Utilization of nutmeg (Myristica fragrans Houtt.) seed hydrodistillation time to produce essential oil fractions with varied compositions and pharmacological effects

© 2020 by the authors. Licensee MDPI, Basel, Switzerland. The intent of this study was to utilize distillation timeframes (DT) of nutmeg (Myristica fragrans) essential oil (EO) to generate fractions with differential chemical compositions and bioactivity. Ten fractions were captured at the following distillation timeframes: 0.0–0.5, 0.5–1.0, 1.0–2.5, 2.5–5.0, 5.0–10, 10–30, 30–60, 60–90, 90–120, and 120–240 min. In addition, a control EO was collected from a straight 0–240 min non-stop distillation. ANOVA and advanced regression modeling revealed that the produced EO fractions possess substantial variation in the concentration of potentially desired compounds. The concentrations (%) of α-phellandrene, 3-carene, p-cymene, limonene, α-thujene, α-pinene, camphene, sabinene, β-pinene, and myrcene decreased, while the concentrations (%) of α-terpinene, γ-terpinene, terpinolene, and myristicin increased in later DT fractions. Nutmeg EO showed some antimalarial activity against Plasmodium falciparum D6, but did not exhibit significant antifungal activity. In general, nutmeg seed oil yields increased with an increase of DT. These results may be utilized by industries using nutmeg EO

Essential Oil Yield and Composition of the Balkan Endemic Satureja pilosa Velen. (Lamiaceae)

© 2020 by the authors. Satureja pilosa Velen. senso lato is a Balkan endemic plant that is not well characterized and is found on rocky outcrops of limestone base in Stara Planina (the Balkan Mountains) and the Rhodope Mountains. The objective of this study was to assess the variability of essential oil (EO) content and composition of S. pilosa collected at 33 locations across the Balkan and Rhodope Mountains in Bulgaria using advanced statistical methods including cluster analysis. The EO content in dried aboveground biomass varied from 0.52% to 2.03%. More than 21 EO constituents were identified, belonging to the groups of monoterpenes and sesquiterpenes. The monoterpenes were the predominant class, comprising 84.8% to 96.1% of the total EO. Thymol and carvacrol were the major constituents of the phenolic monoterpenoids. Thymol varied from 36.6% to 67.1% and carvacrol varied from 52.4% to 93.0% of the total oil. p‐Cymene also varied widely, from 9.6%–34.0%. There were significant variations between locations and within a location in the EO content and composition. This study identified several chemotypes: (1) thymol and p‐cymene; (2) thymol, p-cymene and γ‐terpinene; (3) carvacrol and p‐cymene; (4) carvacrol, p‐cymene and γ‐terpinene; and (5) carvacrol. This is the first comprehensive study on the endemic plant S. pilosa that identified several chemotypes based on the EO composition. The S. pilosa EO from the five different chemotypes exhibited larvicidal and mosquito repellent activity against Aedes aegypti. The identified chemotypes can be utilized for the development of new varieties with desirable compositions to meet specific industry needs and new mosquito management control products

Essential Oil Yield, Composition, and Bioactivity of Sagebrush Species in the Bighorn Mountains

Sagebrush (Artemisia spp.) are dominant wild plants in large areas of the U.S., Canada and Mexico, and they include several species and subspecies. The aim was to determine if there are significant differences in essential oil (EO) yield, composition, and biological activity of sagebrush within the Bighorn Mountains, U.S. The EO yield in fresh herbage varied from 0.15 to 1.69% for all species, including 0.25–1.69% in A. tridentata var. vaseyana, 0.64–1.44% in A. tridentata var. tridentata, 1% in A. tridentata var. wyomingensis, 0.8–1.2% in A. longifolia, 0.8–1% in A. cana, and 0.16% in A. ludoviciana. There was significant variability in the EO profile between species, and subspecies. Some EO constituents, such as α-pinene (0–35.5%), camphene (0–21.5%), eucalyptol (0–30.8%), and camphor (0–45.5%), were found in most species and varied with species and subspecies. The antioxidant capacity of the EOs varied between the species and subspecies. None of the sagebrush EOs had significant antimicrobial, antimalarial, antileishmanial activity, or contained podophyllotoxin. Some accessions yielded EO with significant concentrations of compounds including camphor, eucalyptol, cis-thujone, α-pinene, α-necrodol-acetate, fragranol, grandisol, para-cymene, and arthole. Therefore, chemotypes can be selected and possibly introduced into culture and be grown for commercial production of these compounds to meet specific industry needs

