Search

Using combined chromatographic methods, two new sesquiterpene glucosides, vulgarosides A (1) and B (2), and two known analogs ainsliaside E (3) and pumilaside A (4) were isolated from the aerial parts of Artemisia vulgaris. Their chemical structures were established by spectroscopic methods, including one and two-dimensional nuclear magnetic resonance (1 D and 2 D-NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). In addition, their cytotoxicity on five human cancer cell lines, including KB (epidermoid carcinoma), HepG2 (hepatocarcinoma), MCF7 (breast carcinoma), SK-Mel-2 (melanoma), and LNCaP (prostate cancer) was also evaluated by the SRB assay. However, none of the tested eudesmane sesquiterpene glycosides showed significant cytotoxicity (IC50>100 µM).

Phytochemical investigations of Senna tora seeds led to the isolation of fourteen phenolic glycosides, including three new compounds, namely, sennatorosides A–C (1–3). The chemical structures of the isolated compounds were confirmed by a detailed analysis of the 1D and 2D NMR, HR-ESI-QTOF mass, and ECD spectra. Among the isolated compounds, 1-[(1-( - d -glucopyranosyl)oxy-8-hydroxy-methoxynaphthalen)-6-yl]propan-2-one (11) exhibited strong cytotoxic activity against three tested cancer cell lines, SK-LU-1 (lung cancer), HepG2 (hepatoma cancer), and MCF-7 (breast cancer), with IC50 values of 8.05 ± 0.28, 9.52 ± 1.20, and 8.54 ± 0.85 μM, respectively, whereas compounds 1–4, 6–9, 12, and 14 revealed moderated or weak cytotoxicity, with IC50 values ranging from 44.59 ± 5.03–98.24 ± 2.45 μM.

In the present study, 10 secondary metabolites, including three new asperversilactones A–C (2, 4, and 5) and two new natural metabolites (4Z,6S,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone (1) and (4E,6S,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone (3) were isolated from a culture fermentation of the soybean-derived fungus Aspergillus versicolor IMBC-NMTP02. Their structures were elucidated by comprehensive analyses of spectroscopic methods, including NMR, mass, and ECD spectra. Compounds 5, 6, and 9 were shown to have cytotoxic effects toward the HepG2, KB, HL-60, MCF-7, SK-Mel-2, and LNCaP human cancer cell lines (IC50 = 31.7–81.5 μM), whereas all of the compounds inhibited NO overproduction in LPS-stimulated BV2 cells (IC50 = 19.0–41.9 μM). Furthermore, all of the compounds showed antimicrobial effects against Enterococcus faecalis and Candida albicans, with MIC values in the range of 32–256 μM. Our investigation contributes to clarification of the chemical constituents of the soybean-derived A. versicolor and warrants further studies of some bioactive metabolites for therapeutic uses.

Phytochemical investigations of Blumea balsamifera branches and leaves led to the isolation of ten secondary metabolites, including three new compounds, namely, balsamiferine K (1) and balsamiferosides A (2) and B (3). Structural elucidation was confirmed by detailed analysis of the 1D and 2D NMR spectra as well as HR-ESI-QTOF mass spectra. Among the isolated compounds, blumeaene J (4) exhibited moderate cytotoxicity against LNCaP (IC50 = 44.53 ± 4.95 μM) and SK-Mel2 (IC50 = 46.49 ± 3.84 μM) cell lines and weak effects on HepG2 (IC50 = 61.54 ± 2.98 μM), KB (IC50 = 65.40 ± 4.97 μM), and MCF-7 (IC50 = 70.06 ± 5.65 μM) cell lines, whereas (―)-angelicoidenol 2-O-β- d -glucopyranoside (6) revealed weak activity on all five tested cancer cell lines, with IC50 values ranging from 61.60 ± 5.64–98.73 ± 2.24 μM.

