7-isopentenyloxycoumarin

**7-isopentenyloxycoumarin** is a naturally occurring oxyprenylated derivative of umbelliferone (coumarin), found in members of Rutaceae and Apiaceae (including medicinal and edible plants)[3][1]. It is characterized by a 3,3-dimethylallyl (isopentenyl) side chain at the 7-position of the coumarin core. Recent pharmacological research demonstrates diverse bioactivity: - **Anticancer**: Induces cell cycle arrest at G2/M, DNA fragmentation, chromatin condensation, increased caspase 3 activity (suggesting a proapoptotic effect), inhibition of tumor angiogenesis, and reduction of chemokine CCL2 release in tumor microenvironment. Shows cytotoxicity against certain tumor cell lines and can reverse multidrug resistance[1][3]. - **Neuroprotective**: Reduces activation of microglia and provides protection against dopaminergic neuronal cell death in models of neurodegeneration (e.g., Parkinson’s disease)[1][5]. - **Enzyme inhibition**: Potent inhibitor of butyrylcholinesterase (IC50 ~11.77 μM), with limited acetylcholinesterase activity, and notable π–π stacking interactions with butyrylcholinesterase active site[1]. - **Melanogenesis stimulator**: Significantly increases melanin biosynthesis via strong agonism of estrogen receptor β, upregulation of tyrosinase-related proteins, and microphthalmia-associated transcription factor; potential additional involvement with aryl hydrocarbon receptor[1]. - **Other properties**: Antigenotoxic (reduces DNA damage under oxidative stress), antibacterial, antifungal, antiprotozoal, anti-inflammatory, and antioxidant effects[3]. Toxicity studies demonstrate low toxicity and non-genotoxicity at tested doses[1]. No approved medical uses or commercial formulations are listed; studies are mainly in vitro and in vivo (nonclinical/preclinical).

Other names

isopentenyloxycoumarin3-(3-methylbut-3-enoxy)chromen-2-one