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1.
Front Pharmacol ; 14: 1205414, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-37416061

RESUMEN

Background: Sarcocephalus pobeguinii (Hua ex Pobég) is used in folk medicine to treat oxidative-stress related diseases, thereby warranting the investigation of its anticancer and anti-inflammatory properties. In our previous study, the leaf extract of S. pobeguinii induced significant cytotoxic effect against several cancerous cells with high selectivity indexes towards non-cancerous cells. Aim: The current study aims to isolate natural compounds from S. pobeguinii, and to evaluate their cytotoxicity, selectivity and anti-inflammatory effects as well as searching for potential target proteins of bioactive compounds. Methods: Natural compounds were isolated from leaf, fruit and bark extracts of S. pobeguinii and their chemical structures were elucidated using appropriate spectroscopic methods. The antiproliferative effect of isolated compounds was determined on four human cancerous cells (MCF-7, HepG2, Caco-2 and A549 cells) and non-cancerous Vero cells. Additionally, the anti-inflammatory activity of these compounds was determined by evaluating the nitric oxide (NO) production inhibitory potential and the 15-lipoxygenase (15-LOX) inhibitory activity. Furthermore, molecular docking studies were carried out on six putative target proteins found in common signaling pathways of inflammation and cancer. Results: Hederagenin (2), quinovic acid 3-O-[α-D-quinovopyranoside] (6) and quinovic acid 3-O-[ß-D-quinovopyranoside] (9) exhibited significant cytotoxic effect against all cancerous cells, and they induced apoptosis in MCF-7 cells by increasing caspase-3/-7 activity. (6) showed the highest efficacy against all cancerous cells with poor selectivity (except for A549 cells) towards non-cancerous Vero cells; while (2) showed the highest selectivity warranting its potential safety as a chemotherapeutic agent. Moreover, (6) and (9) significantly inhibited NO production in LPS-stimulated RAW 264.7 cells which could mainly be attributed to their high cytotoxic effect. Besides, the mixture nauclealatifoline G and naucleofficine D (1), hederagenin (2) and chletric acid (3) were active against 15-LOX as compared to quercetin. Docking results showed that JAK2 and COX-2, with the highest binding scores, are the potential molecular targets involved in the antiproliferative and anti-inflammatory effects of bioactive compounds. Conclusion: Overall, hederagenin (2), which selectively killed cancer cells with additional anti-inflammatory effect, is the most prominent lead compound which may be further investigated as a drug candidate to tackle cancer progression.

2.
Nat Prod Res ; 37(24): 4169-4180, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-36757210

RESUMEN

From Rinorea oblongifolia fruits, 3-Nor-4ß-friedelan-24-ol (1) and 3-decyl-6,7,8-trimethoxy-2H,5H-furo[4,3,2-de]isochromene-2,5-dione (4), new derivatives alongside, 28-hydroxyfriedelan-3-one (2), friedelin (3), 3,3',4,4',5'-pentamethylcoruleoellagic acid (5), hexamethylcoruleoellagic acid (6), 3',4,4',5,5'-pentamethylcoruleoellagic acid (7), and fatty compounds 8-11 were isolated and characterized using HRESIMS, EIMS, 1D and 2D NMR. In vitro enzyme inhibition of compounds 1, 2, 4, 5, 6 and 7 were evaluated on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), α-glucosidase, urease and tyrosinase. Against AChE and BChE, the phenolic compounds 4, 5, 6, and 7 had good activity probably due to the phenolic nature and methoxy substituents. Compounds 4, 5, 6 and 7 exhibited good α-glucosidase inhibition especially compound 4 whose IC50 = 42.45 ± 0.46 µg/mL was close that of acarbose (IC50 = 20.52 ± 0.84 µg/mL) standard drug. Urease and tyrosinase were appreciably inhibited by the compounds. Overall results of enzyme inhibitory assays indicate Rinorea oblongifolia, fruits and its constituents as potential remedy for enzymatic disorders.


Asunto(s)
Butirilcolinesterasa , Violaceae , Butirilcolinesterasa/química , Acetilcolinesterasa/química , Monofenol Monooxigenasa , alfa-Glucosidasas , Ureasa , Inhibidores de la Colinesterasa/farmacología , Inhibidores de la Colinesterasa/química , Frutas , Simulación del Acoplamiento Molecular
3.
Nat Prod Res ; 37(11): 1806-1815, 2023 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-36121777

RESUMEN

The bio guided fractionation of the dichloromethane/methanol (1:1) crude extract of the air-dried whole plant of C. aegyptiaca led to the isolation of one new flavone derivative designated conyflavone (1) and one new clerodane diterpene type designated conyclerodane (2) along with five known compounds including two flavonoids Gardenin C (3), chrysosplenetin (4) and two steroids glucoside of ß-sitosterol (5), the mixture of stigmasterol (6) and ß-sitosterol (6') and ent-2b,18,19trihydroxycleroda-3,13-dien-16,15-olide (7). The structures were established by spectroscopic methods including IR, 1D and 2D NMR in conjunction with mass spectroscopy and by comparison to data of related compounds described in literature. The stereocentres in compound 2 were determined by SC-XRD analysis. Crude extract as well as fractions and pure compounds were evaluated in vitro for their antibacterial activities against four pathogenic and two clinical isolate strains using microdilution methods. Extracts and compounds displayed a moderate antibacterial activity with MIC values ranging from 125 to 500 µg/mL.


Asunto(s)
Asteraceae , Conyza , Extractos Vegetales/química , Antibacterianos/química , Glucósidos , Pruebas de Sensibilidad Microbiana
4.
In Silico Pharmacol ; 10(1): 11, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35800001

RESUMEN

Overproduction of Nitric oxide (NO) and many other pro-inflammatory mediators are responsible for many pathological disorders in humans, including Alzheimer's disease (AD). In this study, active fractions isolated from Khaya grandifoliola (Kg) were screened for their inhibitory activities against NO production in lipopolysaccharide (LPS)-activated microglia. Among the 5 fractions tested, Kg25 was the most active and showed potent inhibitory activity towards NO production. The fraction further showed inhibitory effect on iNOS's mRNA expression and other major pro-inflammatory cytokines including TNFα and IL1-ß. Study of the effect of Kg25 on p38MAPKinase and JNK3 showed that the fraction inhibits these signaling pathways known to be involved in cell inflammatory pathways. These observations were confirmed at the protein level with Kg25 inhibiting iNOS and p38MAPK protein expressions in N9 cells. Analysis of Kg25 composition by HPLC identified 3 main compounds, namely: 6 phenyl, 4-(1`oxyehylphenyl) hexane, Carbamic acid, (4-methly-1-phenyl)-1, phenyl, and Benzene, 1 1`-(oxydiethylidene) bis. The above mentionned compounds were further analyzed for their bioactivity against the p38MAPKinase and iNOS receptors using molecular docking. MolDock results showed that 1-phenylethyl N-(4-methylphenyl)carbamate (compound 2) possesses the highest binding affinity (for iNOS); and 1-(1-phenylethoxy)ethylbenzene (compound 3) (for pMAPK) respectively and both compounds interact well with the active site residues. Hence, these compounds could be considered as scaffolds for further development of lead- drugs targeting neuroinflammation in AD.

5.
J Asian Nat Prod Res ; 24(11): 1041-1051, 2022 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34984935

RESUMEN

As part of our search for new secondary metabolites from Macaranga hurifolia Beille, a phytochemical investigation was carried out on the fruits that led to the isolation and characterization of two new prenylated flavonol derivatives named macafolias A (1) and B (2), along with five known compounds. Their chemical structures were established on the basis of extensive analysis of their 1-D and 2-D NMR (1H, 13C, APT, COSY, HSQC and HMBC) in conjunction with mass spectroscopy and by comparison with data from the literature. The in vitro assay of the antibacterial potency of the crude extract, fractions and some pure compounds were evaluated against a wide range of bacteria strains.


