Stachydrine (BioDeep_00000002999)

 

Secondary id: BioDeep_00000230871

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

化学式: C7H13NO2 (143.0946238)
中文名称: 水苏碱
谱图信息: 最多检出来源 Homo sapiens(blood) 0.04%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Stachydrine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/(-)-stachydrine (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000002999). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C[N+]([C@@H](C1)C(=O)[O-])(C)C
InChI: InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3

描述信息

Proline betaine is an osmoprotective compound found in urine. It is thought to serve an osmoprotective role for the kidney. Proline betaine is a glycine betaine analogue found in many citrus foods. Elevated levels of proline betaine in human urine are found after the consumption of citrus fruits and juices (PMID: 18060588). Proline betaine is a biomarker for the consumption of citrus fruits.
Alkaloid from Citrus spp Medicago sativa and Stachys subspecies(alfalfa). L-Stachydrine or also called proline betaine is a biomarker for the consumption of citrus fruits. L-Stachydrine is found in many foods, some of which are capers, pulses, lemon, and alfalfa.

Proline betaine, also known as stachydrine, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Proline betaine exists in all living organisms, ranging from bacteria to humans. Proline betaine is found, on average, in the highest concentration within capers (Capparis spinosa). Proline betaine has also been detected, but not quantified in, several different foods, such as soy beans (Glycine max), crosnes (Stachys affinis), domestic pigs (Sus scrofa domestica), limes (Citrus aurantiifolia), and triticales (X Triticosecale rimpaui). This could make proline betaine a potential biomarker for the consumption of these foods. Proline betaine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Proline betaine.
Stachydrine is a major constituent of Chinese herb leonurus heterophyllus sweet used to promote blood circulation and dispel blood stasis. Stachydrine can inhibit the NF-κB signal pathway.
Stachydrine is a major constituent of Chinese herb leonurus heterophyllus sweet used to promote blood circulation and dispel blood stasis. Stachydrine can inhibit the NF-κB signal pathway.

同义名列表

17 个代谢物同义名

(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate; (S)-2-Carboxylato-1,1-dimethylpyrrolidinium; (2S)-2-Carboxy-1,1-dimethylpyrrolidinium; 1,1-Dimethylpyrrolidinium-2-carboxylate; (S)-2-carboxy-1,1-dimethylpyrrolidinium; stachydrine chloride, (S)-isomer; stachydrine, (+-)-isomer; N,N-dimethyl-L-proline; stachydrine chloride; L-proline betaine; dimethylproline; Homostachydrine; Prestwick-08G03; proline betaine; L-stachydrine; Stachydrine; Stachydrine



数据库引用编号

24 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(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

