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1.
Anthraquinones from the roots of Prismatomeris tetrandra 总被引:1,自引:0,他引:1
Three new anthraquinones, 1-hydroxy-2,3-dimethoxy-7-methyl-9,10-anthraquinone, 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone, and 3-hydroxy-1,5,6-trimethoxy-2-methyl-9,10-anthraquinone, along with five known anthraquinones were isolated from the roots of Prismatomeris tetrandra. Their structures were determined on the basis of spectroscopic data. 相似文献
2.
Iridoids and anthraquinones from the Malaysian medicinal plant,Saprosma scortechinii (Rubiaceae) 总被引:1,自引:0,他引:1
Ling SK Komorita A Tanaka T Fujioka T Mihashi K Kouno I 《Chemical & pharmaceutical bulletin》2002,50(8):1035-1040
A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-beta-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin. 相似文献
3.
Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae)
Osman CP Ismail NH Ahmad R Ahmat N Awang K Jaafar FM 《Molecules (Basel, Switzerland)》2010,15(10):7218-7226
Dichloromethane root extract of Rennellia elliptica Korth. showed strong inhibition of Plasmodium falciparum growth in vitro with an IC?? value of 4.04 μg/mL. A phytochemical study of the dichloromethane root extract has led to the isolation and characterization of a new anthraquinone, 1,2-dimethoxy-6-methyl-9,10-anthraquinone (1), and ten known anthraquinones: 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (2), nordamnacanthal (3), 2-formyl-3-hydroxy-9,10-anthraquinone (4), damnacanthal (5), lucidin-ω-methyl ether (6), 3-hydroxy-2-methyl-9,10-anthraquinone (7), rubiadin (8), 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone (9), rubiadin-1-methyl ether (10) and 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone (11). Structural elucidation of all compounds was accomplished by modern spectroscopic methods, notably 1D and 2D NMR, IR, UV and HREIMS. The new anthraquinone 1, 2-formyl-3-hydroxy-9,10-anthraquinone (4) and 3-hydroxy-2-methyl-9,10-anthraquinone (7) possess strong antiplasmodial activity, with IC?? values of 1.10, 0.63 and 0.34 μM, respectively. 相似文献
4.
A naphthohydroquinone and eight anthraquinones were isolated from the roots of Rubia lanceolata Hayata. Their structures were assigned as mollugin ( 1 ), l-hydroxy-2-methyl-9,10-anthraquinone ( 2 ), 2-methylquinizarin ( 3 ), 3-carbomethoxy-l-hydroxy-9,10-anthraquinone ( 4 ), lucidin ethyl ether ( 5 ), rubiadin ( 6 ), alizarin ( 7 ), ω-hydroxypachybasin ( 8 ) and digiferruginol ( 9 ) on the basis of spectral evidence. Among them, compounds 8 and 9 were isolated for the first time from Rubia species. 相似文献
5.
Cycloaddition of 1-Aryl-3-trimethylsiloxy-1,3-butadienes in the Synthesis of Natural Quinone Analogs
I. V. Nechepurenko E. E. Shul'ts G. A. Tolstikov 《Russian Journal of Organic Chemistry》2001,37(9):1276-1283
7-Hydroxy-5-(2-methoxyphenyl)-2-methyl-6-R-1,4-naphthoquinones, 8-hydroxy-1-(2-methoxyphenyl)-3-oxo-1,2,3,4-tetrahydro-9,10-anthraquinone, and 2-ethoxycarbonyl-8-hydroxy-1-(2-methoxyphenyl)-3-trimethylsiloxy-1,1a,4,4a-tetrahydro-9,10-anthraquinone were synthesized by reactions of 1-(2-methoxyphenyl)-2-R-3-trimethylsiloxy-1,3-butadienes with 2-bromo-5-methyl-1,4-benzoquinone and juglone. 1-Aryl-2-ethoxycarbonyl-3-trimethylsiloxy-1,3-butadienes reacted with 1,4-naphthoquinone to afford 1-aryl-2-ethoxycarbonyl-3-hydroxy-9,10-anthraquinones and their 4,4a-dihydro derivatives. 相似文献
6.
