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Mar. Drugs 2017, 15(9), 285;

Biogenetic Relationships of Bioactive Sponge Merotriterpenoids

Department of Medicinal Chemistry, University of Utah, 30 S. 2000 E., Salt Lake City, UT 84112, USA
Department of Integrative Biology, University of Texas at Austin, 2506 Speedway, NMS 4.216 stop C0930, Austin, TX 78712, USA
Received: 25 July 2017 / Revised: 7 September 2017 / Accepted: 7 September 2017 / Published: 10 September 2017
(This article belongs to the Special Issue Genome Mining and Marine Microbial Natural Products)
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Hydroquinone meroterpenoids, especially those derived from marine sponges, display a wide range of biological activities. However, use of these compounds is limited by their inaccessibility; there is no sustainable supply of these compounds. Furthermore, our knowledge of their metabolic origin remains completely unstudied. In this review, an in depth structural analysis of sponge merotriterpenoids, including the adociasulfate family of kinesin motor protein inhibitors, provides insight into their biosynthesis. Several key structural features provide clues to the relationships between compounds. All adociasulfates appear to be derived from only four different hydroquinone hexaprenyl diphosphate precursors, each varying in the number and position of epoxidations. Proton-initiated cyclization of these precursors can lead to all carbon skeletons observed amongst sponge merotriterpenoids. Consideration of the enzymes involved in the proposed biosynthetic route suggests a bacterial source, and a hypothetical gene cluster was constructed that may facilitate discovery of the authentic pathway from the sponge metagenome. A similar rationale can be extended to other sponge meroterpenoids, for which no biosynthetic pathways have yet been identified. View Full-Text
Keywords: sponge; meroterpenoid; marine natural product; medicinal chemistry; biosynthesis; drug discovery sponge; meroterpenoid; marine natural product; medicinal chemistry; biosynthesis; drug discovery

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Smith, T.E. Biogenetic Relationships of Bioactive Sponge Merotriterpenoids. Mar. Drugs 2017, 15, 285.

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