Asunto(s)
Euphorbiaceae , Flavonoides , Flavonoides/farmacología , Flavonoides/química , Frutas/química , Estructura Molecular , Euphorbiaceae/química , Antibacterianos/farmacología , Antibacterianos/química
6.
Nat Prod Res ; 36(1): 246-255, 2022 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-32530301

RESUMEN

The ethyl acetate fraction, the stem bark and the residual methanolic extracts from the leaves of Cola heterophylla (Sterculiaceae) led to the isolation of two new compounds: Heterophynone (1) and methyl ester of Colic acid (6), along with four known triterpenes: betulinic acid (2), oleanolic acid (3), ursolic acid (4) and chletric acid (5). Structures of compounds were established by different spectroscopic methods that included 1D and 2D NMR experiment. The antimicrobial activity of isolated compounds was evaluated against two yeasts, Candida Albicans NR 29456 and Candida Krusei 1415; and five Gram-positive bacterial, Salmonella enteric Serovar Muenchem, Salmonella enteric Serovar Thyphimurium, Staphylococcus aureus NR 46003, Staphylococcus aureus NR46374 and Pseudomonas aeruginosa HM 601). Among tested compounds, Heterophynone was found to be the most active with significant antimicrobial activity against Salmonella enteric Serovar Thyphimurium (MIC = 7.82 µg/mL and MBC = 62.5 µg/mL) and good activity against Candida Albicans NR 29456 (MIC = 62.5 µg/mL).


Asunto(s)
Antiinfecciosos , Cola/química , Ésteres , Antiinfecciosos/farmacología , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/farmacología , Hojas de la Planta/química
7.
Org Biomol Chem ; 20(1): 98-105, 2021 12 22.
Artículo en Inglés | MEDLINE | ID: mdl-34596204

RESUMEN

A new vobasine-tryptamine-based monoterpene indole alkaloid pseudodimer was isolated from the stem bark of Voacanga africana. As a minor constituent occurring in a thoroughly investigated plant, this molecule was targeted based on a molecular networking strategy and a rational MS2-guided phytochemical investigation led to its isolation. Its structure was formally established based on HRMS, 1D/2D NMR data, and the application of the tool Small Molecule Accurate Recognition Technology (SMART 2.0). Its absolute configuration was assigned by the exciton chirality method and TD-DFT ECD calculations. Besides featuring an unprecedented intermonomeric linkage in the small group of vobasine/tryptamine hybrids, pyrrovobasine also represents the first pyrraline-containing representative in the whole monoterpene indole alkaloids group. Biosynthetic hypotheses possibly underpinning these structural oddities are proposed here.


Asunto(s)
Alcaloides Indólicos/química , Aprendizaje Automático , Monoterpenos/química , Norleucina/análogos & derivados , Pirroles/química , Alquilación , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Norleucina/química , Voacanga/química
8.
J Nat Prod ; 84(10): 2755-2761, 2021 10 22.
Artículo en Inglés | MEDLINE | ID: mdl-34569237

RESUMEN

Voatriafricanines A and B (1 and 2), the first examples of vobasine-aspidosperma-aspidosperma monoterpene trisindole alkaloids, were isolated from the stem barks of Voacanga africana, guided by a molecular networking strategy. Their structures, including absolute configurations, were elucidated by spectroscopic methods and ECD calculations. Compounds 1 and 2 possess intramolecular hydrogen bonding, sufficiently robust to transfer homonuclear and heteronuclear magnetizations. Compound 1 exhibited potent antimycobacterial activity with no discernible cytotoxic activity.


Asunto(s)
Antibacterianos/farmacología , Alcaloides Indólicos/farmacología , Voacanga/química , Antibacterianos/aislamiento & purificación , Camerún , Alcaloides Indólicos/aislamiento & purificación , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Corteza de la Planta/química
9.
Avicenna J Phytomed ; 11(4): 353-366, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34290967

RESUMEN

OBJECTIVE: A fraction from Khaya grandifoliola has recently been shown to inhibit hepatitis C virus (HCV) infection and three limonoids (17-epi-methyl-6-hydroxylangolensate, 7-deacetoxy-7-oxogedunin and 7-deacetoxy-7R-hydroxygedunin) were purified from this fraction. The present study aimed at assessing the inhibitory effect of these limonoids on HCV using cell-culture derived HCV (HCVcc) system. MATERIALS AND METHODS: Cytotoxic effects of the limonoids on Huh7.5 cells were assessed by MTT assay. Huh7.5 cells were transfected with RNA transcripts of the plasmid Jc1/GLuc2a, carrying a Gaussia luciferase reporter gene to rescue the HCVcc particles which were used to infect naïve cells in the presence or absence of the studied limonoids during 72 hr. Infection and replication rates were monitored by luciferase reporter assay and immunofluorescence assay (IFA) while cellular gene expression was analyzed by western blot, respectively. RESULTS: The limonoids inhibited HCV infection mostly by targeting entry and replication stage. Their inhibitory effect on entry step, comparable to that of anti-CD81 antibody, was related to the blocking of CD81 receptor. In the replication step, the limonoids decreased the expression of NS5B similar to danoprevir. These compounds also significantly decreased but up-regulated the expression of Class-III phosphatidylinositol 4-kinase alpha and 2',5'-oligoadenylate synthase-3, respectively. CONCLUSION: The present findings suggest that limonoids from K. grandifoliola are potential anti-HCV agents and may offer an advantage in the treatment of HCV infection.

10.
Acta Crystallogr C Struct Chem ; 77(Pt 6): 312-320, 2021 06 01.
Artículo en Inglés | MEDLINE | ID: mdl-34089255

RESUMEN

The crystal structures of rubescin D (1, C26H30O5) and monadelphin A (2, C30H36O11), bioactive molecules of the vilasinin and gedunin classes of limonoids, respectively, are reported for the first time and the synthons affecting their crystal packings are analyzed on the basis of their occurrences in molecules in the Cambridge Structural Database that share the same moieties. Rubescin D, 1, crystallizes in the space group P21 and its molecular structure consists of three six-membered rings A, C and D having, respectively, envelope, twist-boat and half-chair conformations, and three five-membered rings with half-chair (B and E) and planar conformations (F). Many synthons found in the crystal packing of 1 are in agreement with expectations derived from molecules displaying the same moieties. However, the secondary alcohol-ketone O-H...O=C synthon, which has a low occurrence (2.9%), contributes much to the layered packing, while the furan-ketone Csp2-H...O=C and secondary alcohol-epoxide O-H...OC2 synthons usually found in these compounds (occurrences of 20.6 and 17.6%, respectively) are missing. The packing of 1 is close to that of ceramicine B (3), but is completely different from that of TS3 (4), suggesting that the absence of the epoxide group in 3 would have favoured the furan-secondary alcohol Csp2-H...OH synthon and that the missing hydroxy group in 4, a strong hydrogen-bond donor, would have favoured the involvement of water molecules in the crystal packing. The molecular structure of monadelphin A, 2, consists of four six-membered fused rings (A, B, C and D) and one five-membered ring (E); they have twist-boat (A and C), chair (B), screw-boat (D) and planar (E) conformations. The molecule crystallizes in the space group P212121 with the contribution of many synthons usually found in compounds having the same moieties. However, the secondary alcohol-acetate O-H...OOC and secondary alcohol-ketone O-H...O=C synthons (occurrences of 16.7% each in these compounds) are missing. The furan-acetate Csp2-H...OOC synthon not observed in these compounds greatly contributes to the layered packing of 2. The layered packing is very close to those of 7-oxogedunin (5) and 6-dehydro-7-deacetoxy-7-oxogedunin (6), which both crystallize in the space group P21.


