Next Article in Journal
COSMO-RS Based Prediction for Alpha-Linolenic Acid (ALA) Extraction from Microalgae Biomass Using Room Temperature Ionic Liquids (RTILs)
Next Article in Special Issue
Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives
Previous Article in Journal
A Pharmacological Comparison of Two Isomeric Nicotinic Receptor Agonists: The Marine Toxin Isoanatabine and the Tobacco Alkaloid Anatabine
Previous Article in Special Issue
Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species
Open AccessArticle

New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis

1
GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany
2
Senckenberg Research Institute and Natural History Museum, Senckenberganlage 25, D-60325 Frankfurt, Germany
3
Faculty of Mathematics and Natural Sciences, Kiel University, Christian-Albrechts-Platz 4, 24118 Kiel, Germany
*
Author to whom correspondence should be addressed.
Mar. Drugs 2020, 18(2), 107; https://doi.org/10.3390/md18020107
Received: 28 January 2020 / Revised: 5 February 2020 / Accepted: 7 February 2020 / Published: 11 February 2020
(This article belongs to the Special Issue Advances in Marine Alkaloids)
Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n-hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (−)-(1R,2R,6R,8S,6’S)-discorhabdin B dimer (1) and two new derivatives, (−)-(1S,2R,6R,8S,6’S)-discorhabdin B dimer (2) and (−)-(1R,2R,6R,8S,6’S)-16’,17’-dehydrodiscorhabdin B dimer (3). The chemical structures of compounds 13 were elucidated by means of HR-ESIMS, NMR, [α]D, ECD spectroscopy, and a comparison with the previously reported discorhabdin analogs. Compounds 1 and 2 showed significant in vitro anticancer activity against the human colon cancer cell line (HCT-116), with IC50 values of 0.16 and 2.01 µM, respectively. Compared to monomeric discorhabdins, dimeric discorhabdins are very rare in Nature. This study adds two new discorhabdin dimers (2 and 3) to this small pyrroloiminoquinone subfamily. This is also the first report of compound 1 as a natural product and the first assessment of its in vitro anticancer activity. View Full-Text
Keywords: Latrunculia biformis; discorhabdin B dimer; deep-sea sponge; Antarctica; anticancer activity; ECD spectroscopy Latrunculia biformis; discorhabdin B dimer; deep-sea sponge; Antarctica; anticancer activity; ECD spectroscopy
Show Figures

Graphical abstract

MDPI and ACS Style

Li, F.; Janussen, D.; Tasdemir, D. New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis. Mar. Drugs 2020, 18, 107.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop