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Application of HPLC-NMR in the identification of plocamenone and isoplocamenone from the marine red alga Plocamium angustum.

Timmers MA, Dias DA, Urban S - Mar Drugs (2012)

Bottom Line: A combination of on-line HPLC-NMR and off-line chemical investigations has resulted in the identification of the previously reported polyhalogenated monoterpene plocamenone, together with the new structural analogue isoplocamenone from the crude extract of the marine alga Plocamium angustum.On-flow and stop-flow HPLC-NMR analyses (including the acquisition of WET 2D NMR spectra) rapidly assisted in the identification of the major component plocamenone and in the partial identification of its unstable double bond isomer isoplocamenone.Conventional off-line isolation and structural characterization techniques were employed to unequivocally confirm both structures, leading to a structural revision for plocamenone, as well as to obtain sufficient quantities for biological testing.

View Article: PubMed Central - PubMed

Affiliation: School of Applied Sciences, Health Innovations Research Institute (HIRi), RMIT University, GPO Box 2476V, Melbourne, Victoria 3001, Australia. michael.timmers@rmit.edu.au

ABSTRACT
A combination of on-line HPLC-NMR and off-line chemical investigations has resulted in the identification of the previously reported polyhalogenated monoterpene plocamenone, together with the new structural analogue isoplocamenone from the crude extract of the marine alga Plocamium angustum. On-flow and stop-flow HPLC-NMR analyses (including the acquisition of WET 2D NMR spectra) rapidly assisted in the identification of the major component plocamenone and in the partial identification of its unstable double bond isomer isoplocamenone. Conventional off-line isolation and structural characterization techniques were employed to unequivocally confirm both structures, leading to a structural revision for plocamenone, as well as to obtain sufficient quantities for biological testing.

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Representative polyhalogenated monoterpenes from marine algae.
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marinedrugs-10-02089-f001: Representative polyhalogenated monoterpenes from marine algae.

Mentions: A major focus of the Marine And Terrestrial NAtural Product (MATNAP) research group at RMIT University is the study of the chemical diversity and biological activities of Australian marine flora. Plocamium is a genus of red algae that is known to produce a vast array of acyclic and cyclic polyhalogenated monoterpenes for which the main differences are associated with the position, orientation and degree of halogen incorporation [1,7]. The species P. angustum is endemic to New Zealand and Australia and has not been as widely studied, with only four secondary metabolites having been reported (1–4) to date (Figure 1) [8,9]. An extract of the red alga P. angustum was selected for chemical investigation on the basis of the potent cytotoxicity and significant antimicrobial activities displayed by the crude extract. In addition, chemical investigation of the alga was motivated by the fact that this genus is known to produce a wide array of polyhalogenated monoterpenes, some of which possess bioactive properties, together with the fact that this species has not been extensively studied [10,11,12,13,14,15,16,17].


Application of HPLC-NMR in the identification of plocamenone and isoplocamenone from the marine red alga Plocamium angustum.

Timmers MA, Dias DA, Urban S - Mar Drugs (2012)

Representative polyhalogenated monoterpenes from marine algae.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3475275&req=5

marinedrugs-10-02089-f001: Representative polyhalogenated monoterpenes from marine algae.
Mentions: A major focus of the Marine And Terrestrial NAtural Product (MATNAP) research group at RMIT University is the study of the chemical diversity and biological activities of Australian marine flora. Plocamium is a genus of red algae that is known to produce a vast array of acyclic and cyclic polyhalogenated monoterpenes for which the main differences are associated with the position, orientation and degree of halogen incorporation [1,7]. The species P. angustum is endemic to New Zealand and Australia and has not been as widely studied, with only four secondary metabolites having been reported (1–4) to date (Figure 1) [8,9]. An extract of the red alga P. angustum was selected for chemical investigation on the basis of the potent cytotoxicity and significant antimicrobial activities displayed by the crude extract. In addition, chemical investigation of the alga was motivated by the fact that this genus is known to produce a wide array of polyhalogenated monoterpenes, some of which possess bioactive properties, together with the fact that this species has not been extensively studied [10,11,12,13,14,15,16,17].

Bottom Line: A combination of on-line HPLC-NMR and off-line chemical investigations has resulted in the identification of the previously reported polyhalogenated monoterpene plocamenone, together with the new structural analogue isoplocamenone from the crude extract of the marine alga Plocamium angustum.On-flow and stop-flow HPLC-NMR analyses (including the acquisition of WET 2D NMR spectra) rapidly assisted in the identification of the major component plocamenone and in the partial identification of its unstable double bond isomer isoplocamenone.Conventional off-line isolation and structural characterization techniques were employed to unequivocally confirm both structures, leading to a structural revision for plocamenone, as well as to obtain sufficient quantities for biological testing.

View Article: PubMed Central - PubMed

Affiliation: School of Applied Sciences, Health Innovations Research Institute (HIRi), RMIT University, GPO Box 2476V, Melbourne, Victoria 3001, Australia. michael.timmers@rmit.edu.au

ABSTRACT
A combination of on-line HPLC-NMR and off-line chemical investigations has resulted in the identification of the previously reported polyhalogenated monoterpene plocamenone, together with the new structural analogue isoplocamenone from the crude extract of the marine alga Plocamium angustum. On-flow and stop-flow HPLC-NMR analyses (including the acquisition of WET 2D NMR spectra) rapidly assisted in the identification of the major component plocamenone and in the partial identification of its unstable double bond isomer isoplocamenone. Conventional off-line isolation and structural characterization techniques were employed to unequivocally confirm both structures, leading to a structural revision for plocamenone, as well as to obtain sufficient quantities for biological testing.

Show MeSH