In this paper it will be argued that systems functioning, even at abstract levels, can trace its roots to principles extracted from the biological tradition as well as non-tradition. This would ideally clarify, by picturing a non-coincidental analogue found in the natural world, the play between elements and relations as the precondition for the origin of a system and its evolution. The methodology presents the juxtaposition of Lovelock’s (1982) Gaia hypothesis which depicts life as operating through homeostasis, and Luhmann’s system theory, where closed systems reproduce and operate through autopoiesis (1995). The alignment is possible, it is argued, despite Luhmann’s affirmation that one cannot reduce a system to a mere analogy of an organism in terms of causality. According to the extensionality principle enunciated by Sebeok (2000), abstract forms are complex derivatives of concrete, simpler forms of which the natural world abounds, especially in their iconic relations with their object referents. This is a reiteration of the fact that abstract systems, characterized by communication, are derivative of more concrete natural systems based on semiosis. The evolving of a subsystem such as art can therefore be related to that of a natural subsystem such as a specific ecosystem. Today, art has acquired the status of a self-referential, self-reproductive system based on a dynamic equilibrium (also characterizing established ecosystems) which is self-maintained and auto-regulated, but has reached a state of, according to Luhmann’s words, "minimalism and radical simplicity". Therefore one may argue that a burst of complexity in the system, obviously coming from inside and not from an external agent, may be similar to that of a catastrophic natural event. Furthermore, it triggers, if not destruction, evolution. With regard to the future of the art system, Luhmann concludes that "Sooner or later one may once again demand a maximum amount of complexity from the individual work." Such change will originate in internal autopoietic mechanisms and will, perhaps, lead to further evolution of both art forms and communications.