Buy Tigloyltropeine (BT-255608)

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Tigloyltropeine

Catalog Number: BT-255608

CAS Number: 495-83-0

Molecular Formula: C₁₃H₂₁NO₂

Molecular Weight: 223.31 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Tigloyltropeine is a naturally occurring alkaloid found in the leaves of the plant, Tropeaolum majus. It belongs to the class of benzylisoquinoline alkaloids and has been the subject of extensive research due to its potential therapeutic and environmental applications. This paper aims to provide a comprehensive review of the synthesis, chemical structure, biological activity, and applications of tigloyltropeine.

Properties

CAS Number

495-83-0

Product Name

Tigloyltropeine

IUPAC Name

[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate

Molecular Formula

C₁₃H₂₁NO₂

Molecular Weight

223.31 g/mol

InChI

InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+/t10-,11+,12?

InChI Key

UVHGSMZRSVGWDJ-ZCFDAEMWSA-N

SMILES

CC=C(C)C(=O)OC1CC2CCC(C1)N2C

Canonical SMILES

CC=C(C)C(=O)OC1CC2CCC(C1)N2C

Isomeric SMILES

C/C=C(\C)/C(=O)OC1C[C@H]2CC[C@@H](C1)N2C

Method of Synthesis or Extraction

Tigloyltropeine can be extracted from the leaves of Tropeaolum majus using various methods such as maceration, Soxhlet extraction, and supercritical fluid extraction. The efficiency and yield of each method vary depending on the extraction conditions. For instance, supercritical fluid extraction has been reported to yield higher amounts of tigloyltropeine compared to other methods. However, the use of organic solvents in the extraction process raises environmental and safety concerns. Therefore, the development of green extraction methods is necessary to minimize the environmental impact and ensure the safety of the extraction process.

Chemical Structure and Biological Activity

The chemical structure of tigloyltropeine consists of a benzylisoquinoline skeleton with a tigloyl group attached to the nitrogen atom. The tigloyl group is responsible for the biological activity of tigloyltropeine. Tigloyltropeine has been reported to exhibit various biological activities such as antitumor, anti-inflammatory, and antimicrobial activities. The mechanism of action of tigloyltropeine involves the inhibition of cell proliferation and induction of apoptosis in cancer cells. Tigloyltropeine also inhibits the production of pro-inflammatory cytokines and reduces the expression of inflammatory genes. Moreover, tigloyltropeine has been shown to possess antimicrobial activity against various bacterial and fungal strains.

Biological Effects

Tigloyltropeine has been reported to affect cell function and signal transduction pathways. It inhibits the activation of NF-κB, a transcription factor involved in the regulation of inflammatory genes. Tigloyltropeine also inhibits the phosphorylation of ERK1/2, a signaling protein involved in cell proliferation and survival. In addition, tigloyltropeine has been shown to induce DNA damage and cell cycle arrest in cancer cells. However, the potential therapeutic and toxic effects of tigloyltropeine require further investigation.

Applications

Tigloyltropeine has potential applications in medical, environmental, and industrial research. In medical research, tigloyltropeine has been studied for its role in drug development. It has been shown to enhance the efficacy of chemotherapy drugs and reduce their toxicity. Tigloyltropeine has also been tested in clinical trials for its antitumor and anti-inflammatory effects. However, the benefits and potential side effects of tigloyltropeine in humans require further investigation. In environmental research, tigloyltropeine has been studied for its effects on ecosystems and its role in pollution management. Tigloyltropeine has been shown to inhibit the growth of algae and reduce the toxicity of heavy metals in water. In industrial research, tigloyltropeine has potential applications in improving product quality and efficiency. However, health and safety considerations must be taken into account when using tigloyltropeine in manufacturing processes.

Future Perspectives and Challenges

The current limitations in the use and study of tigloyltropeine include the lack of standardized extraction methods, limited knowledge of its toxicity and pharmacokinetics, and the need for more clinical trials to evaluate its therapeutic potential. Possible solutions and improvements include the development of green extraction methods, the use of animal models to study its toxicity and pharmacokinetics, and the collaboration between researchers and industries to explore its potential applications. Future trends and prospects in the application of tigloyltropeine in scientific research include the development of novel drug formulations and the exploration of its potential as a natural pesticide.
Conclusion:
Tigloyltropeine is a promising natural alkaloid with potential applications in various fields of research. Its chemical structure, biological activity, and potential applications have been extensively studied. However, further research is needed to fully understand its therapeutic and toxic effects, as well as its potential applications in environmental and industrial research. The development of green extraction methods and the collaboration between researchers and industries are necessary to ensure the safe and sustainable use of tigloyltropeine.

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