Journal articles: 'Piperitone'

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Milenković, Marina, Jelena Stošović, and Violeta Slavkovska. "Synergy between Essential Oils of Calamintha Species (Lamiaceae) and Antibiotics." Natural Product Communications 13, no. 3 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300325.

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The subject of the study was the investigation of the chemical composition and antimicrobial activity of the essential oils (EOs) isolated from Calamintha sylvatica, C. vardarensis, C. nepeta and C. glandulosa, as well as their antibacterial activity in combination with antibiotics. The quantitative and qualitative analysis of EOs was performed using the GC/FID and GC/MS methods. The antimicrobial activity of EOs against six standard bacterial strains and one strain of yeast was tested using the broth microdilution method, while the antimicrobial activity of a combination of essential oils and gentamicin/ciprofloxacin was tested by the checkerboard method. The dominant components (> 10%) of the essential oils were: cis-piperitone epoxide and menthone ( C. sylvatica), pulegone and menthone ( C. vardarensis), pulegone and piperitenone ( C. nepeta), pulegone, piperitenone, menthone and piperitone ( C. glandulosa). EOs did not exhibit significant antimicrobial activity except the essential oil of C. vardarensis which was selectively active against Staphylococcus aureus (MIC - 21.25 μg/mL). The overall effect of essential oil-antibiotic combinations varied from synergistic (FICI ≤ 0.5) to antagonistic (FICI ≥ 2) depending on the bacterial strain tested.

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Fuchs, Sabine, Andrea Gross, Thomas Beck, and Armin Mosandl. "Monoterpene biosynthesis inMentha�piperita L.: bioconversion of piperitone and piperitenone." Flavour and Fragrance Journal 15, no. 2 (2000): 84–90. http://dx.doi.org/10.1002/(sici)1099-1026(200003/04)15:2<84::aid-ffj870>3.0.co;2-v.

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Barrientos Ramírez, Lucia, José Antonio Silva Guzmán, Edison Antonio Osorio Muñoz, et al. "Chemical Composition, Antioxidant Properties, and Antibacterial Activity of Essential Oils of Satureja macrostema (Moc. and Sessé ex Benth.) Briq." Molecules 28, no. 12 (2023): 4719. http://dx.doi.org/10.3390/molecules28124719.

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Satureja macrostema is a plant that is located in various regions of Mexico and is used in a traditional way against illness. Essential oils (EOs) were obtained from leaves Satureja macrostema and the chemical composition was evaluated by gas chromatography–mass spectrometry (GC-MS). The antioxidant effect of the oil was assayed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and by Trolox Equivalent Antioxidant Capacity (TEAC). In vitro antibacterial activity against Escherichia coli and Staphylococcus aureus was determined using a broth microdilution assay and thin layer chromatography–direct bioautography (TLC-DB) to identify active antibacterial compounds. The EOs analysis showed 21 compounds, 99% terpenes, and 96% oxygenated monoterpenes, with trans-piperitone epoxide (46%), cis-piperitone epoxide (22%), and piperitenone oxide (11%) as more abundant compounds. Likewise, S. macrostema EOs showed an antioxidant activity of DPPH = 82%, with 50% free radical scavenging (IC50) = 7 mg/mL and TEAC = 0.005, an antibacterial effect against E. coli of 73% inhibition, and 81% over S. aureus at dose of 100 µL of undiluted crude oil. The TLC-DB assay showed that the most active compounds were derived from piperitone. The comparison with other studies on S. macrostema shows variability in the compounds and their abundances, which can be attributed to climatic factors and the maturity of plants with similar antioxidant and antibacterial activities.

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Shevchuk, O. M., S. A. Feskov, N. A. Bagrikova, and I. V. Tania. "Chemotypical diversity of Mentha longifolia L. oil." Bulletin of the State Nikitsky Botanical Gardens, no. 140 (November 17, 2021): 130–39. http://dx.doi.org/10.36305/0513-1634-2021-140-130-139.

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The article presents data on the content and composition of the essential oil of Mentha longifolia (L.) L. plants growing in natural phytocenoses on the territory of Crimea and Abkhazia. It was found that dry raw materials in two samples from natural phytocenoses of Crimea contain 1.27 and 1.76% of essential oil per wet weight, three samples from phytocenoses of Abkhazia contain less essential oil - 0.68, 0.98 and 1.19 %. About 60 components have been identified. Two new chemotypes were identified for Crimea: carvone-piperitone (mass fraction of carvone is 66.65%, piperitone oxide - 14.37%) and piperitone-sabinene (mass fraction of piperitone oxide - 55.19% and cis-sabinene hydrate - 23.51%), and two for Abkhazia: terpene-caryophyllene (α-terpinyl acetate - 51.48%; β-caryophyllene - 9.26%), piperitone-non-petalactone (piperitone oxide - 46.29%; nepetalactone 4aa, 7a, 7aa - 34.85%). These Mentha longifolia chemotypes are promising for use in the food, chemical, pharmaceutical and perfume industries.

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Sharopov, Farukh S., Muhamadsho A. Kukaniev, and William N. Setzer. "Composition of the Essential Oil of Origanum tyttanthum from Tajikistan." Natural Product Communications 6, no. 11 (2011): 1934578X1100601. http://dx.doi.org/10.1177/1934578x1100601137.

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Origanum tyttanthum Gontsch. was collected from two different sites in south-central Tajikistan. The essential oils were obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. A total of 52 compounds were identified representing 99.0-100% of total oil compositions. The major components of Origanum tyttanthum Gontsch. oil were carvacrol (34.3-59.2%), thymol (10.8-46.4%), p-cymene (0.7-7.3%), β-thujone (1.9-4.1%), piperitenone oxide (0.1-3.8%), γ-terpinene (0.3-3.5%), cis-piperitone epoxide (0.8-3.3%), carvacrol acetate (0.4-2.4%), menthone (0.6-2.1%) and borneol (1.0-2.3%).

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Malankina, Elena L., Alexey N. Кuzmenko, Aleksandr А. Evgrafov, Svetlana L. Evgrafova, Boris T. Zaychik та Aleksandr O. Ruzhitskiy. "СHEMICAL FEATURES OF VARIETIES LONG-LEAVED MINT (MENTHA LONGIFOLIA L.)". Lomonosov chemistry journal 66, № 1, 2025 (2025): 72–80. https://doi.org/10.55959/msu0579-9384-2-2025-66-1-72-80.

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The work determined the content of phenolic compounds and essential oil of 4 samples of of Mentha longifolia L. of various origins. As a result of the GC-MS analysis of the essential oil, signifi cant intraspecifi c variability in the component composition was revealed. Mentha longifolia L. accumulates predominantly oxygenated monoterpenes formed according to the following scheme limonene – piperitеnone – piperitone or pulegone, and their derivatives, in most cases without synthesizing in large quantities the following in the chain of biosynthesis, menthone and menthol, which are characteristic of peppermint.

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Chiou, Tai-Ying, Shiori Nomura, Masaaki Konishi, et al. "Conversion and Hydrothermal Decomposition of Major Components of Mint Essential Oil by Small-Scale Subcritical Water Treatment." Molecules 25, no. 8 (2020): 1953. http://dx.doi.org/10.3390/molecules25081953.

