Aplysinopsins - Marine Indole Alkaloids: Chemistry, Bioactivity and Ecological Significance

Abstract

Aplysinopsins are tryptophan-derived marine natural products isolated from numerous genera of sponges and scleractinian corals, as well as from one sea anemone and one nudibranch. Aplysinopsins are widely distributed in the Pacific, Indonesia, Caribbean, and Mediterranean regions. Up to date, around 30 analogues occurring in Nature have been reported. Natural aplysinopsins differ in the bromination pattern of the indole ring, variation in the structure of the C ring, including the number and position of N-methylation, the presence and configuration of the C-8-C-1′ double bond, and the oxidation state of the 2-aminoimidazoline fragment. Aplysinopsins can also occur in the form of dimers. This review summarizes 30 years’ research on aplysinopsins. The origin, isolation sources, chemistry, bioactivity, and ecological functions of aplysinopsins are comprehensively reviewed.

<i>Tubastraea coccinea</i>: A Non-Indigenous Coral (Cnidaria, Scleractinia) Collected at Arvoredo Island, South of Brazil with Potential MRSA and VRE Antimicrobial Activity

“…The TLC fingerprint of the bioactive fraction showed the presence of compounds with alkaloids profile after Dragendorff nebulization (data not shown). This result is in agreement to literature data that reports stony scleratinian corals, Tubastraea (Dendrophylliidae) genus as a source of biologically active alkaloid derivatives including aplysinopsin and (bis)-indole alkaloids [20]- [23].…”

Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones

“…The N- 1-unsubstituted aplysinopsins have generated considerable interest due to their potentially useful medicinal properties. 2 Aplysinopsin has been reported as a potent cytotoxic agent against the Kβ-cell line by Hollenbeak et al 3 , and Kondo et al have reported the anti-cancer activity of aplysinopsin and methyl-aplysinopsins against L-1210- and Kβ-cell lines. 4 Wen-Tai et al reported the synthesis and biological evaluation of N -heterocyclic indolyl-glyoxylamides as orally active anticancer agents.…”

Synthesis and In Vitro Screening of Novel Heterocyclic Compounds as Potential Breast Cancer Agents

“…The parent aplysinopsin was isolated for the first time (Kazlauskas, et al, 1977) as the major metabolite of eight Indo-Pacific sponge species, which are representatives of the genus Thorecta. The N-1-unsubstituted aplysinopsins have generated considerable interest due to their potentially useful medicinal properties (Dobroslawa, et al, 2009). Aplysinopsin has been reported as a potent cytotoxic agent against the Kβ-cell line and methyl-aplysinopsins against L-1210 and Kβ-cell lines has been reported as potent cytotoxic agents (Hollenbeak & Schmitz, 1977), and the anticancer activities of aplysinopsin and methyl-aplysinopsins against both 1210-and Kβ-cells has also been reported (Kondo et al 1994).…”