A new cytotoxic polychlorinated sulfolipid from contaminated Adriatic mussels

Ciminiello, Patrizia; Dell’Aversano, Carmela; Fattorusso, Ernesto; Forino, Martino; Magno, Silvana; Meglio, Paola Di; Ianaro, Angela; Poletti, Roberto

doi:10.1016/j.tet.2003.12.072

Cited by 48 publications

(39 citation statements)

References 14 publications

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“…The digestive glands (5000 g of dry weight after extraction) were removed, homogenized with a Waring blender, and extracted with CH 3 CN/H 2 O (8:2 + 0.1 % HCOOH) twice at room temperature. The combined extracts, after filtration, were concentrated in vacuo to give a residue that was dissolved in CH 3 …”

Section: Methodsmentioning

confidence: 99%

“…Our ongoing research on toxic mussels from the Adriatic Sea carried out over the past two decades has allowed us to isolate and stereostructurally characterize not only several marine biotoxins, some of which have never been reported before, [1] but also new and intriguing classes of cytotoxic compounds, such as polychlorosulfolipids [2][3] and oxazin- ins [4][5][6] (Figure 1). Oxazinins represent a class of molecules featuring a typical oxazinine ring that resembles the oxazinone skeleton common to a number of bioactive natural products, such as bassiatin, [7] lateritin, [8] metacytofilin, [9] and javanicunin.…”

Section: Introductionmentioning

confidence: 99%

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Stereostructural Determination by a Synthetic and NMR‐Based Approach of Three Oxazinins Isolated from Adriatic Mussels

et al. 2007

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Two oxazinins, namely oxazinin‐5 and ‐6, along with a related linear precursor (preoxazinin‐7) were isolated from toxic mussels collected along the Northern Adriatic coasts in October 2005. Determination of the planar structure of these novel compounds was achieved through extensive NMR spectroscopic analysis, whereas a synthetic approach was crucial for their absolute stereochemical elucidation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Stereostructural Determination by a Synthetic and NMR‐Based Approach of Three Oxazinins Isolated from Adriatic Mussels

et al. 2007

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“…Mytilipin A is a member of the chlorosulpholipid family isolated from Adriatic mussels [131][132][133]. Its interesting structure has garnered much attention from the synthetic organic community [134][135][136][137][138][139][140].…”

Section: Stereoselective Olefin Metathesis In Synthetic Applicationsmentioning

confidence: 99%

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

2017

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Olefin metathesis is a prevailing method for the construction of organic molecules. Recent advancements in olefin metathesis have focused on stereoselective transformations. Ruthenium olefin metathesis catalysts have had a particularly pronounced impact in the area of stereoselective olefin metathesis. The development of three categories of Z-selective olefin metathesis catalysts has made Z-olefins easily accessible to both laboratory and industrial chemists. Further design enhancements to asymmetric olefin metathesis catalysts have streamlined the construction of complex molecules. The understanding gained in these areas has extended to the employment of ruthenium catalysts to stereoretentive olefin metathesis, the first example of a kinetically E-selective process. These advancements, as well as synthetic applications of the newly developed catalysts, are discussed.

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“…It is likely that these cytotoxic compounds originate, just like typical biotoxins, from harmful microalgae that are accumulated by the continuous filter-feeding process of mussels. The first isolated compound is a hexachloromonosulfate (1), [87] while 2 [88] and 3, [89] characterized very recently, contain eleven chlorines and a fatty acid acyl moiety.…”

Section: Chlorosulfolipidsmentioning

confidence: 99%

Shellfish Toxins − Chemical Studies on Northern Adriatic Mussels

Ciminiello

Fattorusso

2004

Eur J Org Chem

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During our investigation on toxic mussels from the Northern Adriatic sea, initiated about ten years ago, a number of polyether toxins have been isolated and characterized, some of which represent new additions to the diarrhetic shellfish poisoning (DSP) class of biotoxins and seem to be specific to the Adriatic. In addition, we have also isolated new types of toxins, oxazinins and chlorosulfolipids, whose structures were elucidated by extensive use of 1D and 2D NMR spectroscopic techniques. Some of them could represent a further risk to public health due to their cytotoxic activity. A liquid‐chromatography mass‐spectrometry (LC‐MS) method was proposed for the sensitive, specific and direct detection of yessotoxin and its analogs. In addition, the proposed method allows us highlight the possible presence of new analogs, and enables us to propose an effective structural hypothesis even when full structural elucidation of new toxins by NMR spectroscopy is hampered by the limited amount of material available. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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A new cytotoxic polychlorinated sulfolipid from contaminated Adriatic mussels

Cited by 48 publications

References 14 publications

Stereostructural Determination by a Synthetic and NMR‐Based Approach of Three Oxazinins Isolated from Adriatic Mussels

Stereostructural Determination by a Synthetic and NMR‐Based Approach of Three Oxazinins Isolated from Adriatic Mussels

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

Shellfish Toxins − Chemical Studies on Northern Adriatic Mussels

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