Levoglucosan (BioDeep_00000018649)

 

Secondary id: BioDeep_00000398310, BioDeep_00000872217

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.

化学式: C6H10O5 (162.052821)
中文名称: 1,6-脱水-β-D-葡萄糖, 1,6-内醚-D-半乳糖
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.07%

分子结构信息

SMILES: C1C2C(C(C(C(O1)O2)O)O)O
InChI: InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2

描述信息

Levoglucosan is an anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It is formed from the pyrolysis of carbohydrates, such as starch and cellulose. As a result, levoglucosan is often used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. Levoglucosan in urine has been shown to be highly correlated with regional fires and as a biomarker for wood smoke exposure (PMID: 19165390). This is because the gas emitted by the pyrolysis of wood (biomass) contains significant amounts of levoglucosan. The hydrolysis of levoglucosan generates the fermentable sugar glucose, and therefore lignocellulosic material exhibits great potential as a renewable feedstock for the production of bioethanol. Levoglucosan can also be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers. Levoglucosan is also produced via caramelization of sugar. Consumption of caramel or caramel-containing sweets can lead to a short-term 5X increase in urinary levels of levoglucosan (from 20 uM/mM creatinine to 100 uM/mM creatinine) (PMID: 19707249). Urinary levoglucosan levels increase within 2 h of caramel consumption and return to pre-exposure levels within 24 h. These data suggest that diet is a major factor in determining urinary levoglucosan levels and that recent dietary history needs to be taken into account to use levoglucosan as a marker for wood smoke exposure. Excretory levels of levoglucosan vary widely from zero up to 5.3 mmol/L (PMID: 3757263, 16448658, 16317539).
Levoglucosan (1,6-Anhydro-β-D-glucopyranose) is an anhydrosugar produced through glucan pyrolysis and is widely found in nature[1].

同义名列表

25 个代谢物同义名

6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.; (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol; 6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.; 6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol; 1,6-Anhydro-beta-delta-glucopyranose; 1,6-Anhydro-beta-D-glucopyranose; 1,6-Anhydro-beta-glucopyranose; 1,6-Anhydro-beta-delta-glucose; 1,6-Anhydro-b-D-glucopyranose; 1,6-Anhydro-b-glucopyranose; 1,6-Anhydro-β-glucopyranose; 1,6-Anhydro-beta-D-glucose; 1,6-Anhydro-delta-glucose; 1,6-Anhydro-β-D-glucose; 1,6-Anhydro-b-D-glucose; 1,6-Anhydro-D-galactose; Anhydro-delta-mannosan; 1,6-Anhydro-D-glucose; 1,6-Anhydroglucose; Anhydro-D-mannosan; Leucoglucosan; Levoglucosan; L-Glucosan; Glucosan; 1,6-Anhydro-β-D-glucopyranose



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(0)

PlantCyc(0)

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)

