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《Phytochemistry》1987,26(12):3339-3341
Three quinoline alkaloids and two lignan lactones were isolated from Haplophyllum tuberculatum. Physicochemical and spectral evidence established the structures of two of the alkaloids as a new quinoldione, 3-(1′,1′-dimethylallyl)-3-(3″,3″-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione and the known 4-(3′,3′-dimethylallyloxy)-3-(3″,3″-dimethylallyl)-2(1H)-quinolone. The former was shown to undergo facile [3,3]-sigmatotropic transformation into the latter. The remaining compounds were identified as the known Polygamain, kusunokinin and 1-methyl-2-n-nonyl-4(1H)-quinolone. 相似文献
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The structures of two new 2-quinolone alkaloids from the stem bark of Vepris louisii, N-methylpreskimmianine [7,8 - dimethoxy - 3 - (3 - methylbut - 2 - enyl) - 1 - methyl - 2 - quinolone] and veprisine (7,8 - dimethoxy - N - methylflindersine) have been deduced from their spectral data and confirmed by partial synthesis from known compounds. Two minor indolopyridoquinazoline alkaloids were also isolated and identified as the already known 1-hydroxyrutaecarpine and the hitherto unknown 7,8-dehydro derivative of 1-hydroxyrutaecarpine. 相似文献
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Quinoline alkaloids are abundant in the Rutaceae, and many have exhibited cytotoxic activity. Because structurally related
antitumor alkaloids such as camptothecin and fagaronine are known to function as intercalative topoisomerase poisons, it is
hypothesized that cytotoxic Stauranthus alkaloids may also serve as intercalative topoisomerase inhibitors. To test this hypothesis theoretically, ten Stauranthus quinoline alkaloids were examined for potential intercalation into DNA using a molecular docking approach. Four of the alkaloids
(stauranthine, skimmianine, 3′,6′-dihydroxy-3′,6′-dihydrostauranthine, and trans-3′,4′-dihydroxy-3′,4′-dihydrostauranthine) were able to intercalatively dock consistently into DNA. In order to probe the
intermolecular interactions that may be responsible for intercalation of these quinoline alkaloids, density functional calculations
have been carried out using both the B3LYP and M06 functionals. M06 calculations indicated favorable π–π interactions between
either skimmianine or stauranthine and the guanine–cytosine base pair. Furthermore, the lowest-energy face-to-face orientation
of stauranthine with guanine is consistent with favorable dipole–dipole orientations, favorable electrostatic interactions,
and favorable frontier molecular orbital interactions. Likewise, the lowest-energy face-to-face orientation of stauranthine
with the guanine–cytosine base pair reveals favorable electrostatic interactions as well as frontier molecular orbital interactions.
Thus, not only can quinoline alkaloids dock intercalatively into DNA, but the docked orientations are also electronically
favorable.
相似文献
5.
A new quinoline alkaloid named sonminine (1) along with nine known quinoline alkaloids dictamnine (2), isodictamnine (3), skimmianine (4), robustine (5), γ-fagarine (6), isopteleine (7), 5-methoxydictamnine (8), haplopine (9), 5-hydroxy-4,8-dimethoxy-furoquinoline (10) and two sesquiterpenes dictamnol (11), radicol (12) were obtained. Among them, compound 8 and 10 were isolated from the genus Dictamnus L. for the first time. Compounds 9, 11 and 12 were obtained from this species for the first time. 相似文献
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Two iridoid glucosides, 8-epi-grandifloric acid and 3′-O-β-glucopyranosyl-stilbericoside, were isolated from the aerial part of Thunbergia laurifolia along with seven known compounds, benzyl β-glucopyranoside, benzyl β-(2′-O-β-glucopyranosyl) glucopyranoside, grandifloric acid, (E)-2-hexenyl β-glucopyranoside, hexanol β-glucopyranoside, 6-C-glucopyranosylapigenin and 6,8-di-C-glucopyranosylapigenin. Strucural elucidation was based on the analyses of spectroscopic data. 相似文献
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Kokusaginine and evolitrine are the major alkaloids present in Sri Lankan Acronychia pedunculata. The Indian variety of Acronychia laurifolia collected in Madras does not contain these alkaloids. 相似文献
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Eskander J Lavaud C Pouny I Soliman HS Abdel-Khalik SM Mahmoud II 《Phytochemistry》2006,67(16):1793-1799
Nine saponins were isolated from the seeds of Mimusops laurifolia. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. Three of them are identified as: 3-O-(beta-d-apiofuranosyl-(1-->3)-beta-d-glucuronopyranosyl)-28-O-(alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl)-16alpha-hydroxyprotobassic acid, 3-O-(beta-d-glucopyranosyl-(1-->3)-beta-d-glucopyranosyl)-28-O-(alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl)-16alpha-hydroxyprotobassic acid and 3-O-(beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl)-28-O-(alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl)-16alpha-hydroxyprotobassic acid. 相似文献
9.
