Oxazinin-1, -2 and -3 − A Novel Toxic Compound and Its Analogues from the Digestive Glands ofMytilus galloprovincialis

Abstract

A chemical investigation of the digestive glands of Mytilus galloprovincialis from North Adriatic Sea led to the isolation of three novel compounds, oxazinin-1 (1), oxazinin-2 (2) and oxazinin-3 (3). Their structures, including the relative stereochemistry, were established by spectroscopic means includ- [a]

Screening the Biosphere: The Fungicolous Fungus Trichoderma phellinicola, a Prolific Source of Hypophellins, New 17‐, 18‐, 19‐, and 20‐Residue Peptaibiotics

“…preoxazinin-7, the linear precursor [101], and cyclic oxazinins from the digestive glands of Mytilus galioprovincialis [102] [103]. …”

Screening the Biosphere: The Fungicolous Fungus Trichoderma phellinicola, a Prolific Source of Hypophellins, New 17‐, 18‐, 19‐, and 20‐Residue Peptaibiotics

“…preoxazinin-7, the linear precursor [101], and cyclic oxazinins from the digestive glands of Mytilus galioprovincialis [102] [103]. …”

Marine natural products

“…594 The absolute configuration of 662 was established by chemical conversion to a known diene. The absolute stereochemistry of oxazinin-3 665, from North Adriatic Sea mussels, 595 was established by synthesis, 596 while the structure and absolute stereochemistry of azaspiracid-1 666, originally obtained from Irish collections of Mytilus edulis, 597 has been revised as a consequence of stereoselective total synthesis. 598,599 The structure of cyercene A, a pyrone polypropionate from a Mediterranean Cyerce cristallina, 600 has been confirmed by synthesis.…”

Biological Relevance and Synthesis of C‐Substituted Morpholine Derivatives

“…Three novel compounds were isolated from the digestive glands of toxic mussels Mytilus galloprovincialis from the North Adriatic Sea (Figure 4). 9 The structures of 10, 11, and 12 were elucidated using extensive 2D NMR studies combined with molecular mechanics calculations. Of these three compounds, 10 was the only one that proved to be active in a cytotoxicity analysis.…”

Screening the Biosphere: The Fungicolous Fungus Trichoderma phellinicola, a Prolific Source of Hypophellins, New 17‐, 18‐, 19‐, and 20‐Residue Peptaibiotics

“…preoxazinin-7, the linear precursor [101], and cyclic oxazinins from the digestive glands of Mytilus galioprovincialis [102] [103]. …”

Marine natural products

“…594 The absolute configuration of 662 was established by chemical conversion to a known diene. The absolute stereochemistry of oxazinin-3 665, from North Adriatic Sea mussels, 595 was established by synthesis, 596 while the structure and absolute stereochemistry of azaspiracid-1 666, originally obtained from Irish collections of Mytilus edulis, 597 has been revised as a consequence of stereoselective total synthesis. 598,599 The structure of cyercene A, a pyrone polypropionate from a Mediterranean Cyerce cristallina, 600 has been confirmed by synthesis.…”

Biological Relevance and Synthesis of C‐Substituted Morpholine Derivatives

“…Three novel compounds were isolated from the digestive glands of toxic mussels Mytilus galloprovincialis from the North Adriatic Sea (Figure 4). 9 The structures of 10, 11, and 12 were elucidated using extensive 2D NMR studies combined with molecular mechanics calculations. Of these three compounds, 10 was the only one that proved to be active in a cytotoxicity analysis.…”

Screening the Biosphere: The Fungicolous Fungus Trichoderma phellinicola, a Prolific Source of Hypophellins, New 17‐, 18‐, 19‐, and 20‐Residue Peptaibiotics

“…preoxazinin-7, the linear precursor [101], and cyclic oxazinins from the digestive glands of Mytilus galioprovincialis [102] [103]. …”

Marine natural products

“…594 The absolute configuration of 662 was established by chemical conversion to a known diene. The absolute stereochemistry of oxazinin-3 665, from North Adriatic Sea mussels, 595 was established by synthesis, 596 while the structure and absolute stereochemistry of azaspiracid-1 666, originally obtained from Irish collections of Mytilus edulis, 597 has been revised as a consequence of stereoselective total synthesis. 598,599 The structure of cyercene A, a pyrone polypropionate from a Mediterranean Cyerce cristallina, 600 has been confirmed by synthesis.…”

Biological Relevance and Synthesis of C‐Substituted Morpholine Derivatives

“…Three novel compounds were isolated from the digestive glands of toxic mussels Mytilus galloprovincialis from the North Adriatic Sea (Figure 4). 9 The structures of 10, 11, and 12 were elucidated using extensive 2D NMR studies combined with molecular mechanics calculations. Of these three compounds, 10 was the only one that proved to be active in a cytotoxicity analysis.…”