Plocamenone, a unique halogenated monoterpene from the red alga, plocamium

Stierle, Donald B.; Sims, James J.

doi:10.1016/s0040-4039(00)99827-7

Cited by 11 publications

(14 citation statements)

References 4 publications

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“…The structure of plocamenone ( 4 ) was established by 1D and 2D NMR analysis ( Table 1 ), along with mass spectrometry. 2D NMR experiments confirmed the structure of plocamenone, a marine secondary metabolite previously reported as possessing structure ( 5 ), isolated from P. angustum [ 8 , 9 , 21 , 22 , 23 ].…”

Section: Resultssupporting

confidence: 65%

“…In 1997 the structure was again incorrectly described as 7 [24] and finally in 2010 plocamenone was referred to as plocamenone G ( 5 ) [25]. While all NMR chemical shifts were consistent with those given in literature sources [8,9,23], no complete 2D NMR analysis was reported in the structural elucidation/revisions. We report here the first complete 2D NMR assignment of plocamenone, and the first assignment of its double bond geometry which, has revised the structure of plocamenone from ( 5 ) to ( 4 ).…”

Section: Resultsmentioning

confidence: 99%

“…Plocamenone was first reported in 1979 and proposed as 6 [ 8 ], but in the same year the structure was revised to 5 ( Figure 1 ) [ 21 ]. In 1983 the structure was revised back to 6 , and then in 1984 further revisions to 7 were concluded ( Figure 1 ) [ 9 , 23 ]. This structure was deemed to be incorrect and was again revised back to 5 [ 22 ].…”

Section: Resultsmentioning

confidence: 99%

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Application of HPLC-NMR in the Identification of Plocamenone and Isoplocamenone from the Marine Red Alga Plocamium angustum

2012

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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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Section: Resultssupporting

confidence: 65%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Application of HPLC-NMR in the Identification of Plocamenone and Isoplocamenone from the Marine Red Alga Plocamium angustum

2012

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“…2a,9 For example, the cytotoxic agent plocamenone (E) - 2 has been repeatedly misassigned in the literature, 9b,10 with the closest proposed structure being the (Z) -isomer. 10b More recently, Urban isolated and characterized both double bond isomers from Plocamium angustum and assigned the previously isolated compound, plocamenone, as the (E)- isomer ( (E) - 2 ). The minor isomer, termed isoplocamenone ( (Z) - 2 ) was reportedly prone to decomposition.…”

mentioning

confidence: 99%

Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone

2015

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Over 160 chiral vicinal bromochlorinated natural products have been identified, however a lack of synthetic methods for the selective incorporation of halogens into organic molecules has hindered their synthesis. Here we disclose the first total synthesis and structural confirmation of isoplocamenone and plocamenone, as well as the first selective and scaleable synthesis of the preclinical anticancer natural product halomon. The synthesis of these interhalogenated compounds has been enabled by our recently developed chemo-, regio-, and enantioselective dihalogenation reaction.

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“…The proximity of these two groups gives this molecule some of its interesting chemical reactivity. This may be why plocamenone has been shown to be a potent mutagen in the Ames reversion assay, much more potent than other Plocamium metabolites (Stierle and Sims, 1984).…”

Section: Plocamium Oregonummentioning

confidence: 99%

Volatile halogenated metabolites from marine red algae

2004

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A significant number of halogenated low molecular weight metabolites have exhibited an impressive array of biological properties ranging from antimicrobial to insecticidal activities. Studies on the natural products chemistry of the red seaweeds were recently stimulated by the discovery of the acyclic monoterpene halomon, which exhibits selective antitumor activity in the National Cancer Institute's human tumor and disease oriented in vitro screen.The present review is a taxonomy based compilation of the available literature on the halogenated volatile metabolites (C 1 -C 10 ) produced by red seaweeds, with a short description of the reported ecological and pharmaceutical activities. The review begins with a presentation of simple halogenated hydrocarbons and phenols, showing their wide occurrence in rhodophyta, along with a description of simple halogenated lipids in some of the most frequently investigated red algae species and finally focuses on the chemical composition of individual red algae species.

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Plocamenone, a unique halogenated monoterpene from the red alga, plocamium

Cited by 11 publications

References 4 publications

Application of HPLC-NMR in the Identification of Plocamenone and Isoplocamenone from the Marine Red Alga Plocamium angustum

Application of HPLC-NMR in the Identification of Plocamenone and Isoplocamenone from the Marine Red Alga Plocamium angustum

Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone

Volatile halogenated metabolites from marine red algae

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