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Spande TF, Jain P, Garraffo HM, Pannell LK, Yeh HJC, Daly JW, Fukumoto S, Imamura K, Tokuyama T, Torres JA, Snelling RR, Jones TH. 
“Occurrence and significance of decahydroquinolines from dendrobatid poison frogs and a myrmicine ant: use of 1H and 13C NMR in their conformational analysis”. 
J Nat Prod. 1999 Jan 30;62(1):5-21.
Structures for 2,5-disubstituted decahydroquinolines (DHQs) are reported for the two diastereomeric pairs cis-275B (14) and cis-275B' (15) and 5-epi-trans-269AB (18) and trans-269AB (19), all isolated from skin extracts of dendrobatid frogs, and for 5-epi-cis-275B' (16) and 5-epi-trans-275B (17) found in the extracts of virgin queens of a myrmicine ant [Solenopsis (Diplorhoptrum) azteca]. Detection of such DHQs in an ant, their first reported occurrence, strengthens a dietary hypothesis for the origin of the approximately 30 DHQs that have been detected in extracts of frog skin. NMR data on the two conformers of cis-decahydroquinoline permit assignment of ring conformations and stereochemistry to cis-DHQs of the "N-endo" type or the "N-exo" type. These conformations are also assigned on whether H-8a is equatorial or axial as determined with E-COSY or 1D-HOHAHA spectra.
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