The sorbicillinoid family of natural products: Isolation, biosynthesis, and synthetic studies

Abstract

The sorbicillinoids are a family of hexaketide metabolites that have been isolated from a variety of fungal sources, collected from both marine and terrestrial sources. Since 1948, the family has grown in size to include over 50 members, many of which have complex, highly oxygenated, bicyclic and tricyclic frameworks. In conjunction with their biological activity, the structural complexity of these structures has inspired several synthetic campaigns and has also led to controversy surrounding the biosynthetic pathway responsible for the natural production of these compounds. Through this review, we aim to give a historical perspective to each of these areas and hope to inspire new avenues of research for addressing the knowledge gaps that still exist.

Sorbicillinoids from Fungi and Their Bioactivities

“…Except urea 73 from the genus Paecilomyces, others were isolated from the genus Penicillium. [37] Note: Compounds 74-79 were not included in the last review [1]. …”

“…USF-2690 from a soil sample [44] Clonostachys rosea YRS-06 from a soil sample [13] Note: Compounds 36, 39-41 and 56-60 were not included in the last review [1]. …”

“…In 2011, Harned and Volp reviewed the structures of 62 sorbicillinoids [1]. Since then, many new members of this family were isolated and great progress has been made [4,[10][11][12][13].…”

“…According to the structural features, sorbicillinoids can be divided into four groups: monomeric sorbicillinoids, bisorbicillinoids, trisorbicillinoids, and hybrid sorbicillinoids. Biosynthesis and chemical synthesis have been extensively studied and reviewed [1,11,[14][15][16][17]. In this mini-review, we focus on the occurrence and biological activities of sorbicillinoids, and 28 additional sorbicillinoids were added on the basis of the previous review [1].…”

“…Sorbicillinoids (also called vertinoids) belong to hexaketide metabolites in which the cyclization has taken place on the carboxylate terminus [1]. They have highly diverse bioactivities and have been isolated from either marine [2][3][4] or terrestrial fungi [5][6][7].…”