A New Alkenylphenol from the Propolis of Stingless Bee Trigona minor

2018 ◽  
Vol 13 (1) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Hai Xuan Nguyen ◽  
Truong Nhat Van Do ◽  
Mai Thanh Thi Nguyen ◽  
Phu Hoang Dang ◽  
Le Huu Tho ◽  
...  

A new alkenylphenol, 2-hydroxyl-6-(14' Z -nonadecenyl)benzoic acid (1), was isolated from the ethanolic extract of Vietnamese stingless bee propolis Trigona minor (Meliponini, Apidae), together with two known compounds (2 and 3). Their chemical structures were determined by extensive NMR spectroscopic analysis. All compounds were tested for preferential cytotoxicity against the PANC-1 human pancreatic cell line under nutrition-deprived conditions (NDM). Compound 1 exhibited the strongest preferential cytotoxicity, with a PC50 value of 2.4 μM.

2020 ◽  
Vol 15 (7) ◽  
pp. 1934578X2094235
Author(s):  
Beom-Geun Jo ◽  
Sim-Kyu Bong ◽  
Jonghwan Jegal ◽  
Su-Nam Kim ◽  
Min Hye Yang

The current study was undertaken to isolate and identify anti-inflammatory and antiallergic active compounds in the ethyl acetate and butanol fractions of an ethanolic extract of the aerial parts of Stellera chamaejasme (SCAE). A new maltol glucoside, maltol 3-(6″-(2-( E)-butenoyl)-glucoside) and benzoic acid, daphnoretin (a coumarin), 6 flavonoids (apigenin, genkwanin, taxifolin, apigenin 7- O-glucoside, luteolin 7- O-sambubioside, genkwanin 5- O-glucoside), and 2 lignans (matairesinoside and lariciresinol) were isolated from SCAE by chromatographic separation. Their chemical structures were elucidated by analyzing spectroscopic data, including 1-dimensional and 2-dimensional nuclear magnetic resonance (Fig1). Maltol 3-(6″-(2-( E)-butenoyl)-glucoside) significantly inhibited β-hexosaminidase release by 85.5% in immunoglobulin E and dinitrophenyl/bovine serum albumin (DNP/BSA)-induced RBL-2H3 cells. Benzoic acid from S. chamaejasme inhibited β-hexosaminidase release (by 80.2%) in IgE and DNP/BSA-induced RBL-2H3 cells and interleukin-4 messenger ribonucleic acid expression (by 21.9% inhibition) in propidium iodide-induced RBL-2H3 cells.


Author(s):  
Hai Xuan Nguyen ◽  
Mai Thi Thanh Nguyen ◽  
Nhan Trung Nguyen

Propolis is a natural product produced by bees, and it is a mixture of resins and other bee excretions. The chemical composition of each type of propolis and its associated bioactivities also depend on the geographical regions, its food and the bee species. In Vietnam, propolis has been used in traditional medicine as the remedy to improve health and prevent diseases. From the ethanolic extract of the stingless bee propolis Trigona minor (Meliponini, Apidae), four lignan compounds were isolated. Their chemical structures were determined as (+)-isolariciresinol (1), 5-methoxy-(+)- isolariciresinol (2), (+)-lyoniresinol (3), and 6-(4- hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0] octan-2-one (4) by spectroscopic methods as well as comparing with data in the literature. Among them, compound 4 was the first isolated from natural sources, while others were isolated for the first time from this stingless bee propolis.


2001 ◽  
Vol 33 (1-2) ◽  
pp. 266-267 ◽  
Author(s):  
A Pileggi ◽  
P Cattan ◽  
T Berney ◽  
R.D Molano ◽  
C Vizzardelli ◽  
...  

2020 ◽  
Vol 16 ◽  
pp. 297-304 ◽  
Author(s):  
Amit Raj Sharma ◽  
Enjuro Harunari ◽  
Naoya Oku ◽  
Nobuyasu Matsuura ◽  
Agus Trianto ◽  
...  

A pair of geometrically isomeric unsaturated keto fatty acids, (6E,8Z)- and (6E,8E)-5-oxo-6,8-tetradecadienoic acids (1 and 2), were isolated from the culture broth of an actinomycete of the genus Micrococcus, which was associated with a stony coral, Catalaphyllia sp. Their chemical structures were elucidated by spectroscopic analysis including NMR and MS, with special assistance of spin system simulation studies for the assignment of an E geometry at C8 in 2. As metabolites of microbes, compounds 1 and 2 are unprecedented in terms of bearing a 2,4-dienone system. Both 1 and 2 showed antibacterial activity against the plant pathogen Rhizobium radiobacter and the fish pathogen Tenacibaculum maritimum, with a contrasting preference that 1 is more effective to the former strain while 2 is so to the latter. In addition, compounds 1 and 2 displayed agonistic activity against peroxisome proliferator-activated receptors (PPARs) with an isoform specificity towards PPARα and PPARγ.


Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4488
Author(s):  
Aboagye Kwarteng Dofuor ◽  
Temitayo Samson Ademolue ◽  
Cynthia Mmalebna Amisigo ◽  
Kwaku Kyeremeh ◽  
Theresa Manful Gwira

The search for novel antitrypanosomals and the investigation into their mode of action remain crucial due to the toxicity and resistance of commercially available antitrypanosomal drugs. In this study, two novel antitrypanosomals, tortodofuordioxamide (compound 2) and tortodofuorpyramide (compound 3), were chemically derived from the natural N-alkylamide tortozanthoxylamide (compound 1) through structural modification. The chemical structures of these compounds were confirmed through spectrometric and spectroscopic analysis, and their in vitro efficacy and possible mechanisms of action were, subsequently, investigated in Trypanosoma brucei (T. brucei), one of the causative species of African trypanosomiasis (AT). The novel compounds 2 and 3 displayed significant antitrypanosomal potencies in terms of half-maximal effective concentrations (EC50) and selectivity indices (SI) (compound 1, EC50 = 7.3 μM, SI = 29.5; compound 2, EC50 = 3.2 μM, SI = 91.3; compound 3, EC50 = 4.5 μM, SI = 69.9). Microscopic analysis indicated that at the EC50 values, the compounds resulted in the coiling and clumping of parasite subpopulations without significantly affecting the normal ratio of nuclei to kinetoplasts. In contrast to the animal antitrypanosomal drug diminazene, compounds 1, 2 and 3 exhibited antioxidant absorbance properties comparable to the standard antioxidant Trolox (Trolox, 0.11 A; diminazene, 0.50 A; compound 1, 0.10 A; compound 2, 0.09 A; compound 3, 0.11 A). The analysis of growth kinetics suggested that the compounds exhibited a relatively gradual but consistent growth inhibition of T. brucei at different concentrations. The results suggest that further pharmacological optimization of compounds 2 and 3 may facilitate their development into novel AT chemotherapy.


Author(s):  
Dung Thi Kim Le ◽  
Hao Xuan Bui ◽  
Tuyet Thi Anh Nguyen ◽  
Tuyen Nguyen Kim Pham ◽  
Huy Thuc Duong

Euphorbia tirucalli has not been chemically studied much in Vietnam. This research described the isolation and elucidation of compounds isolated from the plant collected in Binh Thuan. Multiple chromatographic methods were applied, including normal phase silica gel column chromatography and thin-layer chromatography. Seven compounds were isolated and their chemical structures were elucidated by spectroscopic analysis as well as comparing their data with the ones in the literature. They are arjunolic acid (1), eriodictyol (2), quercitrin (3), afzelin (4), scopoletin (5), 3,3′,4- trimethylellagic acid (6), and gallic acid (7). Among them, compound 1 a major component was isolated for the first time in Euphorbia genus, while three compounds 2, 4, and 5 were isolated from this species for the first time.


BMC Cancer ◽  
2018 ◽  
Vol 18 (1) ◽  
Author(s):  
Kate Butcher ◽  
Vinodh Kannappan ◽  
Rajagopal Sharada Kilari ◽  
Mark R. Morris ◽  
Christopher McConville ◽  
...  

2020 ◽  
Vol 21 (22) ◽  
pp. 8820
Author(s):  
Hae-Jun Yang ◽  
Bong-Seok Song ◽  
Bo-Woong Sim ◽  
Yena Jung ◽  
Unbin Chae ◽  
...  

In recent decades, many studies on the treatment and prevention of pancreatic cancer have been conducted. However, pancreatic cancer remains incurable, with a high mortality rate. Although mouse models have been widely used for preclinical pancreatic cancer research, these models have many differences from humans. Therefore, large animals may be more useful for the investigation of pancreatic cancer. Pigs have recently emerged as a new model of pancreatic cancer due to their similarities to humans, but no pig pancreatic cancer cell lines have been established for use in drug screening or analysis of tumor biology. Here, we established and characterized an immortalized miniature pig pancreatic cell line derived from primary pancreatic cells and pancreatic cancer-like cells expressing K-rasG12D regulated by the human PTF1A promoter. Using this immortalized cell line, we analyzed the gene expression and phenotypes associated with cancer cell characteristics. Notably, we found that acinar-to-ductal transition was caused by K-rasG12D in the cell line constructed from acinar cells. This may constitute a good research model for the analysis of acinar-to-ductal metaplasia in human pancreatic cancer.


2017 ◽  
Vol 12 (2) ◽  
pp. 1934578X1701200
Author(s):  
Thanh Tra Nguyen ◽  
Bich Ngan Truong ◽  
Huong Doan Thi Mai ◽  
Marc Litaudon ◽  
Van Hung Nguyen ◽  
...  

Three new compounds, hydnohainanic acid (1), and hydnohainanin A (2) and B (3) were isolated from the fruits of Hydnocarpus hainanensis (Achariaceae). Their structures were determined by spectroscopic analysis, including 2D NMR, and MS. Compounds 1-3 were evaluated for their cytotoxic activity against the KB cell line. Compound 1 had a moderate cytotoxicity with an IC50 value of 32.5 μg/mL, while the two remaining compounds did not exhibit inhibition, even at a concentration of 128 μg/mL.


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