title: 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 been isolated from various marine organisms. A class of pyrroloiminoquinone-related alkaloids, known as bispyrroloquinones, is the focus of this review article. 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 analogs show inhibition of topoisomerases. One additional possible mechanism of anticancer activity of tsitsikammamines analogs that has been 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 evaluation of bioactivities of bispyrroloquinone alkaloids and their analogs.
authors.affiliation: Department of Chemistry, University of Alabama at Birmingham, Birmingham, AL 35294, USA.
authors.forename: Bhavitavya
authors.initials: B
authors.lastname: Nijampatnam
authors.affiliation: Department of Chemistry, University of Alabama at Birmingham, Birmingham, AL 35294, USA.
authors.forename: Shilpa
authors.initials: S
authors.lastname: Dutta
authors.affiliation: Department of Chemistry, University of Alabama at Birmingham, Birmingham, AL 35294, USA. Electronic address: svelu@uab.edu.
authors.forename: Sadanandan E
authors.initials: SE
authors.lastname: Velu
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology; D011758:Pyrroles / Q000737:chemistry / Q000494:pharmacology*; D011804:Quinolines / Q000737:chemistry / Q000494:pharmacology*; D011809:Quinones / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000470:Alkaloids; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D001688:Biological Products; D026121:Indole Alkaloids; D007211:Indoles; D011758:Pyrroles; D011804:Quinolines; D011809:Quinones; C508209:tsitsikammamine A; C508208:wakayin; C505322:zyzzyanone D; C030374:indole
keywords: Anticancer; Antimicrobial; Bispyrroloquinones; Topoisomerase; Tsitsikammamines; Wakayin; Zyzzyanones