1-[2,4-Dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]ethanone (1), and a new aryl ketone, named acrovestenol (2), were isolated as cyclooxygenase-2 (COX-2) inhibitory principles from a CH2Cl2 extract of the bark of Acronychia pedunculata by a bioassay-guided fractionation procedure. Compound 2 inhibited COX-2 with an IC50 value of 142.0+/-2.15 microM, compared to the COX-2 inhibitory reference compound NS-398 with an IC50 value of 11.3+/-1.12 microM. Compound 1 inhibited COX-2-catalyzed PG biosynthesis with 68% at a concentration of 500 microM. The structures were determined by UV, IR, and 1D- and 2D-NMR, including TOCSY, HSQC-DEPT, and HMBC, and MS investigations. 相似文献
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Four pyrrolizidine alkaloids (PA) were isolated from Ageratum houstonianum and their structures elucidated by spectroscopical methods. Besides the already known lycopsamine three new PA were found. Their structures are the 2S-2-hydroxy-2,3-dimethyl-butanoyl-O(9) as well as the O(7) esters of retronecine and the O(9) derivative of heliotridine. 相似文献
13.
L M Li?o P C Vieira E Rodrigues-Filho J B Fernandes M F da Silva 《Phytochemistry》2001,58(8):1205-1207
An investigation of the methanol and ethyl acetate extracts from the roots of Peritassa campestris (Hippocrateaceae) afforded the sesquiterpene pyridine alkaloid, 4-hydroxy-7-epi-chuchuhuanine E-V, and nine known alkaloids, forrestine, euonimine, ebenifoline E-I, wilforine, euojaponine F, euonine, wilforjine, neowilforine, and wilforzine. The structures of the isolates were elucidated on the basis of spectral data, particularly HMQC and HMBC experiments. 相似文献
14.
R J Cole J W Kirksey H G Cutler D M Wilson G Morgan-Jones 《Canadian journal of microbiology》1976,22(5):741-744
Two new isomeric metabolites, toxins A and B, were isolated from culture extracts of Penicillium islandicum. Both toxins had a molecular formula of C16H15O2N2Cl, and physical and chemical analyses indicated that they were indole alkaloids. LD50 of toxin A was about 75-125 mg/kg in day-old cockerels. Insufficient toxin B was available to determine accurate LD50 values. Toxin A moderately inhibited growth of wheat coleoptiles but did not inhibit growth of week-old intact corn and bean plants. Toxin B showed no plant-growth inhibition. 相似文献
15.
Cyclopeptide alkaloids from stems of Paliurus ramossisimus. 总被引:1,自引:0,他引:1
Three 13-membered cyclopeptide alkaloids, paliurines G, H and I, together with six known alkaloids, nummularine H, daechuine-S3, paliurines A-C and F, were isolated from the stem of Paliurus ramossisimus by a combination of centrifugal partition chromatography and preparative TLC. Their structures were characterized and established on the basis of spectral analysis. A preliminary study indicated that nummularine H could shorten the methohexital induced sleeping time. 相似文献
16.
