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1.
Phytochemical investigation of a 90 % ethanol extract of Pachysandra terminalis Sieb. Et Zucc led to the isolation of a novel alkaloid, terminamine T (1); a new pregnane-type alkaloid, terminamine U (2); and four known pregnane-type alkaloids (3-6). The structures of these compounds were elucidated on the basis of nuclear magnetic resonance spectra, mass spectrometry data, single-crystal X-ray diffraction, and by a comparison with data from the literature. All compounds were evaluated for their antibacterial activities against gram-positive (S. aureus, ATCC 29213) and gram-negative (E. coli, ATCC 25922) bacteria. Compounds 2-6 exhibited generally modest to poor antibiotic properties. Furthermore, compound 2 showed antibacterial activity against methicillin-resistant Staphylococcus epidermidis (MRSE), methicillin-resistant Staphylococcus aureus (MRSA), and methicillin-resistant Staphylococcus aureus USA300 (LAC) with a minimal inhibitory concentration (MIC) value of 32 μg/mL (75 μM) and minimum bactericidal concentration (MBC) values of 64, 128, and 128 μg/mL (150, 300, and 300 μM), respectively. 相似文献
2.
Steno L. Oliveira Marcelo S. da Silva Josean F. Tavares José G. Sena‐Filho Hellane F. S. Lucena Marco A. V. Romero José M. Barbosa‐Filho 《化学与生物多样性》2010,7(2):302-326
Erythroxylum, the most representative genus of the Erythroxylaceae family, presents tropane alkaloids as main constituents. This class of compounds greatly contributes to the chemotaxonomic characterization of plants of this genus, and it has important medical uses and shows toxic effects. This review describes 186 tropane alkaloids in the 35 species of Erythroxylum distributed worldwide. In addition, a compilation of their 13C‐NMR spectral data is presented. 相似文献
3.
Elthon G. Ferreira Diego V. Wilke Paula C. Jimenez Julieta R. de Oliveira Otília Deusdênia L. Pessoa Edilberto R. Silveira Francisco A. Viana Cláudia Pessoa Manoel Odorico de Moraes Eduardo Hajdu Letícia Veras Costa‐Lotufo 《化学与生物多样性》2011,8(8):1433-1445
Five guanidine alkaloids, mirabilin B ( 1 ), 8bβ‐hydroxyptilocaulin ( 2 ), ptilocaulin ( 3 ), and a mixture of the 8β‐ and 8α‐epimers, 4 and 5 , of 8‐hydroxymirabilin (1,8a;8b,3a‐didehydro‐8‐hydroxyptilocaulin), were isolated from Monanchora arbuscula colonies collected off the northeastern Brazilian coast. All structures were elucidated by spectroscopic analysis, including 1D (1H‐, 13C‐ (BB), and 13C‐DEPT) and 2D (COSY, HSQC, and HMBC) NMR experiments, and comparison with the literature data. The cytotoxicity of the isolated compounds were evaluated against four tumor cell lines, showing that mirabilin B ( 1 ) and the two epimers were inactive, while 8bβ‐hydroxyptilocaulin ( 2 ) and ptilocaulin ( 3 ) presented IC50 values in the range of 7.9 to 61.5 μM , and 5.8 to 40.0 μM , respectively. Further studies on the mechanism of action of ptilocaulin, using HL‐60 leukemia cells, demonstrated that this guanidine compound induced apoptosis of the treated cells. 相似文献
4.
Phytochemical investigation of the bulbs of Fritillaria hupehensis resulted in the isolation and structural elucidation of four new steroidal penta- and hexacyclic veratraman- and cevan-based alkaloids, respectively, compounds 1-4. They were obtained together with the known constituents ebeinine (5) and zhebeinine (6), which were isolated for the first time from this plant. The structures of the new isolates were established by spectroscopic and mass-spectrometric analyses, in combination with chemical methods. All compounds were assayed for their cytotoxic effects towards HeLa and HepG2 cell lines. Compounds 1 and 2 showed significant inhibitory effects against both types of tumor cells, with IC(50) values in the range 2.52-0.23 microM, similar as those for 5-fluorouracil used as positive control. 相似文献
5.