46 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

  • Yumin Li, Tzung-May Fu, Jian Zhen Yu, Xu Feng, Lijuan Zhang, Jing Chen, Suresh Kumar Reddy Boreddy, Kimitaka Kawamura, Pingqing Fu, Xin Yang, Lei Zhu, Zhenzhong Zeng. Impacts of Chemical Degradation on the Global Budget of Atmospheric Levoglucosan and Its Use As a Biomass Burning Tracer. Environmental science & technology. 2021 04; 55(8):5525-5536. doi: 10.1021/acs.est.0c07313. [PMID: 33754698]
  • Junqi Wang, Siming You, Zhoumin Lu, Rui Chen, Fuqing Xu. Life cycle assessment of bio-based levoglucosan production from cotton straw through fast pyrolysis. Bioresource technology. 2020 Jul; 307(?):123179. doi: 10.1016/j.biortech.2020.123179. [PMID: 32222688]
  • I Gensch, X F Sang-Arlt, W Laumer, C Y Chan, G Engling, J Rudolph, A Kiendler-Scharr. Using δ13C of Levoglucosan As a Chemical Clock. Environmental science & technology. 2018 10; 52(19):11094-11101. doi: 10.1021/acs.est.8b03054. [PMID: 30169962]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Olorunfemi Adetona, Christopher D Simpson, Zheng Li, Andreas Sjodin, Antonia M Calafat, Luke P Naeher. Hydroxylated polycyclic aromatic hydrocarbons as biomarkers of exposure to wood smoke in wildland firefighters. Journal of exposure science & environmental epidemiology. 2017 01; 27(1):78-83. doi: 10.1038/jes.2015.75. [PMID: 26555473]
  • Xiaochao Xiong, Jieni Lian, Xiaochen Yu, Manuel Garcia-Perez, Shulin Chen. Engineering levoglucosan metabolic pathway in Rhodococcus jostii RHA1 for lipid production. Journal of industrial microbiology & biotechnology. 2016 11; 43(11):1551-1560. doi: 10.1007/s10295-016-1832-9. [PMID: 27558782]
  • Willy Maenhaut, Reinhilde Vermeylen, Magda Claeys, Jordy Vercauteren, Edward Roekens. Sources of the PM10 aerosol in Flanders, Belgium, and re-assessment of the contribution from wood burning. The Science of the total environment. 2016 08; 562(?):550-560. doi: 10.1016/j.scitotenv.2016.04.074. [PMID: 27110969]
  • Luis Luque, Valerie C A Orr, Sean Chen, Roel Westerhof, Stijn Oudenhoven, Guus van Rossum, Sascha Kersten, Franco Berruti, Lars Rehmann. Lipid accumulation from pinewood pyrolysates by Rhodosporidium diobovatum and Chlorella vulgaris for biodiesel production. Bioresource technology. 2016 Aug; 214(?):660-669. doi: 10.1016/j.biortech.2016.05.030. [PMID: 27208736]
  • Zia Ul Islam, Yu Zhisheng, El Barbary Hassan, Chang Dongdong, Zhang Hongxun. Microbial conversion of pyrolytic products to biofuels: a novel and sustainable approach toward second-generation biofuels. Journal of industrial microbiology & biotechnology. 2015 Dec; 42(12):1557-79. doi: 10.1007/s10295-015-1687-5. [PMID: 26433384]
  • Anqing Zheng, Zengli Zhao, Sheng Chang, Zhen Huang, Kun Zhao, Guoqiang Wei, Fang He, Haibin Li. Comparison of the effect of wet and dry torrefaction on chemical structure and pyrolysis behavior of corncobs. Bioresource technology. 2015 Jan; 176(?):15-22. doi: 10.1016/j.biortech.2014.10.157. [PMID: 25460979]
  • Daniel Santhanaraj, Marjorie R Rover, Daniel E Resasco, Robert C Brown, Steven Crossley. Gluconic acid from biomass fast pyrolysis oils: specialty chemicals from the thermochemical conversion of biomass. ChemSusChem. 2014 Nov; 7(11):3132-7. doi: 10.1002/cssc.201402431. [PMID: 25204798]
  • Luke P Naeher, Dana Boyd Barr, Olorunfemi Adetona, Christopher D Simpson. Urinary levoglucosan as a biomarker for woodsmoke exposure in wildland firefighters. International journal of occupational and environmental health. 2013 Oct; 19(4):304-10. doi: 10.1179/2049396713y.0000000037. [PMID: 24588036]
  • P Wallner, M Kundi, H Moshammer, S Scharf, M Schmutzer, S Weiss, P Hohenblum, H-P Hutter. Urinary levoglucosan levels in Austrian communities differing in agrarian quota. International journal of hygiene and environmental health. 2013 Jun; 216(3):280-3. doi: 10.1016/j.ijheh.2012.05.001. [PMID: 22647540]
