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1.
Four new 13,14‐seco‐withanolides, minisecolides A – D ( 1  –  4 ), together with three known analogues 5  –  7 , were isolated from the whole plants of Physalis minima. The structures of new compounds were determined on the basis of spectroscopic analysis, including 1H‐, 13C‐NMR, 2D‐NMR (HMBC, HSQC, ROESY), and HR‐ESI‐MS. Evaluation of all isolates for their inhibitory effects on nitric oxide (NO) production was conducted on lipopolysaccaride‐activated RAW264.7 macrophages. Compounds 2 , 3 , 5 , and 6 showed inhibitory activities, especially for compound 5 with IC50 value of 3.87 μm .  相似文献   

2.
Three new alkylated chalcones, villosins A – C ( 1  –  3 ), five known analogues, together with ten known coumarins, were isolated from Fatoua villosa. The structures of the new compounds were elucidated by extensive spectroscopic analysis, including 1D‐, 2D‐NMR, and MS data. Compounds 1  –  3 showed cytotoxicity against five kinds of human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) with IC50 values ranging from 1.4 ± 0.1 to 5.7 ± 0.3 μm .  相似文献   

3.
As part of our search for new bioactive saponins from Cameroonian medicinal plants, two new oleanane‐type saponins, named gummiferaosides D and E ( 1 and 2 ), along with one known saponin, julibroside J8 ( 3 ), were isolated from the roots of Albizia gummifera. Their structures were established on the basis of extensive 1D‐ and 2D‐NMR (1H‐ and 13C‐NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC‐TOCSY, and HMBC) and HR‐ESI‐MS studies, and by chemical evidence. The apoptotic effect of saponins 1  –  3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1  –  3 induced apoptosis of human epidermoid cancer cell (A431) in a dose‐dependent manner.  相似文献   

4.
Three new iridoid glycosides, named involucratosides A – C ( 1  –  3 ), were isolated from the H2O subextract of crude MeOH extract prepared from the aerial parts of Asperula involucrata along with a known iridoid glycoside (adoxoside), three flavone glycosides (apigenin 7‐Oβ‐glucopyranoside, luteolin 7‐Oβ‐glucopyranoside, apigenin 7‐O‐rutinoside) as well as two phenolic acid derivatives (chlorogenic acid and ferulic acid 4‐Oβ‐glucopyranoside). Their chemical structures were established by UV, IR, 1D‐ (1H, 13C and JMOD) and 2D‐ (COSY, HSQC, HMBC and NOESY) NMR experiments and HR‐ESI‐MS. In addition, the crude extract, subextracts and isolates were evaluated for their xanthine oxidase inhibitory and antioxidant activities in in vitro tests. This is the first report on the chemical composition and bioactivities of Ainvolucrata.  相似文献   

5.
Perennial ryegrass (Lolium perenne) is often infected with the fungal‐endophyte Neotyphodium lolii. In addition to the ‘wild‐type’ strain (EWT), several ‘selected’ strains of N. lolii are now being marketed as AR1 (EAR1) and AR37 (EAR37). Each of these strains impact positively on L. perenne's resistance against many insects, including the African black beetles (Heteronychus arator). The impact of volatile oils produced specifically by each strain in the endophyte–grass association in enhancing the grass's resistance to insects is still largely unknown. Keeping these in view, we determined the volatile oil profiles produced by L. perenne infected with either EWT or EAR1 or EAR37 and determined the impacts of these volatiles on the host‐selection behaviour of H. arator adults. In the absence of endophyte infection (E), L. perenne produced 18 different volatile oils. In L. perenne EWT, quantities of 2‐ethyl‐1‐hexanol acetate (Rt = 14.5 min), (Z)‐2‐octen‐1‐ol (Rt = 22.2 min), and butylated hydroxyl toluene (Rt = 23.2 min) were 24, 16 and 26%, respectively, greater than L. perenne E. The strains EAR1 and EAR37 affected differently the quantities of the volatile compounds but not their identity. In the four‐choice bioassay, males and females of H. arator were equally attracted to each strain. In Y‐tube olfactometer, compared against E, H. arator adults were less attracted to L. perenne EWT and EAR1. The attractiveness of EAR37 was similar in effect to E to H. arator. The results indicate that each strain of N. lolii alters the profile of volatile oils in L. perenne differently and that alteration can influence H. arator adult‐host selection.  相似文献   

