Showing papers by "Nhan Trung Nguyen published in 2016"

Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous

Abstract: Tyrosinase is an oxidoreductase that is very important in medicine and cosmetics because the excessive production of melanin causes hyperpigmentation. The development of novel, effective tyrosinase inhibitors has long been pursued. In preliminary tests, we found that an extract of the wood of Artocarpus heterophyllous (AH) potently inhibited tyrosinase activity. Two new flavonoids, artocaepin E (1) and artocaepin F (2), were isolated from the wood of AH, together with norartocarpetin (3), artocarpanone (4), liquiritigenin (5), steppogenin (6), and dihydromorin (7). Their structures were elucidated using one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry. The absolute configuration of 2 was determined from the circular dichroism (CD) spectrum. Artocarpanone (4) had the most potent tyrosinase inhibitory effect, with an IC50 of 2.0 ± 0.1 μM, followed by artocaepin E (1) and steppogenin (6), with IC50 values of 6.7 ± 0.8 and 7.5 ± 0.5 μM, respectively. A kinetic investigation indicated that 1 showed competitive inhibition, with an inhibition constant (K i) of 6.23 μM. These results demonstrate that extracts of the wood of AH and its phytochemical constituents are potential sources for skin-whitening agents. Graphical abstract Artocarmin E (1) and artocarmin F (2) were isolated from the wood of Artocarpus heterophyllous. Their structures were elucidated using nuclear magnetic resonance analysis and mass spectrometric methods

Chemical Constituents of Mangifera indica and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line

Abstract: Human pancreatic cancer cell lines such as PANC-1 have an altered metabolism, enabiling them to tolerate and survive under extreme conditions of nutrient starvation. The search for candidates that inhibit their viability during nutrition starvation represents a novel antiausterity strategy in anticancer drug discovery. A methanol extract of the bark of Mangifera indica was found to inhibit the survival of PANC-1 human pancreatic cancer cells preferentially under nutrient-deprived conditions with a PC50 value of 15.5 μg/mL, without apparent toxicity, in normal nutrient-rich conditions. Chemical investigation on this bioactive extract led to the isolation of 19 compounds (1–19), including two new cycloartane-type triterpenes, mangiferolate A (1) and mangiferolate B (2). The structures of 1 and 2 were determined by NMR spectroscopic analysis. Among the isolated compounds, mangiferolate B (2) and isoambolic acid (12) exhibited potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under...

Design and synthesis of chalcone derivatives as potential non-purine xanthine oxidase inhibitors.

Abstract: Based on some previous research, the chalcone derivatives exhibited potent xanthine oxidase inhibitory activity, e.g. sappanchalcone (7), with IC50 value of 3.9 μM, was isolated from Caesalpinia sappan. Therefore, objectives of this research are design and synthesis of 7 and other chalcone derivatives by Claisen–Schmidt condensation and then evaluate their XO inhibitory activity. Fifteen chalcone derivatives were synthesized by Claisen–Schmidt condensation, and were evaluated for XO inhibitory activity. Nine out of 15 synthetic chalcones showed inhibitory activity (3; 5–8; 10–13). Sappanchalcone derivatives (11) (IC50, 2.5 μM) and a novel chalcone (13) (IC50, 2.4 μM) displayed strong xanthine oxidase inhibitory activity that is comparable to allopurinol (IC50, 2.5 μM). The structure–activity relationship of these chalcone derivatives was also presented. It is the first research on synthesis sappanchalcone (7) by Claisen–Schmidt condensation. The overall yield of this procedure was 6.6 %, higher than that of reported procedure (4 %). Design, synthesis, and evaluation of chalcone derivatives were carried out. This result suggests that the chalcone derivative can be used as potential non-purine XO inhibitors.

α-Glucosidase inhibitors from the bark of Mangifera mekongensis

Abstract: Mangifera mekongensis (Anacardiaceae) is cultivated for its edible fruit and has been used in traditional Vietnamese medicine for its anti-aging properties and for treating diabetes, vermifuge, and dysentery. As part of a search for biologically active compounds with reduction of the rate of glucose absorption, a screening has been initiated to evaluate natural product extracts for the inhibition of enzyme α-glucosidase. A n-hexane extract of the bark of M. mekongensis showed strong α-glucosidase inhibitory activity with IC50 value of 1.71 µg/mL. Thus, the constituents of this plant were examined. Two new steroids named mekongsterol A (1) and mekongsterol B (2), were isolated from the n-hexane extract of the bark of M. mekongensis (Anacardiaceae), together with seven known compounds (3–9). Their chemical structures were elucidated on the basis of spectroscopic data. All compounds possessed significant α-glucosidase inhibitory activity in a concentration-dependent manner, except for 3 and 4. Compounds 1, 2, 5–9 showed more potent inhibitory activity, with IC50 values ranging from 1.2 to 112.0 µM, than that of a positive control acarbose (IC50, 214.5 µM). These results suggested that the traditional use of the bark of M. mekongensis for the treatment of diabetes diseases in Vietnam may be attributable to the α-glucosidase inhibitory activity of its steroid and cycloartane constituents.

Anti-cholinesterases and memory improving effects of Vietnamese Xylia xylocarpa

Abstract: Alzheimer’s disease (AD) is the most common cause of dementia among the elderly and is characterized by loss of memory and other cognitive functions. An increase in AChE (a key enzyme in the cholinergic nervous system) levels around β-amyloid plaques and neurofibrillary tangles is a common feature of AD neuropathology. Amnesic effects of scopolamine (acetylcholine receptor antagonist) can be investigated in various behavioral tests such as Morris water maze, object recognition, Y-maze, and passive avoidance. In the scope of this paper, we report the anti-AChE, anti-BChE properties of the isolated compound and the in vivo effects of the methanolic extract of Xylia xylocarpa (MEXX) on scopolamine-induced memory deficit. In further phytochemistry study, a new hopan-type triterpenoid, (3β)-hopan-3-ol-28,22-olide (1), together with twenty known compounds were isolated (2–21). Compound 1, 2, 4, 5, 7–9, and 11–13 exhibited potent acetylcholinesterase (AChE) inhibitory activity in a concentration-dependent manner with IC50 values ranging from 54.4 to 94.6 μM. Compound 13 was also shown anti-butyrylcholinesterase (BChE) activity with an IC50 value of 42.7 μM. The Morris water Y-maze, Y-maze, and object recognition test were also carried out. It is noteworthy that MEXX is effective when administered orally to mice, experimental results are consistent with the traditional use of this medicinal plant species.

A New Cassane-type Diterpene from the Seed of Caesalpinia sappan.

Abstract: Phytochemical investigation of the CH2Cl2 extract of the Vietnamese medicinal plant Caesalpinia sappan Linn resulted in the isolation of a new cassane-type diterpene named tomocin I (1). Its chemical structure was determined by NMR spectroscopic and mass spectrometric analysis.