10.26686/wgtn.12509912.v1
Joe Bracegirdle
Joe
Bracegirdle
Z Sohail
Z
Sohail
Michael Fairhurst
Michael
Fairhurst
Monica Gerth
Monica
Gerth
Giuseppe Zuccarello
Giuseppe
Zuccarello
M Ali Hashmi
M Ali
Hashmi
Robert Keyzers
Robert
Keyzers
Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum
Open Access Te Herenga Waka-Victoria University of Wellington
2020
halogenated monoterpene
Plocamium angustum
costatone
Mosher's analysis
DFT
ECD
Mosher’s analysis
Plocamium
Staphylococcus aureus
Staphylococcus epidermidis
Hydrocarbons, Halogenated
Monoterpenes
Plant Extracts
Anti-Bacterial Agents
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Molecular Structure
New Zealand
Medicinal & Biomolecular Chemistry
Physical Chemistry (incl. Structural)
Pharmacology and Pharmaceutical Sciences
2020-06-18 21:00:14
Journal contribution
https://openaccess.wgtn.ac.nz/articles/journal_contribution/Costatone_C_A_new_halogenated_monoterpene_from_the_New_Zealand_red_alga_plocamium_angustum/12509912
© 2019 by the authors Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the planar structure of 7 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 8 was determined using Mosher’s method. Compound 7 showed mild antibacterial activity against Staphylococcus aureus and S. epidermidis. The state of Plocamium taxonomy and its implications upon natural product distributions, especially across samples from specimens collected in different countries, is also discussed.