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1.
Chem Biodivers ; 19(7): e202100887, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35653619

RESUMO

Bacterial diseases, such as American Foulbrood (AFB) and European Foulbrood (EFB), are known to have catastrophic effects on honey bees (if left to spread, can wipe out entire colonies), leading to severe financial losses in the beekeeping industry. The aim of this study was to evaluate the pharmacological properties of methanol extract and its fractions (ethyl acetate, hexane, water) derived from Dicranum scoparium Hedw., which could be utilized as a potential drug to prevent the bacterial diseases (AFB and EFB) affecting the honey bees. For this purpose, crude methanol extract and ethyl acetate/hexane/water fractions were prepared from the aerial part of D. scoparium, collected from Trabzon province. Bio-guided fractionation of the extract and its fractions led to the first-time isolation of five compounds. The structure of all compounds was elucidated by nuclear magnetic resonance (NMR) spectroscopy, ultraviolet (UV) spectral analysis, Fourier-transform infrared spectroscopy (FT-IR), liquid chromatography quadrupole time-of-flight mass spectroscopy (LC-QToF-MS), and by comparison of their NMR data with that of literature. The analysis of these compounds revealed significant antibacterial and sporicidal activities against bacteria causing larval diseases in honey bees. The antibacterial activity of these compounds ranged from 0.6 to 60 µg/mL against AFB and EFB causing bacteria. Therefore, the natural raw extract and fractions of D. scoparium could be used as potential therapeutic agents against bacterial agents affecting honey bees.


Assuntos
Infecções Bacterianas , Hexanos , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Abelhas , Metanol , Compostos Fitoquímicos , Espectroscopia de Infravermelho com Transformada de Fourier , Água
2.
Bioorg Chem ; 81: 545-552, 2018 12.
Artigo em Inglês | MEDLINE | ID: mdl-30245236

RESUMO

Some Geranium species have been used to treat diabetes. To evaluate the scientific basis of this ethnopharmacological use, we aimed to isolate potent α-glucosidase inhibitory metabolites of Geranium asphodeloides Burm. through in vitro bioactivity-guided fractionation. All the tested extracts showed high α-glucosidase inhibitory effect compared to acarbose. Among the tested extracts, the ethyl acetate subextract showed the highest activity with an IC50 value of 0.85 ±â€¯0.01 µM. A hydrolysable tannin, 1,2,4-tri-O-galloyl-ß-d-glucopyranose (1), and five flavonoid glycosides, kaempferol-3-O-α-rhamnopyranoside (2), kaempferol-3-O-α-arabinofuranoside (3), quercetin-3-O-ß-glucopyranoside (4), quercetin-3-O-α-rhamnopyranoside (5), and quercetin-3-O-α-rhamnofuranoside (6), were isolated from the ethyl acetate subextract. Their structures were identified by 1D- and 2D-NMR experiments. 1 exhibited the highest α-glucosidase inhibitory effect, approximately 61 times more potent than positive control, acarbose, with an IC50 value of 0.95 ±â€¯0.07 µM. Also, 2 was more potent than acarbose. An enzyme kinetics analysis revealed that compounds 2, 3 and 4 were competitive, whereas 1 and 6 uncompetitive inhibitors. Molecular docking studies were performed to get insights into inhibition mechanisms of the isolated compounds in the light of the enzyme kinetic studies using various binding sites of the enzyme model.


Assuntos
Geranium/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Polifenóis/química , Polifenóis/farmacologia , Proteínas de Saccharomyces cerevisiae/metabolismo , Saccharomyces cerevisiae/enzimologia , alfa-Glucosidases/metabolismo , Simulação de Acoplamento Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia
3.
Nat Prod Res ; 37(7): 1185-1198, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-34736355

