Distillation waste water can modify peppermint (Mentha ×piperita L.) oil composition

We evaluated the effects of foliar sprays made of residual distillation waters from 13 species containing essential oil (Melissa officinalis, Mentha arvensis, M. gracilis, M. ×piperita, M. spicata, Monarda citriodora, Nepeta mussinii, Porophyllum ruderale, Rosmarinus officinalis, Salvia officinalis, Satureja montana, Tagetes lucida, and Thymus vulgaris), hot water extracts from two alkaloid-containing species (Glaucium flavum, Datura innoxia), and three plant hormones (methyl jasmonate, gibberellic acid, and salicylic acid) on growth, productivity, and essential oil content and composition (α-pinene, β-pinene, sabinene, myrcene, l-limonene, 1,8-cineole, l-menthone, menthofuran, d-isomenthone, menthyl acetate, neo-menthol, b-caryophyllene, l-menthol, pulegone, germacrene-d, and piperitone) of peppermint (Mentha ×piperita L.) ‘Black Mitcham’. The results showed significant effects of the treatments on plant height and weight, essential oil content and yield, and essential oil composition. Cluster analysis indicated similarities between the effects of plant hormones and some extracts on peppermint oil composition. None of the distillation waters had strong in vitro antimicrobial activity. The results indicated that residual distillation water of some plant species may influence monoterpene synthesis and accumulation in peppermint and hence may be used for targeted modification of peppermint essential oil composition.     

Evidence for the influence of weeds on corky ringspot persistence in alfalfa and Scotch spearmint rotations

Corky ringspot disease (CRS) of potato is caused by tobacco rattle virus (TRV). The virus is transmitted by the stubby root nematode (Paratrichodorus allius) in the Pacific Northwest potato-producing regions. Alfalfa (Medicago sativa L.) and Scotch spearmint (Mentha cardiaca Baker) rarely serve as hosts for TRV. Therefore,P. allius reared on these plants for 1 to 3 months are cleansed of TRV in greenhouse trials. However, weeds in alfalfa and Scotch spearmint rotation crops may serve as hosts for the virus. In greenhouse trials, hairy nightshade (Solanum sarrachoides), prickly lettuce (Lactuca serriola), henbit (Lamium amplexicaule) and, green foxtail (Setaria viridis) grown alone were found to be suitable hosts ofP. allius, whereas Powell amaranth (Amaranthus powellii) was not. ViruliferousP. allius added to hairy nightshade, prickly lettuce, henbit, green foxtail, or Powell amaranth in mixtures with alfalfa and/or Scotch spearmint occasionally remained viruliferous over a 3-to 4-month period, whereasP. allius maintained on weed-free alfalfa or Scotch spearmint became virus-free after 1 to 2 months. Potato grown in soil containingP. allius that had been maintained on weed-alfalfa or weed-Scotch spearmint mixtures for 3 to 4 months exhibited slight to severe CRS symptoms on new tubers, whereas potato following weed-free Scotch spearmint or alfalfa were free from CRS symptoms. Severe CRS symptoms on potato tubers were only observed when potatoes were grown in soil containingP. allius that were maintained on hairy nightshade or hairy nightshade mixtures with alfalfa or Scotch spearmint. These preliminary data suggest that the presence of weeds that serve as hosts of both TRV and P.allius may nullify the positive effects of growing alfalfa or Scotch spearmint for CRS control. Targeted control efforts of known weed hosts may be required to successfully eliminate CRS from fields using alfalfa and Scotch spearmint rotational crops.     

Mathematical modeling for extraction of essential oil from Baccharis spp. by steam distillation

Baccharis (Compositae-Asteraceae) is a large genus of plants distributed from the USA to Argentina, of which 90% are located in South America. In recent decades, species of the genus have been studied, due to their importance as sources of novel active components with possible applications in the pharmaceutical and chemical industries. This work studied three species of Baccharis: Baccharis uncinella DC, Baccharis anomala DC and Baccharis dentata (Vell) G.M. Barroso collected in São Francisco de Paula in southern Brazil. The aim of this work is the evaluation of the aromatic potential of the essential oil obtained by steam distillation method and the simulation of the extraction data by means of a mathematical model. A mathematical model based on mass transfer fundamentals is developed and applied to correlate the experimental data. This model is based on the existence of the broken and intact cells, in which the oil located in the broken cells is rapidly extracted and the oil from intact cells diffuses slowly to the surface of the vegetal material. The analysis of the essential oil was carried through by GC-MS and the major compounds identified to both processes were α-pinene, β-pinene, and spathulenol (B. uncinella), spathulenol, β-caryophyllene, and β-selinene (B. anomala), and germacrene-D, caryophyllene oxide, and spathulenol (B. dentata).     