Grinding and Fractionation during Distillation Alter Hemp Essential Oil Profile and Its Antimicrobial Activity

The hypothesis of this study was that we can modify the essential oil (EO) profile of hemp (Cannabis sativaL.) and obtain fractions with differential composition and antimicrobial activity. Therefore, the objective was to evaluate the effects of grinding of hemp biomass before EO extraction and fractionation during distillation on EO profile and antimicrobial activity. The study generated a several EO fractions with a diversity of chemical profile and antimicrobial activity. The highest concentrations of beta-pinene and myrcene in the EO can be obtained in the 5-10 min distillation time (DT) of ground material or in the 80-120 min DT of nonground material. High delta-3-carene and limonene EO can be obtained from 0-5 min DT fraction of nonground material. High eucalyptol EO can be sampled either in the 0-5 min DT of the ground material or in the 80-120 min of nonground material. Overall, the highest concentrations of beta-caryophyllene,alpha-(E)-bergamotene, (Z)-beta-farnesene,alpha-humulene, caryophyllenyl alcohol, germacrene D-4-ol, spathulenol, caryophyllene oxide, humulene epoxide 2,beta-bisabolol,alpha-bisabolol, sesquiterpenes, and cannabidiol (CBD) can be obtained when EO is sampled in the 80-120 min DT and the material is nonground. Monoterpenes in the hemp EO can be increased twofold to 85% by grinding the material prior to distillation and collecting the EO in the first 10 min. However, grinding resulted in a slight but significant decrease in the CBD concentration of the EO. CBD-rich oil can be produced by collecting at 120-180 min DT. Different EO fractions had differential antimicrobial activity. The highest antimicrobial activity of EO fraction was found againstStaphylococcus aureussubsp.aureus. THC-free EO can be obtained if the EO distillation is limited to 120 min. The results can be utilized by the hemp processing industry and by companies developing new hemp EO-infused products, including perfumery, cosmetics, dietary supplements, food, and pharmaceutical industries

Micronutrients in the Soil and Wheat: Impact of 84 Years of Organic or Synthetic Fertilization and Crop Residue Management

Crop residues are an important source of plant nutrients. However, information on the various methods of residue management on micronutrients in soil and wheat (Triticum aestivum L.) over time is limited. A long-term (84-year) agroecosystem experiment was assessed to determine the impact of fertilizer type and methods of crop residue management on micronutrients over time under dryland winter wheat-fallow rotation. The treatments were: no N application with residue burning in fall (FB), spring (SB), and no residue burn (NB); 45 kg N ha−1 with SB and NB; 90 kg N ha−1 with SB and NB; pea vines; and farmyard manure (FYM) and a nearby undisturbed grass pasture (GP). Wheat grain, straw, and soil samples from 1995, 2005, and 2015 were used to determine tissue total and soil Mehlich III extractable Mn, Cu, B, Fe, and Zn, and soil pH. After 84 years, extractable Mn and B in the top 10 cm of soil decreased in all plots, except for B in FYM and SB. The FYM plots had the highest extractable Mn (114 mg kg−1) in the top 10 cm soil; however, it declined by 33% compared to the GP (171 mg kg−1). Extractable Zn in the top 10 cm of soil increased with FYM while it decreased with inorganic N application in 2015; however, total Zn in grain increased by 7% with inorganic N (90 kg ha−1) application compared to FYM application. The results suggest that residue management had similar impact on soil micronutrients. Inorganic N and FYM application can be integrated to reduce micronutrient losses from cultivatio