6.
A newly discovered triterpenoid, (2α,3β)‐2,3,23‐trihydroxyurs‐13(18)‐en‐28‐oic acid ( 1 ), along with twelve known compounds ( 2  –  13 ), were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). Their chemical structures were determined by 1D‐ and 2D‐NMR spectra and mass spectrometry (MS). The crude extracts and six main constituents ( 8  –  13 ) were tested for cytochrome P450 (CYPs) enzyme inhibitory activity. The results showed that, except for compound 8 , compounds 9  –  13 had different inhibitory effects on the cytochrome P450 (CYPs) enzyme, and compound 9 significantly inhibited the catalytic activities of CYP3A4 to < 10% of its control activities.  相似文献   

7.
This study was performed to determine the chemical composition, antioxidant and cytotoxic effects of essential oils extracted from the aerial parts of fresh (F‐PSEO) and air‐dried (D‐PSEO) Pallenis spinosa. The composition of the oils was analyzed by gas chromatography (GC) and GC/mass spectrometry, the antioxidant activity by free radical scavenging and metal chelating assays, and their cytotoxicity by a flow cytometry analysis. The primary components in both oils were sesquiterpene hydrocarbons and oxygentated sesquiterpenes. F‐PSEO contained 36 different compounds; α‐cadinol (16.48%), germacra‐1(10),5‐diene‐3,4‐diol (14.45%), γ‐cadinene (12.03%), and α‐muurolol (9.89%) were the principal components. D‐PSEO contained 53 molecules; α‐cadinol (19.26%), δ‐cadinene (13.93%), α‐muurolol (12.88%), and germacra‐1(10),5‐diene‐3,4‐diol (8.41%) constituted the highest percentages. Although both oils exhibited a weak radical scavenging and chelating activity, compared to α‐tocopherol and ascorbic acid, D‐PSEO showed a 2‐fold greater antioxidant activity than F‐PSEO. Furthermore, low doses of F‐PSEO were able to inhibit the growth of leukemic (HL‐60, K562, and Jurkat) and solid tumor cells (MCF‐7, HepG2, HT‐1080, and Caco‐2) with an IC50 range of 0.25 – 0.66 μg/ml and 0.50 – 2.35 μg/ml, respectively. F‐PSEO showed a ca. 2 – 3‐fold stronger cytotoxicity against the tested cells than D‐PSEO. The potent growth inhibitory effect of the plant essential oil encourages further studies to characterize the molecular mechanisms of its cytotoxicity.  相似文献   

8.
Activity‐guided fractionation strategy was used to investigate chemical constituents from the roots of Podocarpus macrophyllus. Successfully, two new norditerpenes, 2β‐hydroxymakilactone A ( 1 ) and 3β‐hydroxymakilactone A ( 2 ), along with ten known analogues ( 3  –  12 ) were isolated. The structures of 1 and 2 were elucidated by spectroscopic analysis including 1D‐, 2D‐NMR, and HR‐ESI‐MS data. The previously reported structure of 2,3‐dihydro‐2α‐hydroxypodolide was revised as 2,3‐dihydro‐2β‐hydroxypodolide ( 3 ) by spectroscopic analysis, and was further confirmed by X‐ray crystallographic analysis. Cytotoxic activities of all isolated compounds against five human solid tumour cell lines (AGS, HeLa, MDA‐MB‐231, HepG‐2, and PANC‐1) were evaluated. All of them exhibited anti‐proliferative activities (IC50 = 0.3 – 27 μm ), except for 10 . Compounds 1 , 4 , 5 , 6 , and 8 exhibited potent inhibitory activities with IC50 < 1 μm against HeLa and AGS cells.  相似文献   

