In Vitro and In Silico Evaluation of ACE2 and LOX Inhibitory Activity of Origanum Essential Oils and Carvacrol.

Origanum spp. are used both for culinary purposes and for their biological activities. In this study, commercial Origanum majorana, Origanum minutiflorum, Origanum vulgare, and Origanum onites essential oils and their prominent constituent carvacrol were evaluated for their in vitro and in silico angiotensin-converting enzyme 2 and lipoxygenase enzyme inhibitory potentials. The essential oils were analysed by gas chromatography-flame ionisation detection and gas chromatography-mass spectrometry, where carvacrol was identified as the major component (62 - 81%), confirming the quality. In vitro enzyme inhibition assays were conducted both with the essential oils (20 µg/mL) and with carvacrol (5 µg/mL). The comparative values of angiotensin-converting enzyme 2 percent inhibition for O. majorana, O. minutiflorum, O. vulgare, and O. onites essential oils were determined as 85.5, 79.1, 74.3, and 42.8%, respectively. As a result of the enzyme assays, carvacrol showed 90.7% in vitro angiotensin-converting enzyme 2 inhibitory activity. The in vitro lipoxygenase inhibition of the essential oils (in the same order) was 89.4, 78.9, 81.1, and 73.5%, respectively, where carvacrol showed 74.8% inhibition. In addition, protein-ligand docking and interaction profiling was used to gain structural and mechanistic insights into the angiotensin-converting enzyme 2 and lipoxygenase inhibitory potentials of major Origanum essential oil constituents. The in silico findings agreed with the significant enzyme inhibition activity observed in vitro. Further in vivo studies are suggested to confirm the safety and efficacy of the oils.

Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey.

Teucrium species that belong to the family Lamiaceae have been traditionally used for their medicinal properties. T. polium is one the most widespread members of the genus for its use in the treatment of several diseases. In this study, the essential oil and phenolic composition of the aerial parts from T. polium were assessed by GC-FID, GC/MS, and LC-MS/MS as well as for its total phenolic content. Several extracts such as n-hexane, chloroform, methanol, and infusion were prepared and their antimicrobial, antioxidant, and also acetylcholinesterase activities were studied. According to GC/MS results, ß -caryophyllene (8.8%), t-cadinol (6.2%), (E)-nerolidol (5%), α -cadinol (5.4%), and α-pinene (4.7%) were identified as main constituents of the essential oil. LC MS/MS analysis of the infusion and the methanol extract showed the presence of 15 phenolic compounds. Moreover, the total phenolic content of each sample was also determined and the infusion had the highest percentage of phenolics. To evaluate the antioxidant properties, the samples were tested by using DPPH" free radical scavenging, FRAP, and CUPRAC activity methods. The infusion showed the strongest radical scavenging activity, whereas n-hexane and chloroform extracts exhibited considerable reducing power effects. The MIC values for all of the examined microorganisms ranged from 15 to 2000 µg/mL with respect to antimicrobial activities.

Review of Studies on Phlomis and Eremostachys Species (Lamiaceae) with Emphasis on Iridoids, Phenylethanoid Glycosides, and Essential Oils.

As the sixth-largest Angiosperm family, Lamiaceae contains more than 245 genera and 7886 species that are distributed worldwide. It is also the third-largest family based on the number of taxa in Turkey where it is represented by 46 genera and 782 taxa with a high endemism ratio (44%). Besides, Lamiaceae are rich in plants with economic and medicinal value containing volatile and nonvolatile compounds. Many aromatic plants of Lamiaceae such as Salvia, Sideritis, Stachys, Phlomis, and Teucrium species are used in traditional herbal medicine throughout Turkey as well as in other Mediterranean countries. Salvia (Sage tea "Adaçayi"), Sideritis (Mountain tea "Dagçayi"), Stachys (Hairy Tea "Tüylü Çay"), and Phlomis (Turkish sage "Çalba or Salba") are the largest genera that are used as herbal teas. This review focuses on the volatile and nonvolatile compounds of Lamiaceae from the genera Phlomis and Eremostachys of the subfamily Lamioideae with emphasis on iridoids, phenylethanoid glycosides, and essential oils.

In vitro Anti-Leishmanial Activity of Essential Oils Extracted from Plants Growing in Northern Cyprus Against Leishmania tropica

Objective: Natural plant products are considered as a source of novel and effective compounds for the treatment of leishmaniasis. In this study, the in vitro activities of essential oils obtained from Origanum dubium (OD), Origanum majorana (OM), Salvia fruticosa (SF) and Laurus nobilis (LN) plants in Northern Cyprus were investigated against Leishmania tropica. Methods: Leishmania tropica strain (MHOM/TR/2012/CBCL-LT) was obtained. RPMI-1640 was added to 96-well plates in 100 µL aliquots, 100 µg/mL essential oil was added to the first well of each row and serial 2-fold dilutions were performed. A promastigote suspension was pipetted into all wells, and the plates were incubated. The promastigotes were enumerated using a haemocytometer. Results: OD essential oil was effective at killing all promastigotes at a minimum inhibitor height (MIC)=0.2 µg/mL and had high activity at the lowest concentrations. Both SF and LN oils had MIC=1.56 µg/mL and LD50=0.78 µg/mL. SF was observed to impair promastigote morphology at the lowest concentrations, while LN did not exert any effect at concentrations <0.2 µg/mL. OM essential oil was found to have a MIC=3.13 µg/mL and a LD50=1.56 µg/mL. Conclusion: All tested essential oils inhibited promastigotes of Leishmania tropica. OD essential oil demonstrated the highest anti-leishmanial activity. Amaç: Bitkilerden elde edilen dogal ürünlerin leishmaniasis tedavisi için yeni ve etkili bilesiklerin üretilmesine öncülük edecegi düsünülmektedir. Çalismamizda, Kuzey Kibris'ta yetisen Origanum dubium (OD), Origanum majorana (OM), Salvia fruticosa (SF) ve Laurus nobilis (LN) bitkilerinden elde edilen uçucu yaglarin Leishmania tropica'ya karsi in vitro etkinlikleri arastirilmistir. Yöntemler: Çalismamizda, Leishmania tropica susu (MHOM/TR/2012/CBCL-LT) kullanildi. Düz tabanli 96'lik plaklarda, tüm kuyucuklara 100 µL RPMI-1640 ve ilk kuyucuklara 100 µg/mL uçucu yaglar eklenerek, seri dilüsyonlari yapildi. Ardindan tüm kuyucuklara Leishmania tropica promastigot süspansiyonundan pipetlendi ve inkübe edildi. Hemositometre yöntemiyle promastigotlarin sayisi incelendi. Bulgular: OD yaginin minimum inhibitör konsantrasyonu (MIK)=0,2 µg/mL'de tüm promastigotlari öldürürken, en düsük konsantrasyonlarda bile etkili oldugu görülmüstür. SF ve LN uçucu yaglarinin ikisinde de MIK=1,56 µg/mL, LD50=0,78 µg/mL olarak saptanmistir. SF'nin en düsük konsantrasyonlarinin bile promastigot morfolojisini bozdugu görülürken, Laurus nobilis'in ise 0,2 µg/mL'den sonraki konsantrasyonlarda etkisini kaybettigi belirlenmistir. OM uçucu yaginin MIK=3,13 µg/mL, LD50=1,56 µg/mL oldugu görülmüstür. Sonuç: Kullanilan tüm uçucu yaglarin Leishmania tropica promastigotlarini inhibe ettigi görülürken, en yüksek anti-leishmanial etkinlik Origanum dubium uçucu yaginda bulunmustur.

Insecticidal and Biting Deterrent Activities of Magnolia grandiflora Essential Oils and Selected Pure Compounds against Aedes aegypti.

