From my newLISP loading on WIN/SketchUp 7 here:
http://www.alh.net/newlisp/phpbb/viewtopic.php?t=2710
There comes the next question:
Sketchup runs also on the MAC.
So it is possible to load the newLISP modul under ruby?
Should be possible, the newLISP library behaves like a normal C library on Mac OS X with cdecl calling conventions.
Not sure if this will help but I wrote some C code to load the newLISP dylib into a C/C++/Obj-C app: Calling newLISP from C (//http)