9.
Four limonoids, 1  –  4 , five alkaloids, 5  –  9 , and four phenolic compounds, 10  –  13 , were isolated from a MeOH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel‐(1R,2R,3R)‐5‐hydroxy‐3‐(4‐hydroxy‐3‐methoxyphenyl)‐6‐methoxy‐1‐(methoxycarbonylmethyl)indane‐2‐carboxylic acid methyl ester (γ‐di(methyl ferulate)) based on the spectrometric analysis. Upon evaluation of compounds 1  –  13 against the melanogenesis in the B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), four compounds, limonin ( 1 ), noroxyhydrastinine ( 6 ), haplopine ( 7 ), and 4‐methoxy‐1‐methylquinolin‐2(1H)‐one ( 8 ), exhibited potent melanogenesis‐inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP‐1, and TRP‐2 in α‐MSH‐stimulated B16 melanoma cells. In addition, when compounds 1  –  13 were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), duodenum (AZ521), and breast (SK‐BR‐3) cancer cell lines, five compounds, berberine ( 5 ), 8 , canthin‐6‐one ( 9 ), α‐di‐(methyl ferulate) ( 12 ), and 13 , exhibited cytotoxicities against one or more cancer cell lines with IC50 values in the range of 2.6 – 90.0 μm . In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC50 2.6 μm ) which was superior to that of the reference cisplatin (IC50 9.5 μm ).  相似文献   

10.
One new chromone 3,3‐dimethylallylspatheliachromene methyl ether ( 1 ), as well as five known chromones, 6‐(3‐methylbut‐2‐enyl) allopteroxylin methyl ether ( 2 ), 6‐(3‐methylbut‐2‐enyl) allopteroxylin ( 3 ), 3,3‐dimethylallylspatheliachromene ( 4 ), 5‐O‐methylcneorumchromone K ( 5 ) and spatheliabischromene ( 6 ), two alkaloids, 8‐methoxy‐N‐methylflindersine ( 7 ) and 8‐methoxyflindersine ( 8 ), and two limonoids, limonin diosphenol ( 9 ) and rutaevin ( 10 ), were isolated from Dictyoloma vandellianum A. Juss (Rutaceae). Cytotoxic activities towards tumor cell lines B16‐F10, HepG2, K562 and HL60 and non‐tumor cells PBMC were evaluated for compounds 1  –  6 . Compound 1 was the most active showing IC50 values ranging from 6.26 to 14.82 μg/ml in B16‐F10 and K562 cell lines, respectively, and presented IC50 value of 11.65 μg/ml in PBMC cell line.  相似文献   

11.
Four new tirucallane triterpenoids, (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxy‐25‐methoxytirucall‐7‐en‐3‐one ( 2 ), (3S,21S,23R,24S)‐21,23‐epoxy‐21,25‐dimethoxytirucall‐7‐ene‐3,24‐diol ( 8 ), (21S,23R,24R)‐21,23‐epoxy‐24‐hydroxy‐21‐methoxytirucalla‐7,25‐dien‐3‐one ( 11 ), and (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxytirucalla‐7,25‐dien‐3‐one ( 12 ), along with 16 known analogues, 1 , 3  –  7 , 9  –  10 , and 13  –  20 , were isolated from the fruits of Melia azedarach. Their structures were elucidated by spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. These compounds were evaluated for their cytotoxicities against HepG2 (liver), SGC7901 (stomach), K562 (leukemia), and HL60 (leukemia) cancer cell lines. Compound 20 exhibited potent cytotoxicity against HepG2 and SGC7901 cancer cells with the IC50 values of 6.9 and 6.9 μm , respectively.  相似文献   

