Reptilian chemistry: Characterization of a family of dianeackerone-related steroidal esters from a crocodile secretion

Zhicai Yang, Authrine Whyte, Athula B. Attygalle, Paul J. Weldon, Thomas Eisner, Jerrold Meinwald

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The African dwarf crocodile, Osteolaemus tetraspis (Crocodilidae, Reptilia), possesses a pair of skin glands, the paracloacal glands, the secretion of which is thought to be used to mark nest sites or attract mates. Ten aromatic steroidal esters were isolated from this secretion and characterized on the basis of NMR spectroscopic investigations, electrospray ionization-MS analyses, and chemical degradation. These esters, which account for more than 90% of the paracloacal glandular secretion, are derived from either cholesterol or cholestanol, esterified with a C-20 or C-22 acid closely related to dianeackerone, the only significant volatile compound found in this secretion.

Original languageEnglish
Pages (from-to)12251-12256
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume96
Issue number22
DOIs
StatePublished - 26 Oct 1999

Keywords

  • Biosynthesis
  • Cholesterol
  • Osteolaemus tetraspis
  • Paracloacal gland

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