The amount and composition of the essential oil from leaves of Hypericum androsaemum L. cultivated in Arouca (Portugal) were determined in six samples harvested during 1 year at intervals of 2 months. The seasonally dependent essential oil content ranged from 0.7 mg/g biomass dry weight in September to 3.4 mg/g in February. The oil contained more than 80 compounds, 70 of which (constituting 88-93% of the total oil) were identified by GC and GC-MS. An approximation of the absolute quantification of each compound and compound class was performed using a GC method with an internal standard. The relative and the absolute content of each compound and compound class changed during the year. At the end of the winter and in the spring, the essential oil was dominated by sesquiterpene hydrocarbons and accumulated a high number of intermediate to long chain n-alkanes and 1-alkenes. In September, the essential oil contained the lowest levels of sesquiterpene hydrocarbons (43%) and the highest levels of 1-octene and 2-hexenal (38%). In February, the essential oil had the highest level of sesquiterpene hydrocarbons (73%) and the highest diversity of intermediate to long chain n-alkanes and 1-alkenes.

The essential oil yields obtained by hydrodistillation of the aerial parts of Hypericum androsaemum cultivated plants varied from 0.94 to 4.09 mg/g of biomass dry weight, depending of the harvest time. The respective analyses performed by gas chromatography and gas chromatography-mass spectrometry revealed more than 80 compounds, 72 of which were identified. Most of the compounds were sesquiterpene hydrocarbons, which, depending of the harvest time, corresponded to 43-78% of the total essential oil. The other compounds were distributed as monoterpene hydrocarbons, oxygen-containing sesquiterpenes, n-alkanes, 1-alkenes, and oxygen-containing monoterpenes, these being a minor group. In H. androsaemum in vitro shoots, sesquiterpene hydrocarbons represented >80% of the respective essential oil. Differences in the essential oil composition were found depending on the harvest time and origin, in vivo versus in vitro, of the plant material. The essential oil sampled in November was characterized by the highest levels of sesquiterpene hydrocarbons and a high number of n-alkanes and 1-alkenes, from C(18) to C(28), whereas that sampled in June of the following year showed the highest levels of n-nonane and 1-octene as well as monoterpene hydrocarbons, the second most representative group.