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Open AccessArticle

Costatone C—A New Halogenated Monoterpene from the New Zealand Red Alga Plocamium angustum

1
School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
2
Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New Zealand
3
Maurice Wilkins Centre for Molecular Biodiscovery, Wellington 6012, New Zealand
4
Department of Life Sciences, University of Management and Technology, C-II, Johar Town Lahore 54770, Pakistan
5
School of Biological Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
6
Department of Chemistry, University of Education, Attock Campus, Attock 43600, Pakistan
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(7), 418; https://doi.org/10.3390/md17070418
Received: 21 June 2019 / Revised: 8 July 2019 / Accepted: 17 July 2019 / Published: 19 July 2019
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Abstract

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. View Full-Text
Keywords: halogenated monoterpene; Plocamium angustum; costatone; Mosher’s analysis; DFT; ECD halogenated monoterpene; Plocamium angustum; costatone; Mosher’s analysis; DFT; ECD
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Bracegirdle, J.; Sohail, Z.; Fairhurst, M.J.; Gerth, M.L.; Zuccarello, G.C.; Ali Hashmi, M.; Keyzers, R.A. Costatone C—A New Halogenated Monoterpene from the New Zealand Red Alga Plocamium angustum. Mar. Drugs 2019, 17, 418.

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