Isolation, crystal structure and synthesis of arsenobetaine, the arsenical constituent of the western rock lobster panulirus longipes cygnus George

Edmonds, John S.; Francesconi, Kevin A.; Cannon, J. R.; Raston, Colin L.; Skelton, Brian W.; White, Allan H.

doi:10.1016/s0040-4039(01)93098-9

Cited by 327 publications

(112 citation statements)

References 8 publications

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“…Since the 1920s, marine organisms have been known to contain substantial amounts of arsenic as a complex arsenic compound. 1 The transformation of inorganic arsenic in the environment has been widely studied, including the production of methylated species by micro-organisms, 2,3 of arsenobetaine (AsB) and arsenocholine (AsC) by marine animals, 4,5 of arsenosugars by seaweed 6 and of arsenolipids by seaweed 7 and marine animals. 8 Arsenic has been found in seaweed in amounts of more than 100 mg kg −1 (dry weight).…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of arsenosugars in marine sediment

Pengprecha

Wilson

Raab

et al. 2005

Appl. Organometal. Chem.

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In the marine environment, arsenic accumulates in seaweed and occurs mostly in the form of arsenoribofuranosides (often called arsenosugars). This study investigated the degradation pathways of arsenosugars from decaying seaweed in a mesocosm experiment. Brown seaweed (Laminaria digitata) was placed on top of a marine sediment soaked with seawater. Seawater and porewater samples from different depths were collected and analysed for arsenic species in order to identify the degradation products using high-performance liquid chomatography-inductively coupled plasma mass spectrometry. During the first 10 days most of the arsenic found in the seawater and the shallow sediment is in the form of the arsenosugars released from the seaweed. Dimethylarsenoylethanol (DMAE), dimethylarsinic acid (DMA(V)) and, later, monomethylarsonic acid (MMA(V)) and arsenite and arsenate were also formed. In the deeper anaerobic sediment, the arsenosugars disappear more quickly and DMAE is the main metabolite with 60-80% of the total arsenic for the first 60 days besides a constant DMA(V) contribution of 10-20% of total soluble arsenic. With the degradation of the soluble DMAE the solubility of arsenic decreases in the sediment. The final soluble degradation products (after 106 days) were arsenite, arsenate, MMA(V) and DMA(V). No arsenobetaine or arsenocholine were identified in the porewater.

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Section: Introductionmentioning

confidence: 99%

Biodegradation of arsenosugars in marine sediment

Pengprecha

Wilson

Raab

et al. 2005

Appl. Organometal. Chem.

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“…The organo-arsenic compound isolated from western rock lobster by Edmonds et al (19) has been identified as arsenobetaine, (CH3)3AM CH2COO.…”

Section: Introductionmentioning

confidence: 99%

Occurrence of arsenic in plaice (Pleuronectes platessa), nature of organo-arsenic compound present and its excretion by man.

Luten¹,

Riekwel-Booy²,

Rauchbaar³

1982

Environ Health Perspect

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The arsenic content in 255 samples of plaice (Pleuronectes platessa) varied between 3 and 166 mg/kg. About 65% of the samples had an arsenic content above 10 mg/kg. High (low) arsenic concentration in the fillet corresponds with a high (low) concentration in milt or roe.An excretion experiment with eight human volunteers showed that after the consumption of plaice, 69-85% of the ingested arsenic was excreted in the urine within five days. The organo-arsenic compound present in plaice was isolated by means of extraction, ion-exchange and thin-layer chromatography. Field desorption mass spectrometry of the isolate showed that arsenic was present as arsenobetaine, (CH3)3AICH2COO-.

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“…On the basis of studies in Weddell seals, we have identifi ed two suitable compounds, arsenobetaine (AsB) and trimethylamine N-oxide (TMAO) (Eisert, 2003;Eisert et al, 2005). Both are specifi c to, and apparently ubiquitous in, marine prey yet are neither stored nor synthesized by higher vertebrates and in mammals are eliminated rapidly from the circulation following ingestion (Edmonds and Francesconi, 1977Yancey et al, 1982;Vahter et al, 1983;Al-Waiz et al, 1987Van Waarde, 1988;Cullen and Reimer, 1989;Brown et al, 1990;Shibata et al, 1992;Smith et al, 1994;Svensson et al, 1994;Zhang et al, 1999;Lehmann et al, 2001). The biomarker method provides information on recent food intake within a timescale of hours to days, in contrast to fatty acid signatures or stable isotopes in fl uids or tissue samples, which integrate food intake over a period of months (Iverson et al, 1997a(Iverson et al, , 1997bBrown et al, 1999).…”

Section: Monitoring Food Consumption During the Lactation Periodmentioning

confidence: 99%