Asunto(s)
Acetatos/química , Furanos/química , Cetonas/química , Cristalización , Cristalografía por Rayos X , Enlace de Hidrógeno , Conformación Molecular
11.
Z Naturforsch C J Biosci ; 75(5-6): 135-144, 2020 May 26.
Artículo en Inglés | MEDLINE | ID: mdl-32229684

RESUMEN

This study aimed to evaluate the selective cytotoxicity of six natural compounds on four cancerous cells (MCF-7, HeLa, Caco-2 and A549) and two normal intestinal and lung cells (Hs1.Int and Wl-38) cells. We also attempted to analyze basically the structure-activity relationships and to understand the mechanism of action of active compounds using the Caspase-Glo® 3/7 kit. Globimetulin B (2) isolated from Globimetula dinklagei was significantly cytotoxic on cancerous cells with 50% inhibitory concentrations (IC50) ranging from 12.75 to 37.65 µM and the selectivity index (SI) values varying between 1.13 and 3.48 against both normal cells. The compound 3-O-ß-d-glucopyranosyl-28-hydroxy-α-amyrin (5) isolated from Phragmanthera capitata exhibited the highest cytotoxic activity on HeLa cells with the IC50 of 6.88 µM and the SI of 5.20 and 8.71 against Hs1.Int and Wl-38 cells, respectively. A hydroxyl group at C-3 of compounds was suggested as playing an important role in the cytotoxic activity. The induction of caspase-3 and -7 activity represents some proof that apoptosis has occurred in treated cells. Globimetulin B (2) selectively killed cancer cells with less toxicity to non-cancerous cells as compared to conventional doxorubicin therapy.


Asunto(s)
Caspasa 3/metabolismo , Caspasa 7/metabolismo , Loranthaceae/química , Neoplasias/metabolismo , Triterpenos Pentacíclicos/farmacología , Células A549 , Células CACO-2 , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Regulación Neoplásica de la Expresión Génica/efectos de los fármacos , Glucósidos/química , Glucósidos/farmacología , Células HeLa , Humanos , Concentración 50 Inhibidora , Células MCF-7 , Neoplasias/tratamiento farmacológico , Triterpenos Pentacíclicos/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Relación Estructura-Actividad
12.
Nat Prod Res ; 34(14): 2014-2021, 2020 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-30784307

RESUMEN

Two new coruleoellagic acid derivatives, 3,4',5,5',-tetramethylcoruleoellagic acid (1); 3',4,4',5,5'-pentamethylcoruleoellagic acid (2) and a new friedelane-type triterpene derivative rinol (5), were isolated from leaves and trunk bark of Rinorea oblongifolia (Violaceae) along with seven known compounds including 3,3',4,4',5'-pentamethylcoruleoellagic acid (3), hexamethylcoruleoellagic acid (4), 28-hydroxyfriedelin (6), friedelin (7), friedelan-3-ol (8), scopoletin (9) and ß-sitosterol-3-O-ß-D-glucopyranoside (10). Their structures were elucidated by means of spectroscopic methods including IR, 1D and 2D NMR in conjunction with mass spectrometry. Crude extracts of leaves and trunk bark as well as compounds 1-4 were evaluated for their antibacterial activities against 7 pathogenic bacterial strains (Streptococcus pneumoniae ATCC49619, Staphylococcus aureus ATCC 43300, Klepsiella pneumoniae ATCC 700603, Haemophilus influenza ATCC 49247, Escherichia coli ATCC 25922, Pseudomonas aeruginosa HM601, Staphylococcus aureus BAA 977). Compound (3) displayed noteworthy activity against Haemophilus influenza with MIC value of 9.38 µg/mL.