151 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

  • Minghui Feng, Yuwen Chen, Jingzhi Chen, Wei Guo, Pei Zhao, Chen Zhang, Xiaoli Shan, Huihua Chen, Ming Xu, Rong Lu. Stachydrine hydrochloride protects the ischemic heart by ameliorating endoplasmic reticulum stress through a SERCA2a dependent way and maintaining intracellular Ca2+ homeostasis. European journal of pharmacology. 2024 Jun; 973(?):176585. doi: 10.1016/j.ejphar.2024.176585. [PMID: 38636799]
  • Xi Zhu, Yingbiao Wu, Xiaogang Zhang, Wei Gu, Zhongping Ning. Stachydrine ameliorates hypoxia reoxygenation injury of cardiomyocyte via enhancing SIRT1-Nrf2 pathway. Journal of cardiothoracic surgery. 2023 Sep; 18(1):265. doi: 10.1186/s13019-023-02363-6. [PMID: 37752609]
  • Shuang Lu, Yueyang Liang, Songru Yang, Mengwei Fu, Xiaoli Shan, Chen Zhang, Huihua Chen, Pei Zhao, Rong Lu. Stachydrine Hydrochloride Regulates the NOX2-ROS-Signaling Axis in Pressure-Overload-Induced Heart Failure. International journal of molecular sciences. 2023 Sep; 24(18):. doi: 10.3390/ijms241814369. [PMID: 37762672]
  • Yueyang Liang, Lei Xia, Shuang Lu, Songru Yang, Shuting Guo, Xiaoli Shan, Pei Zhao, Chen Zhang, Wei Guo, Ming Xu, Huihua Chen, Rong Lu. A new mechanism of therapeutic effect of stachydrine on heart failure by inhibiting myocardial ferroptosis. European journal of pharmacology. 2023 Sep; 954(?):175881. doi: 10.1016/j.ejphar.2023.175881. [PMID: 37385579]
  • Ruixin Gu, Wei Zhang, Dandan Xu. Stachydrine is effective and selective against blast phase chronic myeloid leukaemia through inhibition of multiple receptor tyrosine kinases. Pharmaceutical biology. 2022 Dec; 60(1):700-707. doi: 10.1080/13880209.2022.2044862. [PMID: 35348419]
  • T W Jung, H Kim, S Y Park, W Cho, H Oh, H J Lee, A M Abd El-Aty, A Hacimuftuoglu, J H Jeong. Stachydrine alleviates lipid-induced skeletal muscle insulin resistance via AMPK/HO-1-mediated suppression of inflammation and endoplasmic reticulum stress. Journal of endocrinological investigation. 2022 Nov; 45(11):2181-2191. doi: 10.1007/s40618-022-01866-8. [PMID: 35834165]
  • Yan Zhang, Xin-Ping Cui, Wen-Quan Wang, Jun-Ling Hou, Bin-Bin Yan. [Effects of pH value on stachydrine biosynthesis of hydroponic Leonurus japonicus and its physiological mechanism]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Oct; 47(20):5502-5507. doi: 10.19540/j.cnki.cjcmm.20220712.101. [PMID: 36471966]
  • Eunjung Lee, Sunhee Kang, Ae-Ran Lee, Jae Ho Kim, Tae Wan Kim, Jang Eun Lee, Hye Ryun Kim. Stachydrine derived from fermented rice prevents diet-induced obesity by regulating adipsin and endoplasmic reticulum homeostasis. The Journal of nutritional biochemistry. 2022 09; 107(?):109036. doi: 10.1016/j.jnutbio.2022.109036. [PMID: 35533898]
  • Xiaomei Bao, Yiman Liu, Jiayan Huang, Shuangshuang Yin, Hua Sheng, Xiao Han, Qian Chen, Tao Wang, Sibao Chen, Yuling Qiu, Chunze Zhang, Haiyang Yu. Stachydrine hydrochloride inhibits hepatocellular carcinoma progression via LIF/AMPK axis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jun; 100(?):154066. doi: 10.1016/j.phymed.2022.154066. [PMID: 35366490]
  • Xiangni Chen, Ning Yan. Stachydrine inhibits TGF-β1-induced epithelial-mesenchymal transition in hepatocellular carcinoma cells through the TGF-β/Smad and PI3K/Akt/mTOR signaling pathways. Anti-cancer drugs. 2021 09; 32(8):786-792. doi: 10.1097/cad.0000000000001066. [PMID: 33675608]
  • Feng Li, Sifeng Zhu, Qihui Jiang, Chenhui Hou, Tao Pang, Liang Zhang, Wenbao Li. Novel Stachydrine-Leonurine Conjugate SL06 as a Potent Neuroprotective Agent for Cerebral Ischemic Stroke. ACS chemical neuroscience. 2021 07; 12(13):2478-2490. doi: 10.1021/acschemneuro.1c00200. [PMID: 34180238]
