gamma-Butyrolactone (BioDeep_00000004752)

 

Secondary id: BioDeep_00000405302, BioDeep_00000861552

human metabolite Endogenous blood metabolite


代谢物信息卡片


4-Hydroxy-butanoic acid g-lactone

化学式: C4H6O2 (86.0367776)
中文名称: γ-丁内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.58%

分子结构信息

SMILES: C1CC(=O)OC1
InChI: InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2

描述信息

Gamma-butyrolactone (GBL), also known as 1,4-butanolide or 1,4-lactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. GBL can also be classified as a tetrahydrofuran substituted by an oxo group at position 2. Gamma-butyrolactone is soluble in ethanol and moderately miscible in water. Gamma-butyrolactone is a sweet, caramel, and creamy tasting compound. Gamma-butyrolactone exists in all living species, ranging from bacteria to plants to humans. It can be endogenously produced from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. Outside of the human body, gamma-butyrolactone has been detected, but not quantified in, several different foods, such as pepper (c. annuum), yellow bell peppers, orange bell peppers, soy beans, evergreen blackberries and a variety of wines (at a concentration of 5 ug/mL) (PMID: 15939164). This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. Gamma-butyrolactone is rapidly converted into gamma-hydroxybutyrate by paraoxonase (lactonase) enzymes, found in the blood. Because it can serve as a prodrug for gamma-hydroxybutyrate (GHB), Gamma-butyrolactone is commonly used as a recreational CNS depressant with effects similar to those of barbiturates. Industrially gamma-butyrolactone is used as a common solvent for polymers and alcohols, a chemical intermediate, a raw material for pharmaceuticals, and as a paint stripper, superglue remover, and a stain remover.
Present in morello cherry, melon, pineapple, blackberry, quince, strawberry jam, wine, soybeans, black tea, Bourbon vanilla, wheat bread, crispbread and other breads. Flavour ingredient [DFC]. gamma-Butyrolactone is found in many foods, some of which are yellow bell pepper, pepper (c. annuum), red bell pepper, and pulses.
D012997 - Solvents

同义名列表

54 个代谢物同义名

4-Hydroxy-butanoic acid g-lactone; gamma-Hydroxybutyric acid lactone; 4-Hydroxybutanoic acid lactone; Lactone, 4-hydroxybutyric acid; 4 Hydroxybutyric acid lactone; g-Hydroxybutyric acid lactone; Γ-hydroxybutyric acid lactone; 4-Hydroxybutyric acid lactone; gamma-Hydroxybutyrate lactone; 2,3,4,5-Tetrahydro-2-furanone; 4,5-Dihydro-2(3H)-furanone; gamma-Hydroxybutyrolactone; g-Hydroxybutyrate lactone; 4-Hydroxybutyrate lactone; Γ-hydroxybutyrate lactone; 4-hydroxy-butanoic acid; 4-Hydroxybutanoic acid; Furanone, tetrahydro 2; Γ-hydroxybutyrolactone; Dihydro-2(3H)-furanone; 1-Oxacyclopentan-2-one; g-Hydroxybutyrolactone; Tetrahydro-2-furanone; Tetrahydrofuran-2-one; gamma-Butyryllactone; gamma-Butyrolacetone; 2-Oxotetrahydrofuran; Butyric acid lactone; 4-Deoxytetronic acid; 4-Hydroxy-butanoate; gamma Butyrolactone; gamma-Butyrolactone; gamma-Butanolactone; 4-Hydroxybutanoate; gamma-Butalactone; 4-Deoxytetronate; g-Butyryllactone; Γ-butanolactone; Γ-butyrolactone; 4 Butyrolactone; g-Butanolactone; 4-Butyrolactone; g-Butyrolactone; 1,4 Butanolide; 1,2-Butanolide; 1,4-Butanolide; Paint clean g; g-Butalactone; butyrolactone; oxolan-2-one; 4-Butanolide; 2-Oxolanone; 1,4-Lactone; GBL



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(0)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

