Naphthopyranones – isolation, bioactivity, biosynthesis and synthesis

Abstract

The 1H-naphtho[2,3-c]pyran-1-one (naphthopyranone) moiety forms the structural framework of a group of secondary metabolites that have been isolated from a range of organisms including fungi, bacteria, lichen and plants. This review documents the known naturally occurring naphthopyranones - their isolation, biosynthesis and biological activity. A survey of methods reported for the synthesis of naphthopyranone natural products is presented.

Spatial mapping of lichen specialized metabolites using LDI-MSI: chemical ecology issues for Ophioparma ventosa

“…The reproductive structures are often reported to produce specific lichen compounds or known to be more concentrated in phenols than the remaining thallus13, in accordance with the optimal defense theory114. Haemoventosin belongs to a structural class (quinones) exerting a wide array of biological activities of ecological significance including antibiotic, antifungal15 and cytotoxic properties10. Moreover, haemoventosin putatively acts as a UV screening filter to protect spores during their maturation within asci.…”

Synthesis of Functionalized Arenopyrans and Arenylsulfanes by Reacting Nitroallylic Acetates with Arenols and Arenethiols

“…Naphthopyran moiety is present in a wide range of bioactive heterocycles of natural and synthetic origin Besides exhibiting various biological activities, for instance, antiproliferative activity, naphthopyrans are distinguished structural scaffolds for the development of diverse photochromic materials (Figure )…”

A new naphthopyranone from the sponge‐associated fungus Penicillium sp. XWS02F62

“…Among them, the fungi of the common genus Penicillium are important producers of various SMs with interesting biological activities and novel structures including alkaloids, terpenes, polyketides, and lipopeptides . Naphthopyranones (1 H ‐naphtho‐[2,3‐ c ]pyran‐1‐one) encompass a linear tricyclic skeleton embedding naphthalene and fused δ ‐lactone ( α ‐pyrone) rings, widely encountered in fungi, bacteria, lichen, and plants of polyketide biosynthetic origin . They have been found with a broad range of bioactivities, as exemplified by antimicrobial, cytotoxic, immunoregulatory, and antioxidant activity, arousing considerable interest from both synthetic and biosynthetic chemists …”