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

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.

SUBMITTER: Bracegirdle J

PROVIDER: S-EPMC6669586 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Bracegirdle Joe J Sohail Zaineb Z Fairhurst Michael J MJ Gerth Monica L ML Zuccarello Giuseppe C GC Ali Hashmi Muhammad M Keyzers Robert A RA

Marine drugs 20190719 7

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 ...[more]

PMID: 31330960

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