为探索拟黄花乌头 Aconitum anthoroideum DC. 作为生物农药的应用价值,以拟黄花乌头整株为研究对象,在活性跟踪的基础上,综合应用硅胶柱层析、ODS、Sephadex LH-20等方法对拟黄花乌头甲醇粗提物进行分离纯化,从中分离得到了4个生物碱类化合物,分别为4-hydroxynicotinic acid methyl ester (1)、Ranaconitine (2)、Lappaconitine (3)、13-hydroxylappaconitine (4),其中4-hydroxynicotinic acid methyl ester为首次从天然产物中分离得到。采用点滴法测定4个化合物对褐飞虱 Nilaparvata lugens Stal和白背飞虱Sogatella furcifera Horvath的触杀活性,结果表明4种化合物对褐飞虱和白背飞虱具有显著的触杀活性,处理后48 h的LD50 分别为0.26~0.38 μg/头、0.25~0.33 μg/头。研究结果为进一步研究拟黄花乌头中的杀虫活性成分提供基础数据。 相似文献
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Two new Lycopodium alkaloids, strictumines A (1) and B (2), along with 18 related known compounds were isolated from the whole plant of Lycopodium obscurum L. f. strictum. The structures of the new compounds were established by spectroscopic methods and chemical transformation. This is the first report on chemical constituents of the title plant. All the isolates were evaluated for their inhibitory activity against acetylcholinesterase (AChE), and only a few were found to show slight bioactivity. 相似文献
18.
Microbial Metabolism of Quinoline by Comamonas sp. 总被引:1,自引:0,他引:1
Cui Mingchao Chen Fanzhong Fu Jiamo Sheng Guoying Sun Guoping 《World journal of microbiology & biotechnology》2004,20(6):539-543
An aerobic bacterial strain which can use quinoline as the sole carbon and energy source has been isolated from activated
sludge and identified as Comamonas sp. The microbial metabolism of quinoline by this strain has been investigated. A pH 8 and a temperature of 30 °C were the
optimum degradation conditions of quinoline. Five intermediates including 2-oxo-1,2-dihydroquinoline, 5-hydroxy-6-(2-carboxyethenyl)-1H-2-pyridone, 6-hydroxy-2-oxo-1,2-dihydroquinoline, 5,6-dihydroxy-2-oxo-1,2-dihydroquinoline, and 8-hydroxy-2-oxo-1,2-dihydroquinoline
were found during quinoline biodegradation. The presence of these intermediates suggested that at least two pathways were
involved for quinoline degradation by Comamonas sp. and a reasonable degradation route was proposed to account for the intermediates observed.
This revised version was published online in July 2006 with corrections to the Cover Date. 相似文献
19.
Ten diterpenoid alkaloids, including five new ones, sczukiniline A–E (1-5), were isolated from the root of Aconitum sczukinii. Their structures were elucidated based on the interpretation of spectroscopic data (HRESI-MS, IR, 1D- and 2D-NMR). Among the five new diterpenoid alkaloids, 1-3 are hetidine-type C20-diterpenoid alkaloids, while compounds 4 and 5 are lycoctonine-type C19-diterpenoid alkaloids. Noteworthily, sczukiniline A (1) features a novel ester group between C-12 and C-14, forming a D ring containing a lactone structure, resulting in a new skeleton of hetidine-type C20-diterpenoid alkaloid. 相似文献
20.
Four quinazolinones, new naturally occurring 1 and three known derivatives 2–4, along with previously synthesized 4-phenylbut-3-enamide (5) and three known compounds, 2-acetamido benzamide, 1H-indole-3-carbaldehyde, and 2-phenylacetamide, were isolated from an actinomycete, Streptomyces sp. BCC 21795. The structures were elucidated based on the analysis of NMR spectroscopic and mass spectrometric data. Compound 1 exhibited strong cytotoxic activity to Vero cells with IC50 3.30 μg/mL. 相似文献