EFFECT OF PLANTING DATE, NITROGEN RATE, AND HYBRID ON SUNFLOWER

Sunflower is a potential crop for the southeastern United States for production of cooking oil or biodiesel. In 2007, we evaluated the effect of planting date (PD, 20 April, 20 May, and 20 June), nitrogen (N) application rate (0, 67, 134, and 202 kg ha−1), and hybrid (‘DKF3875’, ‘DKF2990’, ‘DKF3510’, and ‘DKF3901’) on sunflower productivity and oil profile in four Mississippi locations, Newton, Starkville, and two sites in Verona. There was a trend of increased oleic acid concentration with earlier planting dates, especially in hybrids with lower oleic acid concentration. Earlier planting dates of ‘DKF3901’ and ‘DKF2990’ (the hybrid with the lowest oleic acid) actually had 200 to 300 g kg−1 higher concentration of oleic acid when grown in Mississippi vs. the original seed of the same hybrids used for planting and produced at a more northern latitude. This and a recent study in Mississippi suggest that modern hybrids could provide ample yields even when the N fertilization is relatively low

Industrial, CBD, and Wild Hemp: How Different Are Their Essential Oil Profile and Antimicrobial Activity?

Hemp (Cannabis sativa L.) is currently one of the most controversial and promising crops. This study compared nine wild hemp (C. sativa spp. spontanea V.) accessions with 13 registered cultivars, eight breeding lines, and one cannabidiol (CBD) hemp strain belonging to C. sativa L. The first three groups had similar main essential oil (EO) constituents, but in different concentrations; the CBD hemp had a different EO profile. The concentration of the four major constituents in the industrial hemp lines and wild hemp accessions varied as follows: beta-caryophyllene 11-22% and 15.4-29.6%; alpha-humulene 4.4-7.6% and 5.3-11.9%; caryophyllene oxide 8.6-13.7% and 0.2-31.2%; and humulene epoxide 2, 2.3-5.6% and 1.2-9.5%, respectively. The concentration of CBD in the EO of wild hemp varied from 6.9 to 52.4% of the total oil while CBD in the EO of the registered cultivars varied from 7.1 to 25%; CBD in the EO of the breeding lines and in the CBD strain varied from 6.4 to 25% and 7.4 to 8.8%, respectively. The concentrations of delta 9-tetrahydrocannabinol (THC) in the EO of the three groups of hemp were significantly different, with the highest concentration being 3.5%. The EO of wild hemp had greater antimicrobial activity compared with the EO of registered cultivars. This is the first report to show that significant amounts of CBD could be accumulated in the EO of wild and registered cultivars of hemp following hydro-distillation. The amount of CBD in the EO can be greater than that in the EO of the USA strain used for commercial production of CBD. Furthermore, this is among the first reports that show greater antimicrobial activity of the EO of wild hemp vs. the EO of registered cultivars. The results suggest that wild hemp may offer an excellent opportunity for future breeding and the selection of cultivars with a desirable composition of the EO and possibly CBD-rich EO production

Hydrodistillation Extraction Kinetics Regression Models for Essential Oil Yield and Composition in \u3ci\u3eJuniperus virginiana, J. excelsa\u3c/i\u3e, and \u3ci\u3eJ. sabina\u3c/i\u3e

The chemical profile and antioxidant capacity of Juniperus virginiana, J. excelsa, and J. sabina essential oil (EO) fractions as a function of time was the subject of this study. The hypothesis was that, capturing EO in sequential timeframes during hydrodistillation would generate fractions containing unique compositions and antioxidant capacity. In J. virginiana, the highest limonene (43%) was found in the 0–5 min oil fraction, with safrole (37%) being highest in the 10–20 and 20–40 min fractions, and elemol (34%) being highest in the 160–240 min fraction. In J. excelsa, α-pinene (34-36%) was the highest in the 0–5 min fraction and in the control (non-stop 0–240 min distillation) oil, limonene (39%) was the highest in the 0–10 min fractions and cedrol (50-53%) was the highest in the 40–240 min fractions. In J. sabina, sabinene (80%) was highest in the 0–3 min fraction. The highest antioxidant capacity of J. virginiana was demonstrated by the 5–10 min fraction; the one in J. sabina by the 3–10 min fraction; and, the one in J. excelsa, by the control. The kinetics regression models that were developed can predict EO composition of the three juniper species eluted at different timeframes. Various industries could benefit from the results from this study

