Document Detail

Composition of the cloacal gland secretion of tuatara, Sphenodon punctatus.
MedLine Citation:
PMID:  19180453     Owner:  NLM     Status:  MEDLINE    
The lipophilic content of the cloacal gland secretion of the tuatara (Sphenodon punctatus) was investigated. GC/EI-MS Analysis of CH2Cl2 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.), (4E,6Z)-octa-4,6-dienoic (tuataric acid; D), (R)-2,6-dimethylheptanoic (E), (R)-2,6-dimethylhept-5-enoic (F), (Z)-dec-4-enoic (G), (4Z,7Z)-deca-4,7-dienoic (H), (R)-3,7-dimethyloct-6-enoic (I), (R)-4,8-dimethylnon-7-enoic (J), (2R,6S)-2,6,10-trimethylundec-9-enoic (K), and (2R,5E)-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.
Birte Flachsbarth; Matthias Fritzsche; Paul J Weldon; Stefan Schulz
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemistry & biodiversity     Volume:  6     ISSN:  1612-1880     ISO Abbreviation:  Chem. Biodivers.     Publication Date:  2009 Jan 
Date Detail:
Created Date:  2009-02-03     Completed Date:  2009-03-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101197449     Medline TA:  Chem Biodivers     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  1-37     Citation Subset:  IM    
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig.
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MeSH Terms
Cloaca / chemistry*,  secretion*
Fatty Acids / chemistry
Gas Chromatography-Mass Spectrometry
Reptiles / metabolism*
Triglycerides / chemistry
Reg. No./Substance:
0/Fatty Acids; 0/Triglycerides

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