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 ; D/L: 32039-73-9 ;
3D model (JSmol)	L: Interactive image; D: Interactive image;
Beilstein Reference	3542403
ChEBI	L: CHEBI:35280 ; D/L: CHEBI:181246 ; D: CHEBI:134398 ;
ChEMBL	L: ChEMBL1456892 ; D/L: ChEMBL1986864 ; D: ChEMBL3559614 ;
ChemSpider	L: 103115 ;
DrugBank	L: DB04284 ;
EC Number	L: 207-445-1;
KEGG	L: C10172 ; D: C21514;
PubChem CID	L: 115244; D/L: 554; D: 7016562;
UNII	L: S1L688345C ;
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 Key: CMUNUTVVOOHQPW-LURJTMIESA-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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

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Names
Structural formula of stachydrine
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