Acyl tunichlorins: A new class of nickel chlorins isolated from the Caribbean tunicate Trididemnum solidum

Heather L. Sings, Keith C. Bible, Kenneth L. Rinehart

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

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 C(14:0) to C(22:6) 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.

Original languageEnglish (US)
Pages (from-to)10560-10565
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume93
Issue number20
DOIs
StatePublished - Oct 1 1996

Keywords

  • ascidian
  • marine natural product
  • nickel(II)
  • sea squirt

ASJC Scopus subject areas

  • General

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