Representative LC/UV chromatogram under typical analytical conditions (C18 column; mobile phase: 5–100% ACN / H2O (0.05% H3PO4), linear gradient 20 min; flow rate: 0.2 mL/min; detection: 210 nm).
NMR Spectral Data
Representative 1H NMR (500 MHz) spectrum confirming the structure of Geodin. Representative 13C NMR (125 MHz) spectrum supporting structural assignment of Geodin.
Source Organism
Penicillium sp.
Summary
Geodin is a halogenated fungal polyketide displaying antibacterial, antifungal, and insecticidal activities.
Details
(+)-Geodin is a chlorinated polyketide secondary metabolite produced by Aspergillus terreus and related Aspergillus species. It is formed through a regio- and stereospecific oxidative phenol-coupling reaction catalyzed by the blue copper enzyme dihydrogeodin oxidase during biosynthesis. Geodin and its semi-synthetic derivatives exhibit significant antibacterial activity against Staphylococcus aureus and Aeromonas salmonicida, potent antifungal activity against Candida albicans, and measurable insecticidal effects. Structure-activity relationship studies indicate that substitution at the 4-OH position enhances antimicrobial potency. Geodin serves as both a biosynthetic model for copper-dependent oxidative coupling and a scaffold for antimicrobial and agrochemical development.