Laurolitsine | CAS#5890-18-6 | alkaloid

MedKoo Cat#: 146181 | Name: Laurolitsine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Laurolitsine is an aporphine alkaloid derived from certain plant species, notably within the Lauraceae family. It exhibits pharmacological properties such as anti-inflammatory, antioxidant, and neuroprotective effects. Laurolitsine functions primarily by modulating neurotransmitter systems, including dopaminergic and serotonergic pathways, and may inhibit certain enzymes or receptors involved in oxidative stress and inflammation. Due to these actions, it is being explored for potential therapeutic applications in neurodegenerative disorders and cardiovascular diseases.

Chemical Structure

Laurolitsine

CAS#5890-18-6

Theoretical Analysis

MedKoo Cat#: 146181

Name: Laurolitsine

CAS#: 5890-18-6

Chemical Formula: C18H19NO4

Exact Mass: 313.1314

Molecular Weight: 313.35

Elemental Analysis: C, 69.00; H, 6.11; N, 4.47; O, 20.42

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Laurolitsine; Norboldine;

IUPAC/Chemical Name

(S)-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

InChi Key

KYVJVURXKAZJRK-LBPRGKRZSA-N

InChi Code

1S/C18H19NO4/c1-22-15-8-11-10(7-13(15)20)5-12-16-9(3-4-19-12)6-14(21)18(23-2)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3/t12-/m0/s1

SMILES Code

COC1=CC2=C(C[C@@H]3NCCC4=CC(O)=C(OC)C2=C34)C=C1O

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 313.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Yong Z, Ruiqi W, Yanan Y, Ning M, Zhi Z, Yinfeng T, Lin D, Yiying L, Weiying L, Chongming W, Xiaopo Z. Laurolitsine ameliorates type 2 diabetes by regulating the hepatic LKB1-AMPK pathway and gut microbiota. Phytomedicine. 2022 Nov;106:154423. doi: 10.1016/j.phymed.2022.154423. Epub 2022 Aug 31. Erratum in: Phytomedicine. 2023 Jan;108:154533. doi: 10.1016/j.phymed.2022.154533. PMID: 36075181. 2: Cao M, Wang Y, Zhang Y, Zhang C, Chen N, Zhang X. Total Synthesis of the Racemate of Laurolitsine. Molecules. 2024 Feb 5;29(3):745. doi: 10.3390/molecules29030745. PMID: 38338488; PMCID: PMC10856274. 3: Yong Z, Ruiqi W, Yanan Y, Ning M, Zhi Z, Yinfeng T, Lin D, Yiying L, Weiying L, Chongming W, Zhang X. Corrigendum to [Laurolitsine ameliorates type 2 diabetes by regulating the hepatic LKB1-AMPK pathway and gut microbiota]. Phytomedicine. 2023 Jan;108:154533. doi: 10.1016/j.phymed.2022.154533. Epub 2022 Nov 7. Erratum for: Phytomedicine. 2022 Nov;106:154423. doi: 10.1016/j.phymed.2022.154423. PMID: 36356327. 4: Tan YF, Wang RQ, Wang WT, Wu Y, Ma N, Lu WY, Zhang Y, Zhang XP. Study on the pharmacokinetics, tissue distribution and excretion of laurolitsine from Litsea glutinosa in Sprague-Dawley rats. Pharm Biol. 2021 Dec;59(1):884-892. doi: 10.1080/13880209.2021.1944221. PMID: 34219593; PMCID: PMC8259838. 5: Hughes DW, Genest K, Skakum W. Alkaloids of Peumus boldus. Isolation of laurotetanine and laurolitsine. J Pharm Sci. 1968 Sep;57(9):1619-20. doi: 10.1002/jps.2600570935. PMID: 5674407. 6: Kumar N, Singh A, Gulati HK, Bhagat K, Kaur K, Kaur J, Dudhal S, Duggal A, Gulati P, Singh H, Singh JV, Bedi PMS. Phytoconstituents from ten natural herbs as potent inhibitors of main protease enzyme of SARS-COV-2: In silico study. Phytomed Plus. 2021 Nov;1(4):100083. doi: 10.1016/j.phyplu.2021.100083. Epub 2021 Jun 6. 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PMID: 9461651. 11: Sulaiman SN, Mukhtar MR, Hadi AH, Awang K, Hazni H, Zahari A, Litaudon M, Zaima K, Morita H. Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia. Molecules. 2011 Apr 13;16(4):3119-27. doi: 10.3390/molecules16043119. PMID: 21490559; PMCID: PMC6260609. 12: Eliwa D, Ibrahim AS, Kabbash A, El-Aasr M, Tomczyk M, Bin Jardan YA, Batiha GE, Ragab AE. Biotransformation of Modified Benzylisoquinoline Alkaloids: Boldine and Berberine and In Silico Molecular Docking Studies of Metabolites on Telomerase and Human Protein Tyrosine Phosphatase 1B. Pharmaceuticals (Basel). 2022 Sep 28;15(10):1195. doi: 10.3390/ph15101195. PMID: 36297307; PMCID: PMC9611891. 13: Teng CM, Hsueh CM, Chang YL, Ko FN, Lee SS, Liu KC. Antiplatelet effects of some aporphine and phenanthrene alkaloids in rabbits and man. J Pharm Pharmacol. 1997 Jul;49(7):706-11. doi: 10.1111/j.2042-7158.1997.tb06096.x. PMID: 9255715. 14: Chiou CM, Lin CT, Huang WJ, Chang YM, Ho YJ, Su MJ, Lee SS. Semisynthesis and myocardial activity of thaliporphine N-homologues. J Nat Prod. 2013 Mar 22;76(3):405-12. doi: 10.1021/np3007765. Epub 2013 Jan 10. PMID: 23305495. 15: Boustie J, Stigliani JL, Montanha J, Amoros M, Payard M, Girre L. Antipoliovirus structure-activity relationships of some aporphine alkaloids. J Nat Prod. 1998 Apr;61(4):480-4. doi: 10.1021/np970382v. PMID: 9584402. 16: Quiroz-Carreño S, Pastene-Navarrete E, Espinoza-Pinochet C, Muñoz-Núñez E, Devotto-Moreno L, Céspedes-Acuña CL, Alarcón-Enos J. Assessment of Insecticidal Activity of Benzylisoquinoline Alkaloids from Chilean Rhamnaceae Plants against Fruit-Fly Drosophila melanogaster and the Lepidopteran Crop Pest Cydia pomonella. Molecules. 2020 Nov 3;25(21):5094. doi: 10.3390/molecules25215094. PMID: 33153001; PMCID: PMC7663414. 17: Ge YC, Zhang HJ, Wang KW, Fan XF. Aporphine Alkaloids from Illigera aromatica from Guangxi Province, China. Phytochemistry. 2018 Oct;154:73-76. doi: 10.1016/j.phytochem.2018.06.017. Epub 2018 Jul 6. PMID: 30006090. 18: Fernandes DA, Gomes BA, Mendonça SC, Pinheiro CC, Sanchez EOF, Leitão SG, Fuly AL, Leitão GG. Alkaloids from Siparuna (Siparunaceae) are predicted as the inhibitors of proteolysis and plasma coagulation caused by snake venom and potentially counteract phospholipase A2 activity of Bothrops jararaca. J Ethnopharmacol. 2024 Oct 5;332:118349. doi: 10.1016/j.jep.2024.118349. Epub 2024 May 16. PMID: 38762214.