Spirobisnaphthalenes from Fungi, Biological activities and Total Synthesis: A Research Review

Abstract

Spirobisnaphthalenes are a family of natural products containing two naphthalenes connected with spiroketal or dinaphthalene spiroether. This family of natural compounds has a wide range of biological activities and complex structures, and has attracted great attention from synthetic chemists in recent years. Hundreds of novel spirobisnaphthalenes have been identified from the first separation in 1989. Despite the slow pace of research in recent years, since the latest review in 2017, 30 new natural products have been isolated from the endolichenic and endophytic fungus, including Type A, B, D and E, a new special skeleton with a spiro quaternary carbon center, as well as significant breakthroughs are made in the total synthesis. Here, the last research advances in the isolation of new spirobisnaphthalenes, their activities, mode of action and the total synthesis of spirobisnaphthalenes in the last five years were afforded based on our research in this field in this review.

Rare Cladosporols and Spirobisnaphthalenes from the Chinese toad-derived Cladosporium cladosporioides F-10-2-A

“…[12] Additionally, here spirobisnaphthalenes were initially discovered inCladosporium , representing a growing family of rare natural products containing two naphthalene-derived C10 units bridged through a spiroketal linkage. [4,21] Furthermore, the summary of UV absorption profiles for cladosporols and spirobisnaphthalenes provides valuable evidence that may encourage further in-depth investigation of these compounds. Collectively, this study explored the metabolites produced by endophytic fungi found in toad skin and their anti-tumor activity, offering valuable insights for gaining a deeper understanding of the symbiotic relationship between animals and their associated fungi, and its potential implications for host health.…”

Total Synthesis and Biological Activity of (±)-Guignardin A, (±)-Palmarumycin B9, and Their Derivatives

“…Spirobisnaphthalene natural products, which were divided into five types based on the different linkages of the two naphthalenes, have a broad biological activities, such as antifungal, antimicrobial, antitumor, anticancer, antiparasitic, anti-inflammatory, and cytotoxic activity. − Many reports related to the total synthesis, structure revision, and modification, and biological activity evaluation of the spirobisnaphthalene natural products have appeared in recent years, − in which spiromamakone A and its monobenzo analogue (Figure B) showed excellent cytotoxicity against cervical carcinoma HeLa cells with IC 50 value of 0.77 and 0.56 μM, respectively. − Some of works have also been carried out in the total synthesis and biological activities of this family of natural products in our group. − …”