Three new glucosides, ziberthinosides A-C (1-3), and six known compounds, cleomiscosins A-D (4-7), sporogen AO-2 (8) and sapinofuranone A (9), were isolated from a methanol extract of

Two new megastigmane glucosides namely trewiosides A (1) and B (2), along with 20α-hydroxypregn-4-en-3-one β-D-glucopyranoside (3), sugeroside (4), and schizandriside (5) were isolated from the branches and leaves of Alchornea trewioides. The structure elucidation was confirmed by extensive analysis of the one and two dimensional (1 and 2D) NMR, electronic circular dichroism (ECD) as well as high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra. Noteworthily, the isolation of compounds 1 and 2 represents the second finding of megastigmane derivatives with a methoxycarbonyl group at C-5 to date. In addition, compound 3 showed weak cytotoxicity against three human cancer cell lines as A549 (lung carcinoma), HepG2 (hepatocarcinoma), and MCF7 (breast carcinoma). Besides, compounds 2 and 3 exhibited moderate inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells. Whereas, the remaining compounds 1, 4 and 5 showed weak inhibitory activity.

Chemical investigation of a peanut-associated fungal strain Aspergillus niger IMBC-NMTP01 resulted in isolation and identification of 14 secondary metabolites, including two new, epi-aspergillusol (1) and aspernigin (3), and 12 known compounds: pyrophen (2), 2-(hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid (4), aspergillusol A (5), rubrofusarin B (6), nigerasperone A (7), fonsecin (8), TMC-256C1 (9), pyranonigrin A (10), orlandin (11), nigerasperone C (12), asperpyrone A (13), and 5-(hydroxymethyl)-2-furancarboxylic acid (14). Compounds 9, 12-14 showed cytotoxicity toward all six human cancer cell lines, including HepG2, KB, HL-60, MCF-7, SK-Mel2, and LNCaP, with IC50 values ranging from 8.4 to 84.5 µM, compounds 3-5 were cytotoxic against five cancer cell lines except HepG2, whereas 1 exhibited cytotoxicity toward HepG2, KB, and MCF-7 cells. All of the compounds, except 2 and 13, inhibited NO overproduction in LPS-induced RAW264.7 cells. In addition, all of the compounds displayed antimicrobial effects against Enterococcus faecalis, whereas 13 compounds, except 10, significantly inhibited the growth of the yeast Candida albicans.

Two novel secoabietane diterpenoids, oroxindols A (1) and B (2), along with two known flavones oroxylin A (3) and hispidulin (4) were isolated from the stem bark of Oroxylum indicum. Their structures were elucidated by extensive analysis of the 1D and 2D NMR as well as HR-ESI-QTOF mass spectra. Noteworthily, the isolation of compounds 1 and 2 represents the first case of 11β,13;12,13-diepoxy-12,13-secoabietane-type diterpene obtaining reported to date. In addition, compound 3 exhibited significant inhibitory effects on nitric oxide (NO) production in LPS-stimulated BV2 microglial cell line, with an IC50 value of 21.5 ± 1.1 μM.

Phytochemical study of the Codonopsis javanica roots led to isolation of 12 secondary metabolites, including three new sesquiterpenoid glycosides, named codojavanosides A-C (1-3) and nine known compounds, (3R,6E,10S)-2,6,10-trimethyl-3-hydroxydodeca-6,11-diene-2,10-diol (4), (E)-2-hexenyl O-β- d -glucopyranoside (5), oct-1-en-3-ol O-α- l -arabinopyranosyl-(1′′→6′)-O-β- d -glucopyranoside (6), (Z)-3-hexenyl O-α- l -arabinopyranosyl-(1→6)-β- d -glucopyranoside (7), tangshenosides I (8) and II (9), tangshenosides V (10) and VI (11), and corchoionoside C (12). Their structures were identified by comprehensive analyses of the 1D and 2D NMR and mass spectra. Evaluation of their cytotoxic effects toward three human cancer cell lines, including lung (A549), liver (HepG2), and breast (MCF7) revealed that compounds 1, 2, 4 and 11 exhibit weak cytotoxicity toward the A549 cell line, with the induction of cell death ranging from 40.8–66.4 % at the concentration of 100 μM.

