New lupan-type triterpenoids

2016 ◽  
Vol 71 (11-12) ◽  
pp. 381-386 ◽  
Author(s):  
Pierre Mkounga ◽  
Hermine L.D. Maza ◽  
Blandine M.W. Ouahouo ◽  
Lydie N. Tyon ◽  
Hayato Ishikawa ◽  
...  
Keyword(s):  
Spectral Data ◽  
Manihot Esculenta ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Wide Range ◽  
New Compounds ◽  
Chemical Evidence

Abstract 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.

Synthesis and Antimicrobial Activity of Novel 1, 2, 4-Triazolopyrimidofuro- quinazolinones from Natural Furochromones (Visnagenone and Khellinone)

2020 ◽  
Vol 16 ◽  
Author(s):  
Ameen Ali Abu-Hashem ◽  
Hoda A. R. Hussein ◽  
Ahmed S. Aly
Keyword(s):  
2D Nmr ◽  
Antimicrobial Activities ◽  
New Drugs ◽  
Pharmacological Activities ◽  
Efficient System ◽  
Wide Range ◽  
Nmr Techniques ◽  
Analgesic Activities ◽  
New Compounds

Background: Previous and recent scientific research has shown that triazolopyrimidine and furochromones have a wide range of pharmacological activities in the treatment of numerous diseases, including anticancer, antiviral, anti-depressant, antimicrobial, anti-inflammatory, and analgesic activities. Objective: Preparation of new drugs used as antimicrobial activities derived from a natural furochromones as (1- hydrazinyl or methylthio),-furopyrimidoquinazolinone, 1, 2, 4-triazolopyrimidofuroquinazolin-5-one, and quinazolinepyrimidofuro- quinazoline-8, 10-dione and study of their biological activity as antimicrobial. Method: A series of novel N’-furopyrimidoquinazoline-hydrazide; 1, 2, 4-triazolopyrimidofuroquinazolin-5-one; furopyrimidoquinazolin-3-one and quinazoline-pyrimidofuroquinazoline-8, 10-dione derivatives were synthesized from substituted (methylthio)-furopyrimidoquinazolinone (3a-b) and 1-hydrazinyl-furopyrimidoquinazolinone (4a-b) as the starting material. Results: All compounds were synthesized in good yields (71-95%) in a gradually efficient system under the mild condition and some of the procedures were used a microwave oven. The new compounds have been confirmed by means of different spectroscopic ways such as IR, 1D and 2D -NMR techniques and mass spectrum. The in vitro to antimicrobial activities were evaluated for the prepared compounds using many types of bacteria (Gram positive and Gram negative) and fungi. Conclusion: 1, 2, 4-triazolopyrimidofuroquinazolin-5-one derivatives (10a-f, 8a-b, 7a-b and 6a-d) showed the most efficient antimicrobial activities compared with the cefotaxime sodium and nystatin as standard drugs.

scholarly journals Synthesis of thiourea derivatives bearing the benzo[b]thiophene nucleus as potential antimicrobial agents

2005 ◽  
Vol 70 (6) ◽  
pp. 807-815 ◽  
Author(s):  
K.M. Thakar ◽  
D.J. Paghdar ◽  
P.T. Chovatia ◽  
H.S. Joshi
Keyword(s):  
Spectral Data ◽  
1H Nmr ◽  
Antimicrobial Agents ◽  
Antimicrobial Activities ◽  
Mass Spectral Data ◽  
Thiourea Derivatives ◽  
Mass Spectral ◽  
New Compounds

The synthesis of a group of thiohydantoins and thiobarbiturates derived from 2-N-arylthiopyridocarbonyl-3,5-dichlorobenzo[b]thiophene is described. The structures of the new compounds are supported by IR, 1H-NMR and mass spectral data. These compounds were tested in vitro for their antimicrobial activities.

scholarly journals Flavonoid Glycosides and their p-Coumaroyl Esters from Campylospermum calanthum Leaves

2012 ◽  
Vol 67 (5-6) ◽  
pp. 233-243 ◽  
Author(s):  
Savio S. Elo Manga ◽  
Anastasie E. Tih ◽  
Bintou Abderamane ◽  
Raphael T. Ghogomu ◽  
Alain Blond ◽  
...  
Keyword(s):  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Methanol Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Flavonoid Aglycones ◽  
New Compounds ◽  
Related Compounds ◽  
Chemical Evidence

Six new compounds, comprising three flavonoid glycosides and their respective coumaroyl esters, have been isolated and characterized from the methanol extract of the leaves of Campylospermum calanthum, along with three known flavonoid aglycones, 7-O-methyl apigenin (1), 7-O-methyl luteolin (2), and 7-O-methyl quercetin (3). Their structures were elucidated based on chemical evidence as well as spectroscopic analysis including 1D and 2D NMR (1H-1H COSY, HSQC, HMBC, and NOESY) spectroscopy and by comparing their spectral data with those reported for related compounds

Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Srb Assay ◽  
Phenolic Metabolites ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

scholarly journals Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

scholarly journals Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

2021 ◽  
Author(s):  
Chang-An Geng ◽  
Zhen-Tao Deng ◽  
Qian Huang ◽  
Chun-Lei Xiang ◽  
Ji-Jun Chen
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Cell Protein ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
New Compounds