12.
Fish‐mint (Houttuynia cordataThunb .), belonging to family Saururaceae, has long been used as food and traditional herbal medicine. The present study was framed to assess the changes occurring in the essential‐oil composition of H. cordata during annual growth and to evaluate allelopathic, antibacterial, antifungal, and antiacetylcholinesterase activities. The essential‐oil content ranged from 0.06 – 0.14% and 0.08 – 0.16% in aerial parts and underground stem, respectively. The essential oils were analysed by GC‐FID, GC/MS, and NMR (1H and 13C). Major constituents of aerial‐parts oil was 2‐undecanone (19.4 – 56.3%), myrcene (2.6 – 44.3%), ethyl decanoate (0.0 – 10.6%), ethyl dodecanoate (1.1 – 8.6%), 2‐tridecanone (0.5 – 8.3%), and decanal (1.1 – 6.9%). However, major constituents of underground‐stem oil were 2‐undecanone (29.5 – 42.3%), myrcene (14.4 – 20.8%), sabinene (6.0 – 11.1%), 2‐tridecanone (1.8 – 10.5%), β‐pinene (5.3 – 10.0%), and ethyl dodecanoate (0.8 – 7.3%). Cluster analysis revealed that essential‐oil composition varied substantially due to the plant parts and season of collection. The oils exhibited significant allelopathic (inhibition: 77.8 – 88.8%; LD50: 2.45 – 3.05 μl/plate), antibacterial (MIC: 0.52 – 2.08 μl/ml; MBC: bacteriostatic) and antifungal (MIC: 2.08 – 33.33 μl/ml; MFC: 4.16 – 33.33 μl/ml) activities. The results indicate that the essential oil from Hcordata has a significant potential to allow future exploration and exploitation as a natural antimicrobial and allelopathic agent.  相似文献   

13.

Aims

This work was performed to characterize new secondary metabolites with neuraminidase (NA) inhibitory activity from marine actinomycete strains.

Methods and Results

An actinomycete strain IFB‐A01, capable of producing new NA inhibitors, was isolated from the gut of shrimp Penasus orientalis and identified as Streptomyces seoulensis according to its 16S rRNA sequence (over 99% homology with that of the standard strain). Repeated chromatography of the methanol extract of the solid‐substrate culture of S. seoulensis IFB‐A01 led to the isolation of streptoseolactone ( 1 ), and limazepines G ( 2 ) and H ( 3 ). The structures of 1 – 3 were determined by a combination of IR, ESI‐MS, 1D (1H and 13C NMR, and DEPT) and 2D NMR experiments (HMQC, HMBC, 1H‐1H COSY and NOESY). Compounds 1 – 3 showed significant inhibition on NA in a dose‐dependent manner with IC50 values of 3·92, 7·50 and 7·37 μmol l?1, respectively.

Conclusions

This is the first report of two new ( 1 and 2 ) and known ( 3 , recovered as a natural product for the first time in the work) NA inhibitors from the marine‐derived actinomycete S. seoulensis IFB‐A01.

Significance and Impact of the Study

The three natural NA inhibitors maybe of value for the development of drug(s) necessitated for the treatment of viral infections.  相似文献   

14.
LS‐3‐134 is a substituted N‐phenylpiperazine derivative that has been reported to exhibit: (i) high‐affinity binding (Ki value 0.2 nM) at human D3 dopamine receptors, (ii) > 100‐fold D3 versus D2 dopamine receptor subtype binding selectivity, and (iii) low‐affinity binding (Ki > 5000 nM) at sigma 1 and sigma 2 receptors. Based upon a forskolin‐dependent activation of the adenylyl cyclase inhibition assay, LS‐3‐134 is a weak partial agonist at both D2 and D3 dopamine receptor subtypes (29% and 35% of full agonist activity, respectively). In this study, [3H]‐labeled LS‐3‐134 was prepared and evaluated to further characterize its use as a D3 dopamine receptor selective radioligand. Kinetic and equilibrium radioligand binding studies were performed. This radioligand rapidly reaches equilibrium (10–15 min at 37°C) and binds with high affinity to both human (Kd = 0.06 ± 0.01 nM) and rat (Kd = 0.2 ± 0.02 nM) D3 receptors expressed in HEK293 cells. Direct and competitive radioligand binding studies using rat caudate and nucleus accumbens tissue indicate that [3H]LS‐3‐134 selectively binds a homogeneous population of binding sites with a dopamine D3 receptor pharmacological profile. Based upon these studies, we propose that [3H]LS‐3‐134 represents a novel D3 dopamine receptor selective radioligand that can be used for studying the expression and regulation of the D3 dopamine receptor subtype.  相似文献   