In the present study, 14 phenolic glycosides, including one new neolignan glycoside, iodescirrhoside A (1), three new flavonol glycosides, iodescirrhosides B-D (2-4), and 10 known metabolites were obtained from the methanol extract of Iodes cirrhosa leaves. Structural elucidation was performed by interpretating the 1D- and 2D- NMR, HR-ESI-MS, and CD spectra in comparison with literature data. All compounds were noncytotoxic to LU-1, HepG2, MCF-7, SK-Mel-2, and LNCaP cancer cell lines. Compound 11 significantly inhibited the growth of E. faecalis. In contrast, weak inhibition was observed for 1-9 and 14 against E. faecalis, for 1, 6-8, and 11 against S. aureus, for 6 and 13 against B. cereus, and 2, 4, and 6-9 against C. albicans.

Chemical investigation of the roots of Codonopsis javanica resulted in isolation of 12 compounds, including one new polyacetylene, codojavanyol (1), one new phenolic glycoside, codobenzyloside (7), and 10 known compounds, (2E,8E)-9-(tetrahydro-2H-pyran-2-yl)nona-2,8-diene-4,6-diyl-1-ol (2), lobetyol (3), lobetyolin (4), lobetyolinin (5), cordifolioidyne B (6), benzyl-α-L-arabinopyranosyl (1-6)-β-D-glucopyranoside (8), (Z)-8-β-D-glucopyranosyloxycinnamic acid (9), syringin (10), syringaresinol (11), and tryptophan (12). Their structures were elucidated by 1 D and 2 D NMR and MS spectroscopic analyses in comparison with the data reported in the literature. The stereochemistry of the C-2′ position of 1 was identified based on time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculation. Among the isolates, compounds 3-5 were shown to have weak cytotoxicity toward three human carcinoma cell lines, including lung (A549), liver (HepG2), and breast (MCF7), with the induction of 41.4 to 55.6% cell death at the concentration of 100 µM.

Using various chromatographic separations, five iridoid glucosides (1―5) and five phenylethanoid glycosides (6―10) were isolated from the Plantago major whole plants and included two new compounds: 10-acetylarborescoside (1) and plantainoside G (6). Their structures were elucidated by detailed analysis of 1D and 2D NMR data, HR QTOF MS data, and experimental and calculated ECD data. The isolated compounds exhibited moderate inhibitory effects on NO overproduction in LPS-stimulated BV2 microglial cells, with IC50 values ranging from 44.2–62.3 μM.

In this study, with the aim of determining and assessing the influence of several culture conditions on the ligninolytic enzyme (LiP, MnP, and Lac) activity of bacteria, five lignin-degrading bacteria strains were isolated from two different soil samples and cultured on minimum salt medium agar containing alkaline lignin (MSML agar). Among the five isolated strains, DL1 and X3 expressed strong and stable ligninase enzyme activity at various temperature levels (30°C, 37°C, 50°C, and 60°C) and were selected for further study. Notably, at 60°C, the ligninase activity of both strains lasted until the seventh day before decreasing. The effects of the culture medium conditions, namely, carbohydrate sources, nitrogen sources, and pH, on the ligninolytic system illustrated that both X3 and DL1 were able to generate good enzymatic activity at a pH range of 3.0 to 7.0. These strains could use various sources of carbohydrates and nitrogen, derived from glucose, lactose, peptone, meat extract, and yeast extract. In addition, the analyses of biochemical characteristics revealed that X3 was capable of hydrolyzing starch and cellulose, while DL1 was not. Therefore, the results of this study suggested the potential of applying selected lignin-degrading bacterial strains on lignin treatments of agricultural wastes.

