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Article

Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata

1
School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland
2
Organische Chemie 2, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany
3
Pharmacology and Therapeutics, School of Medicine, National University of Ireland Galway, University Road, H91 W2TY Galway, Ireland
4
GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Product Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany
5
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(11), 581; https://doi.org/10.3390/md18110581
Received: 28 October 2020 / Revised: 17 November 2020 / Accepted: 19 November 2020 / Published: 23 November 2020
Brown alga Bifurcaria bifurcata is a prolific source of bioactive acyclic (linear) diterpenes with high structural diversity. In the continuation of our investigations on Irish brown algae, we undertook an in-depth chemical study on the n-hexanes and chloroform subextracts of B. bifurcata that led to isolation of six new (16) and two known (78) acyclic diterpenes. Chemical structures of the compounds were elucidated by a combination of 1D and 2D NMR, HRMS, FT-IR, [α]D and vibrational circular dichroism (VCD) spectroscopy. Compounds 18, as well as three additional linear diterpenes (911), which we isolated from the same seaweed before, were tested against the human breast cancer cell line (MDA-MB-231). Several compounds moderately inhibited the growth of the MDA-MB-231 cell line with IC50 values ranging from 11.6 to 32.0 μg/mL. The present study carried out on the lipophilic extracts of the Irish B. bifurcata shows the enormous capacity of this seaweed to produce a large palette of acyclic diterpenes with diverse oxygenation and substitution patterns and promising bioactivities. View Full-Text
Keywords: Bifurcaria bifurcata; linear diterpene; brown alga; seaweed; VCD; anticancer activity Bifurcaria bifurcata; linear diterpene; brown alga; seaweed; VCD; anticancer activity
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MDPI and ACS Style

Smyrniotopoulos, V.; Merten, C.; Firsova, D.; Fearnhead, H.; Tasdemir, D. Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata. Mar. Drugs 2020, 18, 581. https://doi.org/10.3390/md18110581

AMA Style

Smyrniotopoulos V, Merten C, Firsova D, Fearnhead H, Tasdemir D. Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata. Marine Drugs. 2020; 18(11):581. https://doi.org/10.3390/md18110581

Chicago/Turabian Style

Smyrniotopoulos, Vangelis, Christian Merten, Daria Firsova, Howard Fearnhead, and Deniz Tasdemir. 2020. "Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata" Marine Drugs 18, no. 11: 581. https://doi.org/10.3390/md18110581

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