15.
Phytochemical investigation on the barks of Betula platyphylla var. japonica (Betulaceae) was carried out, resulting in the isolation and identification of three new triterpenoids, 27‐Ocis‐caffeoylcylicodiscic acid ( 1 ), 27‐Ocis‐feruloylcylicodiscic acid ( 2 ), and 27‐Ocis‐caffeoylmyricerol ( 3 ), along with six known triterpenoids, obtusilinin ( 4 ), winchic acid ( 5 ), 27‐Otrans‐caffeoylcylicodiscic acid ( 6 ), uncarinic acid E ( 7 ), myriceric acid B ( 8 ), and 3‐Otrans‐caffeoyloleanolic acid ( 9 ). The structures of the new compounds were elucidated by extensive spectroscopic methods, including 1D‐ and 2D‐NMR, and HR‐ESI‐MS. All of the isolated compounds were evaluated for cytotoxicity against four human tumor cell lines (A549, SK‐OV‐3, SK‐MEL‐2, and Bt549). Compounds 2 , 6 , 8 , and 9 exhibited potent cytotoxicity against all of the tumor cells tested (IC50 < 10.0 μm ), while compounds 3 , 4 , 5 , and 7 showed moderate cytotoxicity against all of the tumor cells tested (IC50 < 20.0 μm ).  相似文献   

16.
Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2‐aryl‐3‐benzofuranone named superbanone ( 1 ), one benzoin, 2‐hydroxy‐1‐(2‐hydroxy‐4‐methoxyphenyl)‐2‐(4‐methoxyphenyl)ethanone ( 2 ), eight pterocarpans ( 3  –  10 ), and eleven isoflavonoids ( 11  –  21 ). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D‐ and 2D‐NMR. The isolated compounds and their derivatives were evaluated for α‐glucosidase inhibitory and antimalarial activities. Compounds 3 , 7 , 8 , and 11 showed promising α‐glucosidase inhibitory activity (IC50 = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 μm , respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC50 = 6.54 ± 0.04 μm ). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure–activity relationships are discussed.  相似文献   

17.
Thanks to the understanding of the relationships between the residence lifetime τM of the coordinated water molecules to macrocyclic Gd‐complexes and the rotational mobility τR of these structures, and according to the theory for paramagnetic relaxation, it is now possible to design macromolecular contrast agents with enhanced relaxivities by optimizing these two parameters through ligand structural modification. We succeeded in accelerating the water exchange rate by inducing steric compression around the water binding site, and by removing the amide function from the DOTA‐AA ligand [1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid mono(p‐aminoanilide)] ( L ) previously designed. This new ligand 10[2(1‐oxo‐1‐p‐propylthioureidophenylpropyl]‐1,4,7,10‐tetraazacyclodecane‐1,4,7‐tetraacetic acid ( L 1 ) was then covalently conjugated to API [O‐(aminopropyl)inulin] to get the complex API ‐(GdL 1 )x with intent to slow down the rotational correlation time (τR) of the macromolecular complex. The evaluation of the longitudinal relaxivity at different magnetic fields and the study of the 17O‐NMR at variable temperature of the low‐molecular‐weight compound ( GdL 1 ) showed a slight decrease of the τM value ( = 331 ns vs.  = 450 ns for the Gd L complex). Consequently to the increase of the size of the API ‐(GdL 1 )x complex, the rotational correlation time becomes about 360 times longer compared to the monomeric GdL 1 complex (τR = 33,700 ps), which results in an enhanced proton relaxivity.  相似文献   