A new rhamnofolane-type diterpenoid (1) and a new phenolic derivative (2), together with eleven known compounds, were isolated from the leaves of E. cochinchinensis Lour. The chemical structures of these compounds were elucidated based on extensive spectroscopic analysis, including HR-QTOF-MS and NMR, and comparison with reported data. The inhibitory effects of compounds 1–13 on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells were evaluated. As the obtained results, compound 9 showed a moderate inhibitory effects on NO production activity with an IC50 of 6.17 ± 0.25 µM, relative to that of the positive control cardamonin.

Chemical investigation of the aerial parts of Andrographis paniculata resulted in isolation of nine compounds, including a new ent-labdane diterpenoid, andrographic acid methyl ester (1), a new chalcone glucoside, pashanone glucoside (5), and seven known metabolites, andrograpanin (2), andrographolide (3), andropanolide (4), andrographidine A (6), andrographidine F (7), 6-epi-8-O-acetyl-harpagide (8), and curvifloruside F (9). Their chemical structures were elucidated based on comprehensive analyses of the spectroscopic data, including NMR and MS. Among the isolated compounds, andropanolide exerted cytotoxicity toward LNCaP, HepG2, KB, MCF7, and SK-Mel2 carcinoma cells, with IC50 values ranging from 31.8 to 45.9 µM. In addition, andropanolide significantly inhibited the overproduction of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with an IC50 value of 13.4 µM.

Using combined chromatographic methods, two new sesquiterpene glucosides, vulgarosides A (

Using combined chromatographic separation techniques, three new triterpenoids named lycomclavatols A-C (

Three new glucosides, ziberthinosides A–C (1–3), and six known compounds, cleomiscosins A–D (4–7), sporogen AO-2 (8) and sapinofuranone A (9), were isolated from a methanol extract of Durio zibethinus fruit peels. Their chemical structures were elucidated by analyses of their 1 D/2D NMR and HR-ESI-MS data as well as by comparison with the literature values. The absolute configuration of sporogen AO-2 (8) was confirmed by ECD calculation. Of the isolates, compounds 8 and 9 were cytotoxic toward all MCF7, HepG2 and SK-LU-1 cell lines, with IC50 values ranging from 10.7 to 34.9 μM. Our results contribute to better understanding of the chemical constituents of the high valued durian fruit and their pharmacological effect, such as cytotoxicity.

Phytochemical investigation of a methanol extract of Panax pseudoginseng flower buds resulted in the isolation of 22 dammarane-type triterpenoid saponins, including three new compounds, pseudoginsenosides A-C (1-3), and 19 known analogs. Their chemical structures were identified by the comprehensive spectroscopic methods, including 1 D and 2 D NMR and mass spectra. In addition, their cytotoxic effects toward three human carcinoma cell lines, including liver (HepG2), breast (MCF7), and lung (A549) were also evaluated.

Two new phenolic glycosides, oroxylumosides A (1) and B (2), along with four known compounds darendoside A (3), leucosceptoside A (4), acteoside (5) and decaffeoylacteoside (6) were isolated from the stem bark of Oroxylum indicum. Their structures were elucidated by extensive analysis of the 1 D and 2 D NMR as well as HR-ESI-QTOF-MS. In addition, compounds 1 − 4 exhibited inhibitory effects on NO production in LPS-stimulated BV2 microglial cell line with IC50 values of 58.2 ± 2.9, 70.6 ± 3.5, 56.8 ± 2.8 and 61.1 ± 3.1 µM, respectively.

Four pregnane-type steroids including the new compound 5-α-pregn-20-en-3,6-dione (1) and two known cholestane-type steroids were isolated from the MeOH extract of the octocoral Dendronephthya mucronata. The structures of the compounds were elucidated using spectral data (PMR and 13C NMR, HSQC, HMBC, 1H−1H COSY, NOESY, HR-QTOF-MS) and comparisons with previously published information. The steroids exhibited moderate or weak inhibitory effects on inflammatory lipopolysaccharide-induced NO formation in RAW264.7 murine macrophage cells.

Phytochemical investigation of a methanol extract of

Chemical investigation of the roots of