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

16 Citations (Scopus)

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

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Urochordata
Nickel
Mass Spectrometry
Esters
Magnetic Resonance Spectroscopy
Fatty Acids
chlorin
tunichlorin

Keywords

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

ASJC Scopus subject areas

  • Genetics
  • General

Cite this

Acyl tunichlorins : A new class of nickel chlorins isolated from the Caribbean tunicate Trididemnum solidum. / Sings, Heather L.; Bible, Keith C.; Rinehart, Kenneth L.

In: Proceedings of the National Academy of Sciences of the United States of America, Vol. 93, No. 20, 01.10.1996, p. 10560-10565.

Research output: Contribution to journalArticle

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