D-Glucaro-1,4-lactone (BioDeep_00000013715)

 

Secondary id: BioDeep_00000015420, BioDeep_00001870709

human metabolite Endogenous Volatile Flavor Compounds


代谢物信息卡片


(2S)-2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid

化学式: C6H8O7 (192.0270018)
中文名称: 糖质酸-1,4-内酯
谱图信息: 最多检出来源 Homo sapiens(blood) 1.13%

分子结构信息

SMILES: C1(C(C(=O)OC1C(C(=O)O)O)O)O
InChI: InChI=1S/C6H8O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11/h1-4,7-9H,(H,10,11)/t1-,2-,3+,4+/m1/s1

描述信息

D-glucaro-1,4-lactone belongs to the family of Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

同义名列表

15 个代谢物同义名

(2S)-2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid; (S)-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl](hydroxy)acetic acid; Saccharolactone, monocalcium salt, (D)-isomer; Saccharolactone, monosodium salt, (D)-isomer; Saccharolactone, (D)-isomer; Glucaric acid-1,4-lactone; D-Glucaro-1,4-lactone; Glucarate-1,4-lactone; 1,4-D-Glucarolactone; 1,4-Glucarolactone; D-Saccharolactone; Saccharolactone; D-Saccharic acid 1,4-lactone; D-galactaro-1,4-lactone; D-Saccharic acid 1,4-lactone



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)

