Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
JJ Chen ◽  
JY Cho ◽  
TL Hwang ◽  
IS Chen
2020 ◽  
Vol 15 (3) ◽  
pp. 1934578X2091369
Author(s):  
Liangliang Yao ◽  
Suyou Zhu ◽  
Ziyi Hu ◽  
Lin Chen ◽  
Muhammad Farrukh Nisar ◽  
...  

Phytochemical investigation of fruits of Chaenomeles speciosa Lindley (Rosaceae) led to the isolation of 20 compounds including 5 flavonoids (1-5), 5 phenylpropanoids (6-10), 3 benzoic acid derivatives (11-13), 2 phloroglucinols (14 and 15), 2 purines (16 and 17), and 3 terpenoids (18–20). Their structures were elucidated by nuclear magnetic resonance analyses and from mass spectrometry data. These compounds were confirmed as catechin (1), epicatechin (2), catechin-5- O-β-d-glucoside (3), procyanidin B1 (4), quercetin-3- O-β-d-glucoside (5), p-coumaric acid (6), ferulic acid (7), caffeic alcohol (8), 1- O-p-coumaroyl-β-d-glucose (9), 1- O-cinnamoyl-β-d-glucose (10), p-hydroxybenzonic acid (11), protocatechuic acid (12), benzoic acid-β-d-gentiobioside (13), phloracetophenone 4′-glucoside (14), 3,5-dihydroxyphenyl β-d-glucopyranoside (15), adenine (16), adenosine (17), betulalbuside A (18), vomifoliol (19), and roseoside (20). Compounds 3-5, 8, 10, and 13-18 were isolated from the genus Chaenomeles and C. speciosa for the first time. Out of all these, compound 17 showed the best anti-inflammatory properties, comparable with those of the already known minocycline.


2007 ◽  
Vol 62 (5-6) ◽  
pp. 331-338 ◽  
Author(s):  
Amira M. Gamal-Eldeen ◽  
Pierre C. Djemgou ◽  
Marguérite Tchuendem ◽  
Bonaventure T. Ngadjui ◽  
Pierre Tane ◽  
...  

Phytochemical investigation of Cassia petersiana Bolle leaves afforded four new compounds, including two chromone derivatives, 7-acetonyl-5-hydroxy-2-methylchromone (petersinone 1, 1) and 7-(propan-2ʹ-ol-1ʹ-yl)-5-hydroxy-2-methylchromone (petersinone 2, 2), two benzoic acid derivatives, 5-methyl-3-(propan-2ʹ-on-1ʹ-yl) benzoic acid (petersinone 3, 3) and 5-(methoxymethyl)-3-(propan-2ʹ-ol-1ʹ-yl) benzoic acid (petersinone 4, 4), and glyceryl- 1-tetracosanoate (6), in addition to the known compound sistosterol-3-β-ᴅ-glycoside (5). The structures of these compounds were determined by comprehensive NMR studies, including DEPT, COSY, HMQC, HMBC, MS and IR.Compounds 1, 2, 5 and 6 were tested for antioxidant, anti-cancer and immunostimulatory properties. The biological investigations indicated that compound 6, among others, possessed the highest anti-cancer activity against hepatocellular carcinoma, immunoproliferative activity via induction of T-lymphocytes and macrophage proliferation, anti-inflammatory activity as indicated by NO inhibition, and antioxidant activity against DPPH radicals. Moreover, compound 5 was the most effective cytotoxic compound against breast carcinoma and stimulated a consistent immunoproliferative effect on lymphocytes and macrophages combined with strong NO inhibitory activity, while compound 1 was promising as immunoproliferative agent and may act as anti-inflammatory agent as a consequence of its NO inhibitory activity.


2008 ◽  
Vol 71 (1) ◽  
pp. 71-75 ◽  
Author(s):  
Jih-Jung Chen ◽  
Jui-Ying Cho ◽  
Tsong-Long Hwang ◽  
Ih-Sheng Chen

2019 ◽  
Author(s):  
K Georgousaki ◽  
N Tsafantakis ◽  
S Gumeni ◽  
V González-Menéndez ◽  
G Lambrinidis ◽  
...  

2019 ◽  
Vol 15 (2) ◽  
pp. 186-195 ◽  
Author(s):  
Samridhi Thakral ◽  
Vikramjeet Singh

Background: Postprandial hyperglycemia can be reduced by inhibiting major carbohydrate hydrolyzing enzymes, such as α-glucosidase and α-amylase which is an effective approach in both preventing and treating diabetes. Objective: The aim of this study was to synthesize a series of 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl] benzoic acid derivatives and evaluate α-glucosidase and α-amylase inhibitory activity along with molecular docking and in silico ADMET property analysis. Method: Chlorosulfonation of 2,4-dichloro benzoic acid followed by reaction with corresponding anilines/amines yielded 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic acid derivatives. For evaluating their antidiabetic potential α-glucosidase and α-amylase inhibitory assays were carried out. In silico molecular docking studies of these compounds were performed with respect to these enzymes and a computational study was also carried out to predict the drug-likeness and ADMET properties of the title compounds. Results: Compound 3c (2,4-dichloro-5-[(2-nitrophenyl)sulfamoyl]benzoic acid) was found to be highly active having 3 fold inhibitory potential against α-amylase and 5 times inhibitory activity against α-glucosidase in comparison to standard drug acarbose. Conclusion: Most of the synthesized compounds were highly potent or equipotent to standard drug acarbose for inhibitory potential against α-glucosidase and α-amylase enzyme and hence this may indicate their antidiabetic activity. The docking study revealed that these compounds interact with active site of enzyme through hydrogen bonding and different pi interactions.


2010 ◽  
Vol 9 (4) ◽  
pp. 198-204 ◽  
Author(s):  
Sadagopan Magesh ◽  
Nongluk Sriwilaijaroen ◽  
Vats Savita ◽  
Hiromune Ando ◽  
Taeko Miyagi ◽  
...  

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