Asunto(s)
Antibacterianos/aislamiento & purificación , Corteza de la Planta/química , Hojas de la Planta/química , Violaceae/química , Antibacterianos/química , Bacterias/efectos de los fármacos , Haemophilus influenzae/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Triterpenos/análisis , Triterpenos/aislamiento & purificación
13.
Z Naturforsch C J Biosci ; 74(7-8): 175-182, 2019 Jul 26.
Artículo en Inglés | MEDLINE | ID: mdl-30903762

RESUMEN

Three new limonoids, designated as rubescins F (1), G (2), and H (3), together with two known compounds of this type, TS1 (4) and trichirubine A (5), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F (1) is the first limonoid from Trichilia spp. with an oxetane ring between C-7 and C-14, which seems to be formed by the isomerization of TS1 (4). The γ-hydroxybutenolide rubescin G (2) is a potential precursor of trichirubine A (5), whereas rubescin H (3) is the first example of a triterpenoid with a single bond between C-7/C-14, forming a cyclopropane ring. The absolute configuration of these limonoids was derived from biosynthetic considerations and ab initio calculations of NMR and optical rotation dispersion data.


Asunto(s)
Limoninas/análisis , Meliaceae/química , Ciclopropanos/química , Limoninas/química , Hojas de la Planta/química
14.
Nat Prod Res ; 33(2): 196-203, 2019 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-29502449

RESUMEN

Two new tetranorterpenoid derivatives named rubescins I (1) and J (2), were isolated along with six known compounds including rubescin D (3), lichexanthone (4), scopoletin (5), scopoletin O-glycoside (6), ß-sitosterol (7) and stigmasterol (8) from the stem bark of Trichilia rubescens (Meliaceae). The structures of the compounds were determined by means of MS, different NMR and by comparison with related data reported in the literature.


Asunto(s)
Limoninas/química , Meliaceae/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Estructura Molecular , Corteza de la Planta/química , Extractos Vegetales/química , Escopoletina/química , Escopoletina/aislamiento & purificación , Estigmasterol/química , Estigmasterol/aislamiento & purificación
15.
Nat Prod Res ; 33(14): 2011-2015, 2019 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-29882428

RESUMEN

A new lactam, oligoamide (1), along with three known compounds (2-4), stigmasterol-3-O-ß-D-glucopyranoside (2), formononetin (3) and (-)-pinitol (4) were isolated from the CH2Cl2/CH3OH (1:1) extract of the leaves of Angylocalyx oligophyllus by chromatographic separation. Their structures were elucidated on the basis of spectroscopic analysis (UV, IR, MS, 1D, and 2D NMR). Compound 1 was found to have weak antioxidant and urease inhibitory potential.


Asunto(s)
Fabaceae/química , Lactamas/aislamiento & purificación , Hojas de la Planta/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , Lactamas/química , Estructura Molecular , Análisis Espectral , Ureasa/antagonistas & inhibidores
16.
Acta Crystallogr E Crystallogr Commun ; 74(Pt 8): 1083-1086, 2018 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-30116567

RESUMEN

The title limonoid compound, C26H28O5·0.5H2O (TS3) [systematic name: (3aS,3bS,4aS,5aS,6S,7aR,8aR,8bS,11aR)-6-(furan-3-yl)-3a,5a,8b,11a-tetra-methyl-3a,4a,5,5a,6,7,7a,8b,11,11a-deca-hydro-oxireno[2',3':4b,5]oxireno[2'',3'':2',3']cyclo-penta-[1',2':7,8]phenanthro[10,1-bc]furan-3(3aH)-one hemihydrate], crystallizes with two independent mol-ecules (1 and 2) in the asymmetric unit and one water mol-ecule. TS3 is composed of three six-membered rings (A, C and D), three five-membered rings (B, E and F) and two epoxide rings. A group of five fused rings (A-E) is bonded to a furan ring (F) with a Csp3-Csp2 bond [1.500 (3) Šin mol-ecule 1 and 1.499 (3) Šin mol-ecule 2]. The absolute structures of the mol-ecules in the crystal were determined by resonant scattering; Flack parameter = 0.05 (5). In the crystal, the individual mol-ecules stack in columns along the b-axis direction. The water mol-ecule bridges mol-ecules 1 and 2 via Owater-H⋯O and C-H⋯Owater hydrogen bonds. Together with further C-H⋯O hydrogen bonds, linking mol-ecules 1 and 2, the columns are linked to form slabs parallel to the ab plane. Within each column, mol-ecules are also linked via C-H⋯π inter-actions involving the five-membered furan (F) rings.

