Polyhalogenated Monoterpenes of the New Zealand Marine Red Alga Plocamium cartilagineum

Blunt, John W.; Bowman, N. J.; Munro, M. H. G.; Parsons, Murray J.; Wright, G. J.; Kon, Yeow Kok

doi:10.1071/ch9850519

Cited by 27 publications

(34 citation statements)

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“…With the planar structure of 7 in hand, the geometry of the alkene and relative configuration of the four chiral centres were deduced from through space 2D ROESY NMR correlations and 1 H NMR coupling constants. The double bond must have an E geometry on the basis of the through-space ROESY correlation between H-1 and H-3, with 13 C NMR data consistent with that of co-isolated compound 8 that also possess a similar E-chloroalkene [14,15]. H-3 and H-5 both show ROESY correlations to the same proton H-4 b (2.15 ppm), with smaller coupling constants (J H-3/H-4b = 2.6 Hz, J H-4b/H-5 = 4.4 Hz) indicative of axial/equatorial relationships, whereas no ROESY correlations were observed to H-4 a , but large coupling constants suggest axial/axial couplings (J H-3/H-4a = 11.7 Hz, J H-4a/H-5 = 12.0 Hz), therefore H-3 and H-5 are syn, corroborated by their shared nOe correlation.…”

Section: Resultsmentioning

confidence: 66%

“…This indicates that additional interesting chemistries could be The dichlorinated bisnor-monoterpene (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8) was also isolated as the major metabolite. Terpene 8 was initially reported from P. cruciferum and was identified here by comparison to the reported NMR and EI-MS data [14,15]. The absolute configuration at C-3 was not determined originally, therefore Mosher's ester analysis was used to derivatise the secondary alcohol [19].…”

Section: Resultsmentioning

confidence: 98%

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Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum

Bracegirdle¹,

Sohail²,

Fairhurst³

et al. 2020

Preprint

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© 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.

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Section: Resultsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 98%

Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum

Bracegirdle¹,

Sohail²,

Fairhurst³

et al. 2020

Preprint

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“…L. gracilis (König & Wright 1994). Distinctly different compounds have been found in morphologically similar samples of Laurencia distichophylla from Northland (Blunt et al 1984b) and Plocamium cartilagineum from Kaikoura (Blunt et al 1978b(Blunt et al , 1985Bates et al 1979). These results may have taxonomic significance.…”

Section: Small Organic Moleculesmentioning

confidence: 84%

History, current status and future of marine macroalgal research in New Zealand: Taxonomy, ecology, physiology and human uses

Hurd

Nelson

Falshaw³

et al. 2004

Phycological Res

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New Zealand has a rich and diverse macroalgal flora that has been studied since James Cook's first voyage to New Zealand in 1769. The New Zealand region ranges from cool temperate seas at southerly latitudes to subtropical waters in the north. Here we review the history of phycological research in New Zealand since 1900, and the current status of research in taxonomy, ecology, physiology and seaweed uses including aquaculture and seaweed extracts. Some 770 species of seaweed are known to New Zealand, of which 22 are alien. Few taxa have received monographic treatment and many remain to be described. Polysaccharides have been identified from over 80 New Zealand seaweeds and many of these compounds have commercial potential. In addition to urgent taxonomic work, future research should include a national program of longterm (> 5 years) monitoring of macroalgal communities, rates of growth and primary production, and the contribution of seaweed-based production to coastal food webs. Solieriaceae sp. indet.Undaria pinnatifida † Numbers of genera and species for the green algae likely to be overestimated.

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“…Sampies of putatively the same taxon may contain different metabolites. Some illustrative examples include the following: a) Sampies of the red alga Plocamium cartilagineum from different geographicallocalities differed in the types of monoterpenoid components (references in [12]), and samples collected in New Zealand from closely similar localities contained quite different halogenated acyclic monoterpenoids [12]: one contained only a chlorinated bisnor monoterpenoid that had previously been reported, whereas the other contained a series of chlorinated and brominated acyclic monoterpenoids.…”

Section: Use Of Field Materialsmentioning

confidence: 97%

Biological Effects and Biosynthesis of Brominated Metabolites

Neilson

2003

The Handbook of Environmental Chemistry

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Abstract. On the basis of halogenated metabolites assembled by Gribble, an attempt is made to provide a hypothesis for the biosynthesis of representative groups. Examples of brominated and iodinated metabolites are drawn from the major classes of terpenoids and acetogenins, and related to the biosynthesis of their putative precursors. Brominated and iodinated carbocyclic and heterocyclic aromatic compounds are discussed as weil as mechanisms for the oxidative coupling of phenolic substrates. A few chlorinated metabolites are introduced for additional illustration. Halogenation by cationoid (Hai+) reactions catalyzed by haloperoxidases is discussed, and attention drawn to the alternative role of anionoid (Hal-) halogenation. The presentation is extended to the biosynthesis of isonitriles and dichloroimines by anionoid reaction of precursors with cyanide. The range of biota that produce brominated substrates is briefly indicated, and comments made on the ecological significance of metabolites and associations among biota.

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Polyhalogenated Monoterpenes of the New Zealand Marine Red Alga Plocamium cartilagineum

Cited by 27 publications

References 0 publications

Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum

Costatone C—A new halogenated monoterpene from the New Zealand red alga plocamium angustum

History, current status and future of marine macroalgal research in New Zealand: Taxonomy, ecology, physiology and human uses

Biological Effects and Biosynthesis of Brominated Metabolites

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