31 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

  • Kaixue Zhang, Wenjuan Liu, Fukui Shen, Guoqing Luan, Yanqi Han, Jun Xu, Cheng Fu, Weidong Wu, Yuanyuan Hou, Min Jiang, Tiejun Zhang, Gang Bai. Ligustilide covalently binds to Cys703 in the pre-S1 helix of TRPA1, blocking the opening of channel and relieving pain in rats with acute soft tissue injury. Journal of ethnopharmacology. 2024 Aug; 330(?):118217. doi: 10.1016/j.jep.2024.118217. [PMID: 38641072]
  • Chun-Lan Xie, Hong-Xiu Xiao, Pei-Fang Song, Qing-Mei Liu, Haoxiang Wei, Liang Wu, Guang-Hao Zhu, Guang-Ming Liu, Yandong Zhang, Ping Wang, Xian-Wen Yang. Lead Optimization of Butyrolactone I as an Orally Bioavailable Antiallergic Agent Targeting FcγRIIB. Journal of medicinal chemistry. 2024 May; 67(9):7504-7515. doi: 10.1021/acs.jmedchem.4c00354. [PMID: 38640354]
  • Matthew E Poynter, Madeleine M Mank, Jennifer L Ather. Obesity-associated inflammatory macrophage polarization is inhibited by capsaicin and phytolignans. American journal of physiology. Regulatory, integrative and comparative physiology. 2024 May; 326(5):R370-R382. doi: 10.1152/ajpregu.00161.2023. [PMID: 38436058]
  • Lianyu Zhou, Peiyan Jiang, Linyang Zhao, Xinghang Fei, Yexi Tang, Yi Luo, Hong Gong, Xiaqing Wang, Xin Li, Song Li, Chunqing Zhang, Hui Yang, Xiaotang Fan. Ligustilide inhibits Purkinje cell ferritinophagy via the ULK1/NCOA4 pathway to attenuate valproic acid-induced autistic features. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Apr; 126(?):155443. doi: 10.1016/j.phymed.2024.155443. [PMID: 38394737]
  • Qinghe Zhang, Juan Tang, Bingli Gao, Cheng Qu, Jinda Wang, Chen Luo, Ran Wang. Overexpression of CYP6CX4 contributing to field-evolved resistance to flupyradifurone, one novel butenolide insecticide, in Bemisia tabaci from China. International journal of biological macromolecules. 2024 Apr; 265(Pt 2):131056. doi: 10.1016/j.ijbiomac.2024.131056. [PMID: 38522686]
  • Renxuan Zou, Xiang Li, Xi Jiang, Dongmei Shi, Qing Han, Hongxia Duan, Qing Yang. Novel Butenolide Derivatives as Dual-Chitinase Inhibitors to Arrest the Growth and Development of the Asian Corn Borer. Journal of agricultural and food chemistry. 2024 Mar; 72(9):5036-5046. doi: 10.1021/acs.jafc.3c06714. [PMID: 38377548]
  • Zhigang Chen, Qiang Zhu, Xingyu Qi, Li-Rong Yang, Yu-Xia Rong, Qi Wei, Shi-Qi Wu, Qian-Wei Lu, Li Li, Ming-Dong Jiang, Hongyi Qi. Dual role of Nrf2/HO-1 pathway in Z-ligustilide-induced ferroptosis against AML cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Feb; 124(?):155288. doi: 10.1016/j.phymed.2023.155288. [PMID: 38183698]
  • Yufeng Jiang, Jiule Wang, Hua Zhang, Xuelu Tian, Zhiqiang Liang, Xinli Xu, Jie Bao, Biao Chen. Biological Activity and Sterilization Mechanism of Marine Fungi-derived Aromatic Butenolide Asperbutenolide A Against Staphylococcus aureus. Chemistry & biodiversity. 2024 Feb; 21(2):e202301826. doi: 10.1002/cbdv.202301826. [PMID: 38155523]
  • Hong-Xu Yang, Xue-Li Jiang, Rong-Mei Zuo, Yan-Ling Wu, Ji-Xing Nan, Li-Hua Lian. Targeting RXFP1 by Ligustilide: A novel therapeutic approach for alcoholic hepatic steatosis. International immunopharmacology. 2024 Jan; 127(?):111460. doi: 10.1016/j.intimp.2023.111460. [PMID: 38157696]
