Stereochemical evaluation of sesquiterpene quinones from two sponges of the genus Dactylospongia and the implication for enantioselective processes in marine terpene biosynthesis

  title={Stereochemical evaluation of sesquiterpene quinones from two sponges of the genus Dactylospongia and the implication for enantioselective processes in marine terpene biosynthesis},
  author={Ken W L Yong and Aroon Jankam and John N A Hooper and Apichart Suksamrarn and Mary J. Garson},
Total Synthesis of Marine Sesquiterpene Quinones (+)‐Cyclospongiaquinone‐1 and (–)‐Dehydrocyclospongiaquinone‐1 with a Tetracyclic Benzo[a]xanthene Skeleton
Two marine sesquiterpene quinones, (+)-cyclospongiaquinone-1 and (−)-dehydrocyclospongiaquinone-1, were efficiently synthesized from commercially available (+)-sclareolide. The overall yields were
Meroterpenoids with diverse ring systems from the sponge-associated fungus Alternaria sp. JJY-32.
On the basis of supplementation experiments with specific enzyme inhibitors and putative precursors, a shikimate-isoprenoid hybrid biosynthetic pathway is proposed.
Sesquiterpene Derivatives and Steroids from the Sponge Dactylospongia elegans Collected from the South China Sea
The antibacterial activity in vitro of the isolated compounds was evaluated against a panel of pathogenic bacterial strains, Staphylococcus aureus, S. albus, Bacillus subtilis, B. cereus, Micrococcus tetragenus, Kocuria rhizophila, Vibrio parahemolyticus, V. anguillarum, and Pseudomonas putida by using a standard screening protocol.
Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring.
This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and
Unified Synthesis of the Marine Sesquiterpene Quinones (+)‐Smenoqualone, (–)‐Ilimaquinone, (+)‐Smenospongine, and (+)‐Isospongiaquinone
Four biologically attractive marine sesquiterpene quinones, (+)-smenoqualone (1), (−)-ilimaquinone (2), (+)-smenospongine (3) and (+)-isospongiaquinone (4), were efficiently synthesized in a unified
Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′‐Isodrimentine A and Related Compounds
Drimentines are a family of tetracyclic alkaloids biosynthetically originating from the condensation of sesquiterpene units onto cyclic dipeptides. A straightforward assembly of the fused
Cytotoxic Terpene Quinones from Marine Sponges
The present review summarizes the structure and cytotoxicity of natural terpenequinones/hydroquinones and their bioactive analogues and derivatives.
Natural Products from Sponges
Development of recombinant microorganisms engineered for efficient production of sponge-derived products is a promising strategy that deserves further attention in future investigations in order to address the limitations regarding sustainable supply of marine drugs.


Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone
The synthesis of the marine sesquiterpene quinone (+)-hyatellaquinone (1) was achieved starting from the sesquiterpene aldehyde (+)-albicanal ((+)-3) (Schemes 3 and 4). Coupling of (+)-albicanal with
5-Epi-isospongiaquinone, a new sesquiterpene/quinone antibiotic from an Australian marine sponge, Spongia hispida.
An Australian marine sponge, Spongia hispida, has been found to contain a new sesquiterpene/quinone identified by detailed spectroscopic analysis and chemical derivatization as the antibiotic 5-epi-isospongiaquinone, which was speculated to be an artifact of the isolation process.
Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage.
Results indicate that the alternate substrates are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization.
Merosesquiterpenes from two sponges of the genus Dysidea.
The chemical study of two sponges of the genus Dysidea collected in the Gulf of California has led to the isolation of the new merosesquiterpenes 20-O-acetyl-21-hydroxy-ent-isozonarol, which showed cytotoxic activity against three human tumor cell lines.