Costatone C-A New Halogenated Monoterpene from the New Zealand Red Alga

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2019 Jul 24

PMID 31330960

Citations 3

Authors

Joe Bracegirdle

Zaineb Sohail

Michael J Fairhurst

Monica L Gerth

Giuseppe C Zuccarello

Muhammad Ali Hashmi

Robert A Keyzers

Affiliations

Soon will be listed here.

Abstract

Red algae of the genus have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (), was isolated from the extract of collected in New Zealand, along with the previously reported (1,5)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (). Elucidation of the planar structure of was achieved through conventional NMR and (-)-HR-APCI-MS techniques, and the absolute configuration by comparison of experimental and DFT-calculated ECD spectra. The absolute configuration of was determined using Mosher's method. Compound showed mild antibacterial activity against and . The state of taxonomy and its implications upon natural product distributions, especially across samples from specimens collected in different countries, is also discussed.

Citing Articles

Naturally Occurring Organohalogen Compounds-A Comprehensive Review.

Gribble G Prog Chem Org Nat Prod. 2023; 121:1-546.

PMID: 37488466 DOI: 10.1007/978-3-031-26629-4_1.

Tongalides, Halogenated Butenolides from an Antarctic sp. Rhodophyte.

Bracegirdle J, Kennedy S, Shan C, Wojtas L, Shaw L, Amsler C J Nat Prod. 2022; 85(7):1886-1891.

PMID: 35771948 PMC: 11809100. DOI: 10.1021/acs.jnatprod.2c00344.

Red Seaweed-Derived Compounds as a Potential New Approach for Acne Vulgaris Care.

Januario A, Felix R, Felix C, Reboleira J, Valentao P, Lemos M Pharmaceutics. 2021; 13(11).

PMID: 34834345 PMC: 8623078. DOI: 10.3390/pharmaceutics13111930.

Update on Monoterpenes from Red Macroalgae: Isolation, Analysis, and Bioactivity.

Cikos A, Jurin M, coz-Rakovac R, Jokic S, Jerkovic I Mar Drugs. 2019; 17(9).

PMID: 31527497 PMC: 6780258. DOI: 10.3390/md17090537.

References

Perdew , Burke , Ernzerhof . Generalized Gradient Approximation Made Simple. Phys Rev Lett. 1996; 77(18):3865-3868. DOI: 10.1103/PhysRevLett.77.3865. View

Cossi M, Rega N, Scalmani G, Barone V . Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem. 2003; 24(6):669-81. DOI: 10.1002/jcc.10189. View

Tomasi J, Mennucci B, Cammi R . Quantum mechanical continuum solvation models. Chem Rev. 2005; 105(8):2999-3093. DOI: 10.1021/cr9904009. View

Weigend F, Ahlrichs R . Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. Phys Chem Chem Phys. 2005; 7(18):3297-305. DOI: 10.1039/b508541a. View

Grimme S . Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem. 2006; 27(15):1787-99. DOI: 10.1002/jcc.20495. View

Marenich A, Cramer C, Truhlar D . Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B. 2009; 113(18):6378-96. DOI: 10.1021/jp810292n. View

Grimme S, Antony J, Ehrlich S, Krieg H . A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys. 2010; 132(15):154104. DOI: 10.1063/1.3382344. View

Grimme S, Ehrlich S, Goerigk L . Effect of the damping function in dispersion corrected density functional theory. J Comput Chem. 2011; 32(7):1456-65. DOI: 10.1002/jcc.21759. View

Timmers M, Dias D, Urban S . Application of HPLC-NMR in the identification of plocamenone and isoplocamenone from the marine red alga Plocamium angustum. Mar Drugs. 2012; 10(9):2089-2102. PMC: 3475275. DOI: 10.3390/md10092089. View

10.

Bruhn T, Schaumloffel A, Hemberger Y, Bringmann G . SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality. 2013; 25(4):243-9. DOI: 10.1002/chir.22138. View

11.

Stamatakis A . RAxML version 8: a tool for phylogenetic analysis and post-analysis of large phylogenies. Bioinformatics. 2014; 30(9):1312-3. PMC: 3998144. DOI: 10.1093/bioinformatics/btu033. View

12.

Polavarapu P, Covington C . Comparison of experimental and calculated chiroptical spectra for chiral molecular structure determination. Chirality. 2014; 26(9):539-52. DOI: 10.1002/chir.22316. View

13.

Motti C, Thomas-Hall P, Hagiwara K, Simmons C, Willis R, Wright A . Accelerated identification of halogenated monoterpenes from Australian specimens of the red algae Plocamium hamatum and Plocamium costatum. J Nat Prod. 2014; 77(5):1193-200. DOI: 10.1021/np500059h. View

14.

Woolner V, Jones C, Field J, Fadzilah N, Munkacsi A, Miller J . Polyhalogenated Indoles from the Red Alga Rhodophyllis membranacea: The First Isolation of Bromo-Chloro-Iodo Secondary Metabolites. J Nat Prod. 2016; 79(3):463-9. DOI: 10.1021/acs.jnatprod.5b00831. View

15.

Pescitelli G, Bruhn T . Good Computational Practice in the Assignment of Absolute Configurations by TDDFT Calculations of ECD Spectra. Chirality. 2016; 28(6):466-74. DOI: 10.1002/chir.22600. View

16.

Felsenstein J . CONFIDENCE LIMITS ON PHYLOGENIES: AN APPROACH USING THE BOOTSTRAP. Evolution. 2017; 39(4):783-791. DOI: 10.1111/j.1558-5646.1985.tb00420.x. View

17.

Lefranc F, Koutsaviti A, Ioannou E, Kornienko A, Roussis V, Kiss R . Algae metabolites: from in vitro growth inhibitory effects to promising anticancer activity. Nat Prod Rep. 2018; 36(5):810-841. DOI: 10.1039/c8np00057c. View