Stachydrine

Stachydrine
Structural formula of stachydrine
Names
IUPAC name
(2S)-1,1-Dimethylpyrrolidin-1-ium-2-carboxylate
Other names
  • Proline betaine
Identifiers
3D model (JSmol)
3542403
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • L: 207-445-1
KEGG
UNII
  • InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1 ☒N
    Key: CMUNUTVVOOHQPW-LURJTMIESA-N ☒N
  • D/L: Key: CMUNUTVVOOHQPW-UHFFFAOYSA-N
  • D: Key: CMUNUTVVOOHQPW-ZCFIWIBFSA-N
  • L: C[N+]1(C)CCC[C@H]1C([O-])=O
  • D: C(=O)([O-])[C@@H]1[N+](CCC1)(C)C
Properties
C7H13NO2
Molar mass 143.186 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stachydrine, also known as proline betaine, is a naturally occurring alkaloid found in citrus, caper, chestnuts, alfalfa, Leonurus japonicus, Maclura tricuspidata, Stachys arvensis and Arisaema heterophyllum. It has been studied for its potential health benefits.[1][2][3]

  1. ^ Cheng, Fang; Zhou, Yanxi; Wang, Miao; Guo, Chuanjie; Cao, Zhixing; Zhang, Ruoqi; Peng, Cheng (2020). "A review of pharmacological and pharmacokinetic properties of stachydrine". Pharmacological Research. 155: 104755. doi:10.1016/j.phrs.2020.104755. PMID 32173585. S2CID 212730377.
  2. ^ He, Zekun; Li, Peng; Liu, Pan; Xu, Ping (2024-08-06). "Exploring stachydrine: from natural occurrence to biological activities and metabolic pathways". Frontiers in Plant Science. 15. doi:10.3389/fpls.2024.1442879. ISSN 1664-462X. PMC 11337228. PMID 39170783.
  3. ^ Heinzmann, Silke S; Brown, Ian J; Chan, Queenie; Bictash, Magda; Dumas, Marc-Emmanuel; Kochhar, Sunil; Stamler, Jeremiah; Holmes, Elaine; Elliott, Paul; Nicholson, Jeremy K (2010). "Metabolic profiling strategy for discovery of nutritional biomarkers: proline betaine as a marker of citrus consumption123". The American Journal of Clinical Nutrition. 92 (2): 436–443. doi:10.3945/ajcn.2010.29672. ISSN 0002-9165. PMC 2904656. PMID 20573794. S2CID 25176124.