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Article

Density Functional Theory (DFT)-Aided Structure Elucidation of Linear Diterpenes from the Irish Brown Seaweed Bifurcaria bifurcata

1
School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland
2
Pharmacology and Therapeutics, School of Medicine, National University of Ireland Galway, University Road, H91 W2TY Galway, Ireland
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Dipartimento di Agraria, Università degli Studi di Napoli Federico II, 80055 Portici (NA), Italy
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Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, 80131 Napoli, Italy
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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
6
Faculty of Mathematics and Natural Sciences, Kiel University, Christian-Albrechts-Platz 4, 24118 Kiel, Germany
*
Author to whom correspondence should be addressed.
Mar. Drugs 2021, 19(1), 42; https://doi.org/10.3390/md19010042
Received: 18 December 2020 / Revised: 12 January 2021 / Accepted: 15 January 2021 / Published: 19 January 2021
Brown alga Bifurcaria bifurcata is an extraordinarily rich source of linear (acylic) diterpenes with enormous structural diversity. As part of our interest into secondary metabolites of the Irish seaweeds, here we report four new acyclic diterpenes (14) and seven known terpenoids (511) from the CHCl3 extract of B. bifurcata. The planar structures of the new metabolites were elucidated by means of 1D and 2D NMR, HRMS, and FT-IR spectroscopy. Since linear diterpenes are highly flexible compounds, the assignment of their stereochemistry by conventional methods, e.g., NOESY NMR, is difficult. Therefore, we employed extensive quantum-mechanical prediction of NMR chemical shifts and optical rotation analyses to identify the relative and absolute configurations of the new compounds 14. Several compounds moderately inhibited the human breast cancer cell line (MDA-MB-231) with IC50 values ranging from 10.0 to 33.5 μg/mL. This study not only demonstrates the vast capacity of the Irish B. bifurcata to produce highly oxygenated linear diterpenoids, but also highlights the potential of new methodologies for assignment of their stereogenic centers. View Full-Text
Keywords: Bifurcaria bifurcata; brown alga; seaweed; linear diterpene; DFT; anticancer activity Bifurcaria bifurcata; brown alga; seaweed; linear diterpene; DFT; anticancer activity
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MDPI and ACS Style

Smyrniotopoulos, V.; Firsova, D.; Fearnhead, H.; Grauso, L.; Mangoni, A.; Tasdemir, D. Density Functional Theory (DFT)-Aided Structure Elucidation of Linear Diterpenes from the Irish Brown Seaweed Bifurcaria bifurcata. Mar. Drugs 2021, 19, 42. https://doi.org/10.3390/md19010042

AMA Style

Smyrniotopoulos V, Firsova D, Fearnhead H, Grauso L, Mangoni A, Tasdemir D. Density Functional Theory (DFT)-Aided Structure Elucidation of Linear Diterpenes from the Irish Brown Seaweed Bifurcaria bifurcata. Marine Drugs. 2021; 19(1):42. https://doi.org/10.3390/md19010042

Chicago/Turabian Style

Smyrniotopoulos, Vangelis, Daria Firsova, Howard Fearnhead, Laura Grauso, Alfonso Mangoni, and Deniz Tasdemir. 2021. "Density Functional Theory (DFT)-Aided Structure Elucidation of Linear Diterpenes from the Irish Brown Seaweed Bifurcaria bifurcata" Marine Drugs 19, no. 1: 42. https://doi.org/10.3390/md19010042

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