RESUMO

Two new dihydroisocoumarins (scorzolongin I (1), and scorzolongin II (2)) and nine known compounds (3',5'-dimethoxy hydrangenol (scorzolongin III, 3), cladantholide (4), dammar-24-ene-3ß-ol (5), taraxasterol (6), ß-sitosterol (7), mangifgerursanone (8), and a mixture of α-amyrenone (9a), ß-amyrenone (9b), and dammar-24-ene-3-one (9c) in about 1:1:2 ratio) were identified from the dichloromethane fraction of Scorzonera longiana. The structure of all compounds (1-9a-c) were elucidated by extensive 1D and 2D NMR (1H, 13C/APT, COSY, HMBC, HSQC, and NOESY) spectroscopy, UV, FT-IR, and LC-QTOF-MS data and by comparison of their NMR data with the literature. These compounds have been isolated from S. longiana for the first time. An antimicrobial assay against eight microorganisms was applied to isolated compounds 1-3. Scorzolongin I, and scorzolongin II, and scorzolongin III showed notable activity against gram (-) (Escherichia coli and Yersinia pseudotuberculosis) and fungi (Candida albicans, Saccharomyces cerevisiae) with 20 mm inhibition zone each. Scorzolongin II (2) exhibited strong activity against E. coli, Y. pseudotuberculosis, Mycobacterium smegmatis C. albicans, S. cerevisiae with MIC value of 33.8 µg/mL.


Assuntos
Anti-Infecciosos , Scorzonera , Scorzonera/química , Terpenos , Turquia , Espectroscopia de Infravermelho com Transformada de Fourier , Escherichia coli , Saccharomyces cerevisiae , Anti-Infecciosos/farmacologia
4.
Vet Res Commun ; 47(3): 1445-1455, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-36892790

RESUMO

Beekeeping is an important agricultural and commercial activity globally practiced. Honey bee is attacked by certain infectious pathogens. Most important brood diseases are bacterial including American Foulbrood (AFB), caused by Paenibacillus larvae (P. larvae), and European Foulbrood (EFB) by Melissococcus plutonius (M. plutonius) in addition of secondary invaders, e.g. Paenibacillus alvei (P. alvei) and Paenibacillus dendritiformis (P. dendritiformis). These bacteria cause the death of larvae in honey bee colonies. In this work, antibacterial activities of extracts, fractions, and isolated certain compounds (nominated 1-3) all originated from moss, Dicranum polysetum Sw. ( D. polysetum), were tested against some honey bee bacterial pathogens. Minimum inhibitory concentration, minimum bactericidal concentration, and sporicidal values ​​of methanol extract, ethyl acetate, and n-hexane fractions ranged between 10.4 and 18.98, 83.4-303.75 & 5.86-18.98 µg/mL against P. larvae, respectively. Antimicrobial activities of the ethyl acetate sub-fractions (fraction) and the isolated compounds (1-3) were tested against AFB- and EFB-causing bacteria. Bio-guided chromatographic separation of ethyl acetate fraction, a crude methanolic extract obtained from aerial parts of D. polysetum resulted in three natural compounds: a novel one, i.e. glycer-2-yl hexadeca-4-yne-7Z,10Z,13Z-trienoate (1, dicrapolysetoate; given as trivial name), in addition to two known triterpenoids poriferasterol (2), and γ-taraxasterol (3). Minimum inhibitory concentration ranges were 1.4-60.75, 8.12-65.0, 2.09-33.44 & 1.8-28.75 µg/mL for sub-fractions, compounds 1, 2, and 3, respectively.


Assuntos
Antibacterianos , Compostos Fitoquímicos , Abelhas , Animais , Larva , Antibacterianos/farmacologia , Extratos Vegetais
5.
Turk J Chem ; 46(4): 1234-1244, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-37538750

RESUMO

The essential oil (EO) of Cota tinctoria var. tinctoria was analyzed using GC-FID / MS. A total of 51 compounds were determined from this taxon, accounting for 99.79% in hydrodistillation. Monoterpenes were the primary chemical class for the volatile organic compounds in the EO (36.1%, 13 compounds). Borneol (18.1%), camphor (14.9%), and ß-pinene (11.3%) were the major components in the EO of C. tinctoria var. tinctoria. The antimicrobial activities of EO and n-hexane, acetonitrile, methanol, and water solvent extracts of the taxon were screened in vitro against ten microorganisms. The EO yielded the best activity (15 mm, 372.5 MIC, 59600 µg/µL) against Mycobacterium smegmatis. The acetonitrile extract was the most active against the Staphylococcus aureus and Bacillus cereus with 274 µg/mL MIC value. IC50 values for the lipase enzyme inhibitory activity of EO and solvent extracts (n-hexane, acetonitrile, methanol, and water) were found to be 59.80 ± 4.3285 µg/mL 68.28 ± 3.1215 µg/mL, 52.60 ± 3.7526 µg/mL, 48.73 ± 2.8265 µg/mL, and 99.50 ± 5.5678 µg/mL, respectively.