  • Jieni Lian, Manuel Garcia-Perez, Shulin Chen. Fermentation of levoglucosan with oleaginous yeasts for lipid production. Bioresource technology. 2013 Apr; 133(?):183-9. doi: 10.1016/j.biortech.2013.01.031. [PMID: 23425586]
  • Su-Hwa Jung, Seon-Jin Kim, Joo-Sik Kim. Characteristics of products from fast pyrolysis of fractions of waste square timber and ordinary plywood using a fluidized bed reactor. Bioresource technology. 2012 Jun; 114(?):670-6. doi: 10.1016/j.biortech.2012.03.044. [PMID: 22513256]
  • Hanns Moshammer, Stefan Weiss, Manfred Neuberger. Woodsmoke marker levoglucosan: kinetics in a self-experiment. International journal of occupational medicine and environmental health. 2012 Jun; 25(2):122-5. doi: 10.2478/s13382-012-0023-9. [PMID: 22528541]
  • Xue F Sang, Iulia Gensch, Werner Laumer, Beatrix Kammer, Chuen Y Chan, Guenter Engling, Andreas Wahner, Holger Wissel, A Kiendler-Scharr. Stable carbon isotope ratio analysis of anhydrosugars in biomass burning aerosol particles from source samples. Environmental science & technology. 2012 Mar; 46(6):3312-8. doi: 10.1021/es204094v. [PMID: 22313249]
  • M G Perrone, B R Larsen, L Ferrero, G Sangiorgi, G De Gennaro, R Udisti, R Zangrando, A Gambaro, E Bolzacchini. Sources of high PM2.5 concentrations in Milan, Northern Italy: molecular marker data and CMB modelling. The Science of the total environment. 2012 Jan; 414(?):343-55. doi: 10.1016/j.scitotenv.2011.11.026. [PMID: 22155277]
  • Kabindra M Shakya, Patrick Louchouarn, Robert J Griffin. Lignin-derived phenols in Houston aerosols: implications for natural background sources. Environmental science & technology. 2011 Oct; 45(19):8268-75. doi: 10.1021/es201668y. [PMID: 21877739]
  • Li-Jung Kuo, Patrick Louchouarn, Bruce E Herbert. Influence of combustion conditions on yields of solvent-extractable anhydrosugars and lignin phenols in chars: implications for characterizations of biomass combustion residues. Chemosphere. 2011 Oct; 85(5):797-805. doi: 10.1016/j.chemosphere.2011.06.074. [PMID: 21762951]
  • Horacio Riojas-Rodriguez, Astrid Schilmann, Adriana Teresa Marron-Mares, Omar Masera, Zheng Li, Lovisa Romanoff, Andreas Sjödin, Leonora Rojas-Bracho, Larry L Needham, Isabelle Romieu. Impact of the improved patsari biomass stove on urinary polycyclic aromatic hydrocarbon biomarkers and carbon monoxide exposures in rural Mexican women. Environmental health perspectives. 2011 Sep; 119(9):1301-7. doi: 10.1289/ehp.1002927. [PMID: 21622083]
  • Jing Ke, Dhrubojyoti D Laskar, Deepak Singh, Shulin Chen. In situ lignocellulosic unlocking mechanism for carbohydrate hydrolysis in termites: crucial lignin modification. Biotechnology for biofuels. 2011 Jun; 4(?):17. doi: 10.1186/1754-6834-4-17. [PMID: 21672247]
  • Ryan W Allen, Chris Carlsten, Barbara Karlen, Sara Leckie, Stephan van Eeden, Sverre Vedal, Imelda Wong, Michael Brauer. An air filter intervention study of endothelial function among healthy adults in a woodsmoke-impacted community. American journal of respiratory and critical care medicine. 2011 May; 183(9):1222-30. doi: 10.1164/rccm.201010-1572oc. [PMID: 21257787]
  • Carol Potera. Wood-burning stoves get help from HEPA filters. Environmental health perspectives. 2011 Apr; 119(4):A164. doi: 10.1289/ehp.119-a164a. [PMID: 21459694]
  • Oliver Fiehn, W Timothy Garvey, John W Newman, Kerry H Lok, Charles L Hoppel, Sean H Adams. Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women. PloS one. 2010 Dec; 5(12):e15234. doi: 10.1371/journal.pone.0015234. [PMID: 21170321]
  • Megan A Bergauff, Tony J Ward, Curtis W Noonan, Christopher T Migliaccio, Christopher D Simpson, Ashley R Evanoski, Christopher P Palmer. Urinary levoglucosan as a biomarker of wood smoke: results of human exposure studies. Journal of exposure science & environmental epidemiology. 2010 Jun; 20(4):385-92. doi: 10.1038/jes.2009.46. [PMID: 19707249]
