Massarinolins A−C:  New Bioactive Sesquiterpenoids from the Aquatic Fungus Massarina tunicata

Abstract

Massarinolins A-C (1-3), three new bioactive sesquiterpenoids possessing rare ring systems, have been isolated from liquid cultures of the aquatic fungus Massarina tunicata Shearer & Fallah. The structures were determined primarily by analysis of NMR data. Metabolites 1-3 are the first compounds to be reported from any member of the genus Massarina.

Secondary metabolite chemistry of the marine-derived fungus Massarina sp., strain CNT-016

“…Six of the marine Massarina species were described from mangroves (Hyde et al, 1992), while two were described from the salt marsh plant Juncus roemerianus (Kohlmeyer et al, 1995a,b). The secondary metabolite chemistry of Massarina species is virtually unexplored; only one freshwater species, M. tunicata Shearer and Fallah, has been investigated and eleven new bioactive compounds have been recorded (Oh et al, 1999(Oh et al, , 2001(Oh et al, and 2003. Although limited data are available, these studies indicate that Massarina species are chemically productive.…”

Oxidative cyclization of γ-alkylidene butenolides. Stereoselective preparation of spirolactones

“…5 It shows biological activity against Bacillus subtilis (ATCC 6501) and Staphylococcus aureus (ATCC 29213). It appears to be biosynthesized from a farnesyl-type precursor and even though its relative stereochemistry was deduced by spectroscopic methods its absolute stereochemistry remains a challenge for synthetic chemists.…”

Screening and isolation of antibacterial activities of the fermentative extracts of freshwater fungi from Yunnan Province, China

“…Among fungi from the diverse environments, the freshwater aquatic fungi have received attention from the scientific community. Consequently several groups of investigators have identified that freshwater fungi contain some unique biologically active metabolites such as decaspirones (Jiao et al, 2006), gliocladines (Dong et al, 2005), resorcylides (Dong et al, 2007), pseudohalonectrins (Dong et al, 2006), massarinolins (Oh et al, 1999), ophiocerins (Reátegui et al, 2005), massarigenins (Oh et al, 2003) etc. There may be many more freshwater fungi, not yet tested, which could prove to be a fruitful source of biologically active secondary metabolites.…”