2015
DOI: 10.3390/md13031389
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New Antimicrobial Bromotyrosine Analogues from the Sponge Pseudoceratina purpurea and Its Predator Tylodina corticalis

Abstract: Bioassay-guided fractionation of extracts from temperate Australian collections of the marine sponge Pseudoceratina purpurea resulted in the isolation and characterisation of two new and six known bromotyrosine-derived alkaloids with antibiotic activity. Surprisingly, a single specimen of the mollusc Tylodina corticalis, which was collected while feeding on P. purpurea, contained only a few of the compounds found in the sponge suggesting selective accumulation and chemical modification of sponge metabolites.

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Cited by 29 publications
(26 citation statements)
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“…The EADP structure has been found in a number of compounds including the moloka'iamines [26], ceratinamines [27], purpurealidines [28] and purealidines [29], that have been isolated from the Verongidae sponges. This compound class has been found to possess a wide range of bioactivities, including anti-fouling [30], anti-microbial [31], acetylcholinesterase (AChE) inhibition [32], apolipoprotein E (ApoE) modulating activity [33], anti-HIV [34] and inhibition of the histamine subtype 3 (H 3 ) receptor [35]. It is interesting to note that the H 3 receptor, ApoE and AChE have all been identified as potential targets for the treatment of various neurodegenerative diseases [36,37].…”
Section: Discussionmentioning
confidence: 99%
“…The EADP structure has been found in a number of compounds including the moloka'iamines [26], ceratinamines [27], purpurealidines [28] and purealidines [29], that have been isolated from the Verongidae sponges. This compound class has been found to possess a wide range of bioactivities, including anti-fouling [30], anti-microbial [31], acetylcholinesterase (AChE) inhibition [32], apolipoprotein E (ApoE) modulating activity [33], anti-HIV [34] and inhibition of the histamine subtype 3 (H 3 ) receptor [35]. It is interesting to note that the H 3 receptor, ApoE and AChE have all been identified as potential targets for the treatment of various neurodegenerative diseases [36,37].…”
Section: Discussionmentioning
confidence: 99%
“…The compound was a simple bromotyrosine derivative with four bromines (m/z 698 (1), 700 (4), 702 (6), 704 (4), 706 (1)) and was consistent with a molecular formula C 21 H 23 Br 4 N 3 O 4 . These data suggest the compound was aplysamine 4 [73] or aplysamine 8 [74].…”
Section: Isolation Of Chitinous Skeleton From the Sponge And Identifimentioning
confidence: 91%
“…(MIC = 6.25-25 µg/mL) [129]; the antimicrobial peptide isolated from the mucus of the hagfish Myxine glutinosa and several structural analogs (MICs = 1.2-50 µM) [130]; bromopyrrole alkaloids agelamadins C-E (IC 50 = 32 µg/mL) from the Okinawan marine sponge Agelas sp. [131]; a new indole diterpenoid from the fungus Aspergillus flavus (MIC = 20.5 µM), isolated from the Chinese prawn Penaeus vannamei [132]; two new bromopyrrole alkaloids isolated from the Okinawan sponge Agelas sp., namely 2-debromomonagelamide U and 2-debromomukanadin G (MIC=32 µg/mL) [133]; seven known and one new sesquiterpene named epoxysubergorgic acid isolated from the Chinese gorgonian coral S. suberosa (MIC>8 µg/mL) [134]; a new bromotyrosine alkaloid aplysamine 8 (MIC=31 µg/mL) from an Australian marine sponge Pseudoceratina purpurea [135], alternariol derivatives (MIC = 50 µg/disk) from the endophytic fungus Alternaria alternata isolated from the Red sea soft coral Litophyton arboretum [136]; new polyketides amphidins C-F (MIC = 16 and 32 µg/mL), isolated from the culture broth of dinoflagellate Amphidinium sp. […”
Section: Antibacterial Activitymentioning
confidence: 99%