  • Inés Domínguez-López, Polina Galkina, Isabella Parilli-Moser, Camila Arancibia-Riveros, Miguel Ángel Martínez-González, Jordi Salas-Salvadó, Dolores Corella, Mireia Malcampo, J Alfredo Martínez, Lucas Tojal-Sierra, Julia Wärnberg, Jesús Vioque, Dora Romaguera, José López-Miranda, Ramon Estruch, Francisco J Tinahones, José Manuel Santos-Lozano, Lluís Serra-Majem, Aurora Bueno-Cavanillas, Josep A Tur, María Rubín-García, Xavier Pintó, Fernando Fernández-Aranda, Miguel Delgado-Rodríguez, Ana Barabash-Bustelo, Josep Vidal, Clotilde Vázquez, Lidia Daimiel, Emilio Ros, Estefania Toledo, Alessandro Atzeni, Eva M Asensio, Natàlia Vera, Antonio Garcia-Rios, Laura Torres-Collado, Napoleón Pérez-Farinós, Marian Zulet, Alice Chaplin, Rosa Casas, Sandra Martín-Peláez, Jessica Vaquero-Luna, Ana Maria Gómez-Pérez, Zenaida Vázquez-Ruiz, Sangeetha Shyam, Carolina Ortega-Azorín, Natàlia Talens, Patricia J Peña-Orihuela, Alejandro Oncina-Canovas, Javier Diez-Espino, Nancy Babio, Montserrat Fitó, Rosa M Lamuela-Raventós. Microbial Phenolic Metabolites Are Associated with Improved Cognitive Health. Molecular nutrition & food research. 2024 Jan; 68(2):e2300183. doi: 10.1002/mnfr.202300183. [PMID: 38062915]
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  • Zhijie Zheng, Mei Tian, Guozhou Liao, Guanghui Chen, Yanru Zhong, Yuan Yang, Guiying Wang. Evaluation of the effects of compound curing agents on the lipid profiles and volatile flavors in Nuodeng ham based on lipidomics and GC-IMS analysis. Food research international (Ottawa, Ont.). 2024 Jan; 176(?):113810. doi: 10.1016/j.foodres.2023.113810. [PMID: 38163715]
  • Kim T Melville, Muhammad Kamran, Jiaren Yao, Marianne Costa, Madeleine Holland, Nicolas L Taylor, Georg Fritz, Gavin R Flematti, Mark T Waters. Perception of butenolides by Bacillus subtilis via the α/β hydrolase RsbQ. Current biology : CB. 2023 Dec; ?(?):. doi: 10.1016/j.cub.2023.12.035. [PMID: 38183985]
  • Pengyu Geng, Jinhui Zhao, Qi Li, Xiaolin Wang, Wangshu Qin, Ting Wang, Xianzhe Shi, Xinyu Liu, Jia Chen, Hongdeng Qiu, Guowang Xu. Z-Ligustilide Combined with Cisplatin Reduces PLPP1-Mediated Phospholipid Synthesis to Impair Cisplatin Resistance in Lung Cancer. International journal of molecular sciences. 2023 Dec; 24(23):. doi: 10.3390/ijms242317046. [PMID: 38069368]
  • Muhammad Kamran, Kim T Melville, Mark T Waters. Karrikin signalling: impacts on plant development and abiotic stress tolerance. Journal of experimental botany. 2023 Nov; ?(?):. doi: 10.1093/jxb/erad476. [PMID: 38001035]
  • Jiming Chen, Diwakar Shukla. Effect of Histidine Covalent Modification on Strigolactone Receptor Activation and Selectivity. Biophysical journal. 2023 Feb; ?(?):. doi: 10.1016/j.bpj.2023.02.012. [PMID: 36798027]
  • Huan Gao, Runyu Zhao, Zeyu Wu, Jinyu Ye, Lijie Duan, Ran Yu. New insights into exogenous N-acyl-homoserine lactone manipulation in biological nitrogen removal system against ZnO nanoparticle shock. Bioresource technology. 2023 Feb; 370(?):128567. doi: 10.1016/j.biortech.2022.128567. [PMID: 36596365]
  • Umang Dhaubhadel, Abiud E Portillo, Ondřej Horáček, Yu-Sheng Sung, Daniel W Armstrong. Unusual enantiomeric D,L-N-acyl homoserine lactones in Pectobacterium atrosepticum and Pseudomonas aeruginosa. PloS one. 2023; 18(3):e0283657. doi: 10.1371/journal.pone.0283657. [PMID: 37000717]
  • Abhishek Shrestha, Casandra Hernández-Reyes, Maja Grimm, Johannes Krumwiede, Elke Stein, Sebastian T Schenk, Adam Schikora. AHL-Priming Protein 1 mediates N-3-oxo-tetradecanoyl-homoserine lactone priming in Arabidopsis. BMC biology. 2022 12; 20(1):268. doi: 10.1186/s12915-022-01464-3. [PMID: 36464707]