Hikoto Ohta Yasuo Seto Noriko Tsunoda 《Journal of chromatography. B, Analytical technologies in the biomedical and life sciences》1997,691(2):527
Determination of four toxic Aconitum alkaloids, aconitine, mesaconitine, hypaconitine and jesaconitine, in blood and urine samples has been established using high-performance liquid chromatography (HPLC) combined with ultraviolet absorbance detection, solid-phase extraction and mass spectrometry (MS). These alkaloids were hydrolyzed rapidly in alkaline solution (half lives (t1/2)<one day), were stable in solutions of acetonitrile, tetrahydrofuran and diluted hydrochloric acid (t1/2>five months) and were unstable in solutions of methanol and ethanol (t1/2<one month). These alkaloids were separated on an octadecylsilica column with isocratic elution using a solvent mixture of tetrahydrofuran and 0.2% trifluoroacetic acid (14:86, v/v), which was found to be the optimal solvent of the elution systems examined. Calibration curves with UV detection were linear on injection of amounts ranging from 2.5 to 500 ng, and the limit of detection was 1 ng (S/N = 3). These four alkaloids in aqueous solution were recovered almost totally by solid-phase extraction using the styrene polymer resin, Sep-Pak Plus PS-1, and were eluted using a mixture of acetonitrile and hydrochloric acid. These Aconitum alkaloids were confirmed by HPLC coupled with fast atom bombardment MS, giving their protonated molecular ions as base peaks. These alkaloids were detected by HPLC with UV detection from blood samples spiked with more than 50 ng ml−1 of alkaloids, but were not detectable from urine samples spiked with 5 μg ml−1 of alkaloids because of severe sample interference. 相似文献
6.
Three new compounds, 17β-cevanin-6-oxo-5α,20β-diol yibeinine (1), 2-(tetrahydro-5-(2-hydroxyphenyl)-2H-pyran-3-yl) phenol (2), 1,3-O-diferuloyl-2-methoxypropane diol (3), as well as four known compounds (4–7), have been isolated from the ethanol extract of dried bulbs of Fritillaria pallidiflora Schrenk. All structures were determined based on their spectroscopic data (1D and 2D NMR (including 1H NMR, 13C NMR, 1H-1H COSY, HMBC, HSQC, HSQC-TOCSY, and NOESY experiments), and MS). Biological evaluation showed that compounds 1–4 inhibited the production of nitric oxide (NO) in LPS-stimulated RAW 264.7 cells with IC50 values of 18.0, 38.7, 29.5, and 47.1 μM, respectively. These results indicated that compound 1 has potential anti-inflammatory activity. 相似文献
7.
Three new mannopyranosides of indole alkaloids, methyl 7‐(β‐D ‐mannopyranosyloxy)‐1H‐indole‐2‐carboxylate ( 1 ), methyl 7‐[(3‐O‐acetyl‐β‐D ‐mannopyranosyl)oxy]‐1H‐indole‐2‐carboxylate ( 2 ), and 2‐methyl‐1H‐indol‐7‐yl β‐D ‐mannopyranoside ( 3 ), were isolated from an EtOH extract of the roots of Zanthoxylum nitidum. Their structures were identified as new compounds on the basis of the spectroscopic analyses. Bioactivity evaluation revealed that these alkaloids possess significant cytotoxicities against all the tested tumor cell lines with IC50 values of less than 30 μM . 相似文献
8.
de Oliveira SL Tavares JF Branco MV Lucena HF Barbosa-Filho JM de F Agra M do Nascimento SC dos S Aguiar J da Silva TG de Simone CA de Araújo-Júnior JX da Silva MS 《化学与生物多样性》2011,8(1):155-165
Three tropane alkaloids, 1-3, were isolated from Erythroxylum caatingae, i.e., 6β-benzoyloxy-3α-[(4-hydroxy-3,5-dimethoxybenzoyl)oxy]tropane (1), a new tropane alkaloid, along with the known alkaloids 3α,6β-dibenzoyloxytropane (2) and 6β-benzoyloxy-3α-[(3,4,5-trimethoxybenzoyl)oxy]tropane (catuabine B; 3). Their structures were determined by 2D- ((1) H and (13) C) NMR. By LC/ESI-MS/MS analysis of the fractions of alkaloids 1-3, it was possible to detect five more alkaloids, 4-8, two of these, 4 and 8, possibly being new natural products. X-Ray crystallography of the chloride derivate of 1, i.e., 6β-benzoyloxy-3α-(4-hydroxy-3,5-dimethoxybenzoyloxy)tropane hydrochloride (1a) confirmed the structure of 1. Cytotoxicity was tested against the cell lines HEp-2, NCI-H292, and KB for the MeOH extract and alkaloid 3, and antitumor activity was tested against Sarcoma 180 only for the MeOH extract. 相似文献
9.