In our natural products screening program for mosquitoes, we tested essential oils extracted from different plant parts of Magnolia grandiflora L. for their insecticidal and biting deterrent activities against Aedes aegypti. Biting deterrence of seeds essential oil with biting deterrence index value of 0.89 was similar to N,N-diethyl-3-methylbenzamide (DEET). All the other oils were active above the solvent control but the activity was significantly lower than DEET. Based on GC-MS analysis, three pure compounds that were only present in the essential oil of seed were further investigated to identify the compounds responsible for biting deterrent activity. 1-Decanol with PNB value of 0.8 was similar to DEET (PNB = 0.8), whereas 1-octanol with PNB value of 0.64 showed biting deterrence lower than 1-decanol and DEET. The activity of 1-heptanol with PNB value of 0.36 was similar to the negative control. Since 1-decanol, which was 3.3% of the seed essential oil, showed biting deterrence similar to DEET as a pure compound, this compound might be responsible for the activity of this oil. In in vitro A & K bioassay, 1-decanol with MED value of 6.25 showed higher repellency than DEET (MED = 12.5). Essential oils of immature and mature fruit showed high toxicity whereas leaf, flower, and seeds essential oils gave only 20%, 0%, and 50% mortality, respectively, at the highest dose of 125 ppm. 1-Decanol with LC50 of 4.8 ppm was the most toxic compound.

Antiprotozoal Activity of Turkish Origanum onites Essential Oil and Its Components.

Essential oil of Origanum species is well known for antimicrobial activity, but only a few have been evaluated in narrow spectrum antiprotozoal assays. Herein, we assessed the antiprotozoal potential of Turkish Origanum onites L. oil and its major constituents against a panel of parasitic protozoa. The essential oil was obtained by hydrodistillation from the dried herbal parts of O. onites and analyzed by Gas Chromatography-Flame Ionization Detector (GC-FID) and Gas Chromatography coupled with Mass Spectrometry (GC-MS). The in vitro activity of the oil and its major components were evaluated against Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum. The main component of the oil was identified as carvacrol (70.6%), followed by linalool (9.7%), p-cymene (7%), γ-terpinene (2.1%), and thymol (1.8%). The oil showed significant in vitro activity against T. b. rhodesiense (IC50 180 ng/mL), and moderate antileishmanial and antiplasmodial effects, without toxicity to mammalian cells. Carvacrol, thymol, and 10 additional abundant oil constituents were tested against the same panel; carvacrol and thymol retained the oil's in vitro antiparasitic potency. In the T. b. brucei mouse model, thymol, but not carvacrol, extended the mean survival of animals. This study indicates the potential of the essential oil of O. onites and its constituents in the treatment of protozoal infections.

Assessment of selected Saudi and Yemeni plants for mosquitocidal activities against the yellow fever mosquito Aedes aegypti.

As part of our continuing investigation for interesting biological activities of native medicinal plants, thirty-nine plants, obtained from diverse areas in Saudi Arabia and Yemen, were screened for insecticidal activity against yellow fever mosquito Aedes aegypti (L.). Out of the 57 organic extracts, Saussurea lappa, Ocimum tenuiflorum, Taraxacum officinale, Nigella sativa, and Hyssopus officinalis exhibited over 80% mortality against adult female Ae. aegypti at 5 µg/mosquito. In the larvicidal bioassay, the petroleum ether extract of Aloe perryi flowers showed 100% mortality at 31.25 ppm against 1st instar Ae. aegypti larvae. The ethanol extract of Saussurea lappa roots was the second most active displaying 100% mortality at 125 and 62.5 ppm. Polar active extracts were processed using LC-MS/MS to identify bioactive compounds. The apolar A. perryi flower extract was analyzed by headspace SPME-GC/MS analysis. Careful examination of the mass spectra and detailed interpretation of the fragmentation pattern allowed the identification of various biologically active secondary metabolites. Some compounds such as caffeic and quinic acid and their glycosides were detected in most of the analyzed fractions. Additionally, luteolin, luteolin glucoside, luteolin glucuronide and diglucuronide were also identified as bioactive compounds in several HPLC fractions. The volatile ketone, 6-methyl-5-hepten-2-one was identified from A. perryi petroleum ether fraction as a major compound.

