the meaning that these words are going to take it's going to depend on the context. Sometimes, these two are not interchangeable, let's see some examples. If you are doing quite good at school, u get good marks, and you take in all lessons faster than the rest of your partners, then somebody can call you listo. In this case, the word acts as a synonym of smart, clever. You are sharing a flat, and when it comes to divide chores, you can choose for you the easiest, or fastest chore to be done, while the rest of your partners will have to spend more time, and much more effort in doing their tasks. In this case, somebody may call you, que listo eres!!! Regarding the word astuto, at times it can have a negative meaning, more or less like deceitful, like somone who use his/her own intelligence for fooling ppl, for taking advantage on others. However, it is not going to take a negative meaning always, it can also be positive, for example if you manage to do something quicker, and more effectively than others, someone may call u que astuto!