Chemical profiles of primary and secondary essential oils of palmarosa (Cymbopogon martinii (Roxb.) Wats var. motia Burk.)

Natural essential oils extracted from aromatic crops through steam distillation are extensively used in fragrance, flavour and pharmaceutical industries and in aromatherapy. During steam distillation, a part of the essential oil becomes dissolved in condensate or distillation water and is lost as this water is discarded. A method was developed to recover the dissolved essential oil from condensate water. Palmarosa (Cymbopogon martinii (Roxb.) Wats. var. motia Burk., family: Poaceae), an important aromatic grass was used as the test crop. The distillation water of palmarosa mixed with hexane in 10:1 proportion was thoroughly shaken for 30 min to trap the dissolved essential oil. Hexane was then distilled to yield ‘secondary’ or ‘recovered’ oil. In palmarosa, the ‘primary’ or ‘decanted’ oil (obtained directly by distilling the crop biomass) accounted for 92% and the recovered oil accounted for 8% of the total oil yield. The solvent loss in this process was 4–7%. Experiments conducted in the laboratory with the essential oil showed that the water solubility of palmarosa oil ranged from 0.12 to 0.15% at 31 °C and 0.15 to 0.20% at 80 °C. Hexane recovered up to 97% of the dissolved essential oil in water. The recovered essential oil was richer in organoleptically important oxygenated compounds linalool (2.6–3.8%), geraniol (91.8–92.8%) and geranial (1.8–2.0%) compared to the primary oil.     

Lavender and hyssop productivity, oil content, and bioactivity as a function of harvest time and drying

Field and laboratory experiments were conducted to evaluate the productivity and essential oil composition of lavender (Lavandula angustifolia Mill.) and hyssop (Hyssopus officinalis L.) as functions of year, harvest time, and drying. Lavender essential oil content ranged from 0.71 to 1.3% (overall average of 0.89%) and hyssop oil content ranged from 0.13 to 0.26% (overall average of 0.19%). Lavender and hyssop essential oil yields increased with time. Hyssop oil yields varied from 7.3 kg ha⁻¹ to 19.6 kg ha⁻¹, and lavender oil yields varied from 7.8 kg ha⁻¹ to 55.5 kg ha⁻¹. The major constituents of lavender oil were linalool (23.3-43.4%) and linalylacetate (20.2-39.6%), while the major constituents of hyssop oil were pinocamphene + isopinocamphene (57-75%) and β-pinene (5-15%). Lavender oil extracted from dry material had higher concentrations of linalyl acetate and caryophyllene but lower concentrations of myrcene than the oil from the fresh material. Delayed harvest of hyssop increased the concentrations of β-pinene, myrcene, and limonene + cineole but reduced pinocamphone + isopinocamphone. The chemical composition of the lavender and hyssop oil produced in Mississippi was similar to commercial oils from Bulgaria, Canada, France, and US. Lavender and hyssop can be established as essential oil crops in areas of the southeastern United States. Lavender and hyssop essential oils did not show significant antimicrobial, antileishmanial, antimalarial activity, and did not alter ruminal fermentation. However, commercial oil from L. latifolia reduced methane production in an in vitro digestibility study. The antioxidant activity of hyssop essential oil was 2039 μmol of TE L⁻¹, whereas the antioxidant activity of lavender essential oil was 328 μmol of TE L⁻¹.     

Comparative analysis of essential oil components of two Cryptomeria species from China

The essential oils obtained by hydrodistillation from leaves of Chinese native Cryptomeria japonica and Cryptomeria fortunei were analyzed by GC and GC-MS. Fifty-seven compounds were identified in the essential oils of C. japonica with α-elemol (20.12%), kaur-16-ene (14.84%), β-phellandrene (5.97%), β-elemene (5.87%), α-eudesmol (5.62%) and β-eudesmol (5.03%) as main constituents. Forty components were identified in the oil of C. fortunei with kaurene (34.04%), α-elemol (13.34%), γ-eudesmol (10.80%), β-eudesmol (10.16%), α-pinene (2.75%) and γ-cadinene (1.92%) as the most abundant components. This study demonstrated the occurrence of α-elemol chemotype in C. japonica and kaurene chemotype in C. fortunei from China. The essential oil compositions of two Cryptomeria samples were shown that they can be used for green plant protection, pharmaceutical, perfume and food industries.     

