Recent advances in isolation, synthesis, and evaluation of bioactivities of bispyrroloquinone alkaloids of marine origin

Abstract

The ocean continues to provide a plethora of unique scaffolds capable of remarkable biological applications. A large number of pyrroloiminoquinone alkaloids, including discorhabdins, epinardins, batzellines, makaluvamines, and veiutamine have already been isolated from marine organisms. A class of pyrroloiminoquinone-related alkaloids known as bispyrroloquinones is the focus of this review. This family of marine alkaloids, which contain an aryl substituted bispyrroloquinone ring system, includes three subclasses of alkaloids namely, wakayin, tsitsikammamines A-B and zyzzyanones A-D. Both wakayin and the tsitsikammamines contain a tetracyclic fused bispyrroloiminoquinone ring system, while zyzzyanones contain a fused tricyclic bispyrroloquinone ring system. The unique chemical structures of these marine natural products and their diverse biological properties, including antifungal and antimicrobial activity, as well as the potent, albeit generally nonspecific and universal cytotoxicities, have attracted great interest of synthetic chemists over the past three decades. Tsitsikammamines, wakayin, and several of their analogues show inhibition of topoisomerases. One additional possible mechanism of anticancer activity of tsitsikammamines analogues that was discovered recently is through the inhibition of indoleamine 2,3-dioxygenase, an enzyme involved in tumoral immune resistance. This review discusses the isolation, synthesis, and bioactivities of bispyrroloquinone alkaloids and their analogues.

Bioactive Compounds from Marine Sources

“…Marine-derived products have a wide range of applications in pharmaceuticals as anti-tumor and anti-viral among others, nutraceuticals as dietary supplements and food additives, agrochemicals with insecticidal, herbicidal, and fungicidal activities and cosmetics as photoprotective and anti-aging compounds. These compounds are believed to be superior to that derived from terrestrial nature in terms of their chemical novelty and their ability to induce potential activities [7]. They are mainly obtained from different marine taxonomic groups including antarctic fungi, bacteria, epiphytic bacteria and fungi, macroalgae or seaweeds, microalgae and mediterranean sponges [8].…”

Design, Synthesis, and Apoptosis-Promoting Effect Evaluation of Rhopaladins’ Analog 4-Arylidene-5-Oxopyrrolidine Derivatives

“…Compounds with a pyrrolidone structure have a wide range of applications in pharmaceutical and chemical fields, especially as basic nuclear structures for anticancer and antiviral drug syntheses ( Carbone et al, 2020 ; Dyshlovoy et al, 2020 ). On the therapeutic front, the superiority of marine natural products over terrestrial natural products is because of their novelty, chemical stability, and strong biological activity ( Nijampatnam et al, 2015 ). Marine alkaloids widely exist in marine organisms and have many physiological activities.…”

Green synthesis, structure optimization and biological evalution of Rhopaladins’ analog 2–styryl–5-oxopyrrolidine-2- carboxamide RPDPRH on CaSki cells

“…Marine natural products have novel structures and a variety of physiological activities, especially the marine alkaloids containing pyrrolidone structure have unique chemical structure and strong antifungal and antibacterial biological characteristics ( Nijampatnam et al, 2015 ). Among them, alkaloid Rhopaladins A-D isolated from marine natural products has obvious anti-tumor activity ( Sato et al, 1998 ).…”