Repellency of the Origanum onites L. essential oil and constituents to the lone star tick and yellow fever mosquito.

The oregano, Origanum onites L., essential oil (EO) was tested in laboratory behavioural bioassays for repellent activity against Amblyomma americanum (L.) and Aedes aegypti (L.). The O. onites EO was characterised using GC-FID and GC-MS. Carvacrol (75.70%), linalool (9.0%), p-cymene (4.33%) and thymol (1.9%) were the most abundant compounds. At a concentration of 0.413 mg oil/cm2 of filter paper, O. onites EO repelled 100% of the ticks tested and at 0.103 mg oil/cm2 of filter paper, 66.7% of the ticks were repelled. At 0.075 mg oil/cm2 filter paper, thymol repelled 66.7% of the ticks compared to 28.7% by carvacrol at that same concentration. Against Ae. aegypti, O. onites EO was repellent at the minimum effective dosage (MED) of 0.011 (±0.00) mg/cm2 in the cloth patch assay compared to the reference control, N,N-dimethyl-3-methylbenzamide (DEET) with a MED = 0.007 ± (0.003) mg/cm2.

Essential Oils of Echinophora lamondiana (Apiales: Umbelliferae): A Relationship Between Chemical Profile and Biting Deterrence and Larvicidal Activity Against Mosquitoes (Diptera: Culicidae).

The essential oils from the flower, leaf, and stem of Echinophora lamondiana B.Yildiz et Z.Bahcecioglu were analyzed by gas chromatography-flame ionization detection and gas chromatography-mass spectrometry. In total, 41, 37, and 44 compounds were identified, which accounted for 98.0, 99.1, and 97.0% of flower, leaf, and stem essential oils, respectively. The monoterpenic hydrocarbons were found to be high in all samples of the essential oils. The major components of essential oils from flower, leaf, and stem of E. lamondiana were δ-3-carene (61.9, 75.0, and 65.9%, respectively), α-phellandrene (20.3, 14.1, and 12.8%, respectively), and terpinolene (2.7, 3.3, and 2.9%, respectively). Flower and leaf essential oils and terpinolene produced biting deterrence similar to 25 nmol/cm(2) N, N-diethyl-meta-toluamide (DEET; 97%) against Aedes aegypti (L.) and Anopheles quadrimaculatus Say. Compounds (+)-δ-3-carene, (R)-(-)-α-phellandrene, and water-distilled essential oils were significantly less repellent than DEET. Among essential oils, leaf oil was the least toxic of the oils, with an LC50 value of 138.3 ppm, whereas flower essential oil killed only 32% larvae, and no mortality of stem oil at highest tested dosages against Ae aegypti was observed. Terpinolene and α-phellandrene showed higher toxicity than δ-3-carene in both the species. In contrast to Ae. aegypti, all the essential oils showed toxicity in An. quadrimaculatus, and toxicity was higher in leaf oil than the other two oils. These results could be useful in finding new, safe, and more effective natural biopesticides and biting deterrent or repellents against Ae. aegypti.

Inhibition of Human Neutrophil Responses by the Essential Oil of Artemisia kotuchovii and Its Constituents.