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Thermal stabilities of four major components (l-menthol, l-menthone, piperitone, and l-menthyl acetate) of Japanese mint essential oil were evaluated via subcritical water treatment. To improve experimental throughput for measuring compound stabilities, a small-scale subcritical water treatment method using ampoule bottles was developed and employed. A mixture of the four major components was treated in subcritical water at 180–240 °C for 5–60 min, and then analyzed by gas chromatography. The results indicated that the order of thermal resistance, from strongest to weakest, was: l-menthyl acetate, l-menthol, piperitone, and l-menthone. In individual treatments of mint flavor components, subsequent conversions of l-menthyl acetate to l-menthol, l-menthol to l-menthone, l-menthone to piperitone, and piperitone to thymol were observed in individual treatments at 240 °C for 60 min. As the mass balance between piperitone and thymol was low, the hydrothermal decomposition of the components was considered to have occurred intensely during, or after the conversion. These results explained the degradation of mint essential oil components under subcritical water conditions and provided the basis for optimizing the extraction conditions of mint essential oils using subcritical water.

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Sharopov, Farukh S., and William N. Setzer. "Chemical Diversity of Ziziphora Clinopodioides: Composition of the Essential oil of Z. clinopodioides from Tajikistan." Natural Product Communications 6, no. 5 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600524.

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The chemical composition of the essential oils of Ziziphora clinopodioides Lam. from the aerial flowering parts, collected during two different years, were obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. Forty-five components representing 100% and 94.7% of the total oil were identified. The main constituents of the essential oils were pulegone (72.8 and 35.0%), neomenthol (6.5 and 23.1%), menthone (6.2 and 13.3%), p-menth-3-en-8-ol (1.7 and 3.5%), piperitenone (2.6 and 1.1%) and piperitone (0.7 and 1.2%). A cluster analysis was carried out on the essential oil compositions of Z. clinopodioides.

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Sani, Abubakar, and Muhammad Sulaiman Rahama. "Synthesis of Piperitone Epoxide and P-Menthane-8-Thiol-3-One from Essential Oils." Volume 5 - 2020, Issue 8 - August 5, no. 8 (2020): 1153–58. http://dx.doi.org/10.38124/ijisrt20aug405.

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Buchu (Barosma betulina) is a small flowering plant found in the family Rutaceae in Western Cape of South Africa, Namibia and Australia, capable of growing up to 2 meters with a simple rounded leaf that produced essential oil of strong peppermint and sweetish smell. The Buchu oil as an essential oil consist of many chemical constituents, the main components includes piperitone, pulegone, piperitone epoxide, iso-menthone, P-menthane-8-thiol3-one, 4-diosphenol. The piperitone epoxide and Pmenthane-8-thiol-3-one constituents in Buchu oil have high commercial values, which extensively used as fragrances in perform, flavor, food additives, tonic and medicinal stimulant in modern medicine in the manufacture of insecticides, antimicrobial, antiinflammatory and antioxidant in cosmetic products. The extinction threat of the plant and chemistry benefit of these chemical constituents initiate scientist with synthetic route for synthesizing the compounds from Eucalyptus dives oil and pennyroyal oil, which are also an essential oils and abundant in nature. In the synthesis, purified piperitone and pulegone from the Eucalyptus dives oil and pennyroyal oil produced two enatiotiomers of piperitone epoxide and P-menthane-8- thiol-3-one respectively. The analytical analysis such infrared and GC-Mc conducted for the starting materials, synthesis processes and synthesize products showed results of significant value in terms chemical reactions and structural re-arrangement.

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LI, HENG YU, XIN CHAO LIU, XU BO CHEN, QI ZHI LIU, and ZHI LONG LIU. "Chemical Composition and Insecticidal Activities of the Essential Oil of Clinopodium chinense (Benth.) Kuntze Aerial Parts against Liposcelis bostrychophila Badonnel." Journal of Food Protection 78, no. 10 (2015): 1870–74. http://dx.doi.org/10.4315/0362-028x.jfp-15-089.

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Water-distilled essential oil from Clinopodium chinense (Labiatae) aerial parts at the flowering stage was analyzed by gas chromatography–mass spectrometry. Thirty-five compounds, accounting for 99.18% of the total oil, were identified, and the main components of the essential oil of C. chinense were spathulenol (18.54%), piperitone (18.9%), caryophyllene (12.04%), and bornyl acetate (8.14%). Based on bioactivity-directed fractionation, bornyl acetate, caryophyllene, and piperitone were identified from the essential oil. The essential oil possessed fumigant toxicity against booklice (Liposcelis bostrychophila) with a 50% lethal concentration (LC50) value of 423.39 μg/liter, while the isolated constituents, bornyl acetate and piperitone, had LC50 values of 351.69 and 311.12 μg/liter against booklice, respectively. The essential oil also exhibited contact toxicity against L. bostrychophila with an LC50 value of 215.25 μg/cm2. Bornyl acetate, caryophyllene, and piperitone exhibited acute toxicity against booklice with LC50 values of 321.42, 275.00, and 139.74 μg/cm2, respectively. The results indicated that the essential oil and its isolated constituents have potential for development into natural insecticides or fumigants for control of insects in stored grains.

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Armas, Kaylin, Janne Rojas, Luis Rojas, and Antonio Morales. "Comparative Study of the Chemical Composition of Essential Oils of Five Tagetes Species Collected in Venezuela." Natural Product Communications 7, no. 9 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700932.

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The leaves and inflorescences of five species of Tagetes, family Asteraceae, were collected from different locations in Mérida state, Venezuela, and their essential oils analyzed by GC and GC/MS. Several differences were observed in the composition of these oils, mainly regarding the major components, which for T. caracasana were trans-ocimenone (64.3%) and cis-tagetone (13.7%), and for T. erecta, piperitone (35.9%) and terpinolene (22.2%). High amounts of trans-anethole (87.5%) and estragole (10.7%) were observed in T. filifolia, while T. subulata essential oil contained terpinolene (26.0%), piperitenone (13.1%) and limonene (10.8%). For T. patula, two different oil samples were analyzed, leaves (TPL) and inflorescences (TPI). The TPL oil showed terpinolene (20.9%) and piperitenone (14.0%) as main components, while the TPI sample was composed mainly of β-caryophyllene (23.7%), terpinolene (15.6%) and cis-β-ocimene (15.5%).

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Cloonan, Kevin R., Wayne S. Montgomery, Teresa I. Narvaez, and Paul E. Kendra. "A New Repellent for Redbay Ambrosia Beetle (Coleoptera: Curculionidae: Scolytinae), a Primary Vector of the Mycopathogen That Causes Laurel Wilt." Plants 12, no. 13 (2023): 2406. http://dx.doi.org/10.3390/plants12132406.

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The redbay ambrosia beetle, Xyleborus glabratus, was detected in Georgia, USA, in 2002 and has since spread to 12 additional states. This wood-boring weevil carries a symbiotic fungus, Harringtonia lauricola, that causes laurel wilt, a lethal disease of trees in the Lauraceae family. Native ambrosia beetles that breed in infected trees can acquire H. lauricola and contribute to the spread of laurel wilt. Since 2002, laurel wilt has devastated native Persea species in coastal forests and has killed an estimated 200,000 avocado trees in Florida. Since laurel wilt is difficult to manage once it has entered a susceptible agrosystem, this study evaluated piperitone as a candidate repellent to deter attacks by X. glabratus and other ambrosia beetles. Additionally, piperitone was compared to the known repellent verbenone as a potential cost-effective alternative. The repellent efficacy was determined by comparing captures in traps baited with commercial beetle lures containing α-copaene versus captures in traps baited with lures in addition to a repellent. In parallel 10-week field tests, the addition of piperitone reduced the captures of X. glabratus in α-copaene-baited traps by 90%; however, there was no significant reduction in the captures of native ambrosia beetles in ethanol-baited traps. In two replicate 10-week comparative tests, piperitone and verbenone both reduced X. glabratus captures by 68–90%, with longevity over the full 10 weeks. This study identifies piperitone as a new X. glabratus repellent with potential for pest management.

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Bazyl'chik, V. V., and T. N. Overchuk. "Improved method of obtaining piperitone." Chemistry of Natural Compounds 28, no. 3-4 (1992): 292–95. http://dx.doi.org/10.1007/bf00630244.

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Kendra, Paul E., Wayne S. Montgomery, Nurhayat Tabanca, et al. "Piperitone (p-Menth-1-En-3-One): A New Repellent for Tea Shot Hole Borer (Coleoptera: Curculionidae) in Florida Avocado Groves." Biomolecules 13, no. 4 (2023): 656. http://dx.doi.org/10.3390/biom13040656.

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The tea shot hole borer, Euwallacea perbrevis, has been recently established in Florida, USA, where it vectors fungal pathogens that cause Fusarium dieback in avocado. Pest monitoring uses a two-component lure containing quercivorol and α-copaene. Incorporation of a repellent into IPM programs may reduce the incidence of dieback in avocado groves, particularly if combined with lures in a push–pull system. This study evaluated piperitone and α-farnesene as potential repellents for E. perbrevis, comparing their efficacy to that of verbenone. Replicate 12-week field tests were conducted in commercial avocado groves. Each test compared beetle captures in traps baited with two-component lures versus captures in traps containing lures plus repellent. To complement field trials, Super-Q collections followed by GC analyses were performed to quantify emissions from repellent dispensers field-aged for 12 weeks. Electroantennography (EAG) was also used to measure beetle olfactory response to each repellent. Results indicated that α-farnesene was ineffective; however, piperitone and verbenone were comparable in repellency, achieving 50–70% reduction in captures, with longevity of 10–12 weeks. EAG responses to piperitone and verbenone were equivalent, and significantly greater than response to α-farnesene. Since piperitone is less expensive than verbenone, this study identifies a potential new E. perbrevis repellent.

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Pal, Mahesh, Anil Kumar, and Krishna Tewari. "Chemical composition and mosquito repellent activity of the essential oil of Plectranthus incanus link." Facta universitatis - series: Physics, Chemistry and Technology 9, no. 1 (2011): 57–64. http://dx.doi.org/10.2298/fupct1101057p.

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The chemical composition of the essential oil obtained from the leaves of Plectranthus incanus Link, with the yield of 0.6% (w/v), was analyzed by GC and GC/MS. A total of 16 constituents, representing 95.2% of the oil, were identified. The major components of the oil were fenchone (6.0%), piperitone oxide (32.4%), piperitenone (3.0%) and piperitenone oxide (41.5%). The repellent activity of the volatile oil at different concentrations was measured by the protection period against the bites of Anopheles stephensi and Culex fatigans. The tested oil had stronger repellent activity than citronella oil, which was used as a positive control. LC50 (30 min) for P. incanus oil against An. stephensi and C. fatigans were 23.8 and 19.6 ?l/L air, respectively, whereas LC50 of citronella oil were 31.7 and 31.0 ?l/L air. Thus, P. incanus may be regarded as a potential valuable source of chemicals that have strong mosquito repellent activity, and could be used for the preparation of mosquito repellent formulations.

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MIYAZAWA, M., H. KAKITA, M. HYAKUMACHI, and H. KAMEOKA. "ChemInform Abstract: Enantioselective Hydroxylation of (.+-.)-Piperitone to (-)-(4R,6S)-6- Hydroxy-piperitone by Rhizoctonia solani." ChemInform 24, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199317226.

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de Souza, Ana, Uiliane dos Santos, Jackson de Sá Carvalho, Bruno Barbosa, Kirley Canuto, and Tigressa Rodrigues. "Chemical Composition of Essential Oil of Leaves from Lippia schaueriana Mart. Collected in the Caatinga Area." Molecules 23, no. 10 (2018): 2480. http://dx.doi.org/10.3390/molecules23102480.

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Lippia schaueriana Mart. (Verbenaceae) is an endemic species of Caatinga with a restricted distribution to the states of Bahia and Pernambuco, which presents itself as a potential source of raw material for extraction of essential oil and exploitation by the chemical and pharmaceutical industries. Considering that there are no reports in the literature of research carried out with this species, this paper aimed to establish—for the first time—the chemical composition of its essential oil. The essential oil of the dry leaves at room temperature was obtained by hydrodistillation after 3 h of extraction and the phytochemical analyzes were done by gas chromatography coupled to mass spectrometry (GC/MS). The main compounds found in the oil of leaves were piperitone oxide (51.25%), caryophyllene (17.76%), limonene (8.06%), spathulenol (6.63%), and piperitone (2.90%). The piperitone oxide is a compound described in the literature that shows antinociceptive, cardiovascular, analgesic, and relaxing activities, as well as fungicidal and insecticidal effect, which gives it an interesting potential for the alternative control of agricultural pests.

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Byers, John A., Yonatan Maoz, Daniela Fefer, and Anat Levi-Zada. "Semiochemicals Affecting Attraction of Ambrosia Beetle Euwallacea fornicatus (Coleoptera: Curculionidae: Scolytinae) to Quercivorol: Developing Push-Pull Control." Journal of Economic Entomology 113, no. 5 (2020): 2120–27. http://dx.doi.org/10.1093/jee/toaa127.

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Abstract Euwallacea fornicatus (Eichhoff), the polyphagous shot hole borer (PSHB), is an ambrosia beetle infesting avocado Persea americana Mill. limbs in North America and Israel. We conducted field experiments with sticky traps in avocado orchards to develop push–pull semiochemical methods of managing PSHB. Traps baited with 10-fold increasing doses (0.01 to 100× or 1.26 µg to 12.6 mg/d) of attractant quercivorol were previously shown to increasingly capture female PSHB (males flightless). We converted trap catch of this relationship to a standardized effective attraction radius (EAR) that predicts capture power of baited-traps regardless of insect flight density. Earlier, piperitone and verbenone were shown to strongly inhibit attraction of PSHB to quercivorol-traps. We tested increasing numbers of 1× piperitone dispensers at 0.75-m distance surrounding a quercivorol-trap and found PSHB catch to decline exponentially. Increasing decadic doses (0.01 to 10×) of either verbenone or piperitone released at 1× quercivorol-traps caused a sigmoidal first-order kinetic-decay in catch. Verbenone (1×) placed at increasing distances (0, 0.25, 0.5, 1, and 2 m) from a 1× quercivorol-trap became increasingly ineffective in reducing catch of PSHB. We found no evidence that ethanol released from 7.5 to 480 mg/d affected attraction of PSHB, but Scobicia chevrieri (Villa and Villa) (Coleoptera: Bostrichidae) was increasingly attracted. Due to their relatively short-range (&lt;0.5 m) inhibition of attractive sources, piperitone, and verbenone dispensers should be placed on avocado trunks where PSHB aggregations occur before the flight season.

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Foganholi, Ana Paula Do Amaral Mônaco, Juliana Feijó de Souza Daniel, Débora Cristina Santiago, Juliane Resges Orives, Jurandir Pinto Pereira, and Terezinha De Jesus Faria. "Composição química e atividade antifúngica do óleo essencial de poejo em diferentes estágios de desenvolvimento." Semina: Ciências Agrárias 36, no. 5 (2015): 3091. http://dx.doi.org/10.5433/1679-0359.2015v36n5p3091.

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The aim of this study was to compare the yield, chemical composition and antifungal activity of the essential oil that is obtained from Mentha pulegium in different developmental stages and cultivated under controlled conditions in southern Brazil. The hydrodistillation of fresh leaves that were collected at 60, 70 and 85 days resulted inessential oil yields of 0.17 %, 0.23 % and 0.17 %, respectively. All of the essential oil samples showed antifungal activity against Cladosporium herbarum. The gas chromatograph (GC) and GC/MS analysis revealed eleven constituents: seven (pulegone, piperitenone, menthone, isomenthone, neoisomenthol, piperitone and 1.1-dimethoxy-2-nonyne) were common to three samples, while menthofuran and myrtenal were detected only in samples of the first and second stages. Pulegone was the main constituent of the essential oil samples from the first and second stages (26.65 %), followed by piperitenone (20.41; 12.60 %). The pulegone concentration increased to 31.05 % in the last collection, while the major constituent was piperitenone (36.32 %). In conclusion, the results demonstrated that M. pulegium essential oil presents potential as an antifungal agent, and its chemical composition depends on the stage of development during which it was extracted.

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Asgarpanah, Jinous, Setareh Bahrani, and Elham Bina. "Volatile Constituents of the Fruit and Roots of Cymbopogon olivieri." Natural Product Communications 10, no. 2 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000242.

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The essential oil contents of the fruit and roots of Cymbopogon olivieri growing wild in south of Iran were found to be 0.7 % and 0.4% (v/w), respectively based on the fresh weight. The oils were analyzed by GC and GC–MS. Forty and twenty six constituents, representing 93.1 % and 93.4% of the oils were identified, respectively. The major components of the C. olivieri fruit oil were identified as piperitone (44.1%), α-terpinene (13.7%), neral (6.3%), elemol (5.6%) and β-eudesmol (5.3%). while the main components of that of roots were characterized as piperitone (20.6%), α-muurolol (9.5%), β-eudesmol (8.5%), selina-6-en-4-ol (7.9%), 5-epi-7-epi-α-eudesmol (6.8%) and elemol (5.8%).

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Bukvički, Danka, Ana Cirić, Marina Soković, et al. "Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa." Natural Product Communications 11, no. 12 (2016): 1934578X1601101. http://dx.doi.org/10.1177/1934578x1601101232.

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The chemical composition, antimicrobial and antiquorum sensing activity of the essential oil of Micromeria thymifolia (Scop.) Fritsch were investigated. Limonene, piperitone epoxide and piperitenone epoxide were found as the main constituents using a gas chromatography-mass spectrometry technique. In vitro antimicrobial activity of the oil was tested against six bacterial and seven fungal strains and high antimicrobial potential was noticed. Minimum inhibitory concentration varied from 0.031 mg/mL to 0.5 mg/mL for bacterial and 0.062 mg/mL to 0.5 mg/mL for fungal strains. The antiquorum properties of the essential oil were evaluated on Pseudomonas aeruginosa PAO1. The oil was tested at subMIC concentrations for anti-quorum sensing activity. The analyses on quorum-sensing functions have been carried out by evaluating twitching and swarming of bacterial cultures and the total amount of pyocyanin production produced by P. aeruginosa. This study showed that M. thymifolia essential oil exhibited antiquorum sensing activity and may be used as an antipathogenic drug.

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Pons, Alexandre, Valérie Lavigne, Philippe Darriet, and Denis Dubourdieu. "Identification and analysis of piperitone in red wines." Food Chemistry 206 (September 2016): 191–96. http://dx.doi.org/10.1016/j.foodchem.2016.03.064.

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Grudniewska, Aleksandra, Radosław Gniłka, and Czesław Wawrzeńczyk. "Enantioselectivity of hydroxylation of racemic piperitone by fungi." Chirality 22, no. 10 (2010): 929–35. http://dx.doi.org/10.1002/chir.20862.

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Djamel Boukhalfa, Nour El Yakine Yaha, and Bachir Nabti. "Phytochemical analysis and biological activity of the essential oil of lemongrass (Cymbopogon schoenanthus (L.) Spreng) from the Algerian Sahara." GSC Biological and Pharmaceutical Sciences 22, no. 3 (2023): 114–22. http://dx.doi.org/10.30574/gscbps.2023.22.3.0103.

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The work focuses on the phytochemical and biological study (antimicrobial activity) of the essential oil (EO) from the underground parts of Cymbopogon schoenanthus, collected from the cultural park of Ahaggar in southern Algeria. The extraction of the essential oil gives a yield of more than 4 ml per 100 g of dry matter (gdm). Chromatographic analysis of the essential oil of this species shows a richness in monoterpenes (59.7%) with a predominance of piperitone (50.25%) and secondarily α-elemol (11.06%). The antimicrobial activity of the essential oil, tested on six microorganisms, shows a strong antifungal and antibacterial action. This bioactivity is mainly due to the richness of this essence in piperitone known for its effectiveness against microbial agents. The limit test of toxicity shows that a dose of 2 g of essential oil/kg of body weight is not toxic.

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Djamel, Boukhalfa, El Yakine Yaha Nour, and Nabti Bachir. "Phytochemical analysis and biological activity of the essential oil of lemongrass (Cymbopogon schoenanthus (L.) Spreng) from the Algerian Sahara." GSC Biological and Pharmaceutical Sciences 22, no. 3 (2023): 114–22. https://doi.org/10.5281/zenodo.7919948.

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The work focuses on the phytochemical and biological study (antimicrobial activity) of the essential oil (EO) from the underground parts of Cymbopogon schoenanthus, collected from the cultural park of Ahaggar in southern Algeria. The extraction of the essential oil gives a yield of more than 4 ml per 100 g of dry matter (gdm). Chromatographic analysis of the essential oil of this species shows a richness in monoterpenes (59.7%) with a predominance of piperitone (50.25%) and secondarily α-elemol (11.06%). The antimicrobial activity of the essential oil, tested on six microorganisms, shows a strong antifungal and antibacterial action. This bioactivity is mainly due to the richness of this essence in piperitone known for its effectiveness against microbial agents. The limit test of toxicity shows that a dose of 2 g of essential oil/kg of body weight is not toxic.

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Djamel BOUKHALFA, Safia BOURKAIB, Bachir NABTI, and Mohamed BELGHOUL. "Contribution to phytochemical study and biological activities of Artemisia judaïca from the Algerian Sahara." GSC Biological and Pharmaceutical Sciences 23, no. 1 (2023): 137–47. http://dx.doi.org/10.30574/gscbps.2023.23.1.0154.

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This study aims to contribute to the valorisation of the Algerian desert flora, particularly the flora of Ahaggar, by conducting a phytochemical and biological investigation of the essential oil of Artemisia judaïca, a traditional aromatic plant used for various garlics in this region. After the extraction of the essential oil, chromatographic analysis and evaluations of antimicrobial and antioxidant activities are performed on this plant. The results show a very high yield of essential oil on average (> 3.5 ml per 100 g of dry plant). The studied essential oil of Artemisia judaïca is characterized by the presence of piperitone (73.65 %). This oil showed strong antifungal and antibacterial activities, probably due to its richness in piperitone. The evaluation of the antioxidant activity of the essential oil gave an IC50 value of 2.77± 0.05 mg/ml. The β-carotene bleaching test confirmed the trapping power of this essential oil.

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Kremer, Dario, Valerija Dunkić, Danijela Stešević, et al. "Micromorphological traits and essential oil of Micromeria longipedunculata Bräuchler (Lamiaceae)." Open Life Sciences 9, no. 5 (2014): 559–68. http://dx.doi.org/10.2478/s11535-014-0294-1.

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AbstractMicromeria longipedunculata Bräuchler (syn. M. parviflora (Vis.) Rchb.) is an endemic Illyric-Balkan plant species from Bosnia and Herzegovina, Montenegro, and Albania. We investigated types and distribution of trichomes, pollen morphology, and chemical composition of essential oil (analysed by GC and GC-MS) in M. longipedunculata. Non-glandular trichomes, peltate trichomes, and two types of capitate trichomes (type 1 composed of one basal epidermal cell, and one head cell with subcuticular space; type 2 composed of one basal epidermal cell, two or three stalk cells, and one head cell with subcuticular space) were observed on leaves, bracteoles, the calyx, corolla, and the stem. The pollen grains had six apertures which were set in the equatorial pollen belt and showed medium reticulate ornamentation. A phytochemical analysis of essential oils from four different localities is characterized by similar chemical composition with spathulenol (23.7–39.5%), piperitone oxide (7.7–12.1%) and piperitone (7.3–8.9%) as the major compounds.

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Ahadi, Nastaran, Marzieh Torabbeigi, Zahra Aghaiee Meibodei, and Fatemeh Safatian. "Volatile Components of Haplophyllum canaliculatum Boiss. by Different Extraction Procedures." Journal of Analytical Methods in Chemistry 2020 (May 30, 2020): 1–7. http://dx.doi.org/10.1155/2020/4202871.

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Volatile components of Haplophyllum canaliculatum Boiss. grown in Iran were extracted by hydrodistillation (HD), solvent-free microwave extraction (SFME), and headspace solid-phase microextraction (HS-SPME). The components were analyzed by means of GC and GC-MS. The extraction time and temperature for HS-SPME, microwave, power, and exposure time of extraction for SFME were optimized. Twenty-five compounds that represent 99.88% of total compounds in the oil were obtained by the HD method, and the major components for this method were identified as β-pinene (18.90%), 1,8-cineole (13.94%), and piperitone (12.22%). However, piperitone (34.50%), caryophyllene oxide (9.94%), and a-eudesmol were the main compounds among twenty-one constituents, representing 99.89% of the total composition that were characterized in volatiles extracted by the SFME method. Moreover, thirteen compounds, representing 99.95% of the total constituents, were characterized in volatile fraction extracted by the HS-SPME method, which were dominated by β-pinene (21.13%), a-pinene (13.07%), limonene (11.65%), and δ-2-carene (10.23%) as major constituents.

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Djamel, BOUKHALFA, BOURKAIB Safia, NABTI Bachir, and BELGHOUL Mohamed. "Contribution to phytochemical study and biological activities of Artemisia judaïca from the Algerian Sahara." GSC Biological and Pharmaceutical Sciences 23, no. 1 (2023): 137–47. https://doi.org/10.5281/zenodo.7925044.

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This study aims to contribute to the valorisation of the Algerian desert flora, particularly the flora of Ahaggar, by conducting a phytochemical and biological investigation of the essential oil of Artemisia judaïca, a traditional aromatic plant used for various garlics in this region. After the extraction of the essential oil, chromatographic analysis and evaluations of antimicrobial and antioxidant activities are performed on this plant. The results show a very high yield of essential oil on average (> 3.5 ml per 100 g of dry plant). The studied essential oil of Artemisia judaïca is characterized by the presence of piperitone (73.65 %). This oil showed strong antifungal and antibacterial activities, probably due to its richness in piperitone. The evaluation of the antioxidant activity of the essential oil gave an IC50 value of 2.77± 0.05 mg/ml. The β-carotene bleaching test confirmed the trapping power of this essential oil.

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Sakirigui, Amoussatou, Fernand Gbaguidi, Urbain C. Kasséhin, Jacques Poupaert, Georges C. Accrombessi, and Simeon O. Kotchoni. "Structural and antitrypanosomal data of different carbasones of piperitone." Data in Brief 9 (December 2016): 1039–43. http://dx.doi.org/10.1016/j.dib.2016.11.044.

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UMEMOTO, Kazuyasu, and Tomoyuki TSUNEYA. "Studies on chemical constituents of wild mints. (Part XIV). Mentha arvensis containing piperitenone oxide and piperitone oxide as major components." Journal of the agricultural chemical society of Japan 62, no. 7 (1988): 1073–76. http://dx.doi.org/10.1271/nogeikagaku1924.62.1073.

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Muñoz-Acevedo, Amner, María C. González, Juan D. Rodríguez, and Yurina Sh De Moya. "New Chemovariety of Lippia alba From Colombia: Compositional Analysis of the Volatile Secondary Metabolites and Some in vitro Biological Activities of the Essential Oil From Plant Leaves." Natural Product Communications 14, no. 7 (2019): 1934578X1986290. http://dx.doi.org/10.1177/1934578x19862905.

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Lippia alba is a plant widely studied due to both chemical diversity and bioactivities related to its ethnobotanical uses. In this work, the composition of the volatile secondary metabolites (volatile fractions/essential oil, EO) of the flower/leaves of L. alba (from northern region of Colombia) was determined by solid phase micro-extraction/distillation-solvent extraction/microwave-hydrodistillation/gas chromatography-mass spectrometry (MWHD/GC-MS), along with some in vitro biological properties (cytotoxicity and acetylcholinesterase enzyme [AChe] inhibition) from leaf EO. Outstanding results were found: (i) cis-piperitone oxide (~13%-46%), germacrene D (~11%-30%), and limonene (~10%-22%) characterized the volatile secondary metabolites from different parts of the plant; (ii) leaf EO showed a moderate hemolytic activity (HC50: 580 ± 1 µg/mL), a significant cytotoxicity on lymphocytes (LC50: 127 ± 3 µg/mL), a high cytotoxicity on HEp2 cell line (LC50: 38 ± 2 µg/mL), and a moderate inhibitory effect on AChE (IC50: 28 ± 2 µg/mL). Based on these results, a new chemovar of L. alba is reported (represented by cis-piperitone oxide) along with its promising cytotoxic and AChE inhibiting properties.

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Whiffin, T., and A. Bouchier. "Chemical and morphological variation within a population of Eucalyptus radiata (Myrtaceae) exhibiting leaf volatile oil chemical forms." Australian Systematic Botany 5, no. 1 (1992): 95. http://dx.doi.org/10.1071/sb9920095.

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Fifty trees were collected from a population of Eucalyptus radiata subsp. radiata known to contain leaf volatile oil chemical forms. These were studied for leaf volatile oil composition, flavonoid composition, and leaf and fruit morphology. Three distinct groups were detected on the basis of leaf volatile oil composition, representing low, medium and high percentages of piperitone, with 43, 3 and 4 plants in each respectively. The low piperitone group contained two subgroups differing in the inversely varying amounts of α-phellandrene and p-cymene. While there was variation in leaf and fruit morphological characters and in flavonoid composition, there was no correlation between any of these characters and the leaf volatile oil chemical groups. Groups could also be distinguished on the basis of morphological characters, especially fruit characters, but these morphological groups were not as distinct as those based on volatile oil characters. There was no association between the morphological groups and the chemical groups on the basis of group membership. The nature and importance of this variation within a Eucalyptus population are discussed.

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Novakovic, Miroslav, Danka Bukvicki, Vlatka Vajs, et al. "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger." Natural Product Communications 13, no. 4 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300425.

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A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six (1–6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7 rebpectively. New uct (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.

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Akdeniz, Yusuf, and Tuba Genç Kesimci. "Chemical Composition and Biocontrol Activity of Different Essential Oils against Soil-Borne Fungal Pathogens." Plant Pathology Journal 40, no. 2 (2024): 192–204. http://dx.doi.org/10.5423/ppj.oa.01.2024.0002.

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In this study, the efficacy of the essential oil of Mentha longifolia, Achillea arabica and Artemisia absinthium plants were evaluated against important soil-borne fungal pathogens as Verticillium dahliae, Rhizoctonia solani, and Fusarium oxysporum. Essential oils were obtained from plants by hydrodistillation method and the chemical components of essential oils were determined by analyzing by gas chromatography-mass spectrometry. The main components found as piperitone oxide (13.61%), piperitenone oxide (15.55%), pulegone (12.47%), 1-menthone (5.75%), and camphor (5.75%) in M. longifolia, á-selinene 13.38%, camphor 13.34%, L-4-terpineneol 8.40%, (–)-á-Elemene 7.01%, 1,8-cineole 4.71%, and (–)-spathulenol 3.84% in A. arabica, and á-thujone (34.64%), 1,8-cineole (19.54%), pulegone (7.86%), camphene (5.31%), sabinene (4.86%), and germacrene-d (3.67%) in A. absinthium. The antifungal activities of the oils were investigated 0.05, 0.1, 0.25, 0.5, 1.00, and 2.00 μl/ml concentrations with the contact effect method. M. longifolia oil (1.00 and 2.00 μl/ml) has displayed remarkable antifungal effect and provided 100% inhibition on mycelial growth of V. dahliae, R. solani and F. oxysporum. The results obtained from this study may contribute to the development of new alternative and safe methods against soil-borne fungal pathogens.

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Alqasoumi, Saleh. "Densitometric HPTLC method for qualitative and quantitative analysis of piperitone." Journal of Planar Chromatography – Modern TLC 26, no. 1 (2013): 93–95. http://dx.doi.org/10.1556/jpc.26.2013.1.14.

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Grudniewska, Aleksandra, Katarzyna Dancewicz, Agata Białońska, Czesław Wawrzeńczyk, and Beata Gabryś. "Piperitone-Derived Saturated Lactones: Synthesis and Aphid Behavior-Modifying Activity." Journal of Agricultural and Food Chemistry 61, no. 14 (2013): 3364–72. http://dx.doi.org/10.1021/jf3052219.

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Kanagapushpam, D., V. Ramamurthy та K. Venkatesan. "Structure of α-benzylidene-(±)-piperitone, an exception to topochemical behaviour". Acta Crystallographica Section C Crystal Structure Communications 43, № 6 (1987): 1128–31. http://dx.doi.org/10.1107/s0108270187092783.

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Hamada, Hiroki, Yoshihiro Fuchikami, Yuka Ikematsu, Toshifumi Hirata, Howard J. Williams, and A. Ian Scott. "Hydroxylation of piperitone by cell suspension cultures of Catharanthus roseus." Phytochemistry 37, no. 4 (1994): 1037–38. http://dx.doi.org/10.1016/s0031-9422(00)89524-2.

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Debbabi, Haïfa, Ridha El Mokni, Ikbal Chaieb, et al. "Chemical Composition, Antifungal and Insecticidal Activities of the Essential Oils from Tunisian Clinopodium nepeta subsp. nepeta and Clinopodium nepeta subsp. glandulosum." Molecules 25, no. 9 (2020): 2137. http://dx.doi.org/10.3390/molecules25092137.

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The present investigation was focused on the study of the chemical composition variability and biological activities of the essential oils from Clinopodium nepeta subsp. nepeta and subsp. glandulosum. Essential oils extraction was performed using hydrodistillation and the separation of the constituents was carried out by gas chromatography coupled with mass spectrometry (GC-MS). Antifungal activities were tested against Aspergillus flavus, Aspergillus terreus, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophytes, and Candida albicans. Toxicity and repellency were evaluated against the stored product pests Tribolium confusum and Sitophilus zeamais. Both essential oils were characterized by a high content of oxygenated monoterpenes. Piperitone ranks first in the subspecies nepeta and piperitenone oxide is the dominant constituent in the subspecies glandulosum. All tested samples displayed noteworthy antifungal properties, with the highest activity observed for the essential oil of C. nepeta subsp. glandulosum, collected in Béni-M’tir, against T. mentagrophytes (MIC = 40 µg/mL). The essential oil samples of C. nepeta subsp. glandulosum were strongly repellent to the insect species (PR > 80%, after 2h) and highly toxic to S. zeamais reaching 97.5%–100% mortality after 24 h of exposure. In conclusion, this study showed considerable intra-specific changes in the quality of C. nepeta essential oils, which is reflected in different rates of antifungal and insecticidal activity.

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Grammatikopoulos, G., R. Karousou, S. Kokkini, and Y. Manetas. "Differential effects of enhanced UV-B radiation on reproductive effort in two chemotypes of Mentha spicata under field conditions." Functional Plant Biology 25, no. 3 (1998): 345. http://dx.doi.org/10.1071/pp97092.

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Seedlings of two chemotypes of mint (Mentha spicata L.), i.e. the piperitone and piperitenone oxide rich wild mint (chemotype I) and the carvone and dihydrocarvone rich spearmint (chemotype II), were grown to maturity in the field under ambient or ambient plus supplemental UV-B radiation, simulating a 15% ozone depletion over Patras (38.3°N, 29.1°E). Enhanced UV-B radiation had no effect on total stem length, photochemical efficiency of PS II, chlorophyll content, UV-B absorbing capacity of epicuticular and internal compounds, photosynthetic capacity at 5% CO2 and relative water content of both chemotypes. However, specific leaf mass in chemotype II, and leaf number in chemotype I were significantly increased under UV-B supplementation, while total leaf area remained unaffected. Dry mass accumulation measured at plant harvest showed a slight, non-significant trend for increased above- and below-ground biomass in both chemotypes, but a particularly significant increase in the biomass allocated to inflorescences in chemotype II was found. Seed yield was significantly improved by supplemental UV-B radiation in both chemotypes, but, again, chemotype II was particularly responsive, increasing the number of seeds by 100%. We conclude that the aromatic species M. spicata is not only resistant to enhanced UV-B radiation, but some chemotypes may be selectively benefited through increased reproductive effort.

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Fedotova, V. V., and D. A. Konovalov. "The analysis of the essential oils of Anethum graveolens L. variety “Scythian” cultivated in Russia." IOP Conference Series: Earth and Environmental Science 1138, no. 1 (2023): 012023. http://dx.doi.org/10.1088/1755-1315/1138/1/012023.

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Abstract Anethum graveolens L. (Dill) is an aromatic, medicinal, and food plant that is widely known in the world. This paper presents the results of the study of the essential oil of A. graveolens, which was cultivated in the Stavropol region (Russia, North Caucasus) to restore its growth. Herb of A. graveolens, variety “Scythian”, was collected in different fields of the limited company “Cossack agriculture “Staropavlovskoe”. The essential oil was obtained by Clevenger distillation. The chemical composition of the essential oils was studied by the GC/MS method. 25 compounds were detected in essential oil: carvone; 3.9-epoxy-1-p-menthene; ipsdienol; 2-hydroxycineol; allyl caprate; carveol; 6-camphenol; 5-isopropenyl-2-methyl-7-oxabicyclo [4.1.0] heptane-2-ol; piperitone oxide; 3-methyl-2-pent-2-enyl-cyclopent-2-enone; cis-p-mentha-2.8-dien-1-ol; 2-cyclol piperitone oxidehydroxy-3-methyl-6-(1- methyleth); limonene-6-ol, pivalate; isopulegol acetate; z-(13,14-epoxy) tetradec-11-en-1-ol acetate. The major component in the oil detected was arvone (36.9–44.5%). The obtained data confirmed the positive result of the cultivation of A.graveolens with the content of carvone in the essential oil of herbs comparable to the content of carvone in fruits.

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Talankova-Sereda, T. E., J. V. Kolomiets, A. F. Likhanov, A. V. Sereda, N. I. Kucenko, and E. O. Shkopinskiy. "Effect of clonal reproduction on quantitative indices and component composition of essential oil of peppermint varieties." Regulatory Mechanisms in Biosystems 9, no. 3 (2018): 340–46. http://dx.doi.org/10.15421/021850.

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Quantitative and qualitative composition of essential oils of peppermint breeds Lebedinaya Pesnya, Lubenchanka, Lidiya, Ukrainskaya Perechnaya, Mama, Chornolista was investigated before and after clonal microreproduction by the method of isolated tissues and bodies culture in vitro. Methods of essential oil steam distillation, capillary gas chromatography and statistical analysis were used in the research. It is established that increase in essential oil quantity was observed for peppermint breeds on which reproduction and improvement іn vіtro technology was applied. As a result of clonal microreproduction of peppermint plants in culture іn vіtro on nutrient medium Murasige and Skug, in which the growth regulators 0.75 mg/l of 6-benzylaminopurine, 0.1 mg/l of adenine, 0.05 mg/l of indolil-3-acetic acid and 0.5 mg/l of gibberellins acid were added and virocide Ribavirin in concentration 10 mg/l, improvement was obtained in comparison with vegetatively reproduced plants; increase in essential oil quantity per hectare was established for the following breeds; Chornolista by 54.2%, Lebedinaya pesnya by 38.2%, Ukrainskaya Perechnaya by 36.7%, Mama by 28.5%, Lubenchanka by 17.1% and Lidiya by 11.6%. For oil content the highest indices were noted for Lubenchanka, Mama and Lebedinaya Pesnya peppermint breeds with product yield 4.02%, 3.98% and 3.84% respectively. It was established that the essential oil component composition in non-clonal peppermint plants raw materials and plants-regenerants after culture in vitro is variable depending on breed. Limonene, cineole, menthone, menthofuran, iso-menthone, menthyl acetate, β-caryophyllene, iso-menthol, menthol, pulegone, germacren, piperitone, carvone were identified in peppermint essential oil. High content of menthol, low content of carvone, piperitone, pulegone (except for Chornolista, Ukrainskaya Perechnaya breeds) and menthofuran (except for Chornolista, Ukrainskaya Perechnaya and Lubenchanka breeds) are characteristic for Ukrainian selection peppermint investigated breeds. A clear tendency to menthol and menthone content ratio increase is observed in plants which were improved in conditions іn vіtro. Pulegone was not detected in essential oil samples of Lebedinaya Pesnya, Lidiya and Mama breeds. Biochemical markers of Lebedinaya Pesnya, Lubenchanka, Mama breeds, which differentiate them within the group of investigated breeds, are higher limonene, piperitone and menthol pool; for Ukrainskaya Perechnaya and Chornolista breeds – pulegone, cineole and menthone; for Lidiya breed – iso-menthone.

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Morales, Carmen Pérez, M. Mar Herrador, José F. Quílez del Moral, and Alejandro F. Barrero. "Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol." Natural Product Communications 10, no. 1 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000103.

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Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

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Sut, Stefania, Irene Ferrarese, Maria Giovanna Lupo, et al. "The Modulation of PCSK9 and LDLR by Supercritical CO2 Extracts of Mentha longifolia and Isolated Piperitone Oxide, an In Vitro Study." Molecules 26, no. 13 (2021): 3886. http://dx.doi.org/10.3390/molecules26133886.

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In the present study the ability of supercritical carbon dioxide (SCO2) extracts of M. longifolia L. leaves to modulate low-density lipoprotein receptor (LDLR) and proprotein convertase subtilisin/kexin type 9 (PCSK9) expression was evaluated in cultured human hepatoma cell lines Huh7 and HepG2. Two SCO2 extracts, one oil (ML-SCO2) and a semisolid (MW-SCO2), were subjected to detailed chemical characterization by mono- and bidimensional nuclear magnetic resonance (1D, 2D-NMR), gas chromatography coupled with mass spectrometry (GC-MS) and liquid chromatography coupled with mass spectrometry (LC-MS). Chemical analysis revealed significant amounts of fatty acids, phytosterols and terpenoids. ML-SCO2 was able to induce LDLR expression at a dose of 60 µg/mL in HuH7 and HepG2 cell lines. Furthermore, ML-SCO2 reduced PCSK9 secretion in a concentration-dependent manner in both cell lines. Piperitone oxide, the most abundant compound of the volatile constituent of ML-SCO2 (27% w/w), was isolated and tested for the same targets, showing a very effective reduction of PCSK9 expression. The overall results revealed the opportunity to obtain a new nutraceutical ingredient with a high amount of phytosterols and terpenoids using the SCO2 extraction of M. longifolia L., a very well-known botanical species used as food. Furthermore, for the first time we report the high activity of piperitone oxide in the reduction of PCSK9 expression.

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Medina-Holguín, Andrea L., Sandra Micheletto, F. Omar Holguín, Jaime Rodriguez, Mary A. O'Connell, and Charles Martin. "Environmental Influences on Essential Oils in Roots of Anemopsis californica." HortScience 42, no. 7 (2007): 1578–83. http://dx.doi.org/10.21273/hortsci.42.7.1578.

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The climate conditions and chemical composition of root essential oils for 17 populations of Anemopsis californica in New Mexico were examined. The objective of this study was to observe the effect of environmental conditions and management conditions on essential oil composition in different populations of A. californica. Chemical concentrations of three abundant compounds—methyleugenol, thymol, and piperitone—were determined. Maximum accumulations of each compound were associated with different mean annual temperatures, precipitation, and elevation. Similar chemical profiles were detected in root samples recollected for four populations, suggesting retention of unique chemical profiles in different populations. Vegetative propagation of wild plants under cultivated conditions did not significantly alter the chemical profile of the root essential oil. The chemical concentrations for six essential oil components of A. californica roots were determined under field conditions with varying irrigation and nitrogen (N) fertilizer regimens. The concentration of only two compounds, thymol and piperitone, was increased by increasing irrigation. The concentration of all other compounds, methyeugenol, elemicin, 1,8-cineole, and myrtenol, were independent of the irrigation rates and N fertilizer rates used in the study. These results suggest that the chemical variability observed among different populations of A. californica is primarily genetically controlled and the environmental conditions in New Mexico are conducive to the production of this medicinal plant as a high-value crop.

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Shahdadi, Fatemeh, Maliheh Faryabi, Haroon Khan, et al. "Mentha longifolia Essential Oil and Pulegone in Edible Coatings of Alginate and Chitosan: Effects on Pathogenic Bacteria in Lactic Cheese." Molecules 28, no. 11 (2023): 4554. http://dx.doi.org/10.3390/molecules28114554.

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Mentha longifolia is a valuable medicinal and aromatic plant that belongs to Lamiaceae family. This study looked at the antibacterial effects of M. longifolia essential oil and pulegone in edible coatings made of chitosan and alginate on the growth of Staphylococcus aureus, Listeria monocytogenes, and Escherichia coli in cheese. For this purpose, first fresh mint plant was collected from the cold region of Jiroft in Kerman province. Plant samples were dried in the shade at ambient temperature, and essential oil was prepared using Clevenger. The essential oil was analyzed by gas chromatography using mass spectrometric (GC/MS) detection. The major composition of M. longifolia oil was pulegone (26.07%), piperitone oxide (19.72%), and piperitone (11.88%). The results showed that adding M. longifolia essential oils and pulegone to edible coatings significantly reduced the growth of bacteria during storage. The bacterial population decreased by increasing the concentration of chitosan, M. longifolia, and pulegone in edible coatings. When the effects of pulegone and M. longifolia essential oils on bacteria were compared, it was found that pulegone had a stronger effect on bacterial population reduction. Coating treatments showed more antibacterial activity on E. coli than other bacteria. In general, the results of this research showed that alginate and chitosan coatings along with M. longifolia essential oil and its active ingredient pulegone had antibacterial effects against S. aureus, L. monocytogenes, and E. coli in cheese.

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Gavalas, Nikos, Artemios Bosabalidis M., and Stella Kokkini. "COMPARATIVE STUDY OF LEAF ANATOMY AND ESSENTIAL OILS OF THE HYBRID MENTHA X VILLOSO-NERVATA AND ITS PARENTAL SPECIES M. LONGIFOLIA AND M. SPICATA." Israel Journal of Plant Sciences 46, no. 1 (1998): 27–33. http://dx.doi.org/10.1080/07929978.1998.10676704.

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Abstract:

Leaves of the hybrid Mentha x villoso-nervata are covered with nonglandular trichomes of intermediate length between those of its parental taxa M. longifolia and M. spicata. Glandular trichomes producing essential oils are more numerous on the lower leaf surface than on the upper one in all three mints. Their number per mm2 is higher in M. spicata and it decreases in M. longifolia and M. x villoso-nervata. Stomata are also more numerous on the lower leaf surface of the three taxa, with M. longifolia predominating. The leaf lamina of M. x villoso-nervata is ca. 83% thicker than that of M. longifolia and ca. 9% thicker than that of M. spicata. The number of chloroplasts per mm2 of mesophyll section (leaf cross section) is higher in M. X villoso-nervata. In leaf paradermal sections, the sizes of the epidermal, palisade, and spongy parenchyma cells of M. X villoso-nervata have intermediate values between those of its parental species M. longifolia and M. spicata. M. x villoso-nervata leaves are the lowest in essential oil content. As concerns the essential oil composition, the hybrid resembles one parent, M. longifolia, in the derivatives of piperitenone and piperitone, and the other parent, M. spicata, in the high amount of limonene. It differs, however, from its parental species in that it contains a higher amount of germacrene D.

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Abadi, Abderazak, and Aicha Hassani. "Chemical Composition of Marrubium Vulgare l. Essential Oil from Algeria." International Letters of Chemistry, Physics and Astronomy 13 (September 2013): 210–14. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.13.210.

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The chemical constituants of the essential oil from aerial parts of Marrubium vulgare, collected in Algeria, were analyzed by GC and GC/MS. The oil yield of the dried plant aerial parts, obtained by hydrodistillation, was 0.04% (w/w). 50 compounds, accounting for 82.46% of the oil, were identified. The major constituants were: 4,8,12,16-Tetramethyl heptadecan-4-olid (16.97%), Germacrene D-4-ol (9.61%), α-pinéne (9.37%) Phytol (4.87%), Dehydro-sabina ketone (4.12 %), Piperitone (3.27%), δ – Cadinene (3.13%), 1-Octen-3-ol (2.35%) and Benzaldehyde (2.31%).

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50

Abadi, Abderazak, and Aicha Hassani. "Chemical Composition of Marrubium Vulgare l. Essential Oil from Algeria." International Letters of Chemistry, Physics and Astronomy 13 (May 3, 2013): 210–14. http://dx.doi.org/10.56431/p-5t09it.

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Abstract:

The chemical constituants of the essential oil from aerial parts of Marrubium vulgare, collected in Algeria, were analyzed by GC and GC/MS. The oil yield of the dried plant aerial parts, obtained by hydrodistillation, was 0.04% (w/w). 50 compounds, accounting for 82.46% of the oil, were identified. The major constituants were: 4,8,12,16-Tetramethyl heptadecan-4-olid (16.97%), Germacrene D-4-ol (9.61%), α-pinéne (9.37%) Phytol (4.87%), Dehydro-sabina ketone (4.12 %), Piperitone (3.27%), δ – Cadinene (3.13%), 1-Octen-3-ol (2.35%) and Benzaldehyde (2.31%).

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Journal articles on the topic 'Piperitone'

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