6.
Turk J Chem ; 45(1): 199-209, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33679163

RESUMO

Chromatographic separation ofn-hexane and ethyl acetate fraction of a crude methanol extract obtained from aerial parts of theScorzonera aucherianaDC collected from Sivas province of Turkey yielded nine natural compounds; two new 3-caffeoyl-quinic acid analogs (1-2), one new taraxasterol oleate (3), and six known triterpenoids taraxasterol (4), taraxasterol acetate (5), ptiloepoxide (6), lupeol (7), lupeol acetate (8), andß-sitosterol (9) were characterized. The structures of the isolated compounds were elucidated on the basis of NMR (1H,13C, COSY, HMBC, HSQC, and TOCSY), UV, FT-IR and LC-Q-TOF-MS spectrometric data.

7.
Iran J Pharm Res ; 20(3): 110-120, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34903974

RESUMO

Volatile organic compositions of the essential oils (EOs), solid-phase microextraction (SPME) and SPME of n-hexane extracts from the flower and stem-leaf of Filipendula vulgaris (F. vulgaris) were analyzed by GC-FID/MS. A total of 107 constituents were characterized, flower and stem-leaf parts of the plant were found to contain different volatile organic compounds. Tricosane (29.6%), n-nonanal (20.5%) were identified as the main components in the essential oil of the flower, while phytol (35.2%) was found to be a major constituent in the essential oil of stem-leaf. Benzaldehyde (56.0%) and n-nonanal (31.6%) were the major groups in the SPME of stem-leaf and flower, respectively. The volatiles for the SPME of n-hexane extracts of the flower and stem-leaf of F. vulgaris were predominated by aromatic compounds (75.0% and 78.5%) and ketones (18.1% and 10.1%), respectively. On the other hand, a total of terpene compounds was found at the most in the EO of the stem-leaf part of the plant (48.6%). In addition, antimicrobial, tyrosinase inhibition, and nitric oxide scavenging activities of the n-hexane (H), methanol (M), aqueous extracts (A) and EOs of F. vulgaris were investigated. EOs and methanol extracts of flower and stem-leaf had high antimicrobial activity against tested various microorganisms. However, n-hexane extracts of the flower and stem-leaf only displayed activity against Mycobacterium smegmatis. Methanol extracts of flower and stem-leaf possessed the best tyrosine inhibition and NO scavenging activity.

8.
Turk J Chem ; 44(6): 1655-1662, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-33488260

RESUMO

The volatile components of essential oil (EO), SPME, and SPME of solvent extracts ( n -hexane, methanol, and water) obtained from fresh Serapias orientalis subsp. orientalis ( Soo ) were analyzed by GC-FID/MS. EO of Soo gave 11 compounds in the percentage of 99.97%; capronaldehyde (37.01%), 2-( E )-hexenal (23.19%), and n -nonanal (19.05%) were found to be major constituents. SPME GC-FID/MS analyses of fresh plant and solvent extracts of Soo revealed 7, 12, 7, and 4 compounds within the range of 99.7% to 99.9%. Limonene (76.5%, 41.7%, and 61.3%) was the major compound in SPMEs of the n -hexane and methanol extracts. α -Methoxy- p -cresol (52.9%) was the main component in its water extract. The antimicrobial activity of EO and the solvent extracts of Soo were screened against 9microorganisms. EO showed the best activity against Mycobacterium smegmatis , with 79.5 µg/mL MIC value. The n -hexane, methanol, and water extracts were the most active against the Staphylococcus aureus within the range of 81.25-125.0 µg/mL (MIC). IC 50 values for the lipase enzyme inhibitory activity of EO and solvent extracts ( n -hexane, methanol, and water) were determined to be 59.87 µg/mL, 64.03 µg/mL, 101.91 µg/mL, and 121.24 µg/mL, respectively.

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