Aplysina is the best representative genus of the family Aplysinidae. Halogenated substances are its main class of metabolites. These substances contribute greatly to the chemotaxonomy and characterization of the sponges belonging to this genus. Due to their pharmacological activities, these alkaloids are of special interest. The chemistry of halogenated substances and of the alkaloids has long been extensively studied in terrestrial organisms, while the number of marine organisms studied has just started to increase in the last decades. This review describes 101 halogenated substances from 14 species of Aplysina from different parts of the world. These substances can be divided into the following classes: bromotyramines (A), cavernicolins (B), hydroverongiaquinols (C), bromotyrosineketals (D), bromotyrosine lactone derivatives (E), oxazolidones (F), spiroisoxazolines (G), verongiabenzenoids (H), verongiaquinols (I), and dibromocyclohexadienes (J). A compilation of their ¹³C NMR data is also part of the review. For this purpose 138 references were consulted.

A novel alkaloid named bowdichine (1), only the third with a diaza-adamantane skeleton containing an unusual N-acetyl enamine moiety, and the known alkaloids acosmine (2), ormosanine (3) and podopetaline (4) have been isolated from the stem bark of Bowdichia virgilioides. The structures were elucidated on the basis of spectral data, mainly 1D and 2D NMR of the diaza-adamantane alkaloids 1 and 2.

An oil produced from Mentha x villosa Huds. by steam distillation of plant material collected in Fortaleza was analyzed by GC/MS and retention indices. The oil was found to be rich in piperitenone oxide (55.4%) and γ-muurolene (13.1%).

Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC₅₀ of 18.97 and 10.95 µg/mL, respectively.