Brominated Aromatic Furanones and Related Esters from the Ascidian Synoicum sp.

Abstract

Nine new compounds, tris-aromatic furanones (1, 2, 3a, 3b, and 4) and related bis-aromatic diesters (5a, 5b, 6a, and 6b), are described from the ascidian Synoicum sp. collected off the coast of Chuja-do, Korea. The structures of these compounds, designated as cadiolides E and G-I (1-4) and synoilides A and B (5 and 6), were determined by extensive spectroscopic analyses. The absolute configuration at the asymmetric center of cadiolide G (2) was assigned by ECD analysis. Of these new compounds, cadiolide I and the synoilides possess unprecedented carbon skeletons. Several of these compounds exhibited significant inhibition against diverse bacterial strains as well as moderate inhibition against the enzymes sortase A, isocitrate lyase, and Na(+)/K(+)-ATPase.

Antiinfective therapy with a small molecule inhibitor of Staphylococcus aureus sortase

“…inoculation of the pathogen (12,13). Earlier work used in vitro (inhibition of fluorogenic substrate cleavage) and virtual screening of compound libraries to identify sortase inhibitors (15,(52)(53)(54)(55)(56). Although these studies identified both competitive and noncompetitive inhibitors (57,58), isolated compounds have not yet been shown to inhibit in vivo sortase activity in staphylococci, i.e., the cleavage of sorting signals or the assembly of surface proteins into the bacterial cell wall (54,(59)(60)(61)(62).…”

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…[40]; new butenolide cadiolides C–F ( 17 – 20 ) from a Korean tunicate Pseudodistoma antinboja [41]; novel tris-aromatic furanones cadiolides G-I ( 21 – 23 ) from the Korean dark red ascidian Synoicum sp. [42]; xanthones citreamicins θ A and B ( 24 , 25 ), isolated from the Red Sea marine Streptomyces caelestis [43]; two new aromatic polyketides, communols A and F ( 26 , 27 ), isolated from the marine Penicillium commune 518, associated with the gorgonian Muricella abnormalis [44]; two dolabellane diterpenes ( 28 , 29 ), isolated from the Greek brown alga Dilophus spiralis [45]; a novel enhygrolide A ( 30 ), isolated from the obligate marine myxobacterium Enhygromyxa salina from a mud sample from Prerow, Germany [46]; a new β-carboline alkaloid eudistomin Y 11 ( 31 ), isolated from a purple-colored ascidian Synoicum sp. [47]; a new capoamycin-type antibiotic fradimycin B ( 32 ), isolated from the marine Streptomyces fradiae strain PTZ0025 [48]; three novel cyclic bis -1,3 dialkylpyridiniums ( 33 – 35 ) from a Korean sponge Halyclona sp.…”

Sortase A: An ideal target for anti-virulence drug development

“…In contrast to other SrtA inhibitors, the halisulfate compounds described in this study were found to be active against Gram-positive and/or Gram-negative bacteria [63]. Other marine invertebrates, such as the ascidian Synoicum sp., were also found to be an interesting source of bioactive compounds, including furarones and beta-carboline alkaloids, which along with cytotoxicity and antimicrobial activity were shown to have moderate SrtA inhibitory activity [64,65].…”