Growing conditions and postharvest management can affect the essential oil of Origanum vulgare L. ssp. hirtum (Link) Ietswaart

Origanum vulgare subsp. hirtum (Link) Ietswaart (Greek oregano) has been cultivated since ancient times thanks to its herbal and therapeutic properties. Currently, it is added in various commercial preparations thanks to its essential oil composition. This group of secondary compounds is affected in quantity and quality by biotic and abiotic factors during the cultivating phase and by the postharvest management. Thus, the aims of the work were to study: (1) how the growing conditions (soil full-light treatment; pot full-light treatment; pot 50%-shade treatment) can affect the essential oil content and the essential oil profile of Greek oregano branches at full-blossoming stage; and (2) how the postharvest management (distillation of the essential oil from fresh herbs, dehumidified herbs or oven-dried herbs) can affect the essential oil content and the essential oil profile of this species. The growing conditions significantly affected the biometrical parameters. The pot full-light treatment contained the highest dry matter percentage (36.5%) and the highest essential oil content, which was directly correlated to the former parameter (r = 0.890**). The postharvest management did not affect the essential oil content. The growing condition significantly affected the characterizing γ-terpinene, cis-sabinene hydrate, 4-terpineol, α-terpinene, linalyl acetate, and β-bisabolene, while it did not affect carvacrol (mean value 15.8%), p-cymene (mean value 6.0%), or sabinene (mean value 3.9%). The postharvest management significantly affected carvacrol, cis-sabinene hydrate, 4-terpineol, p-cymene, α-terpinene, linalyl acetate, and β-bisabolene, while it did not affect γ-terpinene (mean value 14.7%). The response of some compounds to growing conditions led us to hypothesise an essential oil profile of the plants grown in pots at 50%-shade to be more of a vegetative stage type oil than the essential oil profile of the plants grown in soil, although all were at the blossoming stage. The analyses on the individual compounds indicated that, even though the essential oil content in oregano did not change with a change in postharvest management, biochemical changes occurred on the profile. These could be due to enzyme activity, dilution effect or temperature effect during the drying processes. The oven-drying process and the dehumidifying process changed the essential oil profile in a similar way compared to the essential oil profile distilled from fresh herbs. Thus, when it is not possible to extract the essential oil directly from fresh herbs, processors can dry the oregano according to the equipments they have available.     

Changes in phytochemical, antimicrobial and free radical scavenging activities of the Peruvian pepper tree (Schinus molle L.) as influenced by fruit maturation

The effect of stage of maturity on total lipids, fatty acids, yields and essential oil composition and their antimicrobial and free radical scavenging activities of the Schinus molle fruits was investigated. The content of total lipids varied from 2.87 to 5.35% (w/w, dw) and were rich in unsaturated fatty acids particularly linoleic acid. As maturation progress, the essential oil yield dropped from 5.18% to 1.15%. Monoterpene hydrocarbons with α-phellandrene (35.15-40.38%), limonene + β-phellandrene (21.47-36.62%), β-myrcene (7.61-24.96%) and α-pinene (1.92-2.58%) were found to be the main components. At the same time, the essential oils were evaluated for their antimicrobial and free radical scavenging activities. They were found to be active against Bacillus subtilis, Bacillus cereus, Salmonella typhymurium and Escherichia coli but they do not inhibit the growth of Candida albicans. Conversely, they showed very weak activity against the DPPH radical. In both assay, the oil derived from the intermediate stage was reported as more efficient.     

Aroma profiles of the curry leaf, Murraya koenigii (L.) Spreng. chemotypes: Variability in north India during the year

