Two New Benzoquinone Derivatives from Vietnamese Knema globularia Stems.

The chemical investigation of the stems of Knema globularia led to the isolation of two new benzoquinones derivatives, embenones A and B (1 and 2), along with three known compounds (3-5). The structures of the isolated compounds were determined using spectroscopic techniques, including HRESIMS, 1D and 2D NMR, in conjunction with comparison to existing literature data. Compounds 1 and 2 represent new carbon skeletons in nature. Furthermore, all isolated compounds were evaluated for their α-glucosidase inhibitory activity, with compounds 1-3 exhibiting superior potency relative to the positive control (acarbose, IC50 331 µM). Their IC50 values ranged from 1.40 to 96.1 µM.

A new 26-norlanostane from Phlogacanthus turgidus growing in Vietnam.

Chemical investigation on chloroform extract of Phlogacanthus turgidus led to the isolation of one new compound namely turgidol, together with five known triterpenoids, lupeol, lupenone, betulin, betulinic acid, and taraxerol. Their structures and stereochemistry have been determined by 1 D and 2 D NMR analysis, high resolution mass spectrometry, and compared with those in literatures. The relative configuration of turgidol was defined using DFT-NMR chemical shift calculations and subsequent DP4+ probability method. Turgidol, betulin, and betulinic acid were evaluated for cytotoxic activity toward K562 cancer cell line and the alpha-glucosidase inhibition.

Antimicrobial and alpha-glucosidase inhibitory flavonoid glycosides from the plant Mussaenda recurvata: in vitro and in silico approaches.

Seven flavonoid glycosides were isolated from the aerial portions of Mussaenda recurvata during a phytochemical analysis. This comprised one novel component, ecurvoside, and six well-studied compounds, namely astragalin, isoquercitrin, nicotiflorin, rutin, hesperidin, and neohesperidin. The chemical structures of compounds were identified using spectroscopic techniques and a comparison with previously published studies. Alpha-glucosidase inhibition testing was carried out on all isolated compounds. The compounds evaluated have IC50 values between 35.6 and 239.1 g mL-1, indicating a moderate degree of inhibition. In vitro antimicrobial activities of compounds 1-7 have screened against the bacteria Pseudomonas aeruginosa (P. aeruginosa), methicillin-resistant Staphylococcus aureus (MRSA), Streptococcus faecalis (Strep. faecalis), and fungi: Candida albicans (C. albicans), Trichophyton mentagrophytes (T. mentagrophytes), and Microsporum gypseum (M. gypseum), where compound 6 showed excellent activity against fungi T. mentagrophytes with an MIC value of 12.5 µM. In accordance with the molecular docking study, ecurvoside (1) or pose 472 interacted well with the 3TOP enzyme: PDB and the molecular dynamic simulations proved that the complex of ecurvoside and 3TOP has a stable simulation time of 50-100 ns and the significant residual amino acids in 3TOP are relative to interactions more than one time such as Asp 960, Glu 961, Lys 1088, Glu 1095, Arg 1097, Gly 1102, Thr 1103, Gln 1109, Glu 1178: A chain and Glu 1095, Thr 1101, and Asp 1107: B chain. The docking studies of compounds 1-7 to the enzyme 2VF5 explain the general mechanism to inhibit bacteria and proved that compound 6 (pose 370) inhibited stronger than compound 7 (pose 362) and compound 5 (pose 280), and compounds 1 to 4 do not interact well with 2VF5.

Correction: Antimicrobial and alpha-glucosidase inhibitory flavonoid glycosides from the plant Mussaenda recurvata: in vitro and in silico approaches.

[This corrects the article DOI: 10.1039/D4RA00666F.].

In vitro and in silico docking and molecular dynamic of antimicrobial activities, alpha-glucosidase, and anti-inflammatory activity of compounds from the aerial parts of Mussaenda saigonensis.