Jingqun Gao Yuwei Guo Jun Wang Xudong Jin Zhiqiu Wang Tingting Fan Kai Li Yongnan Xu 《Journal of solution chemistry》2011,40(5):876-888
In this paper, three anthraquinones (alizarin (1,2-dihydroxy-9,10-anthraquinone), alizarin-DA (1,2-dihydroxy-9,10-anthraquinone-3-aminomethyl-N,N-diacetic
acid) and alizarin-DA-Fe (1,2-dihydroxy-9,10-anthraquinone-3-aminomethyl-N,N-diacetate-ferric(III))) with a tricyclic anthraquinone
planar structure are used as quenchers, to study their interaction with bovine serum albumin (BSA) molecules by fluorescence
spectroscopy. The results show that these three anthraquinones can bind to BSA molecules efficiently but the stabilities decrease
in the order alizarin, alizarin-DA and alizarin-DA-Fe. In addition, synchronous fluorescence spectroscopy indicates that the
tryptophan (Trp) residues of BSA molecules are more accessible to alizarin and alizarin-DA than the tyrosine (Tyr) residues,
but both have similar accessibility to alizarin-DA-Fe. 相似文献
7.
Shamsipur M Yari A Sharghi H 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2005,62(1-3):372-376
Complexation reactions between 1-amino-9,10-anthraquinone (AA1), 1-amino-2-methyl-9,10-anthraquinone (AA2), 1-amino-2,4-dimethyl-9,10-anthraquinone (AA3) and 1-amino-2-ethyl-9,10-anthraquinone (AA4) and beta-cyclodextrin were studied spectrofluorometrically, under optimized experimental conditions. The formation constants of the resulting 1:1 beta-cyclodextrin complexes were evaluated and found to decrease in the order AA4>AA1>AA3>AA2. Possible reasons for the observed stability sequence are discussed based on the structures proposed for the resulting inclusion complexes. 相似文献
8.
Khan MS Khan ZH 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2003,59(7):1409-1426
Electronic absorption spectra of 1,2-diamino-9,10-anthraquinone (12DAAQ), 1,4-diamino-9,10-anthraquinone (14DAAQ), 1,5-diamino-9,10-anthraquinone (15DAAQ), and 2,6-diamino-9,10-anthraquinone (26DAAQ) are investigated. Molecular geometries of the amino anthraquinones in the ground state are optimized using the semiempirical ZINDO/1 and AM1 methods without imposing any symmetry constraints. The ground state geometries of all the molecular systems are found to be planar. For interpretation of the spectra, ZINDO/S-CI and AM1-CI calculations employing singly excited configuration using the completely optimized geometry are carried out. Such calculations on the electronic spectra of amino anthraquinones are carried out for the first time. On the basis of these calculations, the assignment of the spectra are successfully made. 相似文献
9.
1,8-二羟基-9,10-二氢蒽的合成 总被引:1,自引:0,他引:1
以1,8-二羟基蒽醌为原料,经甲醚化,锌粉和金属钠还原,去甲基等4步反应合成1,8-二羟基-9,10-二氢蒽,总产率为37.1,8-二甲氧基蒽醌用NaBH4/CF3COOH还原生成二聚产物,并测定了其单晶结构. 相似文献
10.
V. A. Osyanin E. A. Ivleva D. V. Osipov Yu. N. Klimochkin 《Chemistry of Heterocyclic Compounds》2011,47(7):845-850
Products of heterocyclization, 9,10-dimethoxy-12,13-dihydro-7aH,15H-naphtho[1',2':5,6][1,3]oxazino-[2,3-a]isoquinolines, were
isolated on condensing 6,7-dimethoxy-3,4-dihydroisoquinoline with 1-dimethylaminomethyl-2-naphthols. In the case of o-hydroxybenzyl alcohols products of a Michael aza reaction, 2-[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenols
were obtained. 相似文献
11.
