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Hypertension is a contributing factor to pathophysiology of vascular damage and accelerated arterial stiffening. Renin-angiotensin-aldosterone system (RAAS) inhibitors are widely used for treatment of persistent hypertension. Along with conventional antihypertensive therapy, nutritional intervention has also gained attention as arterial and vascular complications are closely associated with dietary and lifestyle risk factors. Flavonoids and omega-3 polyunsaturated fatty acids (PUFA) are the key antihypertensive biomolecules emerging to prevent and manage hypertension. In the current study, twelve long chain fatty acid derivatives of isoquercitrin (Q3G) and phloridzin (PZ) were investigated for inhibition of angiotensin-converting enzyme (ACE), renin and aldosterone synthase in comparison to their parent compounds in vitro. The linoleic and α-linolenic esters of PZ were the strongest (IC50 69.9–70.8 μM) while Q3G and PZ (IC50 >200 μM) were the weakest renin inhibitors in vitro (p