13C-NMR of chaetoglobosins

Isolation of flavipin, a fungus compound antagonistic to plant-parasitic nematodes

“…These fractions appeared on thin-layer chromatography to consist primarily of a single UV-active compound that intensi ed in yellow colour after spraying with H 2 SO 4 and charring. The 1 H NMR spectra of fractions 7 and 8 corresponded to that reported by Sekita et al (1982) for avipin (1,2-benzenedicarboxaldehyde -3,4,5-trihydroxy-6-methyl ) (Fig. 3): ± 2.51 (3H, s), 10.39 (1H, s), 10.58 (1H, s).…”

“…Fractions that reduced rootknot nematode egg hatch and J2 mobility consisted primarily of this compound, and bioassays of the synthesised compound con rmed the activity. Flavipin is produced by several Aspergillus and Epicoccum species as well as by Chaetomium globosum (Raistrick & Rudman, 1956;Bamford et al, 1961;Sekita et al, 1982). The compound is toxic to microorganisms, particularly to fungi (Raistrick & Rudman, 1956;Bamford et al, 1961;Baráthová et al, 1969;Burge et al, 1976;Brown et al, 1987;Mallea et al, 1991;Madrigal & Melgarejo, 1995), and was implicated as the mechanism responsible for the biocontrol of Monilinia laxa, a fungal plant pathogen, by Epicoccum nigrum (Madrigal et al, 1991).…”

The chemistry and biology of cytochalasans

“…92 Sekita and co-workers examined the cytological effects of a range of chaetoglobosins and described cytotoxicity against HeLa cells. 24,25,58 Since the production of secondary metabolites strongly depends on the culture conditions applied, 93,94 Frisvad et al investigated whether P. expansum produces chaetoglobosins when grown on fruit or fruit products. By screening 85 different P. expansum strains that had been isolated from fruits or fruit products, vegetables, nuts, cereals or even processed food commodities, they found consistent production of chaetoglobosins, not only in pure culture but also in naturally infected fruits or fruit products.…”

Cytoglobosins A−G, Cytochalasans from a Marine-Derived Endophytic Fungus, Chaetomium globosum QEN-14

“…Cytochalasans are a large group of fungal alkaloids with a wide range of biological activities targeting cytoskeletal processes . Some of them also possess phytotoxic, cytotoxic, and antibiotic activities. – Chaetoglobosins are cytochalasans with the phenyl group in the molecules being replaced by an indolyl group. – The fungal genus Chaetomium , which includes both marine- and terrestrial-derived species, was revealed to be a rich source of chaetoglobosins, and to date around 40 chaetoglobosins and analogues have been isolated and identified from the genus.…”