Acyl tunichlorins: a new class of nickel chlorins isolated from the Caribbean tunicate Trididemnum solidum.
A new class of nickel-containing chlorins (acyl tunichlorins) has been isolated from the Caribbean tunicate Trididemnum solidum. The structures of 28 of these nickel (II) hydroporphyrins were elucidated using mass spectrometry, one- and two-dimensional NMR spectroscopy, and chemical degradation/derivatization. Unique structural features of these compounds include the diversity of aliphatic side chains, which are derived from C14:0 to C22:6 fatty acids, and their location at an unprecedented position at C-2a on the hydroporphyrin nucleus. No chlorins with ester-linked acyl side chains at C-2a have been reported previously. Although the exact biological role that these compounds play in T. solidum remains unknown, acyl tunichlorins represent the only nickel-containing chlorins to be isolated from a living system and are the C-2a acyl derivatives of tunichlorin, a nickel chlorin reported by this laboratory in 1988.
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Roger Adams Laboratory, University of Illinois at Urbana-Champaign 61801, USA.
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Rinehart
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D000818:Animals; D004220:Disulfides / Q000737:chemistry; D004952:Esters; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008665:Metalloporphyrins / Q000737:chemistry*; D009532:Nickel; D010860:Pigments, Biological / Q000737:chemistry; D014561:Urochordata / Q000737:chemistry*
D004220:Disulfides; D004952:Esters; D008665:Metalloporphyrins; D010860:Pigments, Biological; C056010:tunichlorin; C021181:dimethyl disulfide; D009532:Nickel