AbstractTen 3,5-dimethylcoumarins (1–6 and 8‒11) involving six new ones (1–6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro. Graphic Abstract

scholarly journals Four New Pterosins from Pteris cretica and Their Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2767
Author(s):  
Jian Lu ◽  
Caiying Peng ◽  
Shuang Cheng ◽  
Jianqun Liu ◽  
Qinge Ma ◽  
...  
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Pteris Cretica ◽  
Phytochemical Investigation ◽  
Hct 116 ◽  
Hct 116 Cells ◽  
New Compounds

Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 5–9. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively.

scholarly journals Antimicrobial Constituents from Leaves of Dolichandrone spathacea and Their Relevance to Traditional Use

2018 ◽  
Vol 5 (01) ◽  
pp. e14-e23 ◽  
Author(s):  
Phuc-Dam Nguyen ◽  
Amin Abedini ◽  
Sophie Gangloff ◽  
Catherine Lavaud
Keyword(s):  
Antibacterial Activity ◽  
Methanolic Extract ◽  
Iridoid Glycosides ◽  
Folk Medicine ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Traditional Use ◽  
Triterpenoid Saponins ◽  
Methoxycinnamic Acid ◽  
New Compounds

AbstractFive new compounds, three iridoid glycosides (1-3) and two triterpenoid saponins (4, 5), along with thirty-two known compounds were isolated from the methanolic extract of the leaves of Dolichandrone spathacea. This traditional medicinal plant is widely used in Asia and India as antiseptic, for bronchitis and thrush treatment, and the methanolic extract has been shown to possess antibacterial activity against methicillin-resistant Staphylococcus aureus. The new iridoids were esterified derivatives of 6-ajugol and 6-catalpol, and the new saponins were glucosides of two polyhydroxy triterpenes with ursan skeleton. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR experiments and HR-ESI-MS analysis, and from comparison with the literature. This study aimed at investigating extracts and isolated compounds for their antimicrobial activities against bacterial and yeast strains, in order to validate the uses of the plant in folk medicine. The 6-O-esterified iridoids had weaker antibacterial activity; verbascoside and p-methoxycinnamic acid, the major compounds of the methanol extract, possessed strong antibacterial activity, which could account for the traditional antiseptic and anti-infectious uses of the leaves of D. spathacea.

scholarly journals New Compounds from Leaves of Smallanthus sonchifolius

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400
Author(s):  
Xiang Zheng ◽  
Gai Kuo ◽  
Dou De-Qiang ◽  
Kang Ting-Guo ◽  
Shi Yu-Yuan ◽  
...  
Keyword(s):  
Benzyl Alcohol ◽  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Trienoic Acid ◽  
Octadecatrienoic Acid ◽  
Smallanthus Sonchifolius ◽  
New Compounds ◽  
First Time ◽  
Chemical Evidence

A new octadecatrienoic acid and a new benzyl glycoside, along with a known compound, were isolated from the leaves of Smallanthus sonchifolius. The structures of the two new compounds were elucidated as 13(R)-hydroxy-octadeca-(9E,11E,15Z)-trienoic acid (1) and benzyl alcohol 7-O-α-L-arabinopyranosyl(1″→2′)-β-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trienoic acid (3) by comparison of its spectral data with that reported. Compound 3 was isolated for the first time from the title plant.

scholarly journals Cichorins D–F: Three New Compounds from Cichorium intybus and Their Biological Effects

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4160
Author(s):  
Muhammad Farooq Khan ◽  
Fahd A. Nasr ◽  
Omar M. Noman ◽  
Nouf Abdulaziz Alyhya ◽  
Iftikhar Ali ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Cancer Cells ◽  
Breast Cancer Cells ◽  
Biological Effects ◽  
2D Nmr ◽  
Cichorium Intybus ◽  
Traditional Medicines ◽  
Wide Range ◽  
Sarcoma Cells ◽  
New Compounds

Cichorium intybus L., (chicory) is employed in various traditional medicines to treat a wide range of diseases and disorders. In the current investigation, two new naphthalane derivatives viz., cichorins D (1) and E (2), along with one new anthraquinone cichorin F (3), were isolated from Cichorium intybus. In addition, three previously reported compounds viz., β-sitosterol (4), β-sitosterol β-glucopyranoside (5), and stigmasterol (6) were also isolated from Cichorium intybus. Their structures were established via extensive spectroscopic data, including 1D (1H and 13C) and 2D NMR (COSY, HSQC and HMBC), and ESIMS. Cichorin E (2) has a weak cytotoxic effect on breast cancer cells (MDA-MB-468: IC50: 85.9 µM) and Ewing’s sarcoma cells (SK-N-MC: IC50: 71.1 µM); cichorin F (3) also illustrated weak cytotoxic effects on breast cancer cells (MDA-MB-468: IC50: 41.0 µM and MDA-MB-231: IC50: 45.6 µM), and SK-N-MC cells (IC50: 71.9 µM). Moreover compounds 1–3 did not show any promising anthelmintic effects.

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