Roseophilin CAS No. 142386-38-7

Product Description

Roseophilin is a naturally occurring, pyrrole-containing macrolide first isolated from the actinobacterium Streptomyces griseoviridis. Possessing a striking architecture built from a 13-membered macrolactam ring fused to a tricyclic core and an extended polyene/pyrrole side chain, it belongs to the same biosynthetic neighborhood as the prodiginines and has become a celebrated target for total-synthesis campaigns that exploit Paal-Knorr and Nazarov cyclization tactics. Beyond its structural allure, roseophilin exhibits potent cytotoxicity against selected cancer cell lines—an activity thought to arise from mitochondrial disruption and apoptosis induction—and displays mild antibacterial activity against Gram-positive organisms. Although its precise molecular targets remain under investigation and it has not yet advanced to clinical evaluation, ongoing medicinal-chemistry efforts continue to modify the natural scaffold in search of improved pharmacological properties.

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Product Use & Characteristics

1. General Identity

   • Natural pyrrole-containing macrocyclic alkaloid

   • First source: Streptomyces griseoviridis

2. Molecular Data

   • Formula: C₂₇H₃₃ClN₂O₂

   • Molecular weight: 453 g mol⁻¹

   • IUPAC name: (12R,13R)-15-[5-(3-chloro-1H-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-propan-2-yl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene

3. Structural Features

   • 13-membered macrolactam ring fused to a tricyclic core

   • Extended polyene/pyrrole side chain

   • Two pyrrole rings + one furan ring

   • Conjugated system; dimethylaminoethyl side chain

4. Biosynthesis

   • Hybrid polyketide + amino-acid (likely glycine) pathway

   • Encoded by the rph gene cluster in S. griseoviridis

   • Co-produced with cyclic prodigiosins R1, R2, R3

5. Synthesis Methods

   • First total synthesis: Fürstner & Weintritt (JACS 1998)

   • Key reactions: Corey–Chaykovsky, Tsuji–Trost, Friedel–Crafts, Dess–Martin oxidation

   • Alternative tactics: Paal–Knorr pyrrole formation, Nazarov cyclization for stereocontrolled cyclopenta-annulated pyrrole core

   • Synthetic analogues prepared for structure–activity studies

6. Biological Activities

   • Antitumor: cytotoxic against K562, KB, HeLa, HT1080 cell lines (IC₅₀ ≈ 2–3 µM)

   • Mechanism: mitochondrial disruption, induction of apoptosis

   • Antibacterial: mild activity against Gram-positive bacteria

   • Anion transport: synthetic furan-containing analogues tested as transmembrane carriers (lower activity than prodiginines)

7. Uses / Applications

   • Lead compound for anticancer drug discovery

   • Chemical probe for studying mitochondrial function and apoptosis

   • Scaffold for medicinal-chemistry optimization (potency, selectivity, stability)

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