Abstract
The marine sponge Haliclona fulva (previously described as Reniera fulva) is widespread in the Mediterranean Sea. The chemical study of the sponge led to the isolation and identification of a new compound: 3-epi-cladocroic acid (1) alongside the previously reported cladocroic acid (2) and some other known compounds previously isolated. The structure was fully determined on the basis of extensive analysis by 1D and 2D NMR, as well as GC-MS/MS. The absolute configuration was determined by comparison of the experimental electronic circular dichroism (ECD) spectra with theoretically calculated spectra; these results may be extended to other asymetric cyclopropane carboxylic acids.
Highlights
Haliclona (Halichoclona) fulva (Demospongiae, Haplosclerida, Chalinidae), previously described as Reniera fulva, is an orange encrusting sponge, very common in the Mediterranean Sea [1]
The first chemical study of this sponge was performed by Cimino et al and resulted in the isolation of six acetylenic compounds belonging to the renierin family [2]
The most recent study reported the isolation of fulvynes, polyoxygenated acetylenic compounds related to osirisynes isolated from Haliclona osiris [13,14]
Summary
Haliclona (Halichoclona) fulva (Demospongiae, Haplosclerida, Chalinidae), previously described as Reniera fulva, is an orange encrusting sponge, very common in the Mediterranean Sea [1]. During the first isolation of 2, the determination of the absolute configuration suffered from the lack of experimental data, as only the specific optical rotation was reported. This usual pitfall in natural product chemistry has been overcome during the last years with the increasing use of chiroptical data such as electronic or vibrational circular dichroism (ECD and VCD) and theoretical calculations [16,17,18]. Absolute configuration of the previously reported cladocroic acid was addressed using the sign of the specific optical rotation of compound 2a [15]
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