  • Sophie Hellstrand, Filip Ottosson, Einar Smith, Louise Brunkwall, Stina Ramne, Emily Sonestedt, Peter M Nilsson, Olle Melander, Marju Orho-Melander, Ulrika Ericson. Dietary Data in the Malmö Offspring Study-Reproducibility, Method Comparison and Validation against Objective Biomarkers. Nutrients. 2021 May; 13(5):. doi: 10.3390/nu13051579. [PMID: 34065043]
  • Theresa Saenger, Florian Hübner, Viktoria Lindemann, Kristina Ganswind, Hans-Ulrich Humpf. Urinary Biomarkers for Orange Juice Consumption. Molecular nutrition & food research. 2021 01; 65(2):e2000781. doi: 10.1002/mnfr.202000781. [PMID: 33216459]
  • Fei Zhou, Fei Liu, Juan Liu, Yu-Lin He, Qin-Mei Zhou, Li Guo, Cheng Peng, Liang Xiong. Stachydrine promotes angiogenesis by regulating the VEGFR2/MEK/ERK and mitochondrial-mediated apoptosis signaling pathways in human umbilical vein endothelial cells. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Nov; 131(?):110724. doi: 10.1016/j.biopha.2020.110724. [PMID: 32920518]
  • Jiali Zheng, Jing Tian, Sining Wang, Panwei Hu, Qianfu Wu, Xiaoli Shan, Pei Zhao, Chen Zhang, Wei Guo, Ming Xu, Huihua Chen, Rong Lu. Stachydrine hydrochloride suppresses phenylephrine-induced pathological cardiac hypertrophy by inhibiting the calcineurin/nuclear factor of activated T-cell signalling pathway. European journal of pharmacology. 2020 Sep; 883(?):173386. doi: 10.1016/j.ejphar.2020.173386. [PMID: 32712088]
  • Fang Cheng, Yanxi Zhou, Miao Wang, Chuanjie Guo, Zhixing Cao, Ruoqi Zhang, Cheng Peng. A review of pharmacological and pharmacokinetic properties of stachydrine. Pharmacological research. 2020 05; 155(?):104755. doi: 10.1016/j.phrs.2020.104755. [PMID: 32173585]
  • Hui-Hua Chen, Si-Ning Wang, Tong-Tong Cao, Jia-Li Zheng, Jing Tian, Xiao-Li Shan, Pei Zhao, Wei Guo, Ming Xu, Chen Zhang, Rong Lu. Stachydrine hydrochloride alleviates pressure overload-induced heart failure and calcium mishandling on mice. Journal of ethnopharmacology. 2020 Feb; 248(?):112306. doi: 10.1016/j.jep.2019.112306. [PMID: 31626909]
  • Marjo Tuomainen, Olli Kärkkäinen, Jukka Leppänen, Seppo Auriola, Marko Lehtonen, Markku J Savolainen, Kjeld Hermansen, Ulf Risérus, Björn Åkesson, Inga Thorsdottir, Marjukka Kolehmainen, Matti Uusitupa, Kaisa Poutanen, Ursula Schwab, Kati Hanhineva. Quantitative assessment of betainized compounds and associations with dietary and metabolic biomarkers in the randomized study of the healthy Nordic diet (SYSDIET). The American journal of clinical nutrition. 2019 11; 110(5):1108-1118. doi: 10.1093/ajcn/nqz179. [PMID: 31504116]
  • Yan-Qing Wen, Li-Ying Gong, Lin Wang, Nan Zhao, Qi Sun, Mohamed Olounfeh Kamara, Hai-Ying Ma, Fan-Hao Meng. Comparative pharmacokinetics study of leonurine and stachydrine in normal rats and rats with cold-stagnation and blood-stasis primary dysmenorrhoea after the administration of Leonurus japonicus houtt electuary. Journal of separation science. 2019 May; 42(9):1725-1732. doi: 10.1002/jssc.201801257. [PMID: 30839168]
  • Amal Al-Tamimi, Mohamad Khatib, Giuseppe Pieraccini, Nadia Mulinacci. Quaternary ammonium compounds in roots and leaves of Capparis spinosa L. from Saudi Arabia and Italy: investigation by HPLC-MS and 1H NMR. Natural product research. 2019 May; 33(9):1322-1328. doi: 10.1080/14786419.2018.1475376. [PMID: 29781300]
