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Prosche S, Stappen I. Flower Power: An Overview on Chemistry and Biological Impact of Selected Essential Oils from Blossoms. PLANTA MEDICA 2024; 90:595-626. [PMID: 38843799 DOI: 10.1055/a-2215-2791] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/12/2024]
Abstract
Natural raw materials such as essential oils have received more and more attention in recent decades, whether in the food industry, as flavorings and preservatives, or as insecticides and insect repellents. They are, furthermore, very popular as fragrances in perfumes, cosmetics, and household products. In addition, aromatherapy is widely used to complement conventional medicine. This review summarizes investigations on the chemical composition and the most important biological impacts of essential oils and volatile compounds extracted from selected aromatic blossoms, including Lavandula angustifolia, Matricaria recutita, Rosa x damascena, Jasminum grandiflorum, Citrus x aurantium, Cananga odorata, and Michelia alba. The literature was collected from PubMed, Google Scholar, and Science Direct. Blossom essential oils discussed in this work are used in a wide variety of clinical issues. The application is consistently described as safe in studies and meta-analyses, although there are notes that using essential oils can also have side effects, especially dermatologically. However, it can be considered as confirmed that essential oils have positive influences on humans and can improve quality of life in patients with psychiatric disorders, critically ill patients, and patients in other exceptional situations. Although the positive effect of essential oils from blossoms has repeatedly been reported, evidence-based clinical investigations are still underrepresented, and the need for research is demanded.
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Affiliation(s)
- Sinah Prosche
- Department of Pharmaceutical Sciences, University of Vienna, Austria
| | - Iris Stappen
- Department of Pharmaceutical Sciences, University of Vienna, Austria
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2
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Zhou Y, He L, Zhang N, Ma L, Yao L. Photoprotective Effect of Artemisia sieversiana Ehrhart Essential Oil Against UVB-induced Photoaging in Mice. Photochem Photobiol 2021; 98:958-968. [PMID: 34767631 DOI: 10.1111/php.13561] [Citation(s) in RCA: 4] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/11/2021] [Accepted: 11/10/2021] [Indexed: 12/23/2022]
Abstract
Photoaging refers to the extrinsic aging resulting from ultraviolet (UV) irradiation, which impacts skin appearance and is accompanied by the risk of skin carcinoma. Developing natural products as photoprotective agents is of great interest in cosmetic industry nowadays. The present study aimed at investigating the possible use of Artemisia sieversiana Ehrhart essential oil (AEO) for the prevention of photoaging induced by UVB. AEO was characterized by chamazulene, which accounted for 38.92% among total 51 identified compounds. In in vitro assays, AEO was found to be a moderate antioxidant and good UVB filter with photostability. A UVB-induced photoaging mice model was established with three AEO formulations (0.1%, 0.5% and 1.5%, w/w) topically applied prior to UVB irradiation. The activities of catalase, particularly superoxide dismutase of skin increased, while malondialdehyde content decreased in AEO groups as compared with model controls. The production of matrix metalloproteinases (MMP-1 and MMP-3) and depletion of hydroxyproline in skin were inhibited by AEO in a dose-dependent manner. Histological evaluation indicated that AEO decreased epidermal thickness, inflammatory cell infiltration, collagen degradation and elastin aberrance. These findings indicated that AEO could be a promising sunscreen agent in protecting the skin against photoaging.
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Affiliation(s)
- Ying Zhou
- Department of Landscape Architecture, School of Design, Shanghai Jiao Tong University, Shanghai, China.,R&D Center for Aromatic Plants, Shanghai Jiao Tong University, Shanghai, China
| | - Lei He
- R&D Center for Aromatic Plants, Shanghai Jiao Tong University, Shanghai, China.,Department of Resources and Environment, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai, China
| | - Nan Zhang
- Department of Landscape Architecture, School of Design, Shanghai Jiao Tong University, Shanghai, China.,R&D Center for Aromatic Plants, Shanghai Jiao Tong University, Shanghai, China
| | - Li Ma
- Department of Landscape Architecture, School of Design, Shanghai Jiao Tong University, Shanghai, China.,R&D Center for Aromatic Plants, Shanghai Jiao Tong University, Shanghai, China
| | - Lei Yao
- Department of Landscape Architecture, School of Design, Shanghai Jiao Tong University, Shanghai, China.,R&D Center for Aromatic Plants, Shanghai Jiao Tong University, Shanghai, China
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Keltsch N, Munzert V, Zeller K, Siehl H, Berger S, Sicker D. Linderazulen aus einer invasiven Pflanze. CHEM UNSERER ZEIT 2019. [DOI: 10.1002/ciuz.201900868] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/11/2022]
Affiliation(s)
| | | | | | | | | | - Dieter Sicker
- Institut für Organische ChemieUniversität Leipzig Johannisallee 29 D‐04103 Leipzig
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4
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López-Romero D, Izquierdo-Vega JA, Morales-González JA, Madrigal-Bujaidar E, Chamorro-Cevallos G, Sánchez-Gutiérrez M, Betanzos-Cabrera G, Alvarez-Gonzalez I, Morales-González Á, Madrigal-Santillán E. Evidence of Some Natural Products with Antigenotoxic Effects. Part 2: Plants, Vegetables, and Natural Resin. Nutrients 2018; 10:1954. [PMID: 30544726 PMCID: PMC6316078 DOI: 10.3390/nu10121954] [Citation(s) in RCA: 39] [Impact Index Per Article: 5.6] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/28/2018] [Revised: 11/27/2018] [Accepted: 12/03/2018] [Indexed: 02/07/2023] Open
Abstract
Cancer is one of the leading causes of death worldwide. The agents capable of causing damage to genetic material are known as genotoxins and, according to their mode of action, are classified into mutagens, carcinogens, or teratogens. Genotoxins are also involved in the pathogenesis of several chronic degenerative diseases, including hepatic, neurodegenerative, and cardiovascular disorders; diabetes; arthritis; cancer; chronic inflammation; and ageing. In recent decades, researchers have found novel bioactive phytocompounds able to counteract the effects of physical and chemical mutagens. Several studies have shown the antigenotoxic potential of different fruits and plants (Part 1). In this review (Part 2), we present a research overview conducted on some plants and vegetables (spirulina, broccoli, chamomile, cocoa, ginger, laurel, marigold, roselle, and rosemary), which are frequently consumed by humans. In addition, an analysis of some phytochemicals extracted from those vegetables and the analysis of a resin (propolis),whose antigenotoxic power has been demonstrated in various tests, including the Ames assay, sister chromatid exchange, chromosomal aberrations, micronucleus, and comet assay, was also performed.
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Affiliation(s)
- David López-Romero
- Instituto de Ciencias de la Salud, Universidad Autónoma del Estado de Hidalgo, Ex-Hacienda de la Concepción, Tilcuautla, Pachuca de Soto 42080, Hgo, Mexico.
| | - Jeannett A Izquierdo-Vega
- Instituto de Ciencias de la Salud, Universidad Autónoma del Estado de Hidalgo, Ex-Hacienda de la Concepción, Tilcuautla, Pachuca de Soto 42080, Hgo, Mexico.
| | - José Antonio Morales-González
- Escuela Superior de Medicina, Instituto Politécnico Nacional, "Unidad Casco de Santo Tomas". Plan de San Luis y Díaz Mirón s/n, Ciudad de México 11340, Mexico.
| | - Eduardo Madrigal-Bujaidar
- Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, "Unidad Profesional A. López Mateos". Av. Wilfrido Massieu. Col., Lindavista, Ciudad de México 07738, Mexico.
| | - Germán Chamorro-Cevallos
- Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, "Unidad Profesional A. López Mateos". Av. Wilfrido Massieu. Col., Lindavista, Ciudad de México 07738, Mexico.
| | - Manuel Sánchez-Gutiérrez
- Instituto de Ciencias de la Salud, Universidad Autónoma del Estado de Hidalgo, Ex-Hacienda de la Concepción, Tilcuautla, Pachuca de Soto 42080, Hgo, Mexico.
| | - Gabriel Betanzos-Cabrera
- Instituto de Ciencias de la Salud, Universidad Autónoma del Estado de Hidalgo, Ex-Hacienda de la Concepción, Tilcuautla, Pachuca de Soto 42080, Hgo, Mexico.
| | - Isela Alvarez-Gonzalez
- Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, "Unidad Profesional A. López Mateos". Av. Wilfrido Massieu. Col., Lindavista, Ciudad de México 07738, Mexico.
| | - Ángel Morales-González
- Escuela Superior de Cómputo, Instituto Politécnico Nacional, "Unidad Profesional A. López Mateos". Av. Juan de Dios Bátiz. Col., Lindavista, Ciudad de México 07738, Mexico.
| | - Eduardo Madrigal-Santillán
- Escuela Superior de Medicina, Instituto Politécnico Nacional, "Unidad Casco de Santo Tomas". Plan de San Luis y Díaz Mirón s/n, Ciudad de México 11340, Mexico.
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Flemming M, Kraus B, Rascle A, Jürgenliemk G, Fuchs S, Fürst R, Heilmann J. Revisited anti-inflammatory activity of matricine in vitro: Comparison with chamazulene. Fitoterapia 2015; 106:122-8. [PMID: 26304764 DOI: 10.1016/j.fitote.2015.08.010] [Citation(s) in RCA: 24] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/13/2015] [Revised: 08/13/2015] [Accepted: 08/17/2015] [Indexed: 12/15/2022]
Abstract
The proazulene matricine (1) is present in chamomile flower heads and has been proven to exhibit strong in vivo anti-inflammatory activity. In contrast to other secondary metabolites in chamomile preparations like its degradation product chamazulene (2), no plausible targets have been found to explain this activity. Therefore we revisited 1 regarding its in vitro anti-inflammatory activity in cellular and molecular studies. Using ICAM-1 as a marker for NF-κB activation, it was shown that ICAM-1 protein expression induced by TNF-α and LPS, but not by IFN-γ, was remarkably inhibited by 1 in endothelial cells (HMEC-1). Inhibition was concentration-dependent in a micromolar range (10-75 μM) and did not involve cytotoxic effects. At 75 μM expression of the adhesion molecule ICAM-1 was down to 52.7 ± 3.3% and 20.4 ± 1.8% of control in TNF-α and LPS-stimulated HMEC-1, respectively. In contrast, 2 showed no activity. Quantitative RT-PCR experiments revealed that TNF-α-induced expression of the ICAM-1 gene was also reduced by 1 in a concentration-dependent manner, reaching 32.3 ± 6.2% of control at 100 μM matricine. Additional functional assays (NF-κB promotor activity and cytoplasm to nucleus translocation) confirmed the inhibitory effect of 1 on NF-κB signaling. Despite the fact that 1 lacks an α,β-unsaturated carbonyl and is thus not able to act via a Michael reaction with electron rich SH groups of functional biological molecules, data gave strong evidence that 1 inhibits NF-κB transcriptional activity in endothelial cells by an hitherto unknown mechanism and this may contribute to its well-known anti-inflammatory activity in vivo.
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Affiliation(s)
- Marcel Flemming
- Institut für Pharmazie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
| | - Birgit Kraus
- Institut für Pharmazie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
| | - Anne Rascle
- Institut für Immunologie, Universität Regensburg, Franz-Josef-Strauss-Allee 11, 93053 Regensburg, Germany
| | - Guido Jürgenliemk
- Institut für Pharmazie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
| | - Simone Fuchs
- Institut für Pharmazeutische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt am Main, Germany
| | - Robert Fürst
- Institut für Pharmazeutische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt am Main, Germany
| | - Jörg Heilmann
- Institut für Pharmazie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany.
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Madrigal-Santillán E, Madrigal-Bujaidar E, Álvarez-González I, Sumaya-Martínez MT, Gutiérrez-Salinas J, Bautista M, Morales-González &A, González-Rubio MGLY, Aguilar-Faisal JL, Morales-González JA. Review of natural products with hepatoprotective effects. World J Gastroenterol 2014; 20:14787-14804. [PMID: 25356040 PMCID: PMC4209543 DOI: 10.3748/wjg.v20.i40.14787] [Citation(s) in RCA: 220] [Impact Index Per Article: 20.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 11/03/2013] [Revised: 12/11/2013] [Accepted: 04/21/2014] [Indexed: 02/06/2023] Open
Abstract
The liver is one of the most important organs in the body, performing a fundamental role in the regulation of diverse processes, among which the metabolism, secretion, storage, and detoxification of endogenous and exogenous substances are prominent. Due to these functions, hepatic diseases continue to be among the main threats to public health, and they remain problems throughout the world. Despite enormous advances in modern medicine, there are no completely effective drugs that stimulate hepatic function, that offer complete protection of the organ, or that help to regenerate hepatic cells. Thus, it is necessary to identify pharmaceutical alternatives for the treatment of liver diseases, with the aim of these alternatives being more effective and less toxic. The use of some plants and the consumption of different fruits have played basic roles in human health care, and diverse scientific investigations have indicated that, in those plants and fruits so identified, their beneficial effects can be attributed to the presence of chemical compounds that are called phytochemicals. The present review had as its objective the collecting of data based on research conducted into some fruits (grapefruit, cranberries, and grapes) and plants [cactus pear (nopal) and cactus pear fruit, chamomile, silymarin, and spirulina], which are consumed frequently by humans and which have demonstrated hepatoprotective capacity, as well as an analysis of a resin (propolis) and some phytochemicals extracted from fruits, plants, yeasts, and algae, which have been evaluated in different models of hepatotoxicity.
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Capuzzo A, Occhipinti A, Maffei ME. Antioxidant and radical scavenging activities of chamazulene. Nat Prod Res 2014; 28:2321-3. [PMID: 24980540 DOI: 10.1080/14786419.2014.931393] [Citation(s) in RCA: 27] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/25/2022]
Abstract
Essential oils (EOs) of chamomile contain several bioactive compounds, including monoterpenes, sesquiterpenes, triterpenes and fatty acids. Hydrodistillation of chamomile EO induces the formation of chamazulene, a bioactive compound. Chamazulene was isolated from the EO by column chromatography. The total antioxidant capacity confirmed a higher antioxidant activity of chamazulene (IC50 = 6.4 μg mL(- 1)) than of ascorbic acid (IC50 = 12.8 μg mL(- 1)), α-tocopherol (IC50 = 20.5 μg mL(- 1)) and of butylated hydroxytoluene (BHT) (IC50 = 30.8 μg mL(- 1)). Chamazulene was unable to react with DPPH√. However, when chamazulene was assayed with ABTS√, a strong and significantly (P < 0.05) higher free radical scavenging activity was observed (IC50 = 3.7 μg mL(- 1)), with respect to BHT (IC50 = 6.2 μg mL(- 1)) and α-tocopherol (IC50 = 11.5 μg mL(- 1)). The results of this work show that chamazulene is an important factor for the antioxidant power of chamomile oil.
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Affiliation(s)
- Andrea Capuzzo
- a Biosfered S.r.l., Academic Spin-Off of the University of Turin , Via G. Quarello 15/A, 10135 Turin , Italy
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Tomić M, Popović V, Petrović S, Stepanović-Petrović R, Micov A, Pavlović-Drobac M, Couladis M. Antihyperalgesic and antiedematous activities of bisabolol-oxides-rich matricaria oil in a rat model of inflammation. Phytother Res 2013; 28:759-66. [PMID: 23983133 DOI: 10.1002/ptr.5057] [Citation(s) in RCA: 21] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/13/2012] [Revised: 07/05/2013] [Accepted: 07/22/2013] [Indexed: 11/05/2022]
Abstract
From the dried flower heads of Matricaria recutita L., essential oil was isolated by hydrodistillation, and in the obtained blue oil, α-bisabolol oxide A (21.5%), α-bisabolol oxide B (25.5%) and (Z)-spiroether (cis-en-yn-spiroether) (10.3%) were identified as the main compounds, by gas chromatography (GC) and GC-mass spectrometry analyses. The antihyperalgesic effects of this oil were examined in a rat model of inflammation induced by carrageenan, through a modified 'paw-pressure' test. Antiedematous effects were examined in a rat model of inflammation induced by carrageenan, dextran and histamine, through plethysmometry. Matricaria oil (25, 50 and 100 mg/kg, p.o.) exhibited a significant dose-dependent reduction of hyperalgesia and edema induced by carrageenan in both prophylactic and therapeutic treatment schemes. It was more efficacious in the prophylactic treatment scheme, and the corresponding median effective dose (ED50 ) ± standard error of the mean (SEM) values were 49.8 ± 6.0 and 42.4 ± 0.2 mg/kg for antihyperalgesic and antiedematous effects, respectively. Prophylactic treatments with matricaria oil (25, 50 and 100 mg/kg, p.o.) caused a significant dose-dependent antiedematous effect in dextran-induced edema with lower efficacy than in the carrageenan model. In a dose of 100 mg/kg, p.o., matricaria oil caused a slight reduction of histamine-induced edema. These results suggest that bisabolol-oxide-rich matricaria oil may be effective against pain and edema present in various inflammatory conditions, which supports matricaria traditional uses.
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Affiliation(s)
- Maja Tomić
- Department of Pharmacology, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221, Belgrade, Serbia
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Irmisch S, Krause ST, Kunert G, Gershenzon J, Degenhardt J, Köllner TG. The organ-specific expression of terpene synthase genes contributes to the terpene hydrocarbon composition of chamomile essential oils. BMC PLANT BIOLOGY 2012; 12:84. [PMID: 22682202 PMCID: PMC3423072 DOI: 10.1186/1471-2229-12-84] [Citation(s) in RCA: 32] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 04/23/2012] [Accepted: 06/01/2012] [Indexed: 05/20/2023]
Abstract
BACKGROUND The essential oil of chamomile, one of the oldest and agronomically most important medicinal plant species in Europe, has significant antiphlogistic, spasmolytic and antimicrobial activities. It is rich in chamazulene, a pharmaceutically active compound spontaneously formed during steam distillation from the sesquiterpene lactone matricine. Chamomile oil also contains sesquiterpene alcohols and hydrocarbons which are produced by the action of terpene synthases (TPS), the key enzymes in constructing terpene carbon skeletons. RESULTS Here, we present the identification and characterization of five TPS enzymes contributing to terpene biosynthesis in chamomile (Matricaria recutita). Four of these enzymes were exclusively expressed in above-ground organs and produced the common terpene hydrocarbons (-)-(E)-β-caryophyllene (MrTPS1), (+)-germacrene A (MrTPS3), (E)-β-ocimene (MrTPS4) and (-)-germacrene D (MrTPS5). A fifth TPS, the multiproduct enzyme MrTPS2, was mainly expressed in roots and formed several Asteraceae-specific tricyclic sesquiterpenes with (-)-α-isocomene being the major product. The TPS transcript accumulation patterns in different organs of chamomile were consistent with the abundance of the corresponding TPS products isolated from these organs suggesting that the spatial regulation of TPS gene expression qualitatively contribute to terpene composition. CONCLUSIONS The terpene synthases characterized in this study are involved in the organ-specific formation of essential oils in chamomile. While the products of MrTPS1, MrTPS2, MrTPS4 and MrTPS5 accumulate in the oils without further chemical alterations, (+)-germacrene A produced by MrTPS3 accumulates only in trace amounts, indicating that it is converted into another compound like matricine. Thus, MrTPS3, but also the other TPS genes, are good markers for further breeding of chamomile cultivars rich in pharmaceutically active essential oils.
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Affiliation(s)
- Sandra Irmisch
- Institute of Pharmacy, Martin Luther University, Hoher Weg 8, Halle 06120, Germany
- Current address: Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, Jena 07745, Germany
| | - Sandra T Krause
- Institute of Pharmacy, Martin Luther University, Hoher Weg 8, Halle 06120, Germany
| | - Grit Kunert
- Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, Jena 07745, Germany
| | - Jonathan Gershenzon
- Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, Jena 07745, Germany
| | - Jörg Degenhardt
- Institute of Pharmacy, Martin Luther University, Hoher Weg 8, Halle 06120, Germany
| | - Tobias G Köllner
- Institute of Pharmacy, Martin Luther University, Hoher Weg 8, Halle 06120, Germany
- Current address: Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, Jena 07745, Germany
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Gers CF, Rosellen J, Merkul E, Müller TJJ. One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation-decarbonylative alkynylation-cyclocondensation sequences. Beilstein J Org Chem 2011; 7:1173-81. [PMID: 21915223 PMCID: PMC3168959 DOI: 10.3762/bjoc.7.136] [Citation(s) in RCA: 10] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/01/2011] [Accepted: 07/29/2011] [Indexed: 11/23/2022] Open
Abstract
A novel one-pot four-component synthesis of pyrimidyl- and pyrazolylazulenes through the use of glyoxylation-decarbonylative alkynylation-cyclocondensation sequences starting from azulene or guaiazulene as substrates, gives rise to the formation of the target compounds in moderate to good yields.
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Affiliation(s)
- Charlotte F Gers
- Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany
| | - Julia Rosellen
- Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany
| | - Eugen Merkul
- Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany
| | - Thomas J J Müller
- Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany
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Pavesi VCS, Lopez TCC, Martins MAT, Sant'Ana Filho M, Bussadori SK, Fernandes KPS, Mesquita-Ferrari RA, Martins MD. Healing action of topical chamomile on 5-fluoracil induced oral mucositis in hamster. Support Care Cancer 2010; 19:639-46. [PMID: 20424869 DOI: 10.1007/s00520-010-0875-0] [Citation(s) in RCA: 22] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/13/2009] [Accepted: 03/29/2010] [Indexed: 10/19/2022]
Abstract
BACKGROUND Oral mucositis is a common complication in the treatment of cancer. Its management and prevention are seen as high priority in cancer patient care. The aim of the present study was to investigate the effect of topical chamomile in the treatment of oral mucositis induced by 5-fluoracil (5-FU) in hamsters. MATERIALS AND METHODS One hundred five hamsters were randomly separated into three groups (35 animals each): group I--without treatment (control); group II--treatment with chamomile (Ad-Muc®); and group III--treatment with corticoid (betamethasone elixir--Celestone®). The animals received an intraperitoneal injection of 5-FU on days 0 and 2. On days 3 and 4, the buccal mucosa was scratched and therapy was initiated on day 5. Three animals were sacrificed on days 0, 2, 5, 8, 10, 12, 14, and 16, weighed, and the buccal mucosa removed for clinical and histopathological analysis. RESULTS The animals that developed mucositis and were treated with chamomile or the corticoid agent weighed significantly less than those in the control group. The group treated with the corticoid agent exhibited a more severe clinical condition, whereas the group treated with chamomile exhibited mild mucositis throughout the experiment. The group treated with chamomile had a 12-fold greater chance of scoring zero (absence of mucositis) than the control group. Analysis of the histopathological results demonstrated that the group treated with chamomile exhibited a lesser degree of mucositis throughout the evaluation period in comparison to the control and corticoid groups. CONCLUSION Chamomile proved effective in the treatment of oral mucositis in a hamster model. However, well-designed clinical studies are needed to confirm the clinical efficacy of this medicine in humans.
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Nogueira JCR, Diniz MDFM, Lima EO. In vitro antimicrobial activity of plants in Acute Otitis Externa. Braz J Otorhinolaryngol 2008; 74:118-24. [PMID: 18392512 PMCID: PMC9450625 DOI: 10.1016/s1808-8694(15)30761-8] [Citation(s) in RCA: 26] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/19/2006] [Accepted: 09/11/2007] [Indexed: 11/01/2022] Open
Abstract
UNLABELLED Acute Otitis Externa is an inflammation of the outer auditory meatus, and according to popular saying, medicinal plant extracts can be used in its treatment. AIM to assess the in vitro antimicrobial activity of the following plants: Aleolanthus suaveolens; Caryophyllus aromaticus; Cymbopogon citratus; Matricaria chamomila; Pithecellobium avaremotemo; Plectranthus amboinicus and Ruta graveolens on the germs that cause otitis externa. MATERIALS AND METHODS the minimum inhibitory concentration of extracts and oils from these plants was obtained from otitis externa samples. RESULTS Staphylococcus aureus in 10 cultures, Pseudomonas aeruginosa in 8, Pseudomonas aeruginosa and Staphylococcus aureus together in 5 cultures and Candida albicans and Candida krusei in 4 cultures. P. aeruginosa was resistant to all oils and extracts tested; extracts from A. suaveolens, P. avaremotemo and R. graveolens were inactive; the essential oil from C. aromaticus and M. chamomila were active against 3 strains of S. aureus and the Candida strains; seven of the S. aureus strains were sensitive to the P. amboinicus extract; however, the oil was inactive against 4 S. aureus strains and the Candida strains were sensitive to the R. graveolens essential oil. CONCLUSION depending on the etiological agent, some plants presented satisfactory results, however we still need more detailed studies in order to better use these plants.
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Ramadan M, Watzer B. Determination of chamazulene carboxylic acid in serum by high-performance liquid chromatography. J Chromatogr A 2006; 1133:221-5. [PMID: 16942774 DOI: 10.1016/j.chroma.2006.08.035] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/06/2005] [Revised: 08/09/2006] [Accepted: 08/11/2006] [Indexed: 11/21/2022]
Abstract
A new, simple and sensitive high-performance liquid chromatographic (HPLC) method was developed for the determination of chamazulene carboxylic acid (CCA) in serum. The technique is based on a single liquid-liquid extraction of the substance using ibuprofen as internal standard (I.S.). The separation was achieved on a C(18) reversed-phase column using acetonitrile/water (4:6, pH 3) as mobile phase. The effluent was monitored at 221 and 286 nm. The calibration curves were linear over the concentration range of 0.1-30 microg/ml. The intra- and inter-day RSDs were in all cases less than 15 and 11%, respectively. The limit of quantitation was 0.1 microg/ml. The assay was developed and validated to be applied in a pharmacokinetic study in healthy volunteers.
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Affiliation(s)
- Mai Ramadan
- Department of Pharmaceutical Chemistry, Philipps University, Marbacher Weg 6, D-35032 Marburg, Germany.
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Ramadan M, Goeters S, Watzer B, Krause E, Lohmann K, Bauer R, Hempel B, Imming P. Chamazulene carboxylic acid and matricin: a natural profen and its natural prodrug, identified through similarity to synthetic drug substances. JOURNAL OF NATURAL PRODUCTS 2006; 69:1041-5. [PMID: 16872141 DOI: 10.1021/np0601556] [Citation(s) in RCA: 50] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/11/2023]
Abstract
Chamazulene carboxylic acid (1) is a natural profen with anti-inflammatory activity and a degradation product of proazulenic sesquiterpene lactones, e.g., matricin. Both 1 and proazulenes occur in chamomile (Matricaria recutita), yarrow (Achillea millefolium), and a few other Asteraceae species. It was isolated in improved yields, characterized physicochemically, and found to be an inhibitor of cyclooxygenase-2, but not of cyclooxygenase-1. It had anti-inflammatory activity in several animal models with local and systemic application. When human volunteers were given matricin orally, plasma levels of 1 were found to be in the micromolar range. Matricin was converted to 1 in artificial gastric fluid, but not in artificial intestinal fluid. Matricin and the yarrow proazulenes are proposed to be anti-inflammatory through conversion to 1. Intriguingly, the biological activity of the natural compound 1 was found because of its similarity to fully synthetic drug substances. This is the reverse process of the common lead function of natural compounds in drug discovery.
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Affiliation(s)
- Mai Ramadan
- Institut fuer Pharmazeutische Chemie, Philipps-Universitaet, 35032 Marburg, Germany
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Wegener T, Wagner H. The active components and the pharmacological multi-target principle of STW 5 (Iberogast). PHYTOMEDICINE : INTERNATIONAL JOURNAL OF PHYTOTHERAPY AND PHYTOPHARMACOLOGY 2006; 13 Suppl 5:20-35. [PMID: 16926095 DOI: 10.1016/j.phymed.2006.07.001] [Citation(s) in RCA: 37] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/11/2023]
Abstract
The therapeutic equivalence of the multi-herbal drug combination STW 5 (Iberogast) with two synthetic standard drugs can be explained by an additive or overadditive pharmacological synergism. A review of the different chemical constituents contained in this fixed combination of nine herbal drug extracts and their dominant mechanisms of action shows that they correlate very well with the clinically relevant overall pharmacological profile of the multi-herbal drug combination. This comprises modulatory effects on gastro-intestinal motility, anti-inflammatory action, inhibitory effects on gastric acid production and anti-oxidative and radical-inhibiting properties. As a multi-drug preparation with a multitude of therapeutic targets relevant in functional gastrointestinal diseases, its pharmacological profile of action in accordance with the multi-target principle.
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Affiliation(s)
- T Wegener
- Consulting Herbal Medicinal Products, Zeisigstrasse 9, 33378 Rheda-Wiedenbrück, Germany
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Sashidhara KV, Verma RS, Ram P. Essential oil composition ofMatricaria recutita L. from the lower region of the Himalayas. FLAVOUR FRAG J 2006. [DOI: 10.1002/ffj.1582] [Citation(s) in RCA: 21] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/06/2022]
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Abraham S, Kumar MS, Sehgal PK, Nitish S, Jayakumar ND. Evaluation of the Inhibitory Effect of Triphala on PMN-Type Matrix Metalloproteinase (MMP-9). J Periodontol 2005; 76:497-502. [PMID: 15857087 DOI: 10.1902/jop.2005.76.4.497] [Citation(s) in RCA: 40] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/13/2022]
Abstract
BACKGROUND This study evaluated the inhibitory activity of triphala on PMN-type matrix metalloproteinase (MMP-9) expressed in adult periodontitis patients and compared its activity with another ayurvedic drug, kamillosan, and doxycycline, which has known inhibitory activity. METHODS Matrix metalloproteinases (MMPs) were extracted from gingival tissue samples from 10 patients (six males, four females) with chronic periodontitis. Tissue extracts were treated with the drug solutions, the inhibition was analyzed by gelatin zymography, and the percentage of inhibition was determined by a gel documentation system. RESULTS The activity of MMPs was significantly decreased with the use of the drugs. Triphala showed a 76.6% reduction of MMP-9 activity, whereas kamillosan showed a 46.36% reduction at a concentration of 1,500 microg/ml (crude extract) and doxycycline showed a 58.7% reduction at a concentration of 300 microg/ml (pure drug). CONCLUSION The present study showed the strong inhibitory activity of triphala on PMN-type MMPs involved in the extracellular matrix (ECM) degradation during periodontitis.
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Affiliation(s)
- Sajith Abraham
- Department of Periodontia, Saveetha Dental College and Hospitals, Chennai, Tamil Nadu, India
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Szoke E, Máday E, Tyihák E, Kuzovkina IN, Lemberkovics E. New terpenoids in cultivated and wild chamomile (in vivo and in vitro). J Chromatogr B Analyt Technol Biomed Life Sci 2004; 800:231-8. [PMID: 14698259 DOI: 10.1016/j.jchromb.2003.09.038] [Citation(s) in RCA: 25] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/26/2022]
Abstract
The effect of Chamomilla recutita (L.) Rauschert is made up by several groups of active substances, among which terpenoids in the inflorescences are of greatest importance. Among cultivated species, the Hungarian BK-2 contains more chamazulene in its essential oil than the German Degumil type, which is mainly cultivated for its (-)-alpha-bisabolol. Both components have important antiinflammatory activities. Among wild chamomile populations in Hungary, a population was found in the area of Szabadkigyós containing significant amounts-on average 48%-of (-)-alpha-bisabolol in its inflorescence oil. In vitro cultures were made from this population to obtain propagation material containing a high number of active substances. The intact roots contained no (-)-alpha-bisabolol but the sesquiterpene alcohol beta-eudesmol as new compound was identified by our group. Sterile plantlets, cultured in vitro, were multiplied for phytochemical investigations. Pharmacologically important compounds of the essential oils were followed in great detail. The amount of in vitro cultured terpenoids and polyin compounds was compared with that of in vivo plants. These volatile compounds were identified by comparing their retention times with those of authentic standards, essential oils of known composition and peak enrichment. The confirmation of identity was done by comparison of their mass spectra with those reported in the literature and reference compounds. The percentage evaluation of each component was made by area normalisation. Gas chromatography (GC) and mass spectrometry (MS) showed that sterile chamomile cultures generated the most important terpenoid and polyin compounds characteristic of the parent plant. We identified germacrene-D, berkheyaradulene, 4-(2', 4', 4'-trimethyl-bicyclo[4.1.0]hept-2'-en-3'-yl)-3-buten-2-one, geranyl-isovalerate and cedrol as new components in these sterile cultures.
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Affiliation(s)
- Eva Szoke
- Department of Pharmacognosy, Ulloi Street 26, Semmelweis University, Budapest H-1085, Hungary.
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Hernández-Ceruelos A, Madrigal-Bujaidar E, de la Cruz C. Inhibitory effect of chamomile essential oil on the sister chromatid exchanges induced by daunorubicin and methyl methanesulfonate in mouse bone marrow. Toxicol Lett 2002; 135:103-110. [PMID: 12243869 DOI: 10.1016/s0378-4274(02)00253-9] [Citation(s) in RCA: 32] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 02/07/2023]
Abstract
Different preparations of chamomile (Matricaria chamomilla) are used to treat various diseases, including inflammation and cancer; however, no studies on the plant's antigenotoxic capacity have been made. The aim of the present work was to determine the inhibitory effect of the chamomile essential oil (CO), on the sister chromatid exchanges (SCEs) produced by daunorubicin and methyl methanesulfonate (MMS) in mouse bone marrow cells. CO was analyzed and was found to contain 13 compounds, mainly bisabolol and its oxides, chamazulene, farnesene, germacrene and other sesquiterpenes. Initially, a toxic and a genotoxic analysis of CO were made; both showed negative results. To determine whether CO can inhibit the mutagenic effects induced by daunorubicin, one group of mice was administered corn oil, another group was treated with the mutagen (10 mg/kg), a third group was treated with 500 mg/kg of CO; three other groups were treated first with CO (5, 50 and 500 mg/kg) and then with 10 mg/kg of daunorubicin. In the case of MMS, the experimental groups consisted of the following: the negative control group which was administered corn oil, a group treated with 25 mg/kg of MMS, a group treated with 1000 mg/kg of CO, and three groups treated first with CO (250, 500 and 1000 mg/kg) and then with MMS (25 mg/kg). The results indicated a dose-dependent inhibitory effect on the SCEs formed by both mutagens. In the case of daunorubicin, a statistically significant result was observed in the three tested doses: from the lowest to the highest dose, the inhibitory values corresponded to 25.7, 63.1 and 75.5%. No alterations were found with respect to the cellular proliferation kinetics, but a reduction in the mitotic index was detected. As regards MMS, the inhibitory values were 24.8, 45.8 and 60.6%; no alterations were found in either the cellular proliferation kinetics or in the mitotic indices. Our results suggest that CO may be an effective antimutagen that could be considered for further study.
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Affiliation(s)
- A Hernández-Ceruelos
- Laboratorio de Genética, Escuela Nacional de Ciencias Biológicas, IPN. Carpio y Plan de Ayala Sto Tomas, 11340 DF, Mexico, Mexico
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Abstract
Though essential oils are a proven antiseptic, little work has investigated their use on chronic wounds. This article describes the progress and problems of a small study of five patients, who were treated with lavender and chamomile essential oils.
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Affiliation(s)
- D Hartman
- Tri-County Hospital, Wadena, Minnesota, USA.
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Glasl S, Gunbilig D, Narantuya S, Werner I, Jurenitsch J. Combination of chromatographic and spectroscopic methods for the isolation and characterization of polar guaianolides from Achillea asiatica. J Chromatogr A 2001; 936:193-200. [PMID: 11761000 DOI: 10.1016/s0021-9673(01)00947-5] [Citation(s) in RCA: 11] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/19/2022]
Abstract
Four polar guaianolides, 8alpha-angeloxy-2alpha,4alpha, 10beta-trihydroxy-6betaH,7alphaH, 11betaH-1(5)-guaien- 12,6alpha-olide; 8alpha-angeloxy-1beta,2beta:4beta,5beta-diepoxy- 10beta-hydroxy-6betaH,7alphaH,11betaH-12,6alpha-guaianolide; 8alpha-angeloxy-4alpha, 10beta-dihydroxy-2-oxo-6betaH, 7alphaH, 11betaH- 1(5)-guaien- 12,6alpha-olide and 8-desacetyl-matricarin, were isolated from Achillea asiatica and characterized by TLC, MS, IR, HPLC and diode array detection. Purified extracts were separated by means of flash chromatography. HPLC separations were achieved using different methanol-water gradients as mobile phase and LiChrospher 100-RP8 5 microm or Zorbax SB-C8 3.5 microm as stationary phases. The chromatographical data are compared to those of the proazulene 8alpha-tigloxy-artabsin which shows antiinflammatory effects. By means of these characteristics the identification of the guaianolides with potential antiphlogistic properties is also possible from other sources.
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Affiliation(s)
- S Glasl
- Institute of Pharmacognosy, University of Vienna, Centre of Pharmacy, Althanstrasse 14, A-1090 Vienna, Austria
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Szentmihályi K, Forgács E, Hajdú M, Then M. In vitro study on the transfer of volatile oil components. J Pharm Biomed Anal 2001; 24:1073-80. [PMID: 11248503 DOI: 10.1016/s0731-7085(00)00542-2] [Citation(s) in RCA: 10] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
Abstract
The following volatile oils were tested in vitro: chamomile (Matricaria recutica L.), peppermint (Mentha piperita L.) and sage (Salvia officinalis L.) to obtain information on which components of volatile oils or minerals are able to pass through the membranes under different conditions. The transfer of chamomile and peppermint oil from aqueous volatile oil to the stomach (pH=1.1) and then to the plasma (pH=7.5) was studied, and the transfer of sage oil through the skin (from pH=5.5 to pH=7.5) was examined. The transfer of some components was more favorable than that of others. The transfer of chamomile oil was faster to buffer pH=1.1 than from buffer pH=1.1 to buffer pH=7.5 and most of the components, except for chamazulene, passed through the membranes. In the case of peppermint the components went through the membranes in the first 15 min although the main components mostly remained in the initial solution. The sage oil transferred showed the same characteristics as the starting oil. A small amount of metal present in the volatile oils also passed through the membranes. The transfer of metals varied, depending on the time, type of the oil, metal quality and the conditions applied.
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Affiliation(s)
- K Szentmihályi
- Chemical Research Center, Hungarian Academy of Sciences, 1525 P.O. Box 17, Budapest, Hungary.
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Zekovic ZP. Chamomile Ligulate Flowers in Supercritical CO2-Extraction. JOURNAL OF ESSENTIAL OIL RESEARCH 2000. [DOI: 10.1080/10412905.2000.9712049] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 10/28/2022]
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Pekic B, Zekovic Z, Petrovic L, Adamovic D. Essential Oil of Chamomile Ligulate and Tubular Flowers. JOURNAL OF ESSENTIAL OIL RESEARCH 1999. [DOI: 10.1080/10412905.1999.9701057] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 10/28/2022]
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Medić-Šarić M, Stanić G, Maleš Ž, Šarić S. Application of numerical methods to thin-layer chromatographic investigation of the main components of chamomile (Chamomilla recutita (L.) Rauschert) essential oil. J Chromatogr A 1997. [DOI: 10.1016/s0021-9673(97)00352-x] [Citation(s) in RCA: 14] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/15/2022]
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Ness A, Metzger JW, Schmidt PC. Isolation, identification and stability of 8-desacetylmatricine, a new degradation product of matricine. ACTA ACUST UNITED AC 1996. [DOI: 10.1016/s0031-6865(96)00026-x] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/25/2022]
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Matos FJ, Machado MI, Alencar JW, Craveiro AA. Constituents of Brazilian Chamomile Oil. JOURNAL OF ESSENTIAL OIL RESEARCH 1993. [DOI: 10.1080/10412905.1993.9698234] [Citation(s) in RCA: 14] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 10/28/2022]
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