Journal
TETRAHEDRON
Volume 57, Issue 33, Pages 7169-7172Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00692-5
Keywords
activated defence; algal sesquiterpene; caulerpenyne; 1,4-bisenol acetate; esterase
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The invasive green macro-alga Caulerpa taxifolia reacts upon wounding with rapid transformation of its main defensive metabolite caulerpenyne. The three acetate groups of this sesquiterpene are enzymatically cleaved within minutes after mechanical damage. Transformation of the 1,4-bis-enol acetate moiety of caulerpenyne results in labile 1,4-dialdehydes after tautomerisation. Normal phase HPLC/APCI-MS measurements of freshly prepared algal extracts allow characterization of these reactive products, which are of the oxytoxin family. Final structural elucidation was achieved after trapping of the aldehydes with 2,4-dinitrophenylhydrazine. The role of wound-induced transformation in activated chemical defence of C. taxifolia is suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.
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