1 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

  • Wenlong Yang, Guanlin Zhou, Shubing Zou, Wentao Yang, Aihong Liu, Shuilin Sun, Baogang Xie. Metabonomics of d-glucaro-1,4-lactone in preventing diethylnitrosamine-induced liver cancer in rats. Pharmaceutical biology. 2018 Dec; 56(1):643-648. doi: 10.1080/13880209.2018.1525414. [PMID: 31070541]
  • Baogang Xie, Yalan Liu, Huiqin Zou, Yong Son, Huiyun Wang, Haipeng Wang, Jianghua Shao. Determination of D-glucaric acid and/or D-glucaro-1,4-lacton in different apple varieties through hydrophilic interaction chromatography. Food chemistry. 2016 Jul; 203(?):1-7. doi: 10.1016/j.foodchem.2016.02.009. [PMID: 26948581]
  • Baogang Xie, Zhirong Zhang, Tao Gong, Ningning Zhang, Huiyun Wang, Huiqing Zou. Application of metabonomic strategy to discover an unreported active ingredient in LiuWeiDiHuang pills suppressing beta-glucuronidase. Analytical and bioanalytical chemistry. 2015 Jan; 407(2):609-14. doi: 10.1007/s00216-014-8253-2. [PMID: 25381611]
  • Baogang Xie, Aihong Liu, Xuejun Zhan, Xinming Ye, Jing Wei. Alteration of gut bacteria and metabolomes after glucaro-1,4-lactone treatment contributes to the prevention of hypercholesterolemia. Journal of agricultural and food chemistry. 2014 Jul; 62(30):7444-51. doi: 10.1021/jf501744d. [PMID: 24972288]
  • Kahkashan Rashid, Semantee Bhattacharya, Parames C Sil. Protective role of D-saccharic acid-1,4-lactone in alloxan induced oxidative stress in the spleen tissue of diabetic rats is mediated by suppressing mitochondria dependent apoptotic pathway. Free radical research. 2012 Mar; 46(3):240-52. doi: 10.3109/10715762.2011.650694. [PMID: 22239106]
  • Pilar Galindo, Isabel Rodriguez-Gómez, Susana González-Manzano, Montserrat Dueñas, Rosario Jiménez, Carmen Menéndez, Félix Vargas, Juan Tamargo, Celestino Santos-Buelga, Francisco Pérez-Vizcaíno, Juan Duarte. Glucuronidated quercetin lowers blood pressure in spontaneously hypertensive rats via deconjugation. PloS one. 2012; 7(3):e32673. doi: 10.1371/journal.pone.0032673. [PMID: 22427863]
  • Semantee Bhattacharya, Prasenjit Manna, Ratan Gachhui, Parames C Sil. D-saccharic acid-1,4-lactone ameliorates alloxan-induced diabetes mellitus and oxidative stress in rats through inhibiting pancreatic β-cells from apoptosis via mitochondrial dependent pathway. Toxicology and applied pharmacology. 2011 Dec; 257(2):272-83. doi: 10.1016/j.taap.2011.09.013. [PMID: 21982801]
  • Carmen Menendez, Montserrat Dueñas, Pilar Galindo, Susana González-Manzano, Rosario Jimenez, Laura Moreno, Maria José Zarzuelo, Isabel Rodríguez-Gómez, Juan Duarte, Celestino Santos-Buelga, Francisco Perez-Vizcaino. Vascular deconjugation of quercetin glucuronide: the flavonoid paradox revealed?. Molecular nutrition & food research. 2011 Dec; 55(12):1780-90. doi: 10.1002/mnfr.201100378. [PMID: 22144045]
  • Semantee Bhattacharya, Srabasti Chatterjee, Prasenjit Manna, Joydeep Das, Jyotirmoy Ghosh, Ratan Gachhui, Parames C Sil. Prophylactic role of D-Saccharic acid-1,4-lactone in tertiary butyl hydroperoxide induced cytotoxicity and cell death of murine hepatocytes via mitochondria-dependent pathways. Journal of biochemical and molecular toxicology. 2011 Nov; 25(6):341-54. doi: 10.1002/jbt.20393. [PMID: 21538728]
  • Semantee Bhattacharya, Prasenjit Manna, Ratan Gachhui, Parames C Sil. Protective effect of kombucha tea against tertiary butyl hydroperoxide induced cytotoxicity and cell death in murine hepatocytes. Indian journal of experimental biology. 2011 Jul; 49(7):511-24. doi: ". [PMID: 21800502]
  • Robert Zółtaszek, Margaret Hanausek, Zofia M Kiliańska, Zbigniew Walaszek. [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy higieny i medycyny doswiadczalnej (Online). 2008 Sep; 62(?):451-62. doi: . [PMID: 18772850]
  • Lauren Oleson, Michael H Court. Effect of the beta-glucuronidase inhibitor saccharolactone on glucuronidation by human tissue microsomes and recombinant UDP-glucuronosyltransferases. The Journal of pharmacy and pharmacology. 2008 Sep; 60(9):1175-82. doi: 10.1211/jpp.60.9.0009. [PMID: 18718121]
  • Joanna Saluk-Juszczak, Beata Olas, Paweł Nowak, Agnieszka Staroń, Barbara Wachowicz. Protective effects of D-glucaro-1,4-lactone against oxidative modifications in blood platelets. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2008 Jul; 18(6):422-8. doi: 10.1016/j.numecd.2007.02.016. [PMID: 17933501]
  • Beata Olas, Joanna Saluk-Juszczak, Barbara Wachowicz. D-glucaro 1,4-lactone and resveratrol as antioxidants in blood platelets. Cell biology and toxicology. 2008 Apr; 24(2):189-99. doi: 10.1007/s10565-007-9028-8. [PMID: 17846905]
