- COUMARINS IN ARTEMISIA CARUIFOLIA
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Isolation of daphnetin 7-methyl ether, daphnetin dimethyl ether, daphnetin methylene ether, daphnetin 7-methyl-8(3,3-dimethylallyl) ether and 3,4-dimethoxy-2-hydroxycinnamic acid from Artemisia caruifolia is reperted. - Key Word Index: Artemisia caruifolia; Compositae; coumarins; daphnetin derivatives; 3,4-dimethoxy-2-hydroxycinnamic acid.
- Barua, Nabin C.,Sharma, Ram P.,Madhusudanan, K. P.,Thyagarajan, Gopalakrishna,Herz, Werner
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- Rare benzonaphthoxanthenones from Chinese folk herbal medicine Polytrichum commune and their anti-neuroinflammatory activities in vitro
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Two new (1–2) as well as five known (3–7) compounds were isolated from Polytrichum commune, a folk herbal medicine in China, and three of them (2, 4, 5) belong to benzonaphthoxanthenones that are rarely found in nature. Their structures were elucidated by the approach to 1D and 2D NMR spectra. The absolute configuration of 2 was assigned by comparing its experimental and calculated ECD data. 1–5 were investigated for their anti-neuroinflammatory activity against LPS-induced BV-2 cells. 1 and 3 exhibited well protective effect at a concentration of 2.5 μmol/mL. Molecular docking studies were adopted to further investigate the possible mechanism, whose results suggested that 1 might exert anti-neuroinflammatory effect by inhibiting activity of p38α, JNK2 and TAK1 to reduce the liberation of pro-inflammatory cytokines.
- Bi, Guang-ming,Guo, Zi-feng,Li, Jia-heng,Meng, Da-li,Zhang, Yun-hong
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- 5-Phenylcoumarin Derivatives: Design, Synthesis, and Vasodilatory Activity
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In continuation of our previous efforts towards the development of coumarin derivatives with potential vasodilatory activity, 5-phenylcoumarin derivatives were designed and synthesized. Target compounds and their precursors exhibited moderately vasodilato
- Wang, Cheng,Li, Youjia,Zhang, Ting,Wei, Di,Hou, Yajing,He, Huaizhen
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- High-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin
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The invention provides a high-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin and belongs to the field of synthesis of natural medicines. The method comprises the steps of subjecting a catechol coumarin compound to a high-selectivity methylation reaction with a methylation reagent in a proper base catalyst added organic reaction system, so as to obtain a 7-hydroxyl mono-methylate, wherein the mole ratio of a base to the catechol coumarin compound is (2.0 to 7.0): 1, the mole ratio of the methylation reagent to the catechol coumarin compound is (1.0 to 3.0): 1, the temperature of the organic reaction system is 0 DEG C to 30 DEG C, and the reaction time is 1.0 to 5.0 hours. The method has the characteristics of simplicity in operation, moderate conditions, good selectivity, high yield and the like and can be applied to the preparation of mono-methylates of coumarin catechols with different types of substituents.
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Paragraph 0040; 0041; 0042
(2017/08/28)
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- Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins
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Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols and propiolic acids used as starting materials in the presence of Yb(OTf)3 hydrate 10% mol as the catalyst.
- Fiorito, Serena,Epifano, Francesco,Taddeo, Vito A.,Genovese, Salvatore
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supporting information
p. 2939 - 2942
(2016/06/14)
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- Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins
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Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases.
- Azelmat, Jabrane,Fiorito, Serena,Taddeo, Vito Alessandro,Genovese, Salvatore,Epifano, Francesco,Grenier, Daniel
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p. 399 - 405
(2015/09/07)
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- Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol
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Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by N
- Cravotto, Giancarlo,Chimichi, Stefano,Robaldo, Bruna,Boccalini, Marco
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p. 8383 - 8386
(2007/10/03)
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- Revision of the structure of a new coumarin isolated from Artemisia carviforia wall
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Four coumarins (1-4) were synthesized by the routes shown in Schemes 2-5, respectively. The previously proposed structure for a new coumarin isolated from Artemisia carviforia was incorrect; the structure of the coumarin is represented by formula (3).
- Harayama, Takashi,Katsuno, Keiko,Nishita, Yoshitaka,Fujii, Masako,Abe, Hitoshi,Takeuchi, Yasuo
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p. 319 - 328
(2007/10/03)
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- Natural Product Chemistry. Part 121. Synthesis of Dicoumarinyl Ethers with the Structures Proposed for Fatagarine and Oreojasmine
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Synthesis of the 7,8'-dicoumarinyl ethers: 7-methoxy-7',8-oxydicoumarin and 6,7-dimethoxy-7',8-oxydicoumarin, established that the structures of fatagarine and oreojasmine for which these two structures have been proposed, have to be revised.Synthesis of 7-methoxy-5,7'-oxydicoumarin and 8-methoxy-7,7'-oxydicoumarin exclude the possibility of these dicoumarinyl ether structures for fatagarine. - Keywords: Dicoumarinyl ethers; 6,7-Dimethoxy-7',8-oxydicoumarin; Fatagarine; 7-Methoxy-5,7'-oxydicoumarin; 8-Methoxy-7,7'-oxydicoumarin; 7-Methoxy-7',8-oxydicoumarin; Oreojasmine; Ruta oreojasme
- Reisch, Johannes,Wickramasinghe, Anura,Kumar, Vijaya
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p. 1333 - 1339
(2007/10/02)
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- CLAISEN REARRANGEMENTS-XV STRUCTURE REVISION OF THE COUMARIN, CELERIN, BY SYNTHESIS
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The four possible structures, 9,12,17 and 26 for celerin have been synthesised and the structure of the natural product revised to 8-hydroxy-7-methoxy-5-(1,1-dimethylallyl)coumarin 26.Efficient alternative synthetic routes to sibiricol 5, coumurrayin 6 and pinnarin 13 have been established.
- Murray, R. D. H.,Jorge, Z. D.
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p. 5229 - 5234
(2007/10/02)
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- COUMARINS OF THREE SPECIES OF THE GENUS Haplophyllum
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The results are given of an investigation of three species of the genus Haplophyllum: H. villosum, H. kowalenskyi, and H. tenue, from which five substances of coumarin nature have been isolated.Of them, two substances (I and II) have been identified as scopoletin and lomatin isovalerate, respectively, while suitable structures have been established for the new compounds tenuidin, villosin, and tenudiol.It has been shown that the coumarin composition of the plants changes with the growth site.
- Abyshev, A. Z.,Isaev, N. Ya.,Kerimov, Yu. B.
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p. 571 - 573
(2007/10/02)
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