New Haloterpenes from the Marine Red Alga Laurencia papillosa: Structure Elucidation and Biological Activity

Mohamed Shaaban; Ghada S E Abou-El-Wafa; Christopher Golz; Hartmut Laatsch

doi:10.3390/md19010035

New Haloterpenes from the Marine Red Alga Laurencia papillosa: Structure Elucidation and Biological Activity

Mar Drugs. 2021 Jan 14;19(1):35. doi: 10.3390/md19010035.

Authors

Mohamed Shaaban^{1

2}, Ghada S E Abou-El-Wafa³, Christopher Golz², Hartmut Laatsch²

Affiliations

¹ National Research Centre, Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, El-Behoos St. 33, Dokki, Cairo 12622, Egypt.
² Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany.
³ Department of Botany, Faculty of Science, Mansoura University, Algomhuria st. 60, El-Mansoura 35516, Egypt.

Abstract

Analysis of the air-dried marine red alga Laurencia papillosa, collected near Ras-Bakr at the Suez gulf (Red Sea) in Egypt delivered five new halogenated terpene derivatives: aplysiolic acid (1), 7-acetyl-aplysiol (2), aplysiol-7-one (3), 11,14-dihydroaplysia-5,11,14,15-tetrol (5a), and a new maneonene derivative 6, named 5-epi-maneolactone. The chemical structures of these metabolites were characterized employing spectroscopic methods, and the relative and absolute configurations were determined by comparison of experimental and ab initio-calculated NMR, NOE, ECD, and ORD data, and by X-ray diffraction of 2 and 6. The antimicrobial activities of the crude extract and compounds 1-3, 5a and 6 were studied.

Keywords: Laurencia papillosa; biological activity; haloterpenes; marine red algae.

MeSH terms

Laurencia / chemistry*
Laurencia / isolation & purification*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular / methods
Rhodophyta / chemistry
Spectroscopy, Fourier Transform Infrared / methods
Terpenes / chemistry*
Terpenes / isolation & purification*

Substances

Terpenes