- Two antimicrobial alkaloids from heartwood of Liriodendron tulipifera L.
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Alcoholic extracts of the heartwood of Liriodendron tulipifera have demonstrated antimicrobial activity against Staphylococcus aureus, Myobacterium smegmatis, Candida albicans, and Aspergillus niger. The antimicrobial activity was associated only with the alkaloidal fraction. Separation of the active alkaloidal fraction by chromatography led to the isolation and identification of dehydroglaucine and liriodenine as the active components. Several other alkaloidal derivatives were prepared and tested. In addition to the active alkaloids, michelalbine was also identified in the tertiary nonphenolic base fraction along with the lignan, lirioresinol B dimethyl ether, and two N acetylnoraporphine alkaloids from the nonbasic fraction.
- Hufford,Funderburk,Morgan,Robertson
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- Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids
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A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.
- Nishimoto, Saeko,Nakahashi, Hiromichi,Toyota, Masahiro
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supporting information
(2020/11/13)
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- Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles
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A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of α-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol. (Figure presented.).
- Guillemard, Lucas,Colobert, Fran?oise,Wencel-Delord, Joanna
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p. 4184 - 4190
(2018/09/25)
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- Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
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Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.
- Zheng, Bo,Qu, Hui-Ya,Meng, Tian-Zhuo,Lu, Xia,Zheng, Jie,He, Yun-Gang,Fan, Qi-Qi,Shi, Xiao-Xin
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p. 28997 - 29007
(2018/08/29)
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- Direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[ de,g ]quinolin-7-ones via reductive photocyclization
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A series of A/D-ring substituted dibenzo[de,g]quinolin-7-ones was produced from the corresponding isoquinolinones and (2-bromophenyl)acetonitriles in four steps. This represents a convenient approach toward the synthesis of tetracyclic alkaloids. A direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[de,g]quinolin-7-ones is the key step in the total synthesis. The yield of the reductive photocyclization depends on the position of the substituents at the isoquinolyl ring and the phenyl group. The mechanism of the reductive photocyclization is also discussed.
- Chuang, Ta-Hsien,Li, Chien-Fu,Lee, Hong-Zin,Wen, Yu-Chia
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p. 4974 - 4984
(2013/06/27)
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- THE SYNTHESIS OF OXOAPORPHINES AND PHENANTHRENEDIONES FROM 7-HYDROXYDEHYDRONORAPORPHINES
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Oxidation of 7-hydroxydehydronoraporphines with air over platinum or palladium yields oxoaporphines in high yield.When the nitrogen is acylated, oxidation with air in the presence of copper ions causes an oxidative ring fragmentation to form phenanthrenediones, also in high yield.
- Costanza, Carl,Lenz, George R.,Lessor, Ralph A.
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p. 465 - 478
(2007/10/02)
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- SYNTHESIS OF NOVEL 7,7'-BIS-6a,7-DEHYDRONORAPORPHINES
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New dimers, (+/-)-bisdehydroanonaine 5a, (+/-)-bisdehydroxylopine 5c, (+/-)-bisdehydronornantenine 5d and (+/-)-7-dehydroxylopinyl-7'-dehydronornantenine 8, and the previously described (+/-)-urabaine 5b, were prepared from dehydroxylopine 3c and known dehydronoraporphines 3a, 3b, and 3d via dimerization at the β-carbon of cyclic secondary enamines.
- Jossang, Akino,Leboeuf, Michel,Cave, Andre
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p. 2191 - 2198
(2007/10/02)
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- A DIRECT CONVERSION OF PHENANTHRENES TO APORPHINOIDS
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We desribe a single-step conversion of phenanthrene alkaloid derivatives into oxoaporphines based on the cyclization of 9,10-phenanthrenediones with ethanamine side-chains under basic conditions.
- Seijas, Julio A.,Lera, Angel Rodriguez de,Villaverde, Carmen,Castedo, Luis
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p. 3079 - 3084
(2007/10/02)
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- Synthetic Photochemistry: Synthesis of Liriodenine
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Bischler-Napieralski cyclisation of N--2'-bromophenylacetamide (3) followed by manganese dioxide oxidation of the crude amine (4) gives 1-(2'-bromobenzoyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline (5) which is aromatis
- Gupta, Y. P.,Yadav, V. S.,Mohammad, Taj
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p. 429 - 431
(2007/10/02)
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- FREMY'S SALT OXIDATION OF SOME ISOQUINOLINE ALKALOIDS. BIOGENETIC CONSIDERATIONS
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Fremy's salt oxidation of benzylisoquinoline and aporphine alkaloids to isoquinolones and oxoaporphines is described.Aminium radicals are suggested to account for the observed results.Their possible involvement in alkaloid biosynthesis is considered.
- Castedo, Luis,Puga, Alberto,Saa, Jose M.,Suau, Rafael
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p. 2233 - 2236
(2007/10/02)
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- Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids
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Liriodenine was evaluated for its antibacterial and antifungal activity against several microorganisms. Other related oxoaporphine alkaloids also were evaluated. Attempts to prepare oxoaporphine alkaloids from N-acetylnoraporphines were unsuccessful, but an unexpected phenanthrene alkaloid was obtained. A novel N-demethylation reaction was noted when oxoglaucine methiodide and liriodenine methiodide were treated with alumina.
- Hufford,Sharma,Oguntimein
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p. 1180 - 1183
(2007/10/02)
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- SYNTHETIC PHOTOCHEMISTRY. SYNTHESIS OF (+/-)OLIVEROLINE AND (+/-)USHINSUNINE
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Sodium borohydride reduction of 1-(2'-Bromobenzoyl)-2-methyl-3,4-dihydro-6,7-methylenedioxyisoquinolinium iodide (4) gave a mixture of alcohols which on irradiation in dil.HCl afforded (+/-) oliveroline and (+/-) ushinsunine.
- Kessar, S.V.,Gupta, Y.P.,Yadav, V.S.,Narula, Mridu,Mohammad, Taj
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p. 3307 - 3308
(2007/10/02)
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- Antimicrobial compositions
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Antimicrobial compositions useful in mammal. An extract of the heartwood of Liriodendron tulipifera L., provides components and derivatives thereof useful as antimicrobial agents; antimicrobial compositions comprising liriodenine, dehydroglaucine liriodenine methiodide and oxoglaucine methiodide compounds of and derivatives and mixtures thereof of alkaloids isolated from the extract of the heartwood of Liriodendron tulipifera L. The antimicrobial compositions being particularly useful against Gram positive bacteria, acid fast bacteria and fungi and yeast.
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