scholarly journals Antiparasitic Indole Alkaloids from Aspidosperma desmanthum and A. spruceanum from the Peruvian Amazonia

2014 ◽  
Vol 9 (8) ◽  
pp. 1934578X1400900
Author(s):  
Matías Reina ◽  
Lastenia Ruiz-Mesia ◽  
Wilfredo Ruiz-Mesia ◽  
Frida Enriqueta Sosa-Amay ◽  
Leonor Arevalo-Encinas ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Indole Alkaloids ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Techniques ◽  
Root Bark ◽  
Antiparasitic Activity ◽  
Specific Cytotoxicity ◽  
First Time ◽  
Selective Activity

Twenty-three indole alkaloids were isolated from Aspidosperma desmanthum and A. spruceanum. Alkaloids 1-4 were isolated from the leaves, 5-8 from the stem bark and 9-15 from the root bark of A. desmanthum. Alkaloids 5, 11, 16, 17 and 19 were isolated from the stem bark, 18 and 20-22 from the root bark and 23 from the flowers of A. spruceanum. Compounds 4, 14, and 15 have not been previously reported as natural products while 16 and 20 have been isolated for the first time from the genus Aspidosperma. Their structures were determined by spectroscopic techniques including 1D and 2D NMR experiments (COSY, NOESY, HSQC, HMBC). The antiparasitic activity of these compounds was tested against Trypanosoma cruzi and Leishmania infantum and their non-specific cytotoxicity on mammalian cells. The most active compounds were 10, 12, 13, and 14 from A. desmanthum, and 19, 21 and 22 from A. spruceanum. Aspidolimine (10) aspidocarpine (12) and tubotaiwine (21) showed selective activity against L. infantum.

Indole Alkaloids from Aspidosperma rigidum and A. schultesii and their Antiparasitic Effects

2011 ◽  
Vol 66 (5-6) ◽  
pp. 225-234 ◽  
Author(s):  
Matías Reina ◽  
Wilfredo Ruiz-Mesia ◽  
Lastenia Ruiz-Mesia ◽  
Rafael Martínez-Díaz ◽  
Azucena González-Coloma
Keyword(s):  
Medicinal Plants ◽  
Trypanosoma Cruzi ◽  
Leishmania Infantum ◽  
Mammalian Cells ◽  
Indole Alkaloids ◽  
Antiparasitic Activity ◽  
Specific Cytotoxicity ◽  
Oxindole Alkaloids

Five oxindole alkaloids, three plumerane-type alkaloids, subtype haplophitine, and one aspidospermatane-type alkaloid, subtype tubotaiwine, were isolated from the medicinal plants Aspidosperma rigidum and A. schultesii. One compound was identified as the transoid conformer of 18-oxo-O-methylaspidoalbine which was not previously described. The antiparasitic activity of all compounds against Trypanosoma cruzi and Leishmania infantum and their non-specific cytotoxicity against mammalian cells were also determined.

scholarly journals Antimicrobial Activity and Interactions of Toddalia asiatica Isolated Coumarins with Two Known Drugs

2020 ◽  
pp. 1-16
Author(s):  
I. Onjero ◽  
B. F. Juma ◽  
J. C. Korir ◽  
R. W. Kamau
Keyword(s):  
Antimicrobial Activity ◽  
Stem Bark ◽  
Additive Effect ◽  
Spectroscopic Techniques ◽  
Root Bark ◽  
Rhizopus Stolonifer ◽  
Toddalia Asiatica ◽  
The Individual ◽  
Coumarin 1 ◽  
First Time

Five coumarins namely, 5, 7-dimethoxy-6-(3'-hydroxy-3'-methylbutan-2-oxo) coumarin coumarin (1), Toddalolactone (2), Coumurrenol (3), gleinadiene (4) and Toddaculin (5) were isolated from either the stem and/or root bark of Toddalia asiatica , with compound 1 being reported for the first time. These were obtained using chromatographic methods and identified using spectroscopic techniques, as well as comparison of their physical data with already published results. Combinations of compound 3 and fluconazole displayed additive effect in inhibiting the growth of Penicillium digitatum with reduced MIC to 125 μg/mL compared to that of fluconazole alone at 250 μg /mL. Combination of compounds 1 and 3 also showed additive effect in inhibiting Rhizopus stolonifer lowering the MIC from 500 μg/mL (for both molecules) to 250 μg /mL. Interaction in antibacterial activity between two isolated compounds 1 and 3 was also evident. These lowered the MIC in action against Staphylococcus aureus to 250 μg/mL compared to individual compounds with MIC of 500 μg/mL while showing additive effect. All the crude extracts apart from that of stem bark hexane and the individual isolated compounds showed considerable activity against all the organisms tested.

scholarly journals A New 3-Prenyl-2-flavene and Other Extractives from Baphia massaiensis and Their Antimicrobial Activities