Distillation Time as Tool for Improved Antimalarial Activity and Differential Oil Composition of Cumin Seed Oil

A steam distillation extraction kinetics experiment was conducted to estimate essential oil yield, composition, antimalarial, and antioxidant capacity of cumin (Cuminum cyminum L.) seed (fruits). Furthermore, regression models were developed to predict essential oil yield and composition for a given duration of the steam distillation time (DT). Ten DT durations were tested in this study: 5, 7.5, 15, 30, 60, 120, 240, 360, 480, and 600 min. Oil yields increased with an increase in the DT. Maximum oil yield (content, 2.3 g/100 seed), was achieved at 480 min; longer DT did not increase oil yields. The concentrations of the major oil constituents α-pinene (0.14–0.5% concentration range), β-pinene (3.7–10.3% range), γ-cymene (5–7.3% range), γ-terpinene (1.8–7.2% range), cumin aldehyde (50–66% range), α-terpinen-7-al (3.8–16% range), and β-terpinen-7-al (12–20% range) varied as a function of the DT. The concentrations of α-pinene, β-pinene, γ-cymene, γ-terpinene in the oil increased with the increase of the duration of the DT; α-pinene was highest in the oil obtained at 600 min DT, β-pinene and γ-terpinene reached maximum concentrations in the oil at 360 min DT; γ-cymene reached a maximum in the oil at 60 min DT, cumin aldehyde was high in the oils obtained at 5–60 min DT, and low in the oils obtained at 240–600 min DT, α-terpinen-7-al reached maximum in the oils obtained at 480 or 600 min DT, whereas β-terpinen-7-al reached a maximum concentration in the oil at 60 min DT. The yield of individual oil constituents (calculated from the oil yields and the concentration of a given compound at a particular DT) increased and reached a maximum at 480 or 600 min DT. The antimalarial activity of the cumin seed oil obtained during the 0–5 and at 5–7.5 min DT timeframes was twice higher than the antimalarial activity of the oils obtained at the other DT. This study opens the possibility for distinct marketing and utilization for these improved oils. The antioxidant capacity of the oil was highest in the oil obtained at 30 min DT and lowest in the oil from 360 min DT. The Michaelis-Menton and the Power nonlinear regression models developed in this study can be utilized to predict essential oil yield and composition of cumin seed at any given duration of DT and may also be useful to compare previous reports on cumin oil yield and composition. DT can be utilized to obtain cumin seed oil with improved antimalarial activity, improved antioxidant capacity, and with various compositions

Oil yield and composition of Juniperus oxycedrus L. from Bulgaria and Serbia

Juniperus oxycedrus L. (Cupressaceae) is widely distributed in countries with a Mediterranean climate. The species is known for its large morphological and chemical variation and its debatable taxonomic status. The objective was to compare the essential oil content and composition of J. oxycedrus plants from Bulgaria and Serbia, and secondly, to quantify morphological variations of leaves. Тhe essential oil content in dried juniper leaves varied from 0.059% (Кopaonik, Serbia) to 0.240% (Markovo, Bulgaria). Around 40 EO constituents were identified, belonging to the groups of monoterpenes, sesquiterpenes, diterpenes, and phenylpropanoids. The monoterpene hydrocarbons and oxygenated monoterpenes were the predominant groups of compounds representing 36.8-66.2% of the total oil, with α-pinene, limonene, sabinene, β-pinene, β-myrcene being the major constituents of this group. Overall, α-pinene was the major oil constituent in plants from all locations. The second largest group was the one of sesquiterpenes (sesquiterpene hydrocarbons, oxygenated sesquiterpenes), ranging from 19.3 tо 33.6%. There was no significant difference between the mean leaf width of the six combinations of location and tree sex, and the overall mean width was 1.24 mm. However, there was a significant difference between the mean leaf lengths. This study contradicts recent reports that the European populations of J. oxycedrus east of Italy belong to a newly identified species J. deltoides. The same reports claimed that ”the leaf oil of J. deltoides was lower in α-pinene and higher in limonene compared to J. oxycedrus”. In this study, none of the studied populations had a higher concentration of limonene than that of α-pinene. Therefore, this study demonstrated that the flora of the two countries includes indeed J. oxycedrus