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Composition of the Cloacal Gland Secretion of Tuatara, Sphenodon punctatus
Author(s) -
Flachsbarth Birte,
Fritzsche Matthias,
Weldon Paul J.,
Schulz Stefan
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800265
Subject(s) - derivatization , glyceride , glycerol , stereochemistry , chemistry , composition (language) , biology , zoology , biochemistry , fatty acid , organic chemistry , high performance liquid chromatography , linguistics , philosophy
The lipophilic content of the cloacal gland secretion of the tuatara ( Sphenodon punctatus ) was investigated. GC/EI‐MS Analysis of CH 2 Cl 2 extracts of the secretions revealed triacylglycerols as major glandular constituents. Twelve major medium‐chain fatty acids were found to be conjugated to glycerol in different combinations, resulting in complex mixtures. These acids were identified by transesterification and subsequent derivatization of natural samples, and their structures were verified by synthesis. The natural glycerides contain predominantly three of the following acids: octanoic ( A ), ( E )‐ and ( Z )‐oct‐4‐enoic ( B and C , resp.), (4 E ,6 Z )‐octa‐4,6‐dienoic (tuataric acid; D ), ( R )‐2,6‐dimethylheptanoic ( E ), ( R )‐2,6‐dimethylhept‐5‐enoic ( F ), ( Z )‐dec‐4‐enoic ( G ), (4 Z ,7 Z )‐deca‐4,7‐dienoic ( H ), ( R )‐3,7‐dimethyloct‐6‐enoic ( I ), ( R )‐4,8‐dimethylnon‐7‐enoic ( J ), (2 R ,6 S )‐2,6,10‐trimethylundec‐9‐enoic ( K ), and (2 R ,5 E )‐2,6,10‐trimethylundeca‐5,9‐dienoic acids ( L ). Several additional acids, occurring in trace amounts only, were tentatively identified by MS. The elucidation of the absolute configuration of the acids was performed by GC on chiral phases. Individual tuatara show specific mixtures of glycerides with up to 100 components. The individual mixtures may permit individual recognition because the bouquets seem to be stable over years.