. doi: 10.1016/j.foodchem.2017.02.074. [PMID: 28372178]
  • Francesca Bot, Monica Anese, M Adília Lemos, Graham Hungerford. Use of time-resolved spectroscopy as a method to monitor carotenoids present in tomato extract obtained using ultrasound treatment. Phytochemical analysis : PCA. 2016 Jan; 27(1):32-40. doi: 10.1002/pca.2584. [PMID: 26289117]
  • Jessica L Cooperstone, Robin A Ralston, Ken M Riedl, Thomas C Haufe, Ralf M Schweiggert, Samantha A King, Cynthia D Timmers, David M Francis, Gregory B Lesinski, Steven K Clinton, Steven J Schwartz. Enhanced bioavailability of lycopene when consumed as cis-isomers from tangerine compared to red tomato juice, a randomized, cross-over clinical trial. Molecular nutrition & food research. 2015 Apr; 59(4):658-69. doi: 10.1002/mnfr.201400658. [PMID: 25620547]
  • Antonio J Meléndez-Martínez, Margot Paulino, Carla M Stinco, Paula Mapelli-Brahm, Xiang-Dong Wang. Study of the time-course of cis/trans (Z/E) isomerization of lycopene, phytoene, and phytofluene from tomato. Journal of agricultural and food chemistry. 2014 Dec; 62(51):12399-406. doi: 10.1021/jf5041965. [PMID: 25426993]
  • Elio Fantini, Giulia Falcone, Sarah Frusciante, Leonardo Giliberto, Giovanni Giuliano. Dissection of tomato lycopene biosynthesis through virus-induced gene silencing. Plant physiology. 2013 Oct; 163(2):986-98. doi: 10.1104/pp.113.224733. [PMID: 24014574]
  • Nikki A Ford, Amy C Elsen, John W Erdman. Genetic ablation of carotene oxygenases and consumption of lycopene or tomato powder diets modulate carotenoid and lipid metabolism in mice. Nutrition research (New York, N.Y.). 2013 Sep; 33(9):733-42. doi: 10.1016/j.nutres.2013.07.007. [PMID: 24034573]
  • Thomas T Y Wang, Alison J Edwards, Beverly A Clevidence. Strong and weak plasma response to dietary carotenoids identified by cluster analysis and linked to beta-carotene 15,15'-monooxygenase 1 single nucleotide polymorphisms. The Journal of nutritional biochemistry. 2013 Aug; 24(8):1538-46. doi: 10.1016/j.jnutbio.2013.01.001. [PMID: 23517913]
  • Lauren E Conlon, Ryan D King, Nancy E Moran, John W Erdman. Coconut oil enhances tomato carotenoid tissue accumulation compared to safflower oil in the Mongolian gerbil ( Meriones unguiculatus ). Journal of agricultural and food chemistry. 2012 Aug; 60(34):8386-94. doi: 10.1021/jf301902k. [PMID: 22866697]
  • B Y Hsu, Y S Pu, B Stephen Inbaraj, B H Chen. An improved high performance liquid chromatography-diode array detection-mass spectrometry method for determination of carotenoids and their precursors phytoene and phytofluene in human serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jun; 899(?):36-45. doi: 10.1016/j.jchromb.2012.04.034. [PMID: 22622065]
  • Nancy J Engelmann, Steven K Clinton, John W Erdman. Nutritional aspects of phytoene and phytofluene, carotenoid precursors to lycopene. Advances in nutrition (Bethesda, Md.). 2011 Jan; 2(1):51-61. doi: 10.3945/an.110.000075. [PMID: 22211189]
  • Ayhan Dogukan, Mehmet Tuzcu, Can Ali Agca, Hasan Gencoglu, Nurhan Sahin, Muhittin Onderci, Ibrahim Hanifi Ozercan, Necip Ilhan, Omer Kucuk, Kazim Sahin. A tomato lycopene complex protects the kidney from cisplatin-induced injury via affecting oxidative stress as well as Bax, Bcl-2, and HSPs expression. Nutrition and cancer. 2011; 63(3):427-34. doi: 10.1080/01635581.2011.535958. [PMID: 21391123]
  • Aviv Shaish, Ayelet Harari, Yehuda Kamari, Etienne Soudant, Dror Harats, Ami Ben-Amotz. A carotenoid algal preparation containing phytoene and phytofluene inhibited LDL oxidation in vitro. Plant foods for human nutrition (Dordrecht, Netherlands). 2008 Jun; 63(2):83-6. doi: 10.1007/s11130-008-0075-y. [PMID: 18443908]
