Recent Advances in Sorbicillinoids from Fungi and Their Bioactivities (Covering 2016–2021)

Abstract

Sorbicillinoids are a family of hexaketide metabolites with a characteristic sorbyl side chain residue. Sixty-nine sorbicillinoids from fungi, newly identified from 2016 to 2021, are summarized in this review, including their structures and bioactivities. They are classified into monomeric, dimeric, trimeric, and hybrid sorbicillinoids according to their basic structural features, with the main groups comprising both monomeric and dimeric sorbicillinoids. Some of the identified sorbicillinoids have special structures such as ustilobisorbicillinol A, and sorbicillasins A and B. The majority of sorbicillinoids have been reported from fungi genera such as Acremonium, Penicillium, Trichoderma, and Ustilaginoidea, with some sorbicillinoids exhibiting cytotoxic, antimicrobial, anti-inflammatory, phytotoxic, and α-glucosidase inhibitory activities. In recent years, marine-derived, extremophilic, plant endophytic, and phytopathogenic fungi have emerged as important resources for diverse sorbicillinoids with unique skeletons. The recently revealed biological activities of sorbicillinoids discovered before 2016 are also described in this review.

Sorbicillinoid Derivatives with the Radical Scavenging Activities from the Marine-Derived Fungus Acremonium chrysogenum C10

“…Sorbicillinoids are a class of structurally diverse hexaketide metabolites with a characteristic sorbyl side chain residue [ 7 , 8 , 9 ]. They were first isolated from Penicillium notatum in 1948 and structurally elucidated by Cram and Tishler [ 10 , 11 ].…”

“…They were first isolated from Penicillium notatum in 1948 and structurally elucidated by Cram and Tishler [ 10 , 11 ]. Up until now, more than 159 naturally occurring sorbicillinoids have been isolated and have displayed good biological activities in cytotoxic, antimicrobial and phytotoxic activities [ 7 , 8 , 9 ]. Because free radicals play an important role in the development of aging and many diseases, including cancer, arthritis and atherosclerosis, exploring the novel radical scavengers is crucial for developing new drugs to slow down the aging process and treat these diseases.…”

“…Additionally, there is an urgent need to find more novel compounds for the emergence of microbial resistance. Some sorbicillinoids showed significant antimicrobial activity, indicating their potential as candidates [ 7 ]. Meanwhile, the sorbicillinoid biosynthetic gene clusters from Penicillium chrysogenum and Trichoderma reesei have been identified and their biosynthetic pathway has been partially revealed [ 12 , 13 , 14 ].…”

UvSorA and UvSorB Involved in Sorbicillinoid Biosynthesis Contribute to Fungal Development, Stress Response and Phytotoxicity in Ustilaginoidea virens

“…Sorbicillinoids are a family of polyketide mycotoxins that are related to the hexaketide sorbicillin, and typically contain a sorbyl side chain in their structures [ 24 ]. To date, at least 159 sorbicillinoids have been identified, and they were found in both terrestrial and marine fungi [ 24 , 25 , 26 ]. The studies of sorbicillinoids have been currently focused on their structural identification [ 24 , 25 , 26 ], biological activities including radical-scavenging activity [ 27 ] and cytotoxic activity [ 23 , 28 ], and biosynthetic pathways [ 29 ], as well as the enzymes related to the sorbicillinoid biosynthesis [ 30 , 31 ].…”

“…To date, at least 159 sorbicillinoids have been identified, and they were found in both terrestrial and marine fungi [ 24 , 25 , 26 ]. The studies of sorbicillinoids have been currently focused on their structural identification [ 24 , 25 , 26 ], biological activities including radical-scavenging activity [ 27 ] and cytotoxic activity [ 23 , 28 ], and biosynthetic pathways [ 29 ], as well as the enzymes related to the sorbicillinoid biosynthesis [ 30 , 31 ]. To the best of our knowledge, the biological functions of sorbicillinoids in U. virens are rarely known.…”