Meleagrin
[CAS# 71751-77-4]

Identification

• Classification: Natural product >> Alkaloid
• Name: Meleagrin
• Synonyms: (1S,9R,14E)-11-hydroxy-14-(1H-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7,10-tetraene-12,15-dione
• Molecular Formula: C₂₃H₂₃N₅O₄
• Molecular Weight: 433.46
• CAS Registry Number: 71751-77-4
• SMILES: CC(C)(C=C)[C@@]12C=C(C(=O)N\3[C@]1(NC(=O)/C3=C\C4=CN=CN4)N(C5=CC=CC=C25)OC)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.718, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

Meleagrin is a naturally occurring alkaloid classified as an indole-based fungal metabolite, recognized for its complex structure and potential bioactivity. The compound was first isolated from fungal species within the Penicillium genus, particularly *Penicillium meleagrinum*, which led to its naming. Discovered in the mid-20th century, meleagrin gained research interest due to its unique chemical framework and potential therapeutic applications. As a secondary metabolite, meleagrin is believed to serve a protective role for the fungi, deterring predation by producing bioactive compounds that may have pharmacological relevance for human use.

One of the primary applications of meleagrin is in the field of antimicrobial research. Studies have shown that meleagrin exhibits inhibitory effects against certain bacterial strains, suggesting it could be a potential lead compound for developing new antibiotics. Given the increasing global challenge of antibiotic resistance, compounds like meleagrin that demonstrate antibacterial properties are valuable starting points for the discovery of novel antimicrobial agents. Research efforts have focused on modifying the core structure of meleagrin to enhance its potency and broaden its range of activity, aiming to synthesize derivatives that can effectively target resistant bacterial pathogens.

Additionally, meleagrin has been investigated for its cytotoxic properties, particularly in the context of cancer research. Preliminary studies have shown that meleagrin may induce apoptosis (programmed cell death) in certain cancer cell lines, which indicates potential as an antitumor agent. This cytotoxic activity, while still under exploration, highlights meleagrin’s promise as a lead compound for the development of cancer therapeutics. Modifications to its structure are being studied to increase its selectivity and reduce potential toxicity, aiming to create safer and more effective antitumor drugs.

In recent years, meleagrin has also gained interest for its role in the synthesis of other indole-based compounds. Researchers value it as a scaffold for creating derivatives with diverse bioactivities, not only against microbes and cancer cells but also in other therapeutic areas such as inflammation and immune modulation. This versatility is due to the compound’s highly functionalized indole and diketopiperazine rings, which offer numerous sites for chemical modifications.

Overall, meleagrin’s unique structure and demonstrated bioactivity have made it a valuable compound in medicinal chemistry. Its potential applications in antibacterial, anticancer, and other therapeutic developments continue to drive research aimed at understanding and enhancing its biological properties for clinical use.