I. Manojlović G. Bogdanović-Dusanović W. Gritsanapan N. Manojlović 《Chemical Papers》2006,60(6):466-468
Five hydroxyanthraquinone derivatives physcion, emodin, fallacinal, teloschistin, and 1,3-dimethoxy-8-hydroxy-6-methyl-9,10-anthraquinone
were isolated from the lichen Caloplaca cerina growing in Serbia. Three anthraquinone derivatives, namely physcion, emodin, and rhein were isolated and identified from
the Thai medicinal plant Cassia tora.
Presented at the 33rd International Conference of the Slovak Society of Chemical Engineering, Tatranské Matliare, 22–26 May
2006. 相似文献
12.
Zoltn A. TthOlavi Raatikainen Toivo Naaranlahti Seppo Auriola 《Journal of chromatography. A》1993,630(1-2):423-428
A high-performance liquid chromatographic method was developed for the determination of the non-glycosidic anthraquinones alizarin (1,2-dihydroxy-9,10-anthracenedione), emodin (1,3,8-trihydroxy-6-methyl-9,10-anthracenedione) and anthraquinone (9,10-anthracenedione). The anthraquinones were separated by isocratic elution on a 125 × 4.6 mm I.D. column containing ODS Hypersil 5 reversed-phase material using methanol-5% acetic acid (pH 3.0) (70:30) as the mobile phase. Free alizarin was determined in plant cell suspension cultures of Rubia tinctorum and free emodin in mushrooms (Dermocybe sanguinea). The effective extraction of anthraquinones from plant cells was achieved with 80% (v/v) ethanol after incubation for 10 h at 80°C. Prepurification and concentration of anthraquinones in the plant cell and mushroom extracts were effected by a solid-phase technique using C8 cartridges. 相似文献
13.
Choudhary MI Nur-E-Alam M Akhtar F Ahmad S Baig I Ondögnii P Gombosurengyin P Atta-ur-Rahman 《Chemical & pharmaceutical bulletin》2001,49(10):1295-1298
Five new peltogynoids, irisoids A-E (1-5), have been isolated from the underground parts of Iris bungei. The structures of the new compounds were established on the basis of spectroscopic methods and were found to be 1,8,10-trihydroxy-9-methoxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (1), 1,8-dihydroxy-9,10-dimethoxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (2), 1,10-dihydroxy-8,9-dimethoxy-[1]benzopyrano-13,2-c][2]-benzopyran-7(5H)-one (3), 1,8-dihydroxy-9,10-methylenedioxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (4), and 1,8,11-trihydroxy-9,10-methylenedioxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (5). The structure of irisoid B (2) was established unambiguously by X-ray diffraction study. 相似文献
14.
Grigoriy A. SeredaDavid G. Akhvlediani 《Tetrahedron letters》2003,44(51):9125-9126
A convenient and environmentally friendly solvent-free procedure has been developed for dimethylation of 1,8-dihydroxy-9,10-anthraquinone with excellent yield. A highly selective monomethylation of 1,8-dihydroxy-9,10-anthraquinone in refluxing tetraglyme makes monomethylated peri-dihydroxy-9,10-anthraquinones easily available. Alternatively, irradiation in a domestic microwave oven has been employed for the solvent-free monomethylation of 1,8-dihydroxy-9,10-anthraquinone. 相似文献
15.
L. Castedo J. A. Granja A. Rodríguez De Lera M. C. Villaverde 《Journal of heterocyclic chemistry》1988,25(5):1561-1566
Total syntheses of 2,9-dihydroxy-1,3-dimethoxy-7-methyl-6a,7-dehydroaporphine 1a and 3,9-dihydroxy-1,2-dimethoxy-7-methyl-6a,7-dehydroaporphine 1b are described. Direct comparison of both with natural goudotianine isolated from Guatteria goudotiana R. E. Fries showed the latter to be identical with 1b . 相似文献
16.
