Sorbicillinoids from Fungi and Their Bioactivities

Abstract

Sorbicillinoids are important hexaketide metabolites derived from fungi. They have a variety of biological activities including cytotoxic, antioxidant, antiviral and antimicrobial activity. The unique structural features of the sorbicillinoids make them attractive candidates for developing new pharmaceutical and agrochemical agents. About 90 sorbicillinoids have been reported in the past few decades. This mini-review aims to briefly summarize their occurrence, structures, and biological activities.

Identification of a Sorbicillinoid-Producing Aspergillus Strain with Antimicrobial Activity Against Staphylococcus aureus: a New Polyextremophilic Marine Fungus from Barents Sea

“…The molecular formulas were deduced by HRESI analysis, and the corresponding structures were tentatively assigned by comparison with literature data (Harned and Volp 2011;Meng et al 2016). The results of this analysis were reported in Table 6.…”

Establishing the True Structure of the Sorbicillinoid‐Derived Isolate Rezishanone C by Total Synthesis

“…These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone Ci sa na rtefact of the isolation process and arises throughaDiels-Alder reactionb etween ethyl vinyl ether and sorbicillinol (3).The sorbicillins are an ever-expanding class of polyketide-derived fungal metabolite [1] that display significant structural diversity and (sometimes)u nusual biological activities. [2] Rezishanone C( sorbivinetone, Figure 1), [3] for which both structures 1 and 2 have been suggested, can be classified as am ember of the so-called hybrid sub-type [2a] of sorbicillins that arise through aD iels-Alder reactionb etween sorbicillinol( 3)a nd variousn on-sorbicillinoid-derived compounds containing ad ienophilic residue. In the case of rezishanone C, it hasb een suggested [3a] that ethyl vinyl ether is the dienophile involved.…”

Diels–Alder Reactions During the Biosynthesis of Sorbicillinoids

“…[7,8] 1a is oxidatively dearomatised to form sorbicillinol (2a;S cheme 1A), [9] which reacts with itself and other compounds to form various sorbicillinoids (Scheme 1), more than 90 of which are known. [10][11][12] Tr ifonov first proposed 2a as the intermediate for self-dimerization due to its dual diene and dienophile character. [2,13,14] This was confirmed by Abe et al through elegant feeding experiments.…”

“…LCMS analysis (DAD 210-600 nm) of A. oryzae NSAR1 (A; control) and transformants expressing sorABC (B) or sorABCD (C) fed with scytolide(12). Dimeric sorbicillinoids are highlighted in yellow; monomeric sorbicillinoids are highlightedi ngrey.…”