Simone Rochfort

Marine nematocides: Tetrahydrofurans from a southern Australian brown alga, Notheia anomala

Chemical analysis of N. anomala collected off rock platforms along the southern coast of Australia yielded a cis-dihydroxytetrahydrofuran (2), the structure for which was assigned by spectroscopic analysis, chemical derivatization and biomimetic synthesis. Tetrahydrofurans from Notheia anomola are reported for the first time as potent and selective inhibitors of the larval development of parasitic nematodes. SAR observations are made on a selection of natural, semi-synthetic and synthetic tetrahydrofurans

A novel aspochalasin with HIV-1 integrase inhibitory activity from Aspergillus flavipes.

A novel aspochalasin, aspochalasin L (1), was isolated from the fermentation broth of a soil-derived fungal culture identified as Aspergillus flavipes (Deuteromycota). Structure elucidation of 1 was accomplished by detailed spectroscopic data analyses and by comparison with related cytochalasins. Aspochalasin L demonstrated activity against HIV integrase with an IC50 of 71.7 µM.

Further Studies on the Chemistry of the Flustra Alkaloids from the Bryozoan Flustra foliacea

Since 1980, over a dozen novel brominated alkaloids, named flustramines, have been isolated from Scandinavian and Canadian collections of the marine bryozoan Flustra foliacea. This paper describes the reisolation of the known compound dihydroflustramine C (1) and the isolation of 11 new flustramines (2-4, 6-13), including two dimers (12, 13) that may be isolation artifacts. Together these compounds, some with an unexpected aryl substitution pattern, reveal an intricate network of metabolites present in the extracts of the bryozoan. The structures of these metabolites were solved using a variety of spectroscopic techniques and chemical derivatization and modification. This work also led to the recognition of an unusual rearrangement reaction that occurred slowly over a number of years.

A Study of the Metabolome of Ricinus communis for Forensic Applications

Investigations were undertaken to ascertain the appropriateness of studying the metabolome of Ricinus communis for cultivar and provenance determination. Seeds from 14 R. communis specimens (a total of 56 seeds) collected from the east coast of Australia were analyzed by high pressure liquid chromatography with UV detection (HPLC-UV), liquid chromatography–mass spectrometry (LC-MS), and 1H NMR spectroscopy. The collected data were then analyzed using principle component analysis (PCA). For HPLC-UV analysis, six R. communis specimens were unambiguously identified by PCA as belonging to separate classes relating to specimen. LC-MS data allowed unique ions to be identified for four specimens. Conversely 10 specimens were unambiguously segregated in the PCA of the 1H NMR data. The ratio of ricinine 1 to demethylricinine analogues 2 and 3 was found to be important for specimen determination. These combined analyses suggested that a combination of HPLC-UV and 1H NMR in conjunction with PCA could allow for specimen differentiation.

The biomimetic synthesis of marine epoxylipids: Bisepoxides to tetrahydrofurans

The biomimetic synthesis of novel lipids 1, 2, 8 and 10 obtained from the southern Australian marine brown alga Notheia anomala has been achieved, and features the acid mediated conversion of methylene interrupted bisepoxides to tetrahydrofurans