Two new isoquinoline alkaloids, 2,10-dimethoxy-3,11-dihydroxy-5,6-dihydroprotoberberine (1) and 1,9-dihydroxy-2,11 -dimethoxy-4,5-dihydro-7-oxoaporphine (2), together with thirteen known alkaloids, were isolated from the ethanolic extracts of the stem and leaves of Miliusa cuneata (Graib). Their structures were elucidated predominantly by spectral evidence. 相似文献
17.
The polarographic behaviour of 9,10-anthraquinone (I) and some of its dihydroxy derivatives, such as alizarin (II), quinizarin (III) and chrisazin (IV) has been studied in the presence of proton donors of HA and HB+ type. After optimization of conditions for reversible reduction of the anthraquinones, various polarographic techniques were used for the determination of anthraquinones in chloroform. In the dc method, the relative standard deviation for the determination of 1mM concentrations was about 1.5%. In the ac method, the detection limit was 0.1 μg/ml and the relative standard deviation for determination at the 0.2 μg/ml level was 2%. The proposed methods are usable for the simultaneous determination of I and II, II and III, II and IV, and have been applied to the determination of 9,10-anthraquinone in papers and black liquors. 相似文献
18.
A new anthraquinone (4) and three known anthraquinones (1-3) were isolated from Galium verum L. Their structures were identified as 1,3-dihydroxy-2-methylanthraquinone (1), physcion (2), 2-hydroxy-1,3-dimethoxyanthraquinone (3), 2,5-dihydroxy-1,3-dimethoxyanthraquinone (4) by means of chemical and spectroscopic analysis. Compound 2 was isolated from the genus Galium for the first time. In addition, compound 4 was assayed for antimicrobial activity in vitro. 相似文献
19.
Since the strategy for the synthesis of 9-, 10- and 11-nitronoracronycine [3,4] could not be applied to the 8-nitronoracronycine 9 , we here report the preparation of the latter by a fusion of methyl 2-amino-6-nitrobenzoate 2 and phloroglucinol 3 . The fusion of 2 and 3 gave 1,3-dihydroxy-8-nitro-9(10H)-acridinone 6 . Subsequent methylation, demethylation and reaction with 2-chloro-2-methyl-3-butyne afforded the desired 8-nitronoracronycine 9 . Compound 9 , 1,3-dimethoxy-10-methyl-8-nitro-9(10H)-acridinone 7 and 1,3-dihydroxy-10-methyl-8-nitro-9(10H)-acridinone 8 were tested by the National Cancer Institute (NCI) for possible anticancer activity. 相似文献
20.
ÇAKIL Erk Erdoğan Erbay 《Journal of inclusion phenomena and macrocyclic chemistry》2000,36(2):229-241
The 9,10-anthraquinone-[12]crown-4, [15]crown-5 and [18]crown-6 derivatives were synthesized from 1,2-dihydroxy-9,10-anthraquinone and 1,8-dihydroxy-9,10-anthraquinone which were condensed with dihalides or ditosylates of polyethylene glycols in alkali carbonate/DMSO. The 9,10-anthraquinone derived polyoxacyclo-alkanes were characterized with IR, mass spectrometry, 1H, 13C spectroscopy and elemental analysis. The cation binding properties were studied with UV-vis spectroscopy. The association constants found in acetonitrile were selectively dependent on the cation radius and macrocycle size as well as the molecular structures. The observed results from UV-vis studies, however, showed the stronger complexing role of 1,2-derived macrocycles compared to those of 1,8-derivatives. The theoretical conformational analysis and the energy optimisations of the 9,10-anthraquinone-macrocycles carried out with MM+ method explained the binding results. 相似文献