  • Jinwei Gao, Jinbo Yu, Panpan Xu, Jinmei Chen, Guanghui Gao, Binglong Li, Lixin Sun. Established UPLC-MS/MS procedure for multicomponent quantitative analysis in rat plasma: A contrastive pharmacokinetics study of Qiangshen tablet in normal and kidney yang deficiency syndrome models. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Feb; 1106-1107(?):35-42. doi: 10.1016/j.jchromb.2018.12.031. [PMID: 30639948]
  • Jinlin Zhang, Aihua Yang, Yu Wu, Wei Guan, Biao Xiong, Xiaoqing Peng, Xiaojin Wei, Chang Chen, Zhaoguo Liu. Stachydrine ameliorates carbon tetrachloride-induced hepatic fibrosis by inhibiting inflammation, oxidative stress and regulating MMPs/TIMPs system in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jan; 97(?):1586-1594. doi: 10.1016/j.biopha.2017.11.117. [PMID: 29378386]
  • Helena Gibbons, Charlotte J R Michielsen, Milena Rundle, Gary Frost, Breige A McNulty, Anne P Nugent, Janette Walton, Albert Flynn, Michael J Gibney, Lorraine Brennan. Demonstration of the utility of biomarkers for dietary intake assessment; proline betaine as an example. Molecular nutrition & food research. 2017 10; 61(10):. doi: 10.1002/mnfr.201700037. [PMID: 28556565]
  • Oscar D Rangel-Huerta, Concepcion M Aguilera, Antonio Perez-de-la-Cruz, Fernando Vallejo, Francisco Tomas-Barberan, Angel Gil, Maria D Mesa. A serum metabolomics-driven approach predicts orange juice consumption and its impact on oxidative stress and inflammation in subjects from the BIONAOS study. Molecular nutrition & food research. 2017 02; 61(2):. doi: 10.1002/mnfr.201600120. [PMID: 27689343]
  • Tong-Tong Cao, Hui-Hua Chen, Zhiwei Dong, Yan-Wu Xu, Pei Zhao, Wei Guo, Hong-Chang Wei, Chen Zhang, Rong Lu. Stachydrine Protects Against Pressure Overload-Induced Cardiac Hypertrophy by Suppressing Autophagy. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2017; 42(1):103-114. doi: 10.1159/000477119. [PMID: 28494450]
  • Mohamad Khatib, Giuseppe Pieraccini, Marzia Innocenti, Fabrizio Melani, Nadia Mulinacci. An insight on the alkaloid content of Capparis spinosa L. root by HPLC-DAD-MS, MS/MS and (1)H qNMR. Journal of pharmaceutical and biomedical analysis. 2016 May; 123(?):53-62. doi: 10.1016/j.jpba.2016.01.063. [PMID: 26874255]
  • Hans Wilhelm Rauwald, Alex Savtschenko, Alexander Merten, Christian Rusch, Kurt Appel, Kenny Kuchta. GABAA Receptor Binding Assays of Standardized Leonurus cardiaca and Leonurus japonicus Extracts as Well as Their Isolated Constituents. Planta medica. 2015 Aug; 81(12-13):1103-10. doi: 10.1055/s-0035-1546234. [PMID: 26218338]
  • Chen Zhang, Xiao-Li Shan, Yue-Ling Liao, Pei Zhao, Wei Guo, Hong-Chang Wei, Rong Lu. Effects of stachydrine on norepinephrine-induced neonatal rat cardiac myocytes hypertrophy and intracellular calcium transients. BMC complementary and alternative medicine. 2014 Dec; 14(?):474. doi: 10.1186/1472-6882-14-474. [PMID: 25488774]
  • Cui Zhang, Ying Lu, Ya-Jie Zhou, Qian-Qian Tong, Chao Qu, Tian-Ji Kang. The effect of stachydrine on the expression of caspase-12 in rats with unilateral ureteral obstruction. The Journal of urology. 2014 Nov; 192(5):1549-54. doi: 10.1016/j.juro.2014.05.046. [PMID: 24840537]
  • Abdallah Bashir, Tamara Hoffmann, Bettina Kempf, Xiulan Xie, Sander H J Smits, Erhard Bremer. Plant-derived compatible solutes proline betaine and betonicine confer enhanced osmotic and temperature stress tolerance to Bacillus subtilis. Microbiology (Reading, England). 2014 Oct; 160(Pt 10):2283-2294. doi: 10.1099/mic.0.079665-0. [PMID: 25012968]
  • Kenny Kuchta, Jutta Ortwein, Lothar Hennig, Hans Wilhelm Rauwald. ¹H-qNMR for direct quantification of stachydrine in Leonurus japonicus and L. cardiaca. Fitoterapia. 2014 Jul; 96(?):8-17. doi: 10.1016/j.fitote.2014.03.023. [PMID: 24704554]