10.
A comparison of the morphology and of the venom alkaloids of the Australian Monomorium rothsteini complex was undertaken. These ants were collected in Australia from western New South Wales, northern Queensland, and northern Northern Territory. Additionally, samples from the M. sordidum complex and M. carinatum complex were examined. Thirteen previously described trans‐2,5‐dialkylpyrrolidines were detected in these ants, along with the novel trans‐2‐ethyl‐5‐[(Z)‐tridec‐4‐enyl]pyrrolidine ( 6 ), whose structure was confirmed by synthesis. The extent of variation and the correlation observed in the morphology and venom chemistry in M. rothsteini samples is very strongly indicative of multiple species in this complex. The presence and location of the C?C bond in 6 reinforces the remarkable structural similarity of the 2‐ethylpyrrolidines in these Monomorium species to the 2‐methylpiperidines in the venoms of many Solenopsis species, and may represent convergent evolution of biosynthetic processes in different genera of solenopsidine ants. 相似文献
11.
A novel diterpene alkaloid named honatisine (1) has been isolated from the whole plants of Delphinium honanense, along with six known alkaloids, siwanine E (2), isoatisine (3), atisine (4), delcorinine (5), uraphine (6), and nordhagenine A (7). Their structures were deduced on the basis of their spectral data. All of them were evaluated by a SRB assay for their cytotoxicity, and compound 1 showed a significant cytotoxic activity (IC(50) =3.16 μM) against the MCF-7 cell line. 相似文献
12.
Chemical studies of the Chinese herb Corydalis saxicola Bunting led to the isolation and identification of 14 alkaloids, 1-14. Seven of these compounds, 4-9 and 11, were obtained from this plant for the first time. Feruloylagmatine (7) is the first guanidine-type alkaloid to be identified in the family Papaveraceae and in dicotyledonous plants. All of the isolated compounds were assayed for inhibitory activity against human DNA topoisomerase I. A DNA cleavage assay demonstrated that these alkaloids specifically inhibit topoisomerase through stabilization of the enzyme-DNA complex. Among the isolated alkaloids, (-)-pallidine (8) and (-)-scoulerine (11) showed strong inhibitory activities toward topoisomerase I that were comparable to camptothecin, a typical topoisomerase I inhibitor. A preliminary structure-activity relationship study suggested that the quaternary ammonium ion might play an important role in topoisomerase I inhibition by the isoquinoline alkaloids. These data indicated that DNA topoisomerase I inhibition represents probably one of the anticarcinogenic mechanisms of C. saxicola. 相似文献
13.
Berberrubine (1a), jatrorubine (2a), and palmatrubine (3a) have been chemically prepared by partial demethylation of berberine (1), jatrorrhizine (2), and palmatine (3), respectively. Their interactions with calf thymus (CT) DNA, poly(dA-dT)poly(dA-dT), poly(dG-dC)poly(dG-dC), and eight AT-rich 12-mer double-stranded DNAs have been investigated by means of competitive ethidium bromide (EB) displacement experiments. The results showed that DNA-binding affinities of these protoberberine alkaloids have been significantly improved by partial demethylation, and that all of these alkaloids have the preferable binding affinities with AT-rich DNA. Especially, the sequence specificities of DNA-binding of demethylated derivatives 1a, 2a, and 3a had changed to a certain extent when compared with the parent alkaloids 1, 2, and 3, respectively. The binding mode of these alkaloids was further confirmed by UV spectroscopic titration experiments. All the compounds bind to double-stranded DNA most probably via an intercalating mode. 相似文献
14.
The first synthesis of 12-oxosoladulcidine (= (3beta,5alpha,22alpha,25R)-3-hydroxyspirosolan-12-one; 4) is reported, and its structure was confirmed by single-crystal X-ray diffraction analysis. Compound 4 was readily obtained in five steps in an overall yield of 31%, starting from hecogenin (5). By slightly modifying the synthetic protocol, eight analogues of 4 were also prepared. The title compound and its derivatives are expected to be potent antitumor alkaloids, since structurally closely related to the known antitumor agents soladulcidine (2) and hecogenin (5). 相似文献
15.