17.
Z Naturforsch C J Biosci ; 73(3-4): 153-160, 2018 Feb 23.
Artículo en Inglés | MEDLINE | ID: mdl-28917086

RESUMEN

Two new limonoids, kostchyienones A (1) and B (2), along with 12 known compounds 3-14 were isolated from the roots of Pseudocedrela kostchyi. Compound (7) was isolated for the first time from a natural source. Their structures were elucidated on the basis of spectroscopic evidence. Compounds 1-6 and 13-14 gave IC50 values ranging from 0.75 to 5.62 µg/mL for antiplasmodial activity against chloroquine-sensitive (Pf3D7) and chloroquine-resistant (PfINDO) strains of Plasmodium falciparum. Compound 5 showed moderate potential cytotoxicity against the HEK239T cell line with an IC50 value of 22.2±0.89 µg/mL. The antiplasmodial efficacy of the isolated compounds supports the medicinal value of this plant and its potential to provide novel antimalarial drugs.


Asunto(s)
Antiprotozoarios/química , Limoninas/química , Meliaceae/química , Extractos Vegetales/química , Antiprotozoarios/toxicidad , Limoninas/toxicidad , Extractos Vegetales/toxicidad , Raíces de Plantas/química , Plasmodium falciparum/efectos de los fármacos
18.
BMC Complement Altern Med ; 17(1): 199, 2017 Apr 04.
Artículo en Inglés | MEDLINE | ID: mdl-28376770

RESUMEN

BACKGROUND: Free radicals have been implicated in the pathogenesis of diverse metabolic disorders including cancer. Therefore, fighting against free radicals has become an important strategy in the prevention or treatment of such diseases, in addition to direct or indirect anticancer chemotherapy. Sarcocephalus pobeguinii has been used traditionally to treat various diseases in which excess production of free radicals is implicated, warranting investigation of its free radical scavenging, anticancer and anti-inflammatory activity. METHODS: In the present study, extracts from leaves, fruits, roots and bark of Sarcocephalus pobeguinii were evaluated on four human cancer cell lines (MCF-7, HeLa, Caco-2 and A549 cells) and a non-cancerous cell line for their antiproliferative potential. The cells were incubated with the plant extracts for 48 h at 37 °C in a 5% CO2 humidified environment and their cytotoxic effect was determined using the tetrazolium-based colorimetric (MTT) assay. The radical inhibition was determined using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) scavenging techniques. The nitric oxide inhibitory activity was determined using LPS-activated RAW 264.7 macrophages. The correlation between radical scavenging capacity and antiproliferative activity was also analysed. RESULTS: The extract from leaves of Sarcocephalus pobeguinii (LSP) exhibited the highest cytotoxic effect on all four of the human cancer cell lines but with some cytotoxicity to the normal Vero cells. However, the LSP extract had the best selectivity index, ranging from 3.15 to 18.28. Also, antioxidant and anti-inflammatory assays indicated that the LSP extract had the highest radical scavenging capacity of all the extracts. A positive linear correlation was found between free radical scavenging ability and antiproliferative activity against the four cancer cell lines, with the highest correlation factor (R2 = 0.9914) obtained between DPPH inhibition and antiproliferative activity against A549 cells. CONCLUSIONS: The high selectivity index of the Sarcocephalus pobeguinii leaf extract indicates the potential of using this extract in cancer therapy. Furthermore, the positive correlation between free radical scavenging and antiproliferative activity suggests that the radical scavenging capacity of extracts may contribute to a prediction of their anticancer property.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Depuradores de Radicales Libres/farmacología , Óxido Nítrico/antagonistas & inhibidores , Extractos Vegetales/farmacología , Rubiaceae/química , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Células CACO-2 , Camerún , Proliferación Celular/efectos de los fármacos , Chlorocebus aethiops , Ensayos de Selección de Medicamentos Antitumorales , Depuradores de Radicales Libres/aislamiento & purificación , Células HeLa , Humanos , Ratones , Fitoquímicos , Plantas Medicinales , Células RAW 264.7 , Células Vero
19.
BMC Microbiol ; 17(1): 41, 2017 Feb 22.
Artículo en Inglés | MEDLINE | ID: mdl-28228111