  • Peter Lorenz, Melanie Berger, Julia Bertrams, Kristian Wende, Kristin Wenzel, Ulrike Lindequist, Ulrich Meyer, Florian C Stintzing. Natural wax constituents of a supercritical fluid CO(2) extract from quince (Cydonia oblonga Mill.) pomace. Analytical and bioanalytical chemistry. 2008 May; 391(2):633-46. doi: 10.1007/s00216-008-2000-5. [PMID: 18418588]
  • Jessica K Campbell, Chad K Stroud, Manabu T Nakamura, Mary Ann Lila, John W Erdman. Serum testosterone is reduced following short-term phytofluene, lycopene, or tomato powder consumption in F344 rats. The Journal of nutrition. 2006 Nov; 136(11):2813-9. doi: 10.1093/jn/136.11.2813. [PMID: 17056806]
  • Jessica K Campbell, Randy B Rogers, Mary Ann Lila, John W Erdman. Biosynthesis of 14C-phytoene from tomato cell suspension cultures (Lycopersicon esculentum) for utilization in prostate cancer cell culture studies. Journal of agricultural and food chemistry. 2006 Feb; 54(3):747-55. doi: 10.1021/jf0581269. [PMID: 16448178]
  • Patrizia Riso, Antonella Brusamolino, Antonia Martinetti, Marisa Porrini. Effect of a tomato drink intervention on insulin-like growth factor (IGF)-1 serum levels in healthy subjects. Nutrition and cancer. 2006; 55(2):157-62. doi: 10.1207/s15327914nc5502_6. [PMID: 17044770]
  • Olivier Aust, Wilhelm Stahl, Helmut Sies, Hagen Tronnier, Ulrike Heinrich. Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2005 Jan; 75(1):54-60. doi: 10.1024/0300-9831.75.1.54. [PMID: 15830922]
  • Myriam Richelle, Karlheinz Bortlik, Stéphanie Liardet, Corinne Hager, Pierre Lambelet, Markus Baur, Lee A Applegate, Elizabeth A Offord. A food-based formulation provides lycopene with the same bioavailability to humans as that from tomato paste. The Journal of nutrition. 2002 Mar; 132(3):404-8. doi: 10.1093/jn/132.3.404. [PMID: 11880563]
  • I Neuman, H Nahum, A Ben-Amotz. Reduction of exercise-induced asthma oxidative stress by lycopene, a natural antioxidant. Allergy. 2000 Dec; 55(12):1184-9. doi: 10.1034/j.1398-9995.2000.00748.x. [PMID: 11117277]
  • I Paetau, D Rao, E R Wiley, E D Brown, B A Clevidence. Carotenoids in human buccal mucosa cells after 4 wk of supplementation with tomato juice or lycopene supplements. The American journal of clinical nutrition. 1999 Oct; 70(4):490-4. doi: 10.1093/ajcn/70.4.490. [PMID: 10500017]
  • G Sandmann, C Schneider, P Böger. A new non-radioactive assay of phytoene desaturase to evaluate bleaching herbicides. Zeitschrift fur Naturforschung. C, Journal of biosciences. 1996 Jul; 51(7-8):534-8. doi: . [PMID: 8810094]
  • M A Ross, L K Crosley, K M Brown, S J Duthie, A C Collins, J R Arthur, G G Duthie. Plasma concentrations of carotenoids and antioxidant vitamins in Scottish males: influences of smoking. European journal of clinical nutrition. 1995 Nov; 49(11):861-5. doi: NULL. [PMID: 8557024]
  • N M Merkle, H Wiedeck, C Herfarth, A Grünert. [Immediate postoperative enteral tube feeding following resection of the large intestine. Experiences with a controlled clinical study]. Der Chirurg; Zeitschrift fur alle Gebiete der operativen Medizen. 1984 Apr; 55(4):267-74. doi: NULL. [PMID: 6426893]
  • J N Thompson. Interference from carotenoids in the fluorometric analysis of serum vitamin A in cancer studies. European journal of cancer & clinical oncology. 1983 Nov; 19(11):1645-6. doi: 10.1016/0277-5379(83)90098-6. [PMID: 6685646]
  • D A BEELER, J W PORTER. The enzymatic conversion of phytoene to phytofluene. Biochemical and biophysical research communications. 1962 Aug; 8(?):367-71. doi: 10.1016/0006-291x(62)90009-8. [PMID: 13866515]
  • L ZECHMEISTER, G KARMAKAR. The occurrence of phytofluene in green plant organs. Archives of biochemistry and biophysics. 1953 Nov; 47(1):160-4. doi: 10.1016/0003-9861(53)90445-7. [PMID: 13114883]
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