The interaction of berberine, palmatine, and coralyne with the B, Z, and HL form of poly[d(G‐C)] was studied. Berberine and palmatine showed moderate binding to the B form, while coralyne showed higher binding, as revealed from spectroscopic and thermodynamic data. Berberine and coralyne binding to the B form was exothermic and enthalpy‐driven, while palmatine showed exothermic binding which was favored by both negative enthalpy and negative entropy changes. Berberine and palmatine neither bind nor converted the Z‐form structure to B form. Coralyne, on the other hand, exhibited a strong binding affinity to Z DNA structure that was enthalpy‐driven. Berberine binding to the HL form was cooperative, exothermic, and favored by both negative enthalpy and negative entropy changes with the formation of an induced CD band. Palmatine showed weak binding, while coralyne showed a strong binding with the HL form. The structural differences in the isoquinoline alkaloids appear to influence the affinity and mode of interactions with these polymorphic DNA structures. 相似文献
16.
A series of natural (i.e., 1-7) and synthetic (i.e., 8-23) protoberberine alkaloids were evaluated for their inhibitory activities towards DNA topoisomerase I. Both the natural, monomeric protoberberine alkaloids and their mono-modified congeners showed only minor activities. In contrast, most of the dimeric protoberberine alkaloids, especially compounds 12-22, were highly active, with a similar cleavage efficiency as camptothecin (CPT), a well-known, potent topoisomerase-I inhibitor. Thus, these dimeric compounds are promising candidates to be further elaborated as anticancer leads. The mechanism of topoisomerase-I inhibition seems to be dependent on drug concentration for the dimeric protoberberines. At low concentration, they exhibit similar characteristics as CPT. At high concentration, this ability is mostly lost, and the dimers inhibit the relaxation activity of topoisomerase I. Thus, we suppose that the active, dimeric protoberberines strongly bind to plasmid DNA at elevated drug concentration. This most likely results in blocking the enzyme's access to plasmid DNA, thus inhibiting its relaxation. 相似文献
17.
Seven benzophenanthridine alkaloids, 1-7, were isolated from the roots of Zanthoxylum nitidum. Among them, two novel alkaloids, named (R)-8-[(R)-1-hydroxyethyl]dihydrochelerythrine (1) and 8-methoxynorchelerythrine (2), were structurally identified as new compounds on the basis of the spectroscopic analysis. Bioactivity evaluation showed that nitidine (3), dihydrochelerythrine (4), oxyavicine (5), 8-methoxychelerythrine (6), and 8-hydroxydihydrochelerythrine (7) exhibit comparable analgesic and anti-inflammatory effects as hydrocortisone. 相似文献
18.
Two new bromotyrosine alkaloids, purealidins T and U (1 and 2, resp.), along with five known bromotyrosines 3-7, were isolated from marine sponge Pseudoceratina sp. Their structures were elucidated on the basis of extensive spectroscopic data (CD, IR, 1D- and 2D-NMR, and MS) analysis. 相似文献
19.
An efficient synthesis of the steroidal alkaloids solasodine (1), O-acetylsolasodine (2), and soladulcidine (3) starting from easily available diosgenin and tigogenin in five or six steps (overall yield 25, 24, and 28%, resp.) is described. Moreover, our synthetic route provides a selective modification at C(3) of 1 and related compounds in order to carry out lead optimization on these natural antitumor steroidal alkaloids. 相似文献
20.
Strictosidine synthase (STR1) catalyzes the stereoselective formation of 3α(S)‐strictosidine from tryptamine and secologanin. Strictosidine is the key intermediate in the biosynthesis of 2,000 plant monoterpenoid indole alkaloids, and it is a key precursor of enzyme‐mediated synthesis of alkaloids. An improved expression system is described which leads to optimized His6‐STR1 synthesis in Escherichia coli. Optimal production of STR1 was achieved by determining the impact of co‐expression of chaperones pG‐Tf2 and pG‐LJE8. The amount and activity of STR1 was doubled in the presence of chaperone pG‐Tf2 alone. His6‐STR1 immobilized on Ni‐NTA can be used for enzymatic synthesis of strictosidines on a preparative scale. With the newly co‐expressed His6‐STR1, novel 3α(S)‐12‐azastrictosidine was obtained by enzymatic catalysis of 7‐azatryptamine and secologanin. The results obtained are of significant importance for application to chemo‐enzymatic approaches leading to diversification of alkaloids with novel improved structures. 相似文献