Bioactive secondary metabolites from Australian invertebrates, Indonesian marine sponges, and an Indonesian terrestrial plant

Swasono, Respati Tri. (2006). Bioactive secondary metabolites from Australian invertebrates, Indonesian marine sponges, and an Indonesian terrestrial plant MPhil Thesis, School of Molecular and Microbial Sciences, The University of Queensland.

       
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Author Swasono, Respati Tri.
Thesis Title Bioactive secondary metabolites from Australian invertebrates, Indonesian marine sponges, and an Indonesian terrestrial plant
School, Centre or Institute School of Molecular and Microbial Sciences
Institution The University of Queensland
Publication date 2006
Thesis type MPhil Thesis
Supervisor Prof Mary Garson
Dr. Joanne Blanchfield
Total pages 125
Language eng
Subjects L
250399 Organic Chemistry not elsewhere classified
780103 Chemical sciences
Formatted abstract

A survey on marine natural products isolated from Indonesian sponges and their associated organisms is presented according to the type of the compounds and their biosynthetic origins.

An Australian marine sponge from South East Queensland yielded the highly unsaturated tetracyclic merosesquiterpene puupehenone while the sponge Darwinella sp. which was collected from the same region yielded the diterpene aplysillin. The later compound was fully characterised and its complete NMR spectra were assigned. Aplysillin showed very strong activity against the larval stages of Haemonchus contortus and Trichostrongylus columbriformis. It displayed 100% inhibition of the development of H. contortus at any concentration tested and 100 % inhibition of development of T. colubriformis at concentrations of 100 µg/mL and 10 µg/mL. In addition, two bromotyrosine derivatives 11,19-dideoxyfistularin 3 and aerothionin were isolated from a verongiid sponge collected near Heron Island. The sponge MOOL-29 which was collected in Mooloolaba was found to contain a furanoterpene pallescensone. An imidazole alkaloid clathridine was isolated from the nudibranch Notodoris gardineri collected near Lizard Island, Great Barrier Reef

A bioassay guided chemistry study of secondary metabolites from Indonesian sponges collected off Gili Trawangan Island in Lombok has been carried out. A Leucetta-like sponge LS-45 yielded two novel imidazole alkaloids deoxypyronaamidine and isopyronaamidine in addition to the known pyronaamidine. Two aromatic bisabolenes (+)-curcuphenol and (+)-curcudiol together with ß-sitosterol were also isolated from the sponge LS-3 (order Halichondrida, family Halichondriidae). Furthermore, a 5ɑ,8ɑ-epidioxysterol was isolated from the sponge LS-4 (order Haploscerida, family Petrosiidae). Structure elucidation of these compounds using ID and 2D NMR analysis was described. All pyronaamidines demonstrated cytotoxic activity against the P388 cell line even at very low concentrations (30-40% inhibition at 1.22 µg/mL) while (+)-curcuphenol and (+)-curcudiol exhibited 99% inhibition with IC50 values of 77.97 and 64.11 µg/mL, respectively.

An investigation on the fruit extract from an Indonesian medicinal plant Garcinia picrorhiza collected at the Botanical Garden in Bogor afforded a polyisoprenylated benzophenone guttiferone F. The structure of this compound was studied based on comparison of the NMR spectra and the physical properties with literature data.

Keyword Bioactive compounds
Plant bioactive compounds
Marine metabolites
Plant metabolites

Document type: Thesis
Collection: UQ Theses (RHD) - UQ staff and students only
 
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