Twelve compounds were isolated from Mussaenda saigonensis aerial parts through phytochemical analysis and the genus Mussaenda is the first place where the compounds 4-6 and 11-12 have been found. Based on the ability to inhibit NO production in RAW264.7 cells, compound 2 has demonstrated the strongest anti-inflammatory activity in vitro with an IC50 of 7.6 µM, as opposed to L-NMMA's IC50 of 41.3 µM. Compound 12 was found to be the most effective inhibitor of alpha-glucosidase enzyme in vitro, with an IC50 value of 42.4 µM (compared to 168 µM for acarbose). Compounds 1-12 were evaluated in vitro for antimicrobial activity using the paper dish method. Compound 11 demonstrated strong antifungal activity against M. gypseum with a MIC value of 50 µM. In silico docking for antimicrobial activity, pose 90 or compound 11 docked well to the 2VF5 enzyme, PDB, which explains why compound 11 had the highest activity in vitro. Entry 2/pose 280 demonstrated excellent anti-inflammatory activity in silico. The stability of the complex between pose 280 and the 4WCU enzyme for anti-inflammatory activity has been assessed using molecular dynamics over a simulation course ranging from 0 to 100 ns. It has been found to be stable from 60 and 100 ns. The Tyr 159 (95%, H-bond via water bridge), Asp 318 (200%, multiple contacts), Met 273 (75%, hydrophobic interaction via water bridge), and Gln 369 (75%, H-bond via water bridge) interacted well within the time range of 0 to 100 ns. It has more hydrophilic or polar pharmacokinetics.

Green synthesis of silver nanoparticles using Nelumbo nucifera seed extract and its antibacterial activity.

Silver nanoparticles (AgNPs) were synthesized using a Nelumbo nucifera dry seed extract, which is a simple, non-toxic, eco-friendly "green material". The synthesized nanoparticles were confirmed by the color changes and characterized by UV-visible spectroscopy. The AgNPs were stable at room temperature for 2 months. Scanning electron microscopy (SEM) revealed the formation of well-dispersed and spherical shapes. Transmission electron microscopy (TEM) of the synthesized AgNPs showed the formation of spherical nanoparticles, 5.03-16.62 nm in size. Fourier transform infrared spectroscopy (FTIR) indicated the involvement of amine, aromatic and alkynes groups in the synthetic process. X-ray diffraction (XRD) confirmed the crystalline nature of AgNPs. These AgNPs were highly toxic to found to Gram negative bacteria.

Recurvataside, a new saponin from aerial parts of Mussaenda recurvata.

A new glycoside, recurvataside (1) and six known compounds, quinovic acid (2), quinovic acid 28-O-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosylquinovic acid (4), 3-O-ß-D-glucopyranosylquinovic acid 28-O-ß-D-glucopyranosyl ester (5), pomolic acid (6), and ursolic acid (7) were isolated from aerial parts of Mussaenda recurvata. The structure of compound 1 was identified from its spectroscopic data and by comparison with the literature. Recurvataside represents the first occurrence of δ-oleanolic acid saponin bearing two D-glucose units at C-3 and C-28 in nature. This is the first time δ-oleanane-type saponin reported in the genus Mussaenda. Compounds 1-7 were evaluated the cytotoxicity against two cancer cell lines MCF-7 and HepG2. Among them, only compound 7 exhibited moderate activity against MCF-7 and HepG2 cell lines with IC50 value of 16.97 ± 1.55 and 20.28 ± 1.00 µM, respectively. Compounds 1-7 were also tested for their inhibitory NO production in LPS-stimulated RAW264.7 cells. Compounds 3, 5, and 7 showed significant reduction of nitrite accumulation in LPS-stimulated RAW 264.7 cells with the IC50 values of 8.81 ± 0.48, 13.42 ± 0.84, and 18.37 ± 0.67 µM, respectively.

In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata.

Bioactive-guided investigation of the aerial parts of Mussaenda recurvata Naiki, Tagane, and Yahara (Rubiaceae) led to the isolation of four triterpenes, including two new triterpenes recurvatanes A and B (1 and 2), along with two known compounds 3ß,6ß,23-trihydroxyolean-12-en-28-oic acid (3) and 3ß,6ß,19α,23-tetrahydroxyolean-12-en-28-oic acid (4). The chemical structures of the compounds were identified from spectroscopic data and by comparison with the literature. A comprehensive review of NMR data of the oleanane-type triterpenes bearing 3-hydroxy and 4-hydroxymethylene groups indicated the characteristic spectroscopic features in this series. Compounds 1-4 were evaluated for the inhibitory NO production in LPS-stimulated RAW264.7 cells. Compounds 2 and 3 showed a moderate reduction of nitrite accumulation with IC50 values of 55.63 ± 2.52 and 60.08 ± 3.17 µM, respectively. Molecular docking model dedicated to compound 3 or pose 420, which is the best candidate among docking poses of compounds 1-4 interacted well with the crystal structure of enzyme 4WCU: PDB. The best ligand molecule, pose 420 in terms of binding energy obtained from docking studies on molecular dynamics (MD) simulations for 100 ns exhibited non-bonding interactions with the protein and remained stable inside the active site.