2018 ◽  
Vol 13 (4) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Ngonye Keroletswe ◽  
Runner R. T. Majinda ◽  
Ishmael B. Masesane
Keyword(s):  
Escherichia Coli ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Spectroscopic Techniques ◽  
Good Activity ◽  
Gram Negative ◽  
E Coli ◽  
Chromatographic Techniques ◽  
Inhibition Zones ◽  
First Time

One new 3-prenyl-2-flavene, named baphiflavene A, 1, and eleven known compounds, 2-12, were isolated and reported for the first time from Baphia massaiensis using several chromatographic techniques. Their structures were elucidated using different spectroscopic techniques; 1D and 2D-NMR, HRMS, GC-MS, UV/Vis, FTIR and by comparison with literature data. The isolates were tested against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli and Candida albicans to establish their preliminary antimicrobial activities. The results revealed that compound 1 had moderate activities against both Gram positive ( B. subtilis and S. aureus) and Gram negative ( E. coli and P. aeruginosa) bacteria, and good activity against C. albicans with inhibition zones of 10–23 mm (compared to 19 mm for chloramphenicol and miconazole standards). To the best of our knowledge, this is the first phytochemical work reported on Baphia massaiensis.

scholarly journals Angustinine – A New Benzopyridoquinolizine Alkaloid from Alangium lamarckii

2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700
Author(s):  
Mumu Chakraborty ◽  
Sibabrata Mukhopadhyay
Keyword(s):  
Spectral Analysis ◽  
2D Nmr ◽  
Stem Bark ◽  
Root Bark

A new benzopyridoquinolizine alkaloid, designated as angustinine (1), was isolated from the root bark of Alangium lamarckii Thwaites, along with the known ipecac alkaloid, emetine. Investigation of the stem bark of the same plant resulted in the isolation of another known ipecac alkaloid, cephaeline. The structure of the new alkaloid (1) was elucidated on the basis of 2D NMR spectral analysis.

scholarly journals Antimycobacterial Activity of the Extract and Isolated Compounds From the Stem Bark of Zanthoxylum leprieurii Guill. and Perr.

2021 ◽  
Vol 16 (8) ◽  
pp. 1934578X2110358
Author(s):  
Benson Oloya ◽  
Jane Namukobe ◽  
Matthias Heydenreich ◽  
Willy Ssengooba ◽  
Bernd Schmidt ◽  
...  
Keyword(s):  
Antimycobacterial Activity ◽  
Stem Bark ◽  
Multidrug Resistant ◽  
Moderate Activity ◽  
Spectroscopic Techniques ◽  
Minimum Inhibitory Concentrations ◽  
Mdr Tb ◽  
Weak Activity ◽  
First Time ◽  
Chloroform Methanol

Zanthoxylum leprieurii Guill. and Perr. (Rutaceae) stem bark is used locally in Uganda for treating tuberculosis (TB) and cough-related infections. Lupeol (1), sesamin (2), trans-fagaramide (3), arnottianamide (4), ( S)-marmesinin (5), and hesperidin (6) were isolated from the chloroform/methanol (1:1) extract of Z. leprieurii stem bark. Their structures were elucidated using spectroscopic techniques and by comparison with literature data. Furthermore, the extract and isolated compounds were subjected to antimycobacterial activity. The extract exhibited moderate activity against the susceptible (H37Rv) TB strain, but weak activity against the multidrug resistant (MDR)-TB strain with minimum inhibitory concentrations (MICs) of 586.0 and 1172.0 μg/mL, respectively. Compound 3 (trans-fagaramide) showed significant antimycobacterial activity against the susceptible (H37Rv) TB strain (MIC 6 μg/mL), but moderate activity against the MDR-TB strain (MIC 12.2 μg/mL). Compounds 2, 5, 6, and 1 showed moderate activities against the susceptible (H37Rv) strain (MIC 12.2-98.0 μg/mL) and moderate to weak activities against the MDR-TB strain (MIC 24.4-195.0 μg/mL). This study reports for the first time the isolation of compounds 1 to 6 from the stem bark of Z leprieurii. trans-Fagaramide (3) may present a vital template in pursuit of novel and highly effective TB drugs.

scholarly journals Four Flavan-3-ol Compounds From The Stembark of Chisocheton balansae C.DC. (MELIACEAE)

Molekul ◽  
2021 ◽  
Vol 16 (1) ◽  
pp. 9
Author(s):  
Unang Supratman ◽  
Mohamad Fajar ◽  
Supriatno Salam ◽  
Rani Maharani ◽  
Desi Harneti ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
13C Nmr ◽  
Chemical Structure ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Endemic Plants ◽  
North Sulawesi ◽  
First Time

Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1), epicatechin (2), epigallocatechin-3-O-gallate (3), and epicatechin-3-O-gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods (1H-NMR, 13C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.