Essential oils were obtained by hydrodistillation of the flowers+leaves and stems of Artemisia kotuchovii Kupr. (AKEO(f+l) and AKEO(stm), respectively) and analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The primary components of the oils were estragole, (E)- and (Z)-ß-ocimenes, methyleugenol, limonene, spathulenol, ß-pinene, myrcene, and (E)-methyl cinnamate. Seventy-four constituents were present at concentrations from 0.1 to 1.0%, and 34 compounds were identified in trace (<0.1%) amounts in one or both plant components. Screening of the essential oils for biological activity showed that AKEO(stm), but not AKEOf+l, inhibited N-formyl-Met-Leu-Phe (fMLF)-stimulated Ca(2+) flux and chemotaxis and phorbol-12-myristate-13-acetate (PMA)-induced reactive oxygen species (ROS) production in human neutrophils. Selected pure constituents, representing >96% of the AKEO(stm) composition, were also tested in human neutrophils and HL-60 cells transfected with N-formyl peptide receptor 1 (FPR1). One component, 6-methyl-3,5-heptadien-2-one (MHDO), inhibited fMLF- and interleukin 8 (IL-8)-stimulated Ca(2+) flux, fMLF-induced chemotaxis, and PMA-induced ROS production in human neutrophils. MHDO also inhibited fMLF-induced Ca(2+) flux in FPR1-HL60 cells. These results suggest that MHDO may be effective in modulating some innate immune responses, possibly by inhibition of neutrophil migration and ROS production.

Chemical composition and biological activity of four salvia essential oils and individual compounds against two species of mosquitoes.

The chemical compositions of essential oils obtained from four species of genus Salvia were analyzed by gas chromatography with a flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The main compounds identified from Salvia species essential oils were as follows: 1,8-cineole (71.7%), α-pinene (5.1%), camphor (4.4%), and ß-pinene (3.8%) in Salvia apiana; borneol (17.4%), ß-eudesmol (10.4%), bornyl acetate (5%), and guaiol (4.8%) in Salvia elegans; bornyl acetate (11.4%), ß-caryophyllene (6.5%), caryophyllene oxide (13.5%), and spathulenol (7.0%) in Salvia leucantha; α-thujene (25.8%), viridiflorol (20.4%), ß-thujene (5.7%), and camphor (6.4%) in Salvia officinalis. In biting-deterrent bioassays, essential oils of S. leucantha and S. elegans at 10 µg/cm(2) showed activity similar to that of DEET (97%, N, N-diethyl-m-toluamide) in two species of mosquitoes, whereas the activities of S. officinalis and S. apiana essential oils were lower than those of the other oils or DEET. Pure compounds ß-eudesmol and guaiol showed biting-deterrent activity similar to DEET at 25 nmol/cm(2), whereas the activity of 13-epi-manool, caryophyllene oxide, borneol, bornyl acetate, and ß-caryophyllene was significantly lower than that of ß-eudesmol, guaiol, or DEET. All essential oils showed larvicidal activity except that of S. apiana, which was inactive at the highest dose of 125 ppm against both mosquito species. On the basis of 95% CIs, all of the essential oils showed higher toxicity in Anopheles quadrimaculatus than in Aedes aegypti. The essential oil of S. leucantha with an LC50 value of 6.2 ppm showed highest toxicity in An. quadrimaculatus.

Chemical composition, larvicidal, and biting deterrent activity of essential oils of two subspecies of Tanacetum argenteum (Asterales: Asteraceae) and individual constituents against Aedes aegypti (Diptera: Culicidae).