18.
Although 2D Ti3C2Tx is a good candidate for supercapacitors, the restacking of nanosheets hinders the ion transport significantly at high scan rates, especially under practical mass loading (>10 mg cm?2) and thickness (tens of microns). Here, Ti3C2Tx‐NbN hybrid film is designed by self‐assembling Ti3C2Tx with 2D arrays of NbN nanocrystals. Working as an interlayer spacer of Ti3C2Tx, NbN facilitates the ion penetration through its 2D porous structure; even at extremely high scan rates. The hybrid film shows a thickness‐independent rate performance (almost the same rate capabilities from 2 to 20 000 mV s?1) for 3 and 50 µm thick electrodes. Even a 109 µm thick Ti3C2Tx‐NbN electrode shows a better rate performance than 25 µm thick pure Ti3C2Tx electrodes. This method may pave a way to controlling ion transport in electrodes composed of 2D conductive materials, which have potential applications in high‐rate energy storage and beyond.  相似文献   

19.
To contribute the development of new products to control plant‐parasitic nematodes, 12 chalcone analogues were synthesized and screened for activity against Meloidogyne incognita. Three caused mortality greater than negative controls in second‐stage juvenile M. incognita, with values varying from 19.9% to 100%. The most active chalcone analogue was (1E,4E)‐1,5‐di(4‐nitrophenyl)‐2‐butylpenta‐1,4‐dien‐3‐one (compound 6 ), which had an LC50 value of 41 µg/ml. Under the same conditions, the commercial nematicide Carbofuran® (2,2‐dimethyl‐2,3‐dihydro‐1‐benzofuran‐7‐yl methylcarbamate) presented an LC50 equal to 101 µg/ml. When this chalcone analogue was applied to tomato plants infested with M. incognita, reductions in the numbers of galls and eggs of 51% and 68% were observed, respectively. According to in silico studies, the enzyme target of compound 6 in M. incongita is cytochrome P450, which is important for the oxidation of several substances in the nematode. Therefore, compound 6 is potentially useful for the development of new products to control M. incongita.  相似文献   

20.
All life requires energy to drive metabolic reactions such as growth and cell maintenance; therefore, fluctuations in energy availability can alter microbial activity. There is a gap in our knowledge concerning how energy availability affects the growth of extreme chemolithoautotrophs. Toward this end, we investigated the growth of thermoacidophile Acidianus ambivalens during sulfur oxidation under aerobic to microaerophilic conditions. Calorimetry was used to measure enthalpy (ΔHinc) of microbial activity, and chemical changes in growth media were measured to calculate Gibbs energy change (ΔGinc) during incubation. In all experiments, Gibbs energy was primarily dissipated through the release of heat, which suggests enthalpy‐driven growth. In microaerophilic conditions, growth was significantly more efficient in terms of biomass yield (defined as C‐mol biomass per mole sulfur consumed) and resulted in lower ΔGinc and ΔHinc. ΔGinc in oxygen‐limited (OL) and oxygen‐ and CO2‐limited (OCL) microaerophilic growth conditions resulted in averages of ?1.44 × 103 kJ/C‐mol and ?7.56 × 102 kJ/C‐mol, respectively, and average ΔHinc values of ?1.11 × 105 kJ/C‐mol and ?4.43 × 104 kJ/C‐mol, respectively. High‐oxygen experiments resulted in lower biomass yield values, an increase in ΔGinc to ?1.71 × 104 kJ/C‐mol, and more exothermic ΔHinc values of ?4.71 × 105 kJ/C‐mol. The observed inefficiency in high‐oxygen conditions may suggest larger maintenance energy demands due to oxidative stresses and a preference for growth in microaerophilic environments.  相似文献   

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