  • Zhihua Qiao, Peiyao Li, Jiaqi Tan, Cheng Peng, Fengwen Zhang, Wei Zhang, Xingyin Jiang. Oxidative stress and detoxification mechanisms of earthworms (Eisenia fetida) after exposure to flupyradifurone in a soil-earthworm system. Journal of environmental management. 2022 Nov; 322(?):115989. doi: 10.1016/j.jenvman.2022.115989. [PMID: 36055090]
  • Xiang-Yu Cao, Qian Zhao, Ya-Na Sun, Ming-Xiang Yu, Fang Liu, Zhe Zhang, Zhen-Hua Jia, Shui-Shan Song. Cellular messengers involved in the inhibition of the Arabidopsis primary root growth by bacterial quorum-sensing signal N-decanoyl-L-homoserine lactone. BMC plant biology. 2022 Oct; 22(1):488. doi: 10.1186/s12870-022-03865-6. [PMID: 36229795]
  • Dejan Orčić, Sanja Berežni, Neda Mimica-Dukić. Quantitative HPLC-UV Study of Lignans in Anthriscus sylvestris. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27186072. [PMID: 36144804]
  • Tanwei Gu, Weihao Chen, Jianglian She, Bin Yang, Lan Tang, Huaming Tao, Jingxia Huang, Xuefeng Zhou. Lipid metabolism regulatory activity and adverse effects of fungi-derived butyrolactone I. Natural product research. 2022 Sep; ?(?):1-5. doi: 10.1080/14786419.2022.2122966. [PMID: 36089911]
  • Yun-Fei Ai, Shu-Hui Dong, Bin Lin, Xiao-Xiao Huang, Shao-Jiang Song. Acylated sucroses and butenolide analog from the leaves of Tripterygium wilfordii Hook. f. and their potential anti-tyrosinase effects. Fitoterapia. 2022 Sep; 161(?):105250. doi: 10.1016/j.fitote.2022.105250. [PMID: 35798062]
  • Nan Fang, Changpeng Zhang, Zhongbin Lu, Zhou Lu, Zhongbei Zhang, Bo Wang, Zhiguang Hou, Xueping Zhao. Dissipation, Processing Factors and Dietary Risk Assessment for Flupyradifurone Residues in Ginseng. Molecules (Basel, Switzerland). 2022 Aug; 27(17):. doi: 10.3390/molecules27175473. [PMID: 36080241]
  • Hong-Wei He, Fei-Yu Wang, Danyang Zhang, Cai-Yun Chen, Dan Xu, Huan Zhou, Xili Liu, Gong Xu. Discovery of Novel α-Methylene-γ-Butyrolactone Derivatives Containing Vanillin Moieties as Antiviral and Antifungal Agents. Journal of agricultural and food chemistry. 2022 Aug; 70(33):10316-10325. doi: 10.1021/acs.jafc.2c03632. [PMID: 35960686]
  • Joe Bracegirdle, Sarah J Kennedy, Chuan Shan, Lukasz Wojtas, Lindsey N Shaw, Charles D Amsler, James B McClintock, Bill J Baker. Tongalides, Halogenated Butenolides from an Antarctic Delisea sp. Rhodophyte. Journal of natural products. 2022 07; 85(7):1886-1891. doi: 10.1021/acs.jnatprod.2c00344. [PMID: 35771948]
  • Hazna Sartiva, Momoka Ishida, Kaori Yoneyama, Hisashi Nishiwaki, Satoshi Yamauchi. Plant Growth Suppressive Activity of (R)-3-(7'-Aryl-9'-hydroxyprop-8'-yl)coumarin, Structural Isomer of Z-2-Hydroxybenzylidene-γ-butyrolactone-type Lignan. Journal of agricultural and food chemistry. 2022 Jul; 70(28):8767-8775. doi: 10.1021/acs.jafc.2c01926. [PMID: 35796683]
  • Nan Fang, Zhongbin Lu, Zhiguang Hou, Changpeng Zhang, Xueping Zhao. Hydrolysis and photolysis of flupyradifurone in aqueous solution and natural water: Degradation kinetics and pathway. Chemosphere. 2022 Jul; 298(?):134294. doi: 10.1016/j.chemosphere.2022.134294. [PMID: 35283145]