RESUMEN

BACKGROUND: Antimicrobial activity of anthraquinone compounds of emodine type has been reported by many authors. These compounds are found in Vismia laurentii (Clusiaceae), a plant used in traditional pharmacopoeia for treatment of microbial infections among others affections. The continuous identification of new compounds has raised the problem of the relation between the structure and antimicrobial properties. RESULTS: The yeast growth kinetics parameters were not influenced by the pH variation as it was the case for the other tested bacteria. Fungicidal activities were noted for all molecules while only few of them had bactericidal activities, mostly on Gram positive bacteria. Mathematical model establishing a quantitative relationship between physicochemical properties of molecules and their fungicidal activities were obtained for Candida albicans and showed that physicochemical properties impacting on antifungal activity were polarizability, partition coefficient, molecular weight and hydrogen bond acceptor. CONCLUSIONS: This work demonstrated that the presence of a long aliphatic chain methoxy group substituted in position two of the emodine structure increased the antibacterial properties of the studied compounds. Moreover this antimicrobial property depends on the pH of the environment, and specifically on the polarizability and number of hydrogen bond acceptors of the compound.


Asunto(s)
Antraquinonas/farmacología , Antiinfecciosos/farmacología , Clusiaceae/química , Extractos Vegetales/farmacología , Relación Estructura-Actividad , Antraquinonas/química , Antibacterianos/química , Antibacterianos/farmacología , Antiinfecciosos/química , Antifúngicos/química , Antifúngicos/farmacología , Bacterias/efectos de los fármacos , Bacterias/crecimiento & desarrollo , Fenómenos Químicos , Hongos/efectos de los fármacos , Hongos/crecimiento & desarrollo , Bacterias Grampositivas/efectos de los fármacos , Enlace de Hidrógeno , Concentración de Iones de Hidrógeno , Cinética , Pruebas de Sensibilidad Microbiana/métodos , Modelos Teóricos , Estructura Molecular , Peso Molecular , Extractos Vegetales/química , Levaduras/efectos de los fármacos , Levaduras/crecimiento & desarrollo
20.
Z Naturforsch C J Biosci ; 71(11-12): 381-386, 2016 Nov 01.
Artículo en Inglés | MEDLINE | ID: mdl-27626765

RESUMEN

Three new lupan-type triterpernoid derivatives, namely globimetulin A (1), B (2) and C (3), were isolated from the shoot of Globimetula dinklagei (Loranthaceae), a hemiparasitic plant growing on Manihot esculenta, along with five known compounds: friedelin (4), friedelan-3-ol (5), 28-hydroxyfriedelin (6), 4-hydroxy-3,5-dimethoxybenzoic acid (7) and (1R,5S,7S)-7-[2-(4-hydroxyphenyl)ethyl]-2,6-dioxabicyclo[3.3.1]nonan-3-one (8). The structures of the new compounds were elucidated by detailed analyses of their MS, IR, 1D and 2D NMR spectral data and chemical evidence. Some of these compounds were evaluated in vitro for their antimicrobial activities against a wide range of microorganisms, but none of them exhibited noticeable activity.


Asunto(s)
Triterpenos/aislamiento & purificación , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Bacterias/efectos de los fármacos , Candida albicans/efectos de los fármacos , Espectroscopía de Resonancia Magnética/métodos , Espectrometría de Masas , Pruebas de Sensibilidad Microbiana , Espectrofotometría Infrarroja , Triterpenos/química , Triterpenos/farmacología
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