Murraya koenigii (L.) Spreng. (Rutaceae) is characterized by a large chemical intraspecific variability among the land races. This fact makes it difficult to detect real changes occurring in their essential oil composition during annual cycle. Based on this, variations of essential oil yield and composition in two chemotypes (‘A’ and ‘B’) of M. koenigii were assessed in spring, summer, rainy, autumn and winter seasons under foot hill conditions of northern India. The essential oil yield ranged from 0.15% to 0.18% in chemotype ‘A’, while it varied from 0.12% to 0.14% in chemotype ‘B’. Essential oils of both chemotypes from different seasons were analysed by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). A total of fifty-eight constituents representing 93.7-98.8% of chemotype ‘A’ and fifty-six constituents forming 96.1-98.7% of the total composition of chemotype ‘B’ were identified. Chemotype ‘A’ was characterized by higher percentages of α-pinene (34.6-41.9%), sabinene (26.1-36.1%), (E)-caryophyllene (2.4-5.4%) and terpinen-4-ol (1.5-5.3%), whereas chemotype ‘B’ was dominated by higher amount of α-pinene (52.7-65.3%), β-pinene (10.7-12.9%), (E)-caryophyllene (3.1-10.3%) and limonene (5.1-7.8%). Comparative results showed considerable variations in the essential oil composition of both chemotypes due to season of collection. Present study concluded that the M. koenigii leaves of desired quality may be obtained by selecting suitable chemotype and season.     

The effects of harvest date,fermentation duration and Tween 20 treatment on essential oil content and composition of industrial oil rose (Rosa damascena Mill.)

The essential oil of Rosa damascena Mill. is one of the most valuable and important base material in the flavor and fragrance industry. The aim of this study was to determine the effects of harvest date, fermentation duration and Tween 20 treatment on the essential oil content and composition of the rose petals. The essential oil content and composition were significantly different in the petals harvested at various dates (May 24, June 1, 8, and 15, 2002). The highest oil content was found on May 24 harvest (0.040%), and then a gradual decrease was observed up to last harvest date (0.032%). The highest percentages of geraniol, nerol, and phenylethyl alcohol were obtained from the petals harvested on May 24. However, the highest percentages of citronellol and linalool were found from the petals harvested on June 8. The petals collected freshly were fermented for various duration (0, 12, 24, and 36 h) at 25 °C in sacks. The highest essential oil content was found in the non-fermented petals. As fermentation duration increased, essential oil content gradually decreased. The most significant changes during the fermentation were observed in citronellol and geraniol contents. Citronellol/geraniol (C/G) ratio increased from 0.57 to 10.31 throughout the fermentation. In the other experiment, Tween 20 was added into the distillation water at various concentrations (0, 1000, 2500, and 5000 ppm). Although Tween 20 generally raised the contents of essential oil, it did not significantly influence the oil composition. The highest oil content (0.045%) was obtained from the distillation treated with 2500 ppm of Tween 20. Oil content had high positive correlations with geraniol and linalool contents (r=0.55 and 0.53, respectively), but high negative correlation with citronellol content (r=−0.48).     

Dual extraction of essential oil and podophyllotoxin from Juniperus virginiana

The leaves (needles) of eastern red cedar (Juniperus virginiana L.) contain two important natural products: essential oil and podophyllotoxin. The hypothesis of this study was that it may be possible to extract both essential oil and podophyllotoxin from the leaves of the tree, by using a dual extraction method. Podophyllotoxin was obtained from the leaves following steam distillation of the leaves to produce the essential oil, indicating that steam distillation did not degrade podophyllotoxin. Furthermore, a product with 6% purity podophyllotoxin was obtained from the steam-distilled plant material, demonstrating the possibility for the establishment of an industrially economic protocol for dual extraction of these two natural products. Our study demonstrated that J. virginiana leaves, currently a waste-product from the timber industry, could be sequentially extracted for essential oil and podophyllotoxin and utilized as a by-product instead. We also found that the J. virginiana heartwood (a traditional source for cedarwood essential oil) does not contain podophyllotoxin. This is the first study to report both podophyllotoxin and essential oil in J. virginiana, and the first report on the dual extraction of these two natural products from the same biomass samples.     

European pennyroyal (Mentha pulegium) from Portugal: Chemical composition of essential oil and antioxidant and antimicrobial properties of extracts and essential oil

There is a growing interest of industry to replace synthetic chemicals by natural products with bioactive properties from plant origin. The aim of this study was to determine the chemical composition of European pennyroyal (Mentha pulegium) essential oil and to characterize the in vitro antioxidant and antimicrobial activities of its water (hot and cold) and ethanolic extracts and of the essential oil. The essential oil revealed menthone, pulegone and neo-menthol as the main constituents, comprising 35.9, 23.2 and 9.2% of the essential oil, respectively. The hot water extract exhibited the highest antioxidant activity and phenol content. In contrast, the extracts were not very effective to inhibit the growth of the seven foodborne spoilage and pathogenic bacteria tested, but the essential oil showed antibacterial activity against all bacterial strains. In conclusion, extracts and essential oil of M. pulegium from Mediterranean origin have huge potential as an alternative to chemical additives for the food industry.     

