Isolaurenidificin and Bromlaurenidificin, Two New C15-Acetogenins from the Red Alga Laurencia obtusa

Nahed O Bawakid; Walied M Alarif; Najla A Alburae; Hajer S Alorfi; Khalid O Al-Footy; Sultan S Al-Lihaibi; Mohamed A Ghandourah

doi:10.3390/molecules22050807

Isolaurenidificin and Bromlaurenidificin, Two New C₁₅-Acetogenins from the Red Alga Laurencia obtusa

Molecules. 2017 May 15;22(5):807. doi: 10.3390/molecules22050807.

Authors

Nahed O Bawakid¹, Walied M Alarif², Najla A Alburae³, Hajer S Alorfi⁴, Khalid O Al-Footy⁵, Sultan S Al-Lihaibi⁶, Mohamed A Ghandourah⁷

Affiliations

¹ Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia. nbawaked@kau.edu.sa.
² Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia. walied1737@yahoo.com.
³ Department of Biology, Faculty of Sciences, King Abdulaziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia. nalbourae@gmail.com.
⁴ Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia. halaorfi@kau.edu.sa.
⁵ Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia. Kalfooti@kau.edu.sa.
⁶ Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia. sallihaibi@kau.edu.sa.
⁷ Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia. mghandourah@kau.edu.sa.

Abstract

Chromatographic fractionation of the CH₂Cl₂/MeOH extract of the Red Sea red alga Laurencia obtusa gave two new hexahydrofuro[3,2-b]furan-based C₁₅-acetogenins, namely, isolaurenidificin (1) and bromlaurenidificin (2). The chemical structures were elucidated based on extensive analyses of their spectral data. Compounds 1 and 2 showed no toxicity (LC₅₀ > 12 mM) using Artemia salina as test organism. Both compounds showed weak cytotoxicity against A549, HepG-2, HCT116, MCF-7, and PC-3 cells, however, they exhibited a relatively potent cytotoxic activity against peripheral blood neutrophils. This can be attributed partly to induction of apoptosis.

Keywords: anti-inflammatory; fatty acids; halogenations; marine algae; spectroscopy.

MeSH terms

Acetogenins / chemistry*
Acetogenins / pharmacology
Animals
Apoptosis / drug effects
Cell Line
HCT116 Cells
Hep G2 Cells
Humans
Laurencia / chemistry*
MCF-7 Cells
Molecular Structure
Neutrophils / drug effects
Nuclear Magnetic Resonance, Biomolecular
Rats

Substances

Acetogenins