  • Kristina D Rogers, Joseph C Cannistra, James B Gloer, Donald T Wicklow. Diplodiatoxin, chaetoglobosins, and diplonine associated with a field outbreak of Stenocarpella ear rot in Illinois. Mycotoxin research. 2014 May; 30(2):61-70. doi: 10.1007/s12550-014-0188-0. [PMID: 24504633]
  • Damon H May, Sandi L Navarro, Ingo Ruczinski, Jason Hogan, Yuko Ogata, Yvonne Schwarz, Lisa Levy, Ted Holzman, Martin W McIntosh, Johanna W Lampe. Metabolomic profiling of urine: response to a randomised, controlled feeding study of select fruits and vegetables, and application to an observational study. The British journal of nutrition. 2013 Nov; 110(10):1760-70. doi: 10.1017/s000711451300127x. [PMID: 23657156]
  • K Kuchta, R B Volk, H W Rauwald. Stachydrine in Leonurus cardiaca, Leonurus japonicus, Leonotis leonurus: detection and quantification by instrumental HPTLC and 1H-qNMR analyses. Die Pharmazie. 2013 Jul; 68(7):534-40. doi: . [PMID: 23923634]
  • Estelle Pujos-Guillot, Jane Hubert, Jean-François Martin, Bernard Lyan, Mercedes Quintana, Sylvain Claude, Bruno Chabanas, Joseph A Rothwell, Catherine Bennetau-Pelissero, Augustin Scalbert, Blandine Comte, Serge Hercberg, Christine Morand, Pilar Galan, Claudine Manach. Mass spectrometry-based metabolomics for the discovery of biomarkers of fruit and vegetable intake: citrus fruit as a case study. Journal of proteome research. 2013 Apr; 12(4):1645-59. doi: 10.1021/pr300997c. [PMID: 23425595]
  • Anja Ekdahl, Maria C Johansson, Martin Ahnoff. Tracing and separating plasma components causing matrix effects in hydrophilic interaction chromatography-electrospray ionization mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Apr; 923-924(?):83-91. doi: 10.1016/j.jchromb.2013.02.013. [PMID: 23500351]
  • Baohong Li, Jindong Wu, Xianglu Li. Simultaneous determination and pharmacokinetic study of stachydrine and leonurine in rat plasma after oral administration of Herba Leonuri extract by LC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2013 Mar; 76(?):192-9. doi: 10.1016/j.jpba.2012.12.029. [PMID: 23348611]
  • Amanda J Lloyd, Manfred Beckmann, Sumanto Haldar, Chris Seal, Kirsten Brandt, John Draper. Data-driven strategy for the discovery of potential urinary biomarkers of habitual dietary exposure. The American journal of clinical nutrition. 2013 Feb; 97(2):377-89. doi: 10.3945/ajcn.112.048033. [PMID: 23269817]
  • Xia Li, Bin Wang, Yuzhu Li, Li Wang, Xiangzhong Zhao, Xianbin Zhou, Yuqi Guo, Guosheng Jiang, Chengfang Yao. The Th1/Th2/Th17/Treg paradigm induced by stachydrine hydrochloride reduces uterine bleeding in RU486-induced abortion mice. Journal of ethnopharmacology. 2013 Jan; 145(1):241-53. doi: 10.1016/j.jep.2012.10.059. [PMID: 23178269]
  • Cui Zhang, Ying Lu, Qian-Qian Tong, Lan Zhang, Yu-Fei Guan, Shu-Jing Wang, Zhi-Hua Xing. Effect of stachydrine on endoplasmic reticulum stress-induced apoptosis in rat kidney after unilateral ureteral obstruction. Journal of Asian natural products research. 2013; 15(4):373-81. doi: 10.1080/10286020.2013.769964. [PMID: 23464629]
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  • Inigo Uriarte-Pueyo, María Goicoechea, Ana Gloria Gil, Adela López de Cerain, Adolfo López de Munain, María Isabel Calvo. Negative evidence for stachydrine or Galeopsis ladanum L. seeds as the causal agents of coturnism after quail meat ingestion. Journal of agricultural and food chemistry. 2009 Nov; 57(22):11055-9. doi: 10.1021/jf902764n. [PMID: 19860419]
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