Water-distilled essential oils from dried aerial parts of Tanacetum argenteum (Lam.) Willd. subsp. argenteum (Lam.) and T. argenteum (Lam.) Willd. subsp. canum (C. Koch) Grierson were analyzed by gas chromatography and gas chromatography-mass spectrometry. In total, 27 and 32 components were identified representing 97.2 and 98.7% of essential oils of subsp. argenteum and canum, respectively. Main compounds of T. argenteum subsp. argenteum were alpha-pinene (67.9%) and beta-pinene (4.8%), whereas alpha-pinene (53.6%), 1, 8-cineole (14.8%), and camphor (4.7%) were the major constituents of subsp. canum. Essential oil of T. argenteum subsp. canum at 10 microg/cm2 with Biting Deterrent Index (BDI) value of 0.73 showed activity similar to N,N-Diethyl-meta-toluamide (DEET) at 25 mol/cm2, whereas the activity of essential oil of subsp. argenteum was lower (BDI = 0.47) than subsp. canum and DEET. Based on 95% CIs, activity of beta-caryophyllene (BDI value = 0.54) and caryophyllene oxide (BDI = 0.66) were significantly lower than DEET. In larval bioassays, essential oil of T. argenteum subsp. argenteum showed LC50 value of 93.34 ppm, whereas T. argenteum subsp. canum killed only 40% of the larvae at the highest dose of 125 ppm. Among the pure compounds, beta-caryophyllene (LC50 = 26 ppm) was the most potent compound followed by caryophyllene oxide (LC50 = 29 ppm), which was also similar to (-)-beta-pinene (LC50 = 35.9 ppm) against 1-d-old Ae. aegypti larvae at 24-h post treatment. Compounds (-)-alpha-pinene and (+)-beta-pinene showed similar larvicidal activity. Activity of (+)-alpha-pinene with LC50 value of was similar to the essential oil of T. argenteum subsp. argenteum.

In vitro antioxidant properties and anthocyanin compositions of elderberry extracts.

In this study, dried elderberry fruits growing wild in Turkey were macerated using different solvents and an infusion was prepared according to traditional methods. All extracts were investigated for their total phenolic content, total monomeric anthocyanins, qualitative-quantitative determination of cyanidin-3-glucoside (by HPLC-UV analysis), anthocyanin compositions (by LC/MS-MS), free radical scavenging activity (DPPH and ABTS) and inhibition of ß-carotene/linoleic acid co-oxidation. An extract with 70% ethanol was found to be richer in cyanidin-3-glucoside when compared to the other extracts. The infusion was found to be as rich as the 70% ethanol extract. Ethanol and acetone extracts (both 70%) were found to be more active in the free radical activity and ß-carotene bleaching assays. Water extract showed good ABTS radical scavenging activity when compared with ascorbic acid.

Bioassay-guided investigation of two Monarda essential oils as repellents of yellow fever mosquito Aedes aegypti.

As part of an ongoing research program to identify active mosquito repellents, Monarda bradburiana Beck and Monarda fistulosa L. essential oils showed good repellent activity with minimum effective dosages (MED) of 0.055 ± 0.036 and 0.078 ± 0.027 mg/cm(2), respectively, compared to reference standard N,N-diethyl-3-methylbenzamide (DEET) (0.039 ± 0.014 mg/cm(2)). Systematic bioassay-guided fractionation of essential oils of both Monarda species was performed to identify the active repellent compounds, and isolated pure compounds were individually tested for repellency. Of the isolated compounds, carvacrol, thymol, eugenol, and carvacrol methyl ether were found to be the repellent compounds with MEDs in the range of 0.013-0.063 mg/cm(2). Active repellent compounds were also tested for larvicidal activity against 1-day-old Aedes aegypti larvae. Thymol was the best larvicide among the tested individual compounds (LD50 of 13.9 ppm). None of the individual compounds showed cytotoxicity against mammalian cells; however, the essential oils were toxic to all cell lines.

Phoenix dactylifera L. spathe essential oil: chemical composition and repellent activity against the yellow fever mosquito.

