Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata
Open Access
- 23 November 2020
- journal article
- research article
- Published by MDPI AG in Marine Drugs
- Vol. 18 (11), 581
- https://doi.org/10.3390/md18110581
Abstract
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 (1–6) and two known (7–8) 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 1–8, as well as three additional linear diterpenes (9–11), 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.Keywords
This publication has 21 references indexed in Scilit:
- Antimycobacterial, antiprotozoal and cytotoxic potential of twenty‐one brown algae (phaeophyceae) from British and Irish watersPhytotherapy Research, 2010
- Antiprotozoal, antimycobacterial and cytotoxic potential of some british green algaePhytotherapy Research, 2010
- Polar acyclic diterpenoids from Bifurcaria bifurcata (Fucales, Phaeophyta)Phytochemistry, 2005
- Trihydroxylated linear diterpenes from the brown alga Bifurcaria bifurcataPhytochemistry, 2004
- Geranylgeraniol-derived diterpenoids from the brown alga Bifurcaria bifurcataPhytochemistry, 1999
- Marine brown algae of family Cystoseiraceae: Chemistry and chemotaxonomyPhytochemistry, 1995
- (S)-13-hydroxygeranylgeraniol-derived furanoditerpenes from Bifurcaria bifurcataPhytochemistry, 1995
- Linear diterpene with antimitotic activity from the brown alga Bifurcaria bifurcataPhytochemistry, 1993
- Eleganolone derived diterpenes from Bifurcaria bifurcataPhytochemistry, 1991
- Polyhydroxyphenyl ethers from Bifurcaria bifurcataPhytochemistry, 1981