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A new iridoid glucoside, cornusoside A (1), and four new natural product iridoid aglycones, cornolactones A–D (2–5), together with 10 known compounds were isolated from the leaves of Cornus florida. The structures of compounds 1–5 were established by interpretation of their spectroscopic data. Cornolactone B (3) is the first natural cis-fused tricyclic dilactone iridoid containing both a five- and a six-membered lactone ring. A biosynthesis pathway is proposed for cornolactones C (4) and D (5), the C-6 epimers of compounds 1–3.