  • Beata Olas, Joanna Saluk-Juszczak, Pawel Nowak, Rafal Glowacki, Edward Bald, Barbara Wachowicz. Protective effects of D-glucaro 1,4-lactone against oxidative/nitrative modifications of plasma proteins. Nutrition (Burbank, Los Angeles County, Calif.). 2007 Feb; 23(2):164-71. doi: 10.1016/j.nut.2006.11.003. [PMID: 17234507]
  • Charu Sudan, Shiva Prakash, Prasanna Bhomkar, Shalu Jain, Neera Bhalla-Sarin. Ubiquitous presence of beta-glucuronidase (GUS) in plants and its regulation in some model plants. Planta. 2006 Sep; 224(4):853-64. doi: 10.1007/s00425-006-0276-2. [PMID: 16652220]
  • L Braun, T Kardon, K El Koulali, M Csala, J Mandl, G Bánhegyi. Different induction of gulonolactone oxidase in aromatic hydrocarbon-responsive or -unresponsive mouse strains. FEBS letters. 1999 Dec; 463(3):345-9. doi: 10.1016/s0014-5793(99)01649-x. [PMID: 10606751]
  • S K Hong, G O Rankin. Biotransformation of 2-chloroaniline in the Fischer 344 rat: identification of urinary metabolites. Xenobiotica; the fate of foreign compounds in biological systems. 1998 Oct; 28(10):985-94. doi: 10.1080/004982598239047. [PMID: 9849645]
  • Z Walaszek, J Szemraj, M Narog, A K Adams, J Kilgore, U Sherman, M Hanausek. Metabolism, uptake, and excretion of a D-glucaric acid salt and its potential use in cancer prevention. Cancer detection and prevention. 1997; 21(2):178-90. doi: . [PMID: 9101079]
  • F M Brunelle, R K Verbeeck. Conjugation-deconjugation cycling of diflunisal via beta-glucuronidase catalyzed hydrolysis of its acyl glucuronide in the rat. Life sciences. 1997; 60(22):2013-21. doi: 10.1016/s0024-3205(97)00166-5. [PMID: 9180355]
  • F M Brunelle, R K Verbeeck. Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Xenobiotica; the fate of foreign compounds in biological systems. 1996 Feb; 26(2):123-31. doi: 10.3109/00498259609046694. [PMID: 8867997]
  • L M Ball, J J Rafter, J A Gustafsson, B E Gustafsson, M J Kohan, J Lewtas. Formation of mutagenic urinary metabolites from 1-nitropyrene in germ-free and conventional rats: role of the gut flora. Carcinogenesis. 1991 Jan; 12(1):1-5. doi: 10.1093/carcin/12.1.1. [PMID: 1988167]
  • A Macfadyen, K J Ho. D-glucaro-1,4-lactone: its excretion in the bile and urine and effect on the biliary secretion of beta-glucuronidase after oral administration in rats. Hepatology (Baltimore, Md.). 1989 Apr; 9(4):552-6. doi: 10.1002/hep.1840090408. [PMID: 2925160]
  • P Mocarelli, P Brambilla, L Colombo, A Marocchi, C Crespi, P Tramacere, A Mondonico. A new method for D-glucaric acid excretion measurement that is suitable for automated instruments. Clinical chemistry. 1988 Nov; 34(11):2283-90. doi: . [PMID: 3180424]
  • Z Walaszek, M Hanausek-Walaszek, T E Webb. Repression by sustained-release beta-glucuronidase inhibitors of chemical carcinogen-mediated induction of a marker oncofetal protein in rodents. Journal of toxicology and environmental health. 1988; 23(1):15-27. doi: 10.1080/15287398809531093. [PMID: 3336058]
  • C Dwivedi, A A Downie, T E Webb. Net glucuronidation in different rat strains: importance of microsomal beta-glucuronidase. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 1987 Oct; 1(4):303-7. doi: 10.1096/fasebj.1.4.3115856. [PMID: 3115856]
  • K K Steinberg, L L Needham. A comparison of two methods for quantifying D-glucaric acid. Journal of analytical toxicology. 1986 Jul; 10(4):139-41. doi: 10.1093/jat/10.4.139. [PMID: 3747452]
  • K Kawahara, T Awaji, K Uda, Y Sakai, Y Hashimoto. Urinary excretion of conjugates of dothiepin and northiaden (mono-N-demethyl-dothiepin) after an oral dose of dothiepin to humans. European journal of drug metabolism and pharmacokinetics. 1986 Jan; 11(1):29-32. doi: 10.1007/bf03189772. [PMID: 3720795]
  • K Jung, D Scholz, G Schreiber. Improved determination of D-glucaric acid in urine. Clinical chemistry. 1981 Mar; 27(3):422-6. doi: 10.1093/clinchem/27.3.422. [PMID: 7471391]
  • K J Ho, L H Ho. Determination of urinary beta-glucuronidase activity. Single-point versus enzyme kinetic measuring system. Enzyme. 1980; 25(6):361-70. doi: NULL. [PMID: 7202386]
  • A Wade, A M Symons, L Martin, D V Parke. Metabolic oxidation of the ethynyl group in 4-ethynylbiphenyl. The Biochemical journal. 1979 Dec; 184(3):509-17. doi: 10.1042/bj1840509. [PMID: 540044]
  • E BOYLAND, D M WALLACE, WILLIAMS. Enzyme activity in relation to cancer: inhibition of urinary beta-glucuronidase of patients with cancer of the bladder by oral administration of 1:4-saccharolactone and related compounds. British journal of cancer. 1957 Dec; 11(4):578-89. doi: 10.1038/bjc.1957.71. [PMID: 13510516]