Effect of drought on the biochemical composition and antioxidant activities of cumin (Cuminum cyminum L.) seeds

This study is designed to examine the yield components, fatty acid, and essential oil compositions and phenolic contents fruit essential oil composition, the total phenolic amounts as well as the antioxidant activities of cumin (Cuminum cyminum L.) seeds under drought. This plant is one of the most common aromatics in the Mediterranean kitchen. Plants were treated with different levels of water deficit: control (C), moderate water deficit (MWD) and severe water deficit (SWD). Our results indicated that MWD improved the number of umbels per plant as well as the number of umbellets per umbel and the seed yield, in comparison to the control, but it decreased under SWD. Fatty acid composition analysis indicated that petroselinic acid was the major fatty acid (55.9%) followed by palmitic (23.82%) and linoleic (12.40%) acids. Water deficit enhanced the palmitic acid percentage and affected the double bound index of the fatty acid pool and thus the oil quality. The essential oil yield was 1.64% based on the dry weight and increased by 1.40 folds under MWD. Nevertheless it decreased by 37.19% under SWD in comparison to the non treated seeds. Drought results on the modification of the essential oil chemotype from γ-terpinene/phenyl-1,2 ethanediol in the control seeds to γ-terpinene/cuminaldehyde in stressed ones. Besides, total phenolic contents were higher in the treated seeds (MWD and SWD). Results suggest that water deficit treatment may regulate the production of bioactive compounds in cumin seeds, influencing their nutritional and industrial values. Besides, antioxidant activities of the extracts were determined by four different test systems, namely DPPH, β-carotene/linoleic acid chelating and reducing power assays and showed that treated seeds (MWD and SWD) exhibited the highest activity.     

Chemical characterization of the essential oil from patchouli accessions harvested over four seasons

The genus Pogostemon of the Lamiaceae family includes several species known for their medicinal and aromatic properties. The species P. cablin is especially notable because the essential oil extracted from its leaves is internationally important and valuable, principally for the perfume and cosmetic industries. Because multiple factors can affect the chemical composition of the essential oil, the aim of this work was to evaluate the chemical variations in the essential oils of nine Pogostemon accessions harvested over four seasons. Two Pogostemon accessions (P. heyneanus, but received as P. cablin) and seven P. cablin accessions from different sources were evaluated. The transplants were planted in January 2008, and the harvests were conducted in May, August, and November 2008 and February 2009. The chemical composition of the essential oils was evaluated quantitatively and qualitatively. Patchoulol was the major compound from the four harvests of all of the P. cablin accessions. The principal compound from the accessions POG-001 and POG-006 was β-pinene. Two clusters were detected by multivariate analyses of the four harvests. Cluster I was formed by the accessions POG-001 and POG-006 (P. heyneanus), and Cluster II was formed by the accessions of P. cablin (POG-002, POG-014, POG-015, POG-016, POG-019, POG-021, and POG-022).     

Repellency of selected biorational insecticides to potato psyllid, Bactericera cockerelli (Hemiptera: Psyllidae)

Bactericera cockerelli has recently become a major concern because of its direct feeding and vectoring of bacterial diseases in many solanaceous crops. The repellency of four biorational insecticides, MOI-201 (a Chinese medicine plant extract), Requiem (a plant extract of Chenopodium ambrosioides), BugOil (a mixture of four plant essential oils), and SunSpray oil (a mineral oil), to B. cockerelli adults was tested on tomato. In a no-choice test, all the insecticides had significant repellency to adults and deterred oviposition as compared with untreated controls. Of the four insecticides, the two oils showed a stronger repellency to adults and deterred oviposition more strongly than Requiem or MOI-201. In a choice test, all insecticides had significant repellency to adults and deterred oviposition compared to untreated controls. Of the four tested insecticides, <1 adults and no eggs were found on the leaves treated with SunSpray Oil, BugOil or Requiem 3 d after treatment. The repellency rates of these three insecticides were 77.2–95.4%. MOI-201 also repelled adults significantly and deterred oviposition compared to untreated controls even though it was the least effective insecticide among the four evaluated. In conclusion, all four insecticides tested showed significant repellency to B. cockerelli adults and deterred oviposition, especially the two oils. The overall repellency to potato psyllid adults can be arranged in a descending order of SunSpray oil > BugOil > Requiem > MOI-201. These insecticides could be used in integrated pest management programs targeted against the potato psyllid on solanaceous crops.     