  • R Neitzel, L P Naeher, M Paulsen, K Dunn, A Stock, C D Simpson. Biological monitoring of smoke exposure among wildland firefighters: a pilot study comparing urinary methoxyphenols with personal exposures to carbon monoxide, particular matter, and levoglucosan. Journal of exposure science & environmental epidemiology. 2009 May; 19(4):349-58. doi: 10.1038/jes.2008.21. [PMID: 18446186]
  • Christopher T Migliaccio, Megan A Bergauff, Christopher P Palmer, Forrest Jessop, Curtis W Noonan, Tony J Ward. Urinary levoglucosan as a biomarker of wood smoke exposure: observations in a mouse model and in children. Environmental health perspectives. 2009 Jan; 117(1):74-9. doi: 10.1289/ehp.11378. [PMID: 19165390]
  • Andrea L Hinwood, Masooma Trout, John Murby, Caroline Barton, Bob Symons. Assessing urinary levoglucosan and methoxyphenols as biomarkers for use in woodsmoke exposure studies. The Science of the total environment. 2008 Aug; 402(1):139-46. doi: 10.1016/j.scitotenv.2008.04.012. [PMID: 18511108]
  • Hongmei Liu, Shuihong Cheng, Jun Liu, Yuguang Du, Zhihui Bai, Yuguo Du. Synthesis of pentasaccharide and heptasaccharide derivatives and their effects on plant growth. Journal of agricultural and food chemistry. 2008 Jul; 56(14):5634-8. doi: 10.1021/jf800326r. [PMID: 18570430]
  • Michael Clark, Michael Paulsen, Kirk R Smith, Eduardo Canuz, Christopher D Simpson. Urinary methoxyphenol biomarkers and woodsmoke exposure: comparisons in rural Guatemala with personal CO and kitchen CO, levoglucosan, and PM2.5. Environmental science & technology. 2007 May; 41(10):3481-7. doi: 10.1021/es061524n. [PMID: 17547167]
  • Russell L Dills, Michael Paulsen, Jacqui Ahmad, David A Kalman, Fady N Elias, Christopher D Simpson. Evaluation of urinary methoxyphenols as biomarkers of woodsmoke exposure. Environmental science & technology. 2006 Apr; 40(7):2163-70. doi: 10.1021/es051886f. [PMID: 16646448]
  • Markus Sillanpää, Sanna Saarikoski, Risto Hillamo, Arto Pennanen, Ulla Makkonen, Zoya Spolnik, René Van Grieken, Tarja Koskentalo, Raimo O Salonen. Chemical composition, mass size distribution and source analysis of long-range transported wildfire smokes in Helsinki. The Science of the total environment. 2005 Nov; 350(1-3):119-35. doi: 10.1016/j.scitotenv.2005.01.024. [PMID: 16227078]
  • R Mungur, A D M Glass, D B Goodenow, D A Lightfoot. Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene. Journal of biomedicine & biotechnology. 2005 Jun; 2005(2):198-214. doi: 10.1155/jbb.2005.198. [PMID: 16046826]
  • Mohammad A Khiyami, Anthony L Pometto Iii, Robert C Brown. Detoxification of corn stover and corn starch pyrolysis liquors by Pseudomonas putida and Streptomyces setonii suspended cells and plastic compost support biofilms. Journal of agricultural and food chemistry. 2005 Apr; 53(8):2978-87. doi: 10.1021/jf048224e. [PMID: 15826048]
  • Pierangela Palma, Achille Cappiello, Elisa De Simonii, Filippo Mangani, Helga Trufelli, Stefano Decesari, Maria Cristina Facchini, Sandro Fuzzi. Identification of levoglucosan and related steroisomers in fog water as a biomass combustion tracer by ESI-MS/MS. Annali di chimica. 2004 Dec; 94(12):911-9. doi: 10.1002/adic.200490113. [PMID: 15689027]
  • P M Fine, G R Cass, B R Simoneit. Chemical characterization of fine particle emissions from fireplace combustion of woods grown in the northeastern United States. Environmental science & technology. 2001 Jul; 35(13):2665-75. doi: 10.1021/es001466k. [PMID: 11452590]
  • C G Nolte, J J Schauer, G R Cass, B R Simoneit. Highly polar organic compounds present in wood smoke and in the ambient atmosphere. Environmental science & technology. 2001 May; 35(10):1912-9. doi: 10.1021/es001420r. [PMID: 11393968]
  • L Dorland, S K Wadman, H Fabery de Jonge, D Ketting. 1,6-Anhydro-beta-D-glucopyranose (beta-glucosan), a constituent of human urine. Clinica chimica acta; international journal of clinical chemistry. 1986 Aug; 159(1):11-6. doi: 10.1016/0009-8981(86)90161-0. [PMID: 3757263]