Bio-active maneonenes and isomaneonene from the red alga Laurencia obtusa

Nahed O Bawakid; Walied M Alarif; Ali I Ismail; Mohamed E El-Hefnawy; Khalid O Al-Footy; Sultan S Al-Lihaibi

doi:10.1016/j.phytochem.2017.08.001

Bio-active maneonenes and isomaneonene from the red alga Laurencia obtusa

Phytochemistry. 2017 Nov:143:180-185. doi: 10.1016/j.phytochem.2017.08.001. Epub 2017 Aug 17.

Authors

Nahed O Bawakid¹, Walied M Alarif², Ali I Ismail³, Mohamed E El-Hefnawy⁴, Khalid O Al-Footy¹, Sultan S Al-Lihaibi⁵

Affiliations

¹ Department of Chemistry, Faculty of Science, King Abdulaziz University, PO. Box 80203, Jeddah 21589, Saudi Arabia.
² Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO. Box 80207, Jeddah 21589, Saudi Arabia. Electronic address: walied1737@yahoo.com.
³ Department of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia.
⁴ Department of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia; Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt.
⁵ Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO. Box 80207, Jeddah 21589, Saudi Arabia.

PMID: 28822320
DOI: 10.1016/j.phytochem.2017.08.001

Abstract

Three previously undescribed compounds, maneonenes and isomaneonene derivatives; in addition to five known compounds, two cuparene, one chamigrene, and two cis-maneonenes were isolated from the Red Sea red alga Laurencia obtusa. The chemical structures of all unknown metabolites were characterized employing spectroscopic methods and then were further confirmed by single crystal X-ray analysis. Jeddahenyne A has C-5-C-12 etheric linkage and C-13-C-14 carbon-carbon double bond; Jeddahenyne B has in addition to the aforementioned etheric linkage a C-13 carbonyl function and absence of halogenation, unusual features for the maneonenes while 12-debromo-12-methoxy isomaneonene A shows unrecorded methoxylation at C-12. The apoptosis-inducing or inhibiting effect of both compounds on apoptosis of peripheral blood neutrophils was studied.

Keywords: Anti-inflammatory; Cyclic enynes; Haloethers; Laurencia obtusa; Red algae; Rhodomelaceae; Spectroscopy; Structure elucidation; X-ray.

MeSH terms

Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Apoptosis / drug effects
Laurencia / chemistry*
Molecular Structure
Neutrophils / drug effects
Nuclear Magnetic Resonance, Biomolecular
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / pharmacology*

Substances

Anti-Inflammatory Agents, Non-Steroidal
Sesquiterpenes
cuparene