Monocerin

Monocerin

Monocerin is a diels-alder adduct of the anthraquinone derivative chrysophanol and the sesquiterpene cadinene. It is a naturally occurring fungal metabolite that exhibits antifungal and phytotoxic properties.

History

Monocerin was first isolated from the fungus Monocillium nordinii in 1972 by researchers at the University of Illinois. Since then, it has been found in several other species of fungi, including Nigrospora sphaerica and Diplodia natalensis.

Structure and Synthesis

The structure of monocerin consists of a chrysophanol moiety and a cadinene moiety, which are connected through a Diels-Alder reaction. The synthesis of monocerin involves the biotransformation of chrysophanol and cadinene by the fungus, followed by a spontaneous Diels-Alder reaction.

Biological Activity

Monocerin has been found to exhibit antifungal activity against several plant pathogenic fungi, including Fusarium oxysporum, Botrytis cinerea, and Rhizoctonia solani. It also shows phytotoxic activity, causing necrosis and chlorosis in plant tissues.

Applications

Due to its antifungal and phytotoxic properties, monocerin has potential applications in agriculture as a natural pesticide. However, further research is needed to determine its safety and efficacy.

See Also

• Anthraquinone
• Diels-Alder reaction
• Fungal metabolites
• Phytotoxicity