Hippophae rhamnoides L. is a perennial shrub of the Elaegnaceae family, which has a significant distribution area (both in cultivation and in the wild) and an annually renewable raw material base (fruits and leaves). The leaves of sea buckthorn are characterized by a high accumulation of various groups of biologically active substances. However, the fraction of lipophilic biologically active substances of this type of medicinal plant material remains poorly understood in terms of composition and pharmacological properties. The aim of the work was to study the phytochemical composition of the lipophilic fractions of sea buckthorn leaves by GC/MS with a predictive in silico assessment of promising types of pharmacological activity of the identified compounds for the subsequent targeted development of medicinal herbal preparations based on this medicinal plant material with a certain spectrum of action. The object of the study was the leaves of three phenological phases of plant life collected in the territory of the Voronezh region and dried by the air-shadow method to a residual moisture content of not more than 10% in 2022. On the chromatograms in the leaves harvested in different phenophases of development, the presence of peaks of about 40 compounds is observed – 20 each in the preparations removed from the leaves of phases I and III; 16 – phases II of blanks, of which 14 compounds were identified – 7, 8, and 10 in phenophases I, II, and III, respectively.The greatest number of compounds of the group of sugars, sterols, aliphatic and alicyclic alcohols was typical for the leaves of the phenological phase III – the phase of technical maturity of the fruit, which is due to the accumulation of these biologically active substances in the process of life. However, leaves already in the first phase of harvesting can be considered as a potential source of vitamins and sterols due to their significant accumulation. The results of the in silico study position phytosterols (betulin and γ-sitosterol) as the target group of biologically active substances in the lipophilic fraction of the leaves of the third phase of the harvest due to the large accumulation and the presence of a high probability of hypolipidemic, hypocholesterolemic and hepatoprotective activities. At the same time, the maximum accumulation of this fraction in the leaves during the harvesting period of fruits, the main pharmacopoeial valuable raw material of this plant, contributes to the possibility of waste-free rational use of plant resources.