Stachydrine

Stachydrine

Structural formula of stachydrine
Names
IUPAC name (2S)-1,1-Dimethylpyrrolidin-1-ium-2-carboxylate
Other names Proline betaine
Identifiers
CAS Number	L: 471-87-4  N D/L: 32039-73-9  N
3D model (JSmol)	L: Interactive image D: Interactive image
Beilstein Reference	3542403
ChEBI	L: CHEBI:35280  N D/L: CHEBI:181246  N D: CHEBI:134398  N
ChEMBL	L: ChEMBL1456892  N D/L: ChEMBL1986864  N D: ChEMBL3559614  N
ChemSpider	L: 103115  N
DrugBank	L: DB04284  N
EC Number	L:207-445-1
KEGG	L: C10172  N D: C21514
PubChem CID	L: 115244 D/L: 554 D: 7016562
UNII	L: S1L688345C  N
CompTox Dashboard (EPA)	L: DTXSID50274274
InChI 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
SMILES L:C[N+]1(C)CCC[C@H]1C([O-])=O D:C(=O)([O-])[C@@H]1[N+](CCC1)(C)C
Properties
Chemical formula	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). Infobox references

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]} Neonatology researchers from the Masonic Institute for the Developing Brain at the University of Minnesota demonstrated that both stachydrine and the related molecule, homostachydrine, displayed lowered CSF and blood levels in Rhesus Macaques with early-life iron deficiency providing a possible diagnostic biomarker in humans. ^{[4] [5]}

References

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 1442879. Bibcode:2024FrPS...1542879H. 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.
4. Sandri, Brian J; Kim, Jonathan; Lubach, Gabriele R; Lock, Eric F; Ennis-Czerniak, Kathleen; Kling, Pamela J; Georgieff, Michael K; Coe, Christopher L; Rao, Raghavendra B (March 2024). "Prognostic Performance of Hematological and Serum Iron and Metabolite Indices for Detection of Early Iron Deficiency Induced Metabolic Brain Dysfunction in Infant Rhesus Monkeys". The Journal of Nutrition. 154 (3): 875–885. doi:10.1016/j.tjnut.2023.10.031. PMC   10942850 . PMID   38072152.
5. Rao, Raghavendra B. (2024-04-08). "Biomarkers of Brain Dysfunction in Perinatal Iron Deficiency". Nutrients. 16 (7): 1092. doi: 10.3390/nu16071092 . ISSN   2072-6643. PMC   11013337 . PMID   38613125.