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.

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.

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.

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.

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.

Sixteen sesquiterpenoids (1 – 16), including two new compounds namely saussucostusosides A and B (1 and 2), were isolated from the roots of Saussurea costus by various chromatographic separations. Their structures were elucidated by 1 D and 2 D NMR and HR-QTOF-MS experiments. Among isolated compounds, costunlide (6), 3β-[4-hydroxymethacryloyloxy]-8α-hydroxycostunolide (10) and 11β,13-dihydrozaluzanin C (16) exhibited potent inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 7.08 ± 0.34, 2.40 ± 0.06 and 5.55 ± 0.24 µM, respectively.

Phytochemical investigation of the whole plant of Scutellaria barbata resulted in the isolation of three new neo-clerodane diterpenoids, named scutebarbatolides A-C (1–3), along with six known analogues as 14-deoxy-11,12-didehydroandrographolide (4), scutehenanine H (5), 14β-hydroxyscutolide K (6), scutebata O (7), scutebartines H (8) and I (9). Their structures were elucidated by spectroscopic analyses, including 1D and 2D NMR and mass spectra in comparison with the data reported in the literature. Cytotoxicity of the isolates was evaluated toward five human cancer cell lines, including LNCaP, HepG2, KB, MCF7, and SK-Mel2 cells. Of the isolates, compounds 1 and 6 were shown to have moderate cytotoxicity toward all the cancer cell lines, with IC50 values ranging from 30.8 to 51.1 μM. Our results contribute to more insightful clarification of the use of S. barbata in the prevention and treatment of cancer.

Using various column chromatographic methods, 5 triterpene tetraglycosides (1−5), including one new compound, namely holothurin A6 (1), were obtained from the water soluble part of the methanol extract of the sea cucumber Stichopus herrmanni. Their structures were confirmed by careful analysis of the 1D and 2D NMR, and HR ESI QTOF mass spectra. Noteworthily, 24-dehydroechinoside A (3) showed potent cytotoxicity to 5 human cancer cell lines {HepG2 (hepatoma cancer), KB (epidermoid carcinoma), LNCaP (prostate cancer), MCF7 (breast cancer), and SK-Mel2 (melanoma)} with IC50 values ranging from 0.19 ± 0.03 to 1.17 ± 0.18 µM.

Using various chromatographic separations, three new acylated flavonoid glycosides, namely barringosides G–I (1–3), were isolated from the water-soluble extract of Barringtonia racemosa branches and leaves. The structure elucidation was performed by extensive analysis of the 1D and 2D NMR and HR-QTOF-MS data. Of the isolated compounds, barringoside I (3) showed moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells with an IC50 of 52.48 ± 1.04 µM.

Phytochemical investigation of the branches and leaves of Alchornea annamica led to isolation of ten secondary metabolites, including two new megastigmane glucosides alnamicosides A (1) and B (2). The structure elucidation was confirmed by 1 D and 2 D NMR, ECD as well as HR-QTOF-MS experiments. The megastigmane derivatives 1 − 3 exhibited inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 78.72 ± 1.90, 77.40 ± 9.40 and 82.16 ± 4.56 µM, respectively. This is the first report on chemical constituents and biological activity of the plant A. annamica.

Chemical investigation of the marine-derived endophytic fungus Ascomycota sp. VK12 resulted in isolation and identification of a new compound, (3R)-(3′,5′-dihydroxyphenyl)butan-2-one (1) and five known ones: AGI-7 (2), sescandelin (3), sescandelin-B (4), 4-hydroxybenzaldehyde (5), and hydroxysydonic acid (6). The absolute configuration of 1 was determined by time-dependent density functional theory electronic circular dichroism, specific optical rotation, and NMR calculations. Compounds 1 and 2 showed cytotoxicity towards HepG2, MCF-7, and SK-Mel2 carcinoma cells, with IC50 values ranging from 48.6 to 96.5 µM. Compounds 1, 2, 4–6 displayed NO inhibitory effects in LPS-stimulated BV2 cells, with IC50 values in a range from 24.2 to 76.5 µM. Compound 2 further inhibited PGE2 overproduction, with an IC50 value of 25.3 µM. The inhibitory effects of 2 towards NO and PGE2 overproduction were found to have a close relationship with its suppression of iNOS and COX-2 protein expression, respectively.