Nervione, a new benzofuran derivative from Nervilia concolor.

A new benzofuran derivative, nervione (1), was isolated from Nervilia concolor (Blume) Schltr. (Orchidaceae). Eight previously reported compounds were also isolated: 5,7-dimethoxyflavone (2), 3,5,7-trimethoxyflavone (3), 7-methoxyflavone (4), 3,7-dimethoxy-5-hydroxyflavone (5), tetramethylscutellarein (4',5,6,7-tetramethoxyflavone) (6), 5,7-dimethoxy-4'-hydroxyflavone (7), rhamnetin (8), and 5,7-dihydroxy-3',4'-dimethoxyflavone (9). The structures were elucidated by 1D, 2D NMR, and HRESIMS spectroscopy in addition to the literature. The relative configuration of 1 was defined using DP4+ probability while its absolute configuration was defined by comparison of the ECD spectrum of 1 with those of previously reported compounds. All isolated compounds were evaluated for alpha-glucosidase inhibition, revealing weak or no activity.[Formula: see text].

Cytotoxic activity and phytochemical composition of Stereospermum binhchauensis V.S. Dang leaves.

For the first time, the cytotoxic and phytochemical investigation of the leaves of Stereospermum binhchauensis V.S. Dang, a new species discovered in Viet Nam were finalized and led to purify nine compounds, including one furancoumarin (1), one chromone (3), two triterpenoids (2, 4), two flavonoids (5, 8), two flavanoids (6, 7) and one iridoid (9) using various chromatography methods. Their structures were verified by HR-ESI-MS, NMR experiments and compared with previous literatures. For the first time, compounds (5-8) were realized from the genus Stereospermum, while compounds (1, 2, 3, 4 & 9) were designated from the species S. binhchauensis. Furthermore, the furancoumarin, chromone and flavanoid classes were notified for the first time from the genus Stereospermum.

Synthesis, Docking Study, Cytotoxicity, Antioxidant, and Anti-microbial Activities of Novel 2,4-Disubstituted Thiazoles Based on Phenothiazine.

A series of novel 1,3-thiazole derivatives (5a-i) with a modified phenothiazine moiety were synthesized and tested against cancer cell line MCF-7 for their cytotoxicity. Most of them (5a-i) were less cytotoxic or had no activity against MCF-7 cancer cell line. MATERIAL AND METHODS: The IC50 value of compound (4) was 33.84 µM. The compounds (5a-i) were also evaluated for antimicrobial activities, but no significant activity was observed. The antioxidant activity was conducted for target compounds (5a-i). The IC50 value of compound (5b) was 0.151mM. RESULTS: The total amount of energy, ACE (atomic contact energy), energy of receptor (PDB: 5G5J), and ligand interaction of structure (4) were found to be 22.448 Kcal.mol-1 , -247.68, and -91.91 Kcal.mol-1, respectively. The structure (4) is well binded with the receptor because the values of binding energy, steric energy, and the number of hydrogen bondings are -91.91, 22.448 kcal.mol-1, and 2, respectively. It shows that structure (4) has good cytotoxicity with MCF-7 in vitro. CONCLUSION: The increasing of docking ability of structures (5a-i) with the receptor is presented in increasing order as (5f)>(5e)>(5g)>(5a)>(5b)>(5d)>(5c)>(5i)>(5h). The structure bearing substitution as thiosemicarbazone (4), nitrogen heterocyclic (5f), halogen (5e), and azide (5g) showed good cytotoxicity activity in vitro.

New cerebroside and chondrocyte proliferation activity of Caryota mitis L.

Caryota mitis L., a flowering plant, belongs to the family Arecaceae. In Vietnam, its fruits were used to treat joint pain. The present study was designed to investigate the phytochemicals and chondrocyte proliferation activity of C. mitis L. fruits on young human chondrocyte. The results showed that all of extracts (crude extract as well as n-hexane, chloroform, ethyl acetate and methanol fractions) were stimulated the growth of chondrocyte at 0.1 µg/mL; 0.01 µg/mL concentrations, of which the n-hexane and methanol fractions significantly increased the proliferation of chondrocyte by 30.75 and 24.42% at concentrations of 0.01 µg/mL, respectively. Repeated chromatography of the methanol fraction on silica gel, Sephadex LH-20 and ODS columns afforded a new cerebroside and eight known ones. Their structures were elucidated by analysis of spectral data and in comparison with the published reports.

