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Admiral Luther Whitetree offered prune juice to Klingon Captain Krenn while visiting the Federation, though he quickly thought better of it, noting that the Medical Corps would object. (TOS novel: The Final Reflection)
Guinan introduced Worf to prune juice in 2366. He pronounced it "a warrior's drink," and it thereafter became a favorite drink of his, on both the USS Enterprise and Deep Space 9. (TNG episode: "Yesterday's Enterprise" DS9 episode: "The Way of the Warrior", et. al.)