Haliclorensin, a Novel Diamino Alkaloid from the Marine Sponge Haliclona tulearensis

Abstract

Haliclorensin (1), a novel diamino alkaloid possessing an azacyclodecane ring, has been isolated from the sponge Haliclona tulearensis. Its structure was elucidated on the basis of spectroscopic data, as well as by comparison with gamma-amino azacycloalkanes.

A concise formation of N-substituted 3,4-diarylpyrroles – synthesis and cytotoxic activity

“…14 was chosen as the primary amine component (see Scheme 2), instead of the isohaliclorensin moiety of halitulin. 16 The thirteen-membered macrocyclic amine was selected due to its rapid access starting from the commercially available laurolactam (Scheme 9), 17 and also because this achiral moiety is present in motuporamine A, another cytotoxic alkaloid isolated from the marine sponge Xestospongia exigua (Kirckpatrick). 18 In addition, it seemed interesting to see the role of this hydrophobic part of the molecule in the biological activity.…”

1,5-Diazacyclohenicosane, a New Cytotoxic Metabolite from the Marine Sponge Mycale sp.

“…Its structure resembles that of other cyclic amines previously characterized from sponge samples such as the motuporamines isolated from the Papua New Guinea sponge Xestospongia exigua [11–12] or halichlorensin obtained from South African specimens of Halichlona tulearensis [13–14]. This structural similarity together with the interesting anti-invasive and anti-angiogenic properties displayed by the motuporamine family suggest that further studies to assess the potential of our compound in this area of research are merited.…”

Recent N-Atom Containing Compounds from Indo-Pacific Invertebrates

“…Halitulin and haliclorensin are two unique alkaloids isolated in our group from the marine sponge Haliclona tulearensis collected in Sodwana Bay, Durban, South Africa [45,46]. The significant cytotoxicity of haliclorensin against P-388 mouse leukemia cells and that of halitulin against several tumor cell lines has stimulated studies toward the total syntheses of both molecules [47–49].…”

“…Together with halitulin and haliclorensin, an additional related compound was isolated from the same sponge [45,46]. Because this compound was isolated in minute amounts and was highly sensitive to light and air, the structure elucidation was not accomplished.…”