A new benzofuran derivative from the leaves of Ficus pumila L.

A new benzofuran derivative, pumiloside (1), together with seven known flavonoid glycosides, afzelin (2), astragalin (3), quercitrin (4), isoquercitrin (5), kaempferol 3-O-rutinoside (6), rutin (7) and kaempferol 3-O-sophoroside (8) were isolated from the leaves of Ficus pumila. Their structures were established by spectroscopic data and comparison with the literature values.

A Study on Corrosion Inhibitor for Mild Steel in Ethanol Fuel Blend.

The main aim of this study is to investigate Aganonerion polymorphum leaf-ethyl acetate extract (APL-EAE) and its inhibiting effect for steel in ethanol fuel blend. The immersion test, electrochemical and surface analysis techniques were successfully carried out in this research. Scanning electron microscope images indicated that the ethanol fuel blend induced pitting corrosion of steel. Remarkably, the surface of the sample containing 1000 ppm APL-EAE is smoother than the others submerged in different conditions. The electrochemical impedance spectroscopy result shows that APL-EAE has formed a good protective layer, preventing corrosive factors from hitting the steel surface. The potentiodynamic polarization data argue that the corrosion inhibition efficiency was strengthened with the increase of APL-EAE concentration. The Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy demonstrated less intensity of Fe peaks, higher intensity of C1s peak and the appearance of organic peaks (N1s, P2p, O1s) from specimens with and without APL-EAE addition. Therefore, the results suggest the formation of the protective film on steel surface and affirm that APL-EAE has served as an effective corrosion inhibitor for steel in ethanol fuel blend.

New naphthalene derivative from the leaves of Cassia grandis L.

Cassia grandis is used for the treatment of skin disorders, back pain, aches, etc. in Vietnamese traditional medicine. In this paper, phytochemicals of the leaves were investigated. A new naphthalene derivative (1, cassgranon D) and, seven known compounds rutin (2), afzelin (3), quercitrin (4), epicatechin (5), (-)-epiafzelechin (6), isoquercitrin (7) and aloe emodin (8) were isolated from the ethyl acetate and methanol extracts. Their structures were elucidated by spectral evidences (UV, IR, MS, 1H, 13C, DEPT, HSQC and HMBC NMR), as well as by comparing with published data.

A new flavan from the Drynaria bonii H. Christ rhizomes.

In Vietnam, the medicinal plant Drynaria bonii H. Christ is used for the treatment of osteoporosis, bone fractures, and stimulate the growth of hair, treat tinnitus (Ho 2002; Loi 2004). In this article, experiments were designed to investigate the proliferation activity of ethanol, n-hexane, chloroform, ethyl acetate and methanol extracts from D. bonii rhizomes on MG-63 human osteoblast-like cells. The results showed that methanol and hexane extracts had the ability to proliferate MG-63 cells at the concentration varying from 0.1 to 0.01 µg/mL. In particular, at the concentration of 0.01 µg/mL, hexane and methanol extracts illustrated the highest proliferation ratio with 9.31% and 6.16%, respectively. By column chromatography, a new compound named drynaether A (1) and five known compounds uracil (2), 4'-hydroxy-7-methoxyflavan (3), kaempferol (4), indole-3-carboxylic acid (5) and protocatechuic acid (6) were isolated and identified from the methanol extract.

Chemical constituents from the leaves of Manglietia phuthoensis and their effects on osteoblastic MC3T3-E1 cells.

Two new phenyl glycosides, mangliesides A and B (1, 2), a new ionol glycoside, manglieside C (3), two new lignan glycosides, mangliesides D and E (4, 5), were isolated from the leaves of Manglietia phuthoensis, along with two known lignans, 3-methoxymagnolol (6) and obovatol (7). Their structures were established by means of 1D and 2D NMR, electrospray ionization (ESI)-MS and HR-ESI-MS experiments. Among them, compounds 2 and 5 significantly (p<0.05) increased the growth and differentiation of osteoblastic MC3T3-E1 cells in vitro.