Date palm, Phoenix dactylifera L. (Arecaceae), grows commonly in the Arabian Peninsula and is traditionally used to treat various diseases. The aim of the present study was to identify chemical composition of the essential oil and to investigate the repellent activity. The essential oil of P. dactylifera was obtained by hydrodistillation from the spathe, a specialized leaf structure that surrounds the pollinating organs of the palm. The oil was subsequently analyzed by GC-FID and GC-MS. The oil showed promising repellent activity against yellow fever mosquito - Aedes aegypti. Sixteen components were characterized, constituting 99% of the oil. The main components were 3,4-dimethoxytoluene (73.5%), 2,4-dimethoxytoluene (9.5%), ß-caryophyllene (5.5%), p-cresyl methyl ether (3.8%), and caryophyllene oxide (2.4%). The minimum effective dosage (MED) for repellency for the P. dactylifera oil was 0.051mg/cm(2), which had moderately lower potency compared to reference standard N,N-diethyl-3-methylbenzamide, DEET (0.018mg/cm(2)) in the "cloth patch assay". The five major compounds were individually assayed for repellency to determine to what extent each is responsible for repellency from the oil. 3,4-Dimethoxytoluene and 2,4-dimethoxytoluene showed the best repellent activity with the same MED value of 0.063mg/cm(2), respectively. The results indicate that these two constituents which comprise a large proportion of the P. dactylifera oil (83%) are likely responsible for the observed repellent activity. In this aspect, the P. dactylifera spathe oil is a sustainable, promising new source of natural repellents.

Composition, mosquito larvicidal, biting deterrent and antifungal activity of essential oils of different plant parts of Cupressus arizonica var. glabra ('Carolina Sapphire').

Essential oils obtained by hydrodistillation of female cones (FC), male cones (MC), needle-twigs (NT) and wood-bark (WB) of 'Carolina Sapphire' [Cupressus arizonica var glabra (Sudw.) Little] were analyzed simultaneously by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS). The main constituents of the investigated essential oils were as follows: FC: alpha-pinene 68.5% and myrcene 11.9%; MC: alpha-pinene 22.5%, epi-zonarene 9.9%, zonarene 6.9%, limonene 6.8% and cadina-3,5-diene 6.1%; NT: alpha-pinene 20.7%, epi-zonarene 10.4%, zonarene 7.6%, limonene 5.9% umbellulone 5.8% and cadina-3,5-diene 5.8%; WB: alpha-pinene 40.7%, limonene 3.2% and umbellulone 2.9%. Essential oils were evaluated for antifungal activity against the strawberry anthracnose causing fungal plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides. Only WB essential oil showed moderate activity when compared with the commercial antifungal standards. Carolina Sapphire essential oils exhibited biting deterrent activity at 10 microg/cm2 with Biting Deterrence Index (BDI) values of 0.64, 0.59, 0.65 and 0.72, for FC, MC, NT and WB, respectively, and were significantly lower (P < or = 0.05) than the synthetic insect repellent, DEET (N,N-diethyl-meta-toluamide), at 25 nmol/cm2 against Aedes aegypti. The biting deterrence of NT and WB oils at 100 microg/cm2 with BDI values of 1.04 and 1.01, respectively, were similar, whereas the activity of MC (BDI = 0.88) and FC (BDI = 0.62) essential oils was lower than DEET at 25 nmol/cm2. Essential oil from FC with LD50 of 33.7 ppm was most toxic against 1-day-old Ae. aegypti larvae at 24-h post treatment. Female cone essential oil was significantly more toxic than MC (LD50 = 53.6 ppm), NT (LD50 = 55.5 ppm) and WB (LD50 = 44.6 ppm) essential oils.

Insecticidal and biting deterrent activity of rose-scented geranium (Pelargonium spp.) essential oils and individual compounds against Stephanitis pyrioides and Aedes aegypti.

