Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate Synoicum sp

• Published in: Marine drugs Vol. 20; no. 3; p. 196
• Main Authors: Kokkaliari, Sofia, Pham, Kim, Shahbazi, Nargess, Calcul, Laurent, Wojtas, Lukasz, Wilson, Nerida G, Crawford, Alexander D, Baker, Bill J
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 08-03-2022; MDPI
• Subjects: Alkaloids; Animals; Antarctic Regions; ascidians; Biodiversity; Biological activity; Biological assays; Carbon; Cruises; Deep sea; Deep water; Embryo, Nonmammalian - abnormalities; Embryo, Nonmammalian - drug effects; Embryos; Freshwater fishes; indole alkaloids; Indole Alkaloids - chemistry; Indole Alkaloids - toxicity; Invertebrates; Lipophilic; Marine invertebrates; meridianins; Metabolites; Nitrogen; Polar environments; Pyrimidines - chemistry; Pyrimidines - toxicity; Spectrum analysis; Substitutes; Synoicum; Urochordata - chemistry; Zebrafish; Antarctic Regions; Antarctica; meridianins; indole alkaloids; zebrafish; ascidians
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md20030196

Five new alkaloids have been isolated from the lipophilic extract of the Antarctic tunicate
sp. Deep-sea specimens of
sp. were collected during a 2011 cruise of the R/V
to the southern Scotia Arc, Antarctica. Crude extracts from the invertebrates obtained during the cruise were screened in a zebrafish-based phenotypic assay. The
sp. extract induced embryonic dysmorphology characterized by axis truncation, leading to the isolation of aminopyrimidine substituted indolone (
-
) and indole (
-
) alkaloids. While the primary bioactivity tracked with previously reported meridianins A-G (
-
), further investigation resulted in the isolation and characterization of australindolones A-D (
-
) and the previously unreported meridianin H (
).