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Lamellarin Sulfates from the Pacific Tunicate Didemnum ternerratum
Joe Bracegirdle, Luke P Robertson1,2, Paul A Hume
1Environmental Futures Research Institute , Griffith University , Southport 4222 , Gold Coast , Australia.
Journal of Natural Products
|July 16, 2019
Summary
Six new lamellarin sulfates were discovered in a Pacific tunicate. Lamellarin D-8-sulfate showed moderate cytotoxicity against colon cancer cells, indicating potential for drug development.
Area of Science:
- Marine Natural Products Chemistry
- Chemical Biology
Background:
- Marine natural products, particularly from tunicates, are a rich source of bioactive compounds.
- Lamellarins are a class of alkaloids known for diverse biological activities.
Purpose of the Study:
- To isolate and characterize new lamellarin sulfates from the tunicate *Didemnum ternerratum*.
- To evaluate the cytotoxic potential of isolated compounds against human colon carcinoma cells.
Main Methods:
- Isolation guided by mass spectrometric molecular networking (GNPS platform).
- Structure elucidation using Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS).
- Determination of absolute configurations via experimental and calculated Electronic Circular Dichroism (ECD) spectra and computational analysis.
Main Results:
- Six new lamellarin sulfates (compounds 1-6) were successfully isolated and identified.
- The absolute configurations and energetic barriers to racemization for atropisomers 2-5 were determined.
- Lamellarin D-8-sulfate (compound 5) demonstrated moderate cytotoxicity against the HCT-116 cell line with an IC50 of 9.7 μM.
Conclusions:
- The study expands the known chemical diversity of lamellarins.
- Lamellarin D-8-sulfate shows promise as a lead compound for further investigation in colon cancer therapy.
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