  • Zhiguo Mao, Liyu Tian, Jiao Liu, Qian Wu, Ning Wang, Guangyun Wang, Yang Wang, Saiwang Seto. Ligustilide ameliorates hippocampal neuronal injury after cerebral ischemia reperfusion through activating PINK1/Parkin-dependent mitophagy. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jul; 101(?):154111. doi: 10.1016/j.phymed.2022.154111. [PMID: 35512628]
  • Zicen Fang, Zhenhui Luo, Yanying Ji, Rihong Yang, Jintian Gao, Nana Zhang. A network pharmacology technique used to investigate the potential mechanism of Ligustilide's effect on atherosclerosis. Journal of food biochemistry. 2022 07; 46(7):e14146. doi: 10.1111/jfbc.14146. [PMID: 35365921]
  • Yan-Fang Deng, Qian-Qian Xu, Tian-Qi Chen, Jia-Xiong Ming, Ya-Fen Wang, Li-Na Mao, Jia-Jun Zhou, Wei-Guang Sun, Qun Zhou, Hong Ren, Yong-Hui Zhang. Kinsenoside alleviates inflammation and fibrosis in experimental NASH mice by suppressing the NF-κB/NLRP3 signaling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jun; 104(?):154241. doi: 10.1016/j.phymed.2022.154241. [PMID: 35749827]
  • Destiny A Mullens, Ivan Ivanov, Meredith A J Hullar, Timothy W Randolph, Johanna W Lampe, Robert S Chapkin. Personalized Nutrition Using Microbial Metabolite Phenotype to Stratify Participants and Non-Invasive Host Exfoliomics Reveal the Effects of Flaxseed Lignan Supplementation in a Placebo-Controlled Crossover Trial. Nutrients. 2022 Jun; 14(12):. doi: 10.3390/nu14122377. [PMID: 35745107]
  • Yujie Lu, Jie Ji, Simeng Chu, Fukui Shen, Wen Yang, Wei Lei, Min Jiang, Gang Bai. CaMKII, that binds with ligustilide, as a potential drug target of Suxiao jiuxin pill, a traditional Chinese medicine to dilate thoracic aorta. Clinical and translational medicine. 2022 06; 12(6):e907. doi: 10.1002/ctm2.907. [PMID: 35678102]
  • Dong Peng, Han-Zi Qiao, Hong-Yu Tan, Yi-Xue Wang, Dan Luo, Li-Jun Qiao, Ye-Feng Cai, Shi-Jie Zhang, Qi Wang, Li Guan. Ligustilide ameliorates cognitive impairment via AMPK/SIRT1 pathway in vascular dementia rat. Metabolic brain disease. 2022 06; 37(5):1401-1414. doi: 10.1007/s11011-022-00947-0. [PMID: 35420377]
  • Ziyu Wang, Yifei Zheng, Mengke Ji, Xu Zhang, Huan Wang, Yuemeng Chen, Qiong Wu, Guo-Qiang Chen. Hyperproduction of PHA copolymers containing high fractions of 4-hydroxybutyrate (4HB) by outer membrane-defected Halomonas bluephagenesis grown in bioreactors. Microbial biotechnology. 2022 05; 15(5):1586-1597. doi: 10.1111/1751-7915.13999. [PMID: 34978757]
  • Qian Wu, Jiao Liu, Li-Yu Tian, Ning Wang. [Mitophagy mediated by ligustilide relieves OGD/R-induced injury in HT22 cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Apr; 47(7):1897-1903. doi: 10.19540/j.cnki.cjcmm.20211029.404. [PMID: 35534260]
  • Yanping Li, Fenglei Wang, Jun Li, Kerry L Ivey, Jeremy E Wilkinson, Dong D Wang, Ruifeng Li, Gang Liu, Heather A Eliassen, Andrew T Chan, Clary B Clish, Curtis Huttenhower, Frank B Hu, Qi Sun, Eric B Rimm. Dietary lignans, plasma enterolactone levels, and metabolic risk in men: exploring the role of the gut microbiome. BMC microbiology. 2022 03; 22(1):82. doi: 10.1186/s12866-022-02495-0. [PMID: 35350985]
  • Ming Xiang, Tingting Liu, Cheng Tian, Kun Ma, Jing Gou, Rongrong Huang, Senlin Li, Qing Li, Chuanrui Xu, Lei Li, Chih-Hao Lee, Yonghui Zhang. Kinsenoside attenuates liver fibro-inflammation by suppressing dendritic cells via the PI3K-AKT-FoxO1 pathway. Pharmacological research. 2022 03; 177(?):106092. doi: 10.1016/j.phrs.2022.106092. [PMID: 35066108]
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