Ajwa, a variety of date palm Phoenix dactylifera L., produces the most expensive date fruits. Percentages of seed, moisture, fructose, glucose, soluble protein, and fiber in Ajwa dates were 13.24, 6.21, 39.06, 26.35, 1.33, and 11.01, respectively. The ethyl acetate, methanolic, and water extracts of Ajwa dates, active at 250 μg/mL in the MTT assay, inhibited lipid peroxidation (LPO) by 88, 70, and 91% at 250 μg/mL and cyclooxygenase enzymes COX-1 by 30, 31, and 32% and COX-2 by 59, 48, and 45% at 100 μg/mL, respectively. Bioactivity-guided purifications afforded compounds 1–7, in addition to phthalates and fatty acids. Compounds 1–3 showed activity at 100 μg/mL in the MTT assay; inhibited COX-1 enzyme by 59, 48, amd 50% and COX-2 enzyme by 60, 40, amd 39% at 50 μg/mL; and inhibited LPO by 95, 58, amd 66% at 100 μg/mL, respectively. The soluble protein fraction was also very active in both antioxidant and anti-inflammatory assays.