Autoclaved spent substrate of hatakeshimeji mushroom (Lyophyllum decastes Sing.) and its water extract protect cucumber from anthracnose

The protective effect of fresh spent mushroom substrate (SMS) of hatakeshimeji (Lyophyllum decastes Sing.), a popular culinary-medicinal mushroom, and its water extract against anthracnose of cucumber was investigated. Plants were treated with water extract from SMS or autoclaved water extract by spraying the whole plant or by dipping the first true leaf, and inoculated with Colletotrichum orbiculare seven days later. Plants treated with either of the extracts showed a significant reduction of necrotic lesions. On the other hand, when plants were grown in a mixture (1:2, v/v) of SMS or autoclaved SMS and soil, a disease reduction of over 70% was observed in autoclaved SMS. The water extract showed no antifungal activity against spore germination and mycelial growth of the pathogen. Real-time PCR analyses of chitinase and β-1,3-glucanase genes revealed a significant increase of expressions after 24 h of pathogen inoculation in water extract-treated plants compared with the control plants. These results suggest that water-soluble and heat-stable compounds in SMS enhance the state of systemic acquired resistance and protect cucumbers from anthracnose. Thus, the use of SMS for disease control may offer a new technology for the recycling and management of waste from mushroom cultivation.     

Water deficit effects on caraway (Carum carvi L.) growth, essential oil and fatty acid composition

The Mediterranean region suffers of drought which affects plant behaviour regarding biochemical responses. Accordingly, the effects of water deficit on growth, essential oil and fatty acid composition of caraway (Carum carvi L.) seeds were investigated. Plants were treated with different levels of water deficit: control, moderate water deficit and severe water deficit. Plant growth (height, fresh and dry matter weight) was significantly reduced by severe water deficit. This last caused also important reductions of the seed yield and yield components. Drought decreased significantly seed total fatty acid contents and particularly the petroselinic ones whose proportions decreased significantly by 12.17 and 18.47%, in comparison with the control, under moderate water deficit and severe water deficit, respectively. Besides, moderate water deficit increased the essential oil yield (expressed as g/100 g on the basis of dry matter weight). The main essential oil constituents were carvone and limonene which showed an increasing of their contents under water deficit levels. Thus, water deficit induced a significant reduction in growth parameters and fatty acid content, and an increase in the essential oil compounds. These bioactive compounds have been required in many industrial products.     

Variation in concentrations of major bioactive compounds in Hypericum perforatum L. from Lithuania

The growing demand for the medicinal plant, Hypericum perforatum, is not being met by available supply in many countries. The conditions for obtaining quality crude drug should be thoroughly studied to ensure adequate supply. The current study describes the variation of major bioactive compounds in different accessions of H. perforatum (Hypericaceae) in two floral development stages. Two extraction procedures were evaluated for the quantification of the major bioactive compounds in H. perforatum. The Soxhlet extraction technique was demonstrated to be more effective with higher extraction yields. The contents of rutin, hyperoside, quercitrin, quercetin, and 3,8″-biapigenin were determined by high performance liquid chromatography (HPLC). This procedure was used to establish the variation in the contents of flavonoids in the field-growing H. perforatum and to evaluate factors predetermining that variation with some practical implications for utilization. A significant difference in flavonoid contents between two floral development stages was detected. The results of the study showed that rutin prevailed during the budding stage, whereas quercitrin, quercetin, and 3,8″-biapigenin were dominant during the full-flowering stage. The contents of hyperoside were similar in both developmental stages of the plants. The highest amounts of the most bioactive compounds were observed in the full-flowering stage, which could therefore be considered the best stage for the harvesting of the raw material of H. perforatum, known as Hyperici herba in pharmaceutics. The study revealed evident intraspecific variations in the flavonoid contents of H. perforatum. Several chemotypes were recognized by qualitative and quantitative differences in flavonoids. Qualitative analysis of the flavonoid contents confirmed the presence of the chemotype of H. perforatum containing no rutin, though the chemotype with higher levels of both rutin and hyperoside was more frequent. The accessions of H. perforatum also showed remarkable differences in chemical composition depending on the origin of plants. Therefore, employing the correct developmental stage for the harvesting of the selected accessions of H. perforatum is highly recommended for the quality production of the drug Hyperici herba.