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No matter what type of sauce you are serving with a pudding or cake dessert; always apply the sauce just before serving. I am not sure what you mean when you say that the pineapple juice will cause red wine to breakdown?...There is nothing in red wine that would breakdown.
If it's fresh pineapple cubes or slices, the red wine will discolor it and become soggy. Like loubaby said, apply the sauce (and in this case fresh pineapple) just before serving. Good luck!