Viaticene A – An Unusual Tetraterpene Cuticular Lipid Isolated from the Springtail Hypogastrura viatica

Abstract

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.

Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry

“…The IR spectrum was similar to that of synthetic (E,E,E)-geranylgeraniol (5) (Figure S34, SI), whereas it differed compared to (E,E)-geranyllinalool (Figure S35, SI) in the fingerprint region, missing for example the band at 921 cm À 1 . Therefore, compound F was identified as ( E,E,E,E,E)-farnesylfarnesol (30), whereas E was assigned to be ( E,E,E,E)-farnesylnerolidol (31). These assignments were verified by I data, shown in E,E,E,E)-β-farnesylfarnesene (28) , (E,E,E,E,E)α-farnesylfarnesene (29) , (E,E,E,E,E)-farnesylfarnesol (30) , and (E,E,E,E)-farnesylnerolidol (31).…”

“…Therefore, compound F was identified as ( E,E,E,E,E)-farnesylfarnesol (30), whereas E was assigned to be ( E,E,E,E)-farnesylnerolidol (31). These assignments were verified by I data, shown in E,E,E,E)-β-farnesylfarnesene (28) , (E,E,E,E,E)α-farnesylfarnesene (29) , (E,E,E,E,E)-farnesylfarnesol (30) , and (E,E,E,E)-farnesylnerolidol (31). Table 3.…”

“…Figure 8. The linear [6]-terpenes (E,E,E,E)-β-farnesylfarnesene(28), (E,E,E,E,E)α-farnesylfarnesene(29), (E,E,E,E,E)-farnesylfarnesol(30), and (E,E,E,E)-farnesylnerolidol(31).…”

“…As a more complex example, squalene is a [3 1 + 3 1 ]-terpene. See Ref [31]. for a detailed description.…”

Head and Tail Oxidized Terpenoid Esters from Androconia of Heliconius erato Butterflies

“…We recently investigated the CSG contents of over 100 individuals of H. erato and showed differences in composition between individuals belonging to different mimicry groups . Different from many other heliconiines, H. erato showed a high variability in compounds originating from the terpene biosynthetic pathway, including linear terpenes containing up to seven consecutively arranged isoprene units, so-called [7]-terpenes . During this project we also analyzed the corresponding androconia and detected two compounds in larger amounts than the known constituents, eluting very late during gas chromatographic analysis on an apolar phase.…”