scholarly journals Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6626
Author(s):  
Edwin R. Sukandar ◽  
Sutin Kaennakam ◽  
Pia Raab ◽  
Xuehong Nöst ◽  
Kitiya Rassamee ◽  
...  
Keyword(s):  
2D Nmr ◽  
Stem Bark ◽  
No Production ◽  
Hep G2 ◽  
Pharmacological Studies ◽  
Ic50 Values ◽  
Hela S3 ◽  
Anti Inflammatory ◽  
First Time ◽  
Mcf 7

Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

scholarly journals Antialactone: A New γ-Lactone from Antiaris Africana, and its Absolute Configuration Determined from TDDFT CD Calculations

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Vouffo Bertin ◽  
Hidayat Hussain ◽  
Simeon F. Kouam ◽  
Etienne Dongo ◽  
Gennaro Pescitelli ◽  
...  
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Betulinic Acid ◽  
Spectroscopic Data ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Stem Bark ◽  
Cd Spectra ◽  
2D Nmr Spectra ◽  
First Time

Four compounds were isolated from the stem bark of Antiaris africana. One of them, a γ-lactone named antialactone (1a), is reported for the first time as a natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectra and EI MS data. The absolute configuration of antialactone acetate (1b) was established by TDDFT CD calculations and comparison with measured CD spectra. The remaining three known compounds were identified, by comparing their spectroscopic data with those reported in the literature, as lichenxanthone, β-sitosterol, and betulinic acid.

scholarly journals Biologically Active Secondary Metabolites from Asphodelus Microcarpus

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Mohammed M. Ghoneim ◽  
Guoyi Ma ◽  
Atef A. El-Hela ◽  
Abd-Elsalam I. Mohammad ◽  
Saeid Kottob ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Biologically Active ◽  
Naphthoic Acid ◽  
Bioassay Guided Fractionation ◽  
Resistant Strains ◽  
Asphodelus Microcarpus ◽  
First Time

Bioassay guided fractionation of the ethanolic extract of Asphodelus microcarpus Salzm.et Vivi (Asphodelaceae) resulted in the isolation of one new metabolite, 1,6-dimethoxy-3-methyl-2-naphthoic acid (1) as well as nine known compounds: asphodelin (2), chrysophanol (3), 8-methoxychrysophanol (4), emodin (5), 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (6), 10-(chrysophanol-7’-yl)-10-hydroxychrysophanol-9-anthrone (7), aloesaponol-III-8-methyl ether (8), ramosin (9) and aestivin (10). The compounds were identified by 1D and 2D NMR and HRESIMS. Compounds 3, 6 and 10 were isolated for the first time from this species. Compounds 3 and 4 showed moderate to weak antileishmanial activity with IC50 values of 14.3 and 35.1 μg/mL, respectively. Compound 4 exhibited moderate antifungal activity against Cryptococcus neoformans with an IC50 value of 15.0 μg/mL, while compounds 5, 7 and 10 showed good to potent activity against methicillin resistant Staphylococcus aureus (MRSA) with IC50 values of 6.6, 9.4 μg/mL and 1.4 μg/mL respectively. Compounds 5, 8 and 9 displayed good activity against S. aureus with IC50 values of 3.2, 7.3 and 8.5 μg/mL, respectively. Compounds 7 and 9 exhibited a potent cytotoxic activity against leukemia LH60 and K562 cell lines. Compound 10 showed potent antimalarial activities against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum with IC50 values in the range of 0.8-0.7 μg/mL without showing any cytotoxicity to mammalian cells.

scholarly journals Chemical Constituents of Cichorium intybus and their Inhibitory Effects against Urease and α-Chymotrypsin Enzymes

2011 ◽  
Vol 6 (8) ◽  
pp. 1934578X1100600
Author(s):  
Sumayya Saied ◽  
Shazia Shah ◽  
Zulfiqar Ali ◽  
Ajmal Khan ◽  
Bishnu P. Marasini ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
Cichorium Intybus ◽  
Spectroscopic Techniques ◽  
Inhibitory Effects ◽  
Isolation And Identification ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Hydroxyphenylacetic Acid ◽  
First Time

Phytochemical investigation of the aerial parts of Cichorium intybus L. resulted in the isolation and identification of two new natural metabolites, 2,6-di[but-3( E)-en-2-onyl]naphthalene (1), and 3,3′,4,4′-tetrahydroxychalcone (2), along with nine known compounds. Their structures were determined by spectroscopic techniques including 1D and 2D NMR. The known compounds were identified as scopoletin (3), 4-hydroxyphenylacetic acid (4), 3-hydroxy-4-methoxybenzoic acid (5), 4,4′-dihydroxychalcone (6), 6,7-dihydroxycoumarine (7), 1-triacontanol (8), lupeol (9), β-sitosterol (10), and β-sitosterol-3- O-β-glucopyranoside (11). Compounds 4-6 and 8 are reported for the first time from C. intybus. Compounds 2 and 3 showed weak inhibitory activities against urease and α-chymotrypsin enzymes, respectively.

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