Marine metabolites represent an extraordinary pre-assembled pool of biologically active molecular diversity, programmed by evolution to be potent and selective modulators of key biopolymers, cells, tissues, organs, and animals. Over the past half-century the study of these metabolites (Marine Natural Products Chemistry) has evolved into a multidisciplinary endeavour, rich in complementary technologies and methodologies, and embracing diverse objectives and outcomes.
Hoffmann–la Roche supported a marine zoologist in the late 1960s, but the company’s deepening interest in the prospect of ‘drugs from the sea’ led them to establish the Roche Research Institute of Marine Pharmacology (RRIMP) at Dee Why, New South Wales, Australia. It opened in 1974 and closed in 1981.
The alkaloid psammopemmin A, originally reported from the Antarctic sponge Psammopemma sp., was synthesized. Based on comparison with spectral data from meridianin A, isolated from the Antarctic tunicate Synoicum sp., we provide evidence that the two compounds are identical.
Psammaplin N (8) is a new sulfoxide-containing metabolite isolated together with psammaplins A, I, and J from Aplysinella rhax. The NMR spectral features of psammaplin I are fully consistent with the revised structure (4a) recently reported for this metabolite. An NMR study on psammaplin J (2) reveals its facile conversion to psammaplins A and I on exposure to methanol..
Chemical fractionation of a southern Australian marine sponge, Trachycladus laevispirulifer, yielded 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide as the first recorded natural occurrence of a nucleoside disulfide, and only the second of a xylo-nucleoside.
A new cyclic peroxide plakortisinic acid (1), and a new ketone derivative (2), in addition to six known compounds were isolated from a Jamaican Plakortis sponge. The structures were elucidated by interpretation of NMR and mass spectrometry data and comparison of literature data. The isolated compounds have been evaluated for their antimicrobial, antimalarial, anticancer, anti-Mtb and anti HIV-1 activity.
A method based on LC-PDA-MS was developed for dereplication of bromotyrosine-derived metabolites. The results indicated that the chemical profile of the 14 specimens of Aplysina spp. presented practically the same dibromotyrosine-derived compounds, and suggested a possible biogenetic pathway for the formation of dibromotyrosine-derived compounds of wide occurrence in Verongida sponges.
Four new diterpenoids, australins E–H (1–4), have been isolated from the marine soft coral Cladiella sp. collected in Pohnpei. The structures of 1–4 were elucidated by analysis of their NMR and MS data combined with an X-ray diffraction analysis of australin E (1). Australin E (1) activates the inositol 5-phosphatase SHIP1 in vitro.
Fuscol and the related fuscosides are diterpenes isolated from the octocoral Eunicea fusca which exhibit potent anti-inflammatory activity. This report describes the isolation and characterization of the diterpene cyclase product, eunicene A, leading to these natural products.
Three new brominated triterpene polyethers, aplysiols C–E (1–3), were isolated from Chondria armata. 1D and 2D NMR techniques were used to determine the planar structures, while stereochemistry was determined from biogenetic considerations and NOESY experiments that support a revision of the stereochemistry at two chiral centres in aplysiol B.
Four higher unsaturated 9-N-methyladeninium bicyclic diterpenoid derivatives were isolated from the marine sponge Agelas sp. collected in Papua New Guinea. Their structures were elucidated through detailed physical data analyses and comparison with literature properties. All pure compounds were evaluated for inhibitory activity against Trypanosoma brucei and cytotoxicity against Jurkat cells.
Triacylglycerol concentrates of eicosapentaenoic and docosahexaenoic omega-3 fatty acids were synthesized by esterification of glycerol with the corresponding ethyl ester or free fatty acid concentrates. The reactions were catalyzed using a newly developed food grade immobilized Candida antarctica lipase B system (ONC294). Free fatty acids were shown to react more efficiently with glycerol than did ethyl esters in the presence of this catalyst, at both laboratory and production scale.
Six new anthraquinone-γ-pyrones, saliniquinones A–F (1–6), related to metabolites of the pluramycin/altromycin class, have been isolated from a fermentation broth of the marine actinomycete Salinispora arenicola (strain CNS-325). Their structures, relative, and absolute configurations have been determined by NMR and optical rotation analyses. Saliniquinone A (1) exhibited potent inhibition of the human colon adenocarcinoma cell line (HCT-116) with an IC50 of 9.9 nM.
Sagittamides C–F are new long-chain, α,ω-difunctionalized polyketide-amino acid conjugates with an intriguing, mid-chain contiguous hexa-acetoxyl stereo-hexad. NMR and symmetry arguments were exploited in their configurational assignments.
A new 3D coordination polymer of MOF [(LaL)·3H2O]n (L = chelidamic acid) (1), was obtained through the hydrothermal reaction. Complex 1 exhibits an unusual (3,6)-connected topology with symbol (42.6)2(44.62.87.102). The optical study suggests that 1 has good luminescent property.
Hydrogen sulfide-releasing drugs have potential as cytoprotective and anti-inflammatory drugs with reduced gastrotoxicity. We report the synthesis of various 5-aryl-dithiolethiones and 5-aryl-dithiole-3-ones and evaluation of their selectivity for cyclooxygenase-2. A highly selective coxib was identified and its hydrogen sulfide-releasing properties were investigated.
This paper describes the synthesis and general characterization of compounds with the general formula [MCl2(L)2]; where M = Zn, Cd, or Hg; and L is a N,O hybrid pyrazole ligand.The structure of complex [ZnCl2(L)2] was determined by single-crystal structure analysis and the intermolecular interactions have been studied. Moreover, we have determined the fluorescent properties of these complexes..
Geometrical changes, from octahedral to square pyramidal, occur when copper complex of the benzimidazole-containing octadentate carboxylic acid ligand investigated here are deprotonated to give the corresponding carboxylate. The coordinating properties of the ligands with CuII are analyzed by density functional theory (DFT) and molecular orbital studies to determine what dictates the geometrical changes. TD-DFT is used to analyze the unseparated electronic spectroscopic bands of the complexes.
The publication rate on RAFT polymerization continues to increase with the latest publication of a third update. Freely access the three reviews previously written by CSIRO scientists Moad, Rizzardo, and Thang on this subject in Australian Journal of Chemistry.