Three new crinane-type alkaloids, namely, 6-methoxyundulatine (1), 6-methoxycrinamidine (2), and undulatine N-oxide (3), along with the known compounds 6-hydroxyundulatine (4), 6-hydroxybuphanidrine (5), undulatine (6), crinamidine (7), ambelline (8), filifoline (9), augustamine (10), and perlolyrine (11), were isolated from the leaves of Crinum latifolium by using various chromatographic separations. Their structures were established by extensive analysis, including 1D and 2D NMR, HR-QTOF-MS, and CD data. Among the isolated compounds, perlolyrine (11) showed significant cytotoxicity against five human cancer cell lines, namely, KB, HepG2, MCF7, SK-Mel2, and LNCaP with the IC50 values ranging from 22.12 ± 2.80 to 28.45 ± 3.75 μM.

In our search for anti-inflammatory constituents from Vietnamese plants, the methanolic extract of Helicteres viscida was found to exhibit inhibitory effect on LPS-induced NO production in RAW264.7 cells. Phytochemical investigation of this plant led to isolation of four sulphated flavones (1���4), including one new compound 5,3���,4���-trihydroxy-7-methoxy-8-O-sulphate flavone (1), and two pregnane-type steroids (5 and 6), including one new compound 7-epi-heligenin B (5). Their structures were elucidated by 1D and 2D NMR as well as HR-QTOF-MS experiments. Among isolated compounds, heligenin B (6) exhibited potent inhibitory effect on LPS-induced NO production in RAW264.7 cells with IC50 of 1.23 �� 0.05 ��M. The activity of 6 was comparable to that of the positive control cardamonin.

Two new and three known polyhydroxysteroid glycosides were isolated from the MeOH extract of the starfish Acanthaster planci. The structures of the isolated compounds were elucidated using NMR and mass spectrometry. The new glycosides had the same aglycon, (24S)-24-methyl-5α-cholestane-3β,4β,6α,8,15β,16β,28-heptaol, and different carbohydrate fragments,2-O-methyl-β-D-xylopyranosyl-(1→2)-β-D-galactofuranose and 5-O-sulfo-α-L-arabinofuranose, bonded to the C-28 position of the 24-methylcholestane side chain.

Eight limonoids (1-8), including 1 new compound named as axillariol A (1), were isolated from the dichloromethane extract of Choerospondias axillaris branches and leaves using various chromatographic separations. Their structures were confirmed by detailed analysis of the 1-dimensional (1D), 2D nuclear magnetic resonance, and high-resolution electrospray ionization quadrupole time-of-flight mass spectra. In addition, toonaciliatins N (6) and toonaciliatins O (7) showed selective and significant cytotoxicity on the rhabdomyosarcoma human cancer cell line with half-maximal inhibitory concentration values of 9.12 and 7.79 µM, respectively.

Five polar steroid derivatives, including one new glycosylated polyhydroxysteroid namely polyacanthoside A (1), were isolated from the water-soluble materials from the MeOH extract of the Vietnamese starfish Astropecten polyacanthus using various chromatographic separations. The structure elucidation was confirmed by spectroscopic experiments such as HR-ESI-MS, 1D and 2D NMR. Among the isolated compounds, (20R,24S)-3β,6α,8,15β,24-pentahydroxy-5α-cholestane (3) showed significant cytotoxic effect against five human cancer cell lines as HepG2, KB, LNCaP, MCF7 and SK-Mel2 with the IC50 values from 18.03 ± 2.63 to 21.59 ± 3.23 μM.

Using various chromatographic separations, three triterpene tetraglycosides (1–3), including one new compound, namely stichorrenoside E (1) along with thelenotoside B (2) and deacetyl thelenotoside B (3), were isolated from the MeOH extract of the Vietnamese sea cucumber Stichopus horrens. Their structures were confirmed by spectroscopic experiments, such as 1D and 2D NMR and HR-ESI-MS. Deacetylated thelenotoside B (3) is firstly isolated as a natural product. Among these compounds, thelenotoside B (2) showed strong cytotoxicities against five human cancer cell lines as HepG2, KB, LNCaP, MCF7 and SK-Mel2 with the IC50 values from 0.95 ± 0.08 to 1.90 ± 0.13 μM, whereas stichorrenoside E (1) and deacetyl thelenotoside B (3) exhibited significant activities with the IC50 values from 6.87 ± 0.25 to 11.62 ± 1.05 μM.

A new endoperoxysesquiterpene lactone, 10α-hydroxy-1α,4α-endoperoxy-guaia-2-en-12,6α-olide ( 1 ), together with a flavanone, eriodictyol ( 2 ), