- Composition and antimicrobial activity of Anemopsis californica leaf oil
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Isolation and characterization of leaf volatiles in Anemopsis californica (Nutt.) Hook. and Am. (A. californica) was performed using steam distillation, solid-phase microextraction, and supercritical fluid extraction. Thirty-eight compounds were detected and identified by gas chromatography; elemicin was the major component of the leaf volatiles. While the composition of the leaf volatiles varied with method of extraction, α-pinene, sabinene, β-phellandrene, 1,8-cineole, piperitone, methyl eugenol, (E)-caryophyllene, and elemicin were usually present in readily detectable amounts. Greenhouse-reared clones of a wild population of A. californica had an identical leaf volatile composition with the parent plants. Steam-distilled oil had antimicrobial properties against 3 (Staphylococcus aureus, Streptococcus pneumoniae, and Geotrichim candidum) of 11 microbial species tested. Some of this bioactivity could be accounted for by the α-pinene in the oil.
- Medina, Andrea L.,Lucero, Mary E.,Holguin, F. Omar,Estell, Rick E.,Posakony, Jeff J.,Simon, Julian,O'Connell, Mary A.
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- Antibacterial mode of action of the daucus carota essential oil active compounds against campylobacter jejuni and efflux-mediated drug resistance in gram-negative bacteria
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Today, an alarming rise of bacterial gastroenteritis in humans resulting from consuming Campylobacter-tainted foods is being observed. One of the solutions for mitigating this issue may be the antibacterial activity of essential oils. In the present research, we propose to study the antibacterial activity against Campylobacter and other Gram-negative bacteria of Daucus carota essential oil and its active molecules. In addition, a few chemically synthesized molecules such as (E)-methylisoeugenol, Elemicin, and eugenol were also studied. The results showed that the essential oil itself and its most active component, (E)-methylisoeugenol, exhibited bactericidal effects. Similar effects were detected using purified and chemically synthesized molecules. Also, it was observed that the Daucus carota essential oil and its active molecules affected intracellular potassium and intracellular ATP contents in Campylobacter cells. Inhibition of the membrane bound FO F1-ATPase was also observed. Eventually, for the first time, the efflux mechanism of active molecules of Daucus carota essential oil was also identified in gamma proteobacteria and its specific antibacterial activity against Campylobacter jejuni was associated with the lack of this efflux mechanism in this species.
- Berti, Liliane,Bolla, Jean Michel,Brunel, Jean Michel,Dedieu, Luc,Lorenzi, Vanina,Muselli, Alain
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- Synthesis and biological activity of novel phenol-conjugates of isoxazolidines
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1,3-Dipolar cycloadditions of the phosphonylnitrone with selected allylbenzenes produced mixtures of diastereoisomeric (3-diethoxyphosphoryl)isoxazolidines with good trans/cis diastereoselectivities (d.e. 80%) and good to excellent overall yields. No inhibitory activity against a broad panel of DNA and RNA viruses was detected for (3-diethoxyphosphoryl)isoxazolidines at 250 μM. Isoxazolidines trans-3k : cis-3k (95: 5) slightly reduced human embryonic lung (HEL) cell viability (CC50 = 45 μM). Four out of ten isoxazolidines inhibited the growth of Staphylococcus epidermidis ATCC 12228 (up to 40% for the most active compound). They were also inhibitory against Staphylococcus aureus ATCC 6538 although inhibition did not exceeded 25%. None of the isoxazolidines affected Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 15442 growth.
- Piotrowska, Dorota G.,Wróblewski, Andrzej E.,Balzarini, Jan,Andrei, Graciela,Schols, Dominique,Snoeck, Robert,Felczak, Aleksandra,Wrońska, Natalia,Lisowska, Katarzyna,G?owacka, Iwona E.
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p. 1091 - 1100
(2017/08/01)
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- A detour route for meta functionalization of phenols
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Cyclohexadienones participate in a two-step procedure, a Michael addition followed by aromatization, providing hitherto difficult-to-synthesize meta-functionalized phenol derivatives in good yield. Application of the developed approach is exemplified by synthesizing C-aryl acetophenones, C-aryl glycines, and elemicin - an allylphenol natural product. Georg Thieme Verlag Stuttgart · New York.
- Chittimalla, Santhosh Kumar,Kuppusamy, Rajesh,Bandi, Chennakesavulu
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p. 1991 - 1996
(2014/11/08)
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- Discovery of structurally simplified analogs of colchicine as an immunosuppressant
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We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg.
- Chang, Dong-Jo,Kim, Wan-Joo
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p. 3121 - 3125
(2014/06/24)
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- SYNTHESIS OF ELEMICIN AND TOPICAL ANALGESIC COMPOSITIONS
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The present invention is directed to the synthesis of elemicin and its isomeric form, and their use in topical analgesic formulations, including for dental and veterinary use. Various compositions include gels, films, dressings, cavity filling gels, having analgesic and/or antifungal properties.
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- Sterically controlled alkylation of arenes through iridium-catalyzed C-H borylation
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Complementary chemistry: A one-pot method for the site-selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir-catalyzed C-H borylation, followed by Pd- or Ni-catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel-Crafts alkylation; meta-selective alkylation of a broad range of arenes with various electronic properties and functional groups occurs in good yield with high site selectivity. Copyright
- Robbins, Daniel W.,Hartwig, John F.
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p. 933 - 937
(2013/02/25)
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- Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates
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This paper highlights Ni-catalyzed allylation of electron-rich aryl bromides with a variety of substituted allylic carbonates using zinc as the terminal reductant, affording E-alkenes regioselectively in good to excellent yields by the addition of aryl to the less hindered allylic carbon. The electron-deficient aryl bromides and chlorides are also highly efficient coupling partners. The Royal Society of Chemistry 2013.
- Cui, Xiaozhan,Wang, Shulin,Zhang, Yuwei,Deng, Wei,Qian, Qun,Gong, Hegui
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supporting information
p. 3094 - 3097
(2013/05/23)
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- Nickel-catalyzed reductive coupling of aryl halides with secondary alkyl bromides and allylic acetate
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A room-temperature Ni-catalyzed reductive method for the coupling of aryl bromides with secondary alkyl bromides has been developed, providing C(sp 2)-C(sp3) products in good to excellent yields. Slight modification of this protocol allows efficient coupling of activated aryl chlorides with cyclohexyl bromide and aryl bromides with allylic acetate.
- Wang, Shulin,Qian, Qun,Gong, Hegui
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supporting information; experimental part
p. 3352 - 3355
(2012/08/08)
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- Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
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This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%).
- Gerbino, Dario C.,Mandolesi, Sandra D.,Schmalz, Hans-Guenther,Podesta, Julio C.
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experimental part
p. 3964 - 3972
(2010/02/27)
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- Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases
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Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.
- Rudroff, Florian,Rydz, Joanna,Ogink, Freek H.,Fink, Michael,Mihovilovic, Marko D.
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p. 1436 - 1444
(2008/09/17)
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- Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure
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Nine bioactive allylphenol (anisole) derivatives (e.g. eugenol, safrole and asaricin) present in several plants of the genus Piper have been synthesized in medium to high yield via aryl cation intermediates. This expeditious metal-free procedure involves the irradiation of the corresponding chlorophenols or chloroanisoles in a polar solvent (MeCN or, better, TFE or aqueous acetonitrile) in the presence of allyltrimethylsilane. Estragole has also been synthesized starting from the corresponding fluoroderivative and diazonium salt, though in a lower yield. The Royal Society of Chemistry 2005.
- Protti, Stefano,Fagnoni, Maurizio,Albini, Angelo
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p. 2868 - 2871
(2007/10/03)
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- First enantioselective synthesis of the neolignans Rhaphidecursinol A and Virolongin B
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The enantioselective synthesis of the neolignans Rhaphidecursinol A and Virolongin B is reported for the first time. The key reactions in the synthesis were Sharpless asymmetric dihydroxylation and Mitsunobu reaction. The absolute configuration of Rhaphidecursinol A was confirmed.
- Ren, Xinfeng,She, Xuegong,Peng, Kun,Su, Ying,Xie, Xingang,Pan, Xinfu,Zhang, Hongbin
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p. 969 - 974
(2007/10/03)
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- First enantioselective synthesis of Rhaphidecursinol A
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The enantioselective synthesis of Rhaphidecursinol A was reported for the first time and the absolute configuration of Rhaphidecursinol A was confirmed.
- Ren, Xinfeng,She, Xuegong,Peng, Kun,Su, Ying,Xie, Xingang,Pan, Xinfu
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p. 358 - 359
(2007/10/03)
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- Method of causing the reduction of physiological and/or subjective reactivity to stress in humans being subjected to stress conditions
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Described is a method for reducing physiological and/or subjective reactivity to stress in humans being subjected to stress conditions. The method consists of administering to such humans an effective amount of a physiological and/or subjective stress reactivity-reducing substance selected from the group consisting of: (i) Nutmeg Oil; (ii) Mace Extract; (iii) Neroli Oil; (iv) Valerian Oil; (v) Myristicin; (vi) Isoelemicin; and (vii) Elemicin. Administration is through inhalation or transdermally using one or more of the above ingredients alone or in a suitable composition such as ethanol and/or a perfume composition, cologne or perfumed article (e.g., air freshener or deodorant stick). Also described is a method for detecting the reduction of physiological and/or subjective reactivity to stress in a human.
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