BACKGROUND: Rose-scented geranium, Pelargonium spp., essential oils from the cultivars 'Bourbon', 'China', 'Egypt', 'Rober's Lemon Rose' and 'Frensham' were analyzed by GC-FID and GC-MS. A total of 136 compounds were identified from five essential oils, constituting 85.5-99.7% of the oils. Essential oils and pure compounds were evaluated for their insecticidal activity against Stephanitis pyrioides and larvicidal and biting deterrent activity against Aedes aegypti. RESULTS: All five geranium oils were toxic to S. pyrioides, and four of these five were more potent than malathion and neem. Trans-nerolidol (LD50 = 13.4 ppm) was the most toxic compound against one-day-old Ae. aegypti larvae, followed by geraniol (49.3 ppm), citronellol (49.9 ppm) and geranyl formate (58.5 ppm). Essential oil of cultivar 'Egypt' at 100 µg cm(-2) [biting deterrent index (BDI) = 0.8] showed the highest biting deterrent activity, followed by cultivars 'Frensham' (BDI = 0.76), 'China' (BDI = 0.72), 'Rober's Lemon Rose' (BDI = 0.63) and 'Bourbon' (BDI = 0.45) essential oils. Among the pure compounds, the biting deterrent activity of geranic acid (BDI = 0.99) was not significantly different from that of N,N-diethyl-m-toluamide (DEET). CONCLUSION: Essential oils and pure compounds showed insecticidal activity against S. pyrioides and Ae. aegypti. The high biting deterrent activity of geranic acid points to the need for further research.

Biotransformation of (-)-(R)-α-phellandrene: antimicrobial activity of its major metabolite.

Terpene derivatives converted by microbial biotransformation constitute an important resource for natural pharmaceutical, fragrance, and aroma substances. In the present study, the monoterpene α-phellandrene was biotransformed by 16 different strains of microorganisms (bacteria, fungi, and yeasts). The transformation metabolites were initially screened by TLC and GC/MS, and then further characterized by NMR spectroscopic techniques. Among the six metabolites characterized, 6-hydroxypiperitone, α-phellandrene epoxide, cis-p-menth-2-en-1-ol, and carvotanacetone, which originated from (-)-(R)-α-phellandrene, are reported for the first time in this study. Additionally, the substrate and the metabolite 5-p-menthene-1,2-diol were subjected to in vitro antibacterial and anticandidal tests. The metabolite showed moderate-to-good inhibitory activities (MICs=0.125 to >4 mg/ml) against various bacteria and especially against Candida species in comparison with its substrate (-)-(R)-α-phellandrene and standard antimicrobial agents.

Natural product studies of U.S. endangered plants: volatile components of Lindera melissifolia (Lauraceae) repel mosquitoes and ticks.

The number of endangered plant species in the U.S. is significant, yet studies aimed towards utilizing these plants are limited. Ticks and mosquitoes are vectors of significant pathogenic diseases of humans. Repellents are critical means of personal protection against biting arthropods and disease transmission. The essential oil and solvent extracts from Lindera melissifolia (Walt.) Blume (Lauraceae) (pondberry) drupes were gathered and analyzed by GC and GC-MS. The essential oil obtained from this endangered plant showed a significant dose dependent repellency of ticks and a moderate mosquito repellent effect while the subsequent hexanes extract was completely ineffective. Fractional freezing enriched the tick repellent components of the essential oil. Several known tick repellent components were recognized by the GC-MS comparison of the resulting fractions and ß-caryophyllene, α-humulene, germacrene D and ß-elemene warrant evaluations for tick repellency. Identifying pondberry as a potential renewable source for a broad spectrum repellent supports efforts to conserve similar U.S. endangered or threatened plant species.

Anticandidal activity of the essential oil of Nepeta transcaucasica Grossh.

Hydrodistallation of the aerial parts of Nepeta transcaucasica Grossh. (Lamiaceae), collected in Agri, Dogubayazit Province, afforded an essential oil that was characterized by GC and GC/MS analyses. Twenty-seven compounds, representing 97.69% of the total oil composition, were identified, and 4aα,7α,7aß-nepetalactone (1; 39%), 4aα,7α,7aα-nepetalactone (2; 28%), and germacrene D (3; 15%) constituted the major components. The anticandidal effects of the oil were evaluated against seven Candida strains by using the broth microdilution method. The oil showed good inhibitory effects against C. glabrata and C. tropicalis at minimal inhibitory concentrations (MICs) of 0.09 and 0.375 mg/ml, respectively.