Premium
Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)
Author(s) -
Chinta Satya Prabhakar,
Goller Stephan,
Uhl Gabriele,
Schulz Stefan
Publication year - 2016
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.201600020
Subject(s) - wax , spider , chemistry , theridiidae , cuticle (hair) , fatty acid , biosynthesis , stereochemistry , carbon chain , acyl group , fatty alcohol , biochemistry , organic chemistry , biology , group (periodic table) , enzyme , zoology , genetics
The analysis of cuticular extracts from the kleptoparasitic spider Argyrodes elevatus revealed the presence of unusual esters, new for arthropods. These novel compounds proved to be methyl‐branched long‐chain fatty acid esters with methyl branches located either close or remote from the internally located ester group. The GC/MS analysis of the prosoma lipid blend from the male cuticle contained one major component, undecyl 2‐methyltridecanoate ( 1 ). In contrast, four major wax‐type esters, 2‐methylundecyl 2,8‐dimethylundecanoate ( 2 ), 2,8‐dimethylundecyl 2,8‐dimethylundecanoate ( 3 ), heptadecyl 4‐methylheptanoate ( 4 ), and 14‐methylheptadecyl 4‐methylheptanoate ( 5 ), were identified in the lipid blend of female prosomata. Structure assignments were based on mass spectra, gas chromatographic retention indices, and microderivatization. Unambiguous proof of postulated structures was ensured by an independent synthesis of all five esters. Preferentially, odd‐numbered carbon chains pointed to a distinct biosynthetic pathway, different from that of common fatty acids, because one or two C 3 starter units are incorporated during the biosynthesis of all acid and alcohol building blocks present in the five esters. The striking sexual dimorphism together with the unique biosynthesis points to a function of the esters in chemical communication of the spiders, although no behavioral data are currently available to test this assumption.