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Vanitiolide

Catalog Number: BT-253823

CAS Number: 17692-71-6

Molecular Formula: C12H15NO3S

Molecular Weight: 253.32 g/mol

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

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Product Introduction

Description

Vanitiolide is a natural product that belongs to the class of sesquiterpene lactones. It was first isolated from the leaves of the plant Vernonia nitidula, which is native to South America. Vanitiolide has gained significant attention in recent years due to its potential therapeutic and environmental applications. This paper aims to provide a comprehensive review of vanitiolide, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges.

Properties

CAS Number

17692-71-6

Product Name

Vanitiolide

IUPAC Name

(4-hydroxy-3-methoxyphenyl)-morpholin-4-ylmethanethione

Molecular Formula

C12H15NO3S

Molecular Weight

253.32 g/mol

InChI

InChI=1S/C12H15NO3S/c1-15-11-8-9(2-3-10(11)14)12(17)13-4-6-16-7-5-13/h2-3,8,14H,4-7H2,1H3

InChI Key

WQYRHRAZNNRDIA-UHFFFAOYSA-N

SMILES

COC1=C(C=CC(=C1)C(=S)N2CCOCC2)O

Canonical SMILES

COC1=C(C=CC(=C1)C(=S)N2CCOCC2)O

Method of Synthesis or Extraction

Vanitiolide can be extracted from the leaves of Vernonia nitidula using various methods, including maceration, Soxhlet extraction, and supercritical fluid extraction. The efficiency and yield of each method vary depending on the extraction conditions, such as the solvent used, temperature, and time. For instance, the yield of vanitiolide obtained from Vernonia nitidula leaves using supercritical fluid extraction was found to be higher than that obtained using Soxhlet extraction. However, the use of supercritical fluid extraction requires specialized equipment and is relatively expensive. Environmental and safety considerations should also be taken into account when selecting the extraction method, as some solvents may be toxic or harmful to the environment.

Chemical Structure and Biological Activity

Vanitiolide has a unique chemical structure consisting of a sesquiterpene lactone core with a γ-lactone ring and a furan ring. The molecule also contains a hydroxyl group and an ester group. The biological activity of vanitiolide has been extensively studied, and it has been found to exhibit a wide range of pharmacological properties, including anti-inflammatory, anti-tumor, and anti-microbial activities. The mechanism of action of vanitiolide involves the inhibition of various enzymes and signaling pathways, such as NF-κB and MAPK, which are involved in inflammation and cancer.

Biological Effects

Vanitiolide has been shown to have significant effects on cell function and signal transduction. It has been found to induce apoptosis in cancer cells and inhibit the growth of tumor cells. Vanitiolide also exhibits anti-inflammatory effects by reducing the production of pro-inflammatory cytokines and chemokines. However, vanitiolide may also have potential toxic effects, as it has been found to induce DNA damage and oxidative stress in some cell types. Further studies are needed to determine the potential therapeutic and toxic effects of vanitiolide in vivo.

Applications

Vanitiolide has potential applications in various fields, including medical research, environmental research, and industrial research. In medical research, vanitiolide has been studied for its role in drug development, and several clinical trials have been conducted to evaluate its efficacy and safety in treating various diseases, such as cancer and inflammatory disorders. In environmental research, vanitiolide has been found to have effects on ecosystems and may have a role in pollution management and sustainability. In industrial research, vanitiolide has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations should be taken into account when using vanitiolide in industrial applications.

Future Perspectives and Challenges

Despite the promising potential of vanitiolide, there are still several challenges that need to be addressed. One of the main challenges is the limited availability of vanitiolide, as it is mainly obtained from Vernonia nitidula, which is not widely cultivated. Another challenge is the lack of understanding of the pharmacokinetics and pharmacodynamics of vanitiolide in vivo, which hinders its clinical development. Future research should focus on developing efficient and sustainable methods for the synthesis or extraction of vanitiolide and on elucidating its pharmacological properties in vivo.
Conclusion
Vanitiolide is a natural product with significant potential in various fields, including medical research, environmental research, and industrial research. Its unique chemical structure and biological activity make it a promising candidate for drug development and other applications. However, further studies are needed to determine its potential therapeutic and toxic effects in vivo and to address the challenges associated with its synthesis or extraction and clinical development.

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