Natural Science Foundation of China [30530080]; Ministry of Science and Technology of China [2007AA09Z403]; Department of Science and Technology of Shandong Province [2006GG2205023]

http://ir.yic.ac.cn/bitstream/133337/9046/1/Halogenated%20Organic%20Molecules%20of%20Rhodomelaceae%20Origin-Chemistry%20and%20Biology.pdf

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

The marine environment is a seemingly inexhaustible treasury of organisms whose secondary metabolites bear witness to the lavishness and inventiveness with which nature is able to manipulate molecular architecture. But to what purpose are these diverse and often grotesque compounds produced? This review is founded on the premise that some of them may be involved in the uptake and transport of metal ions present in the aquatic milieu. Many metabolites produced by terrestrial organisms are known to act as ionophores, but the case for similar behavior by their marine counterparts is far hazier. Notwithstanding the relative abundance of certain metal ions in the oceans, and of metabolite structures possessing features that should facilitate the chelation of metal ions, few attempts to establish a connection between these two phenomena have been reported. We have whittled down the voluminous literature of natural products derived from marine sources to expose a core of observations and speculations germane to our premise. These facts and fantasies are evaluated in this review. A mere handful of metal-containing complexes has actually been isolated; furthermore, attempts to prepare such complexes in vitro are rare, and spectroscopic evidence for metal–metabolite interactions, whether in vivo or in vitro, is not common. Only with the vanadium-sequestering tunichromes does a logical (but by no means complete) picture begin to emerge. In several other cases, the plausibility of metal chelation, though mooted by authors, remains unsupported by experimental evidence. However, continuing efforts to obtain structural, and particularly conformational, information on the metabolites by means of X-ray crystallography, nuclear magnetic resonance spectroscopy, and molecular mechanics calculations would seem to provide the key to a rational approach to this neglected topic. On the basis of recent studies dealing with such structural aspects, we present a selection of candidate compounds, some of which are the targets of our own synthetic attentions, whose potential for binding to metal cations merits further research.

Marine Metabolites and Metal Ion Chelation: The Facts and the Fantasies

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Thyrsiferol: a squalene-derived metabolite of

Crystal and molecular structure of dibromotris(trimethylphosphine)nickel(II). Electronic structures and stereochemistries of the complexes [NiX2(PMe3)3]