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Viaticene A – An Unusual Tetraterpene Cuticular Lipid Isolated from the Springtail Hypogastrura viatica
Author(s) -
Bello Jan E.,
Stamm Patrick,
Leinaas Hans Petter,
Schulz Stefan
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900224
Subject(s) - chemistry , terpene , derivatization , cuticle (hair) , springtail , cyclopropene , organic chemistry , stereochemistry , environmental chemistry , high performance liquid chromatography , biology , ecotoxicology , genetics
The cuticles of springtails are extremely wear‐ and friction‐resistant, super‐hydrophobic, non‐fouling, and self‐cleaning. As such, the chemistry of the lipids covering these cuticles is of great interest as a model for biomimetic super‐hydrophobic surfaces, although only few of these lipids have been structurally elucidated. Hypogastrura viatica , a surface‐dwelling springtail, produces highly branched tetraterpene hydrocarbons with an unprecedented [6+2]‐terpene connectivity as components of the epicuticular lipid layer. The structure of the major lipid component, viaticene A, was elucidated through isolation, spectroscopic analysis, chemical derivatization, synthesis, as well as stereochemical analysis of the core unit obtained from ozonolysis of the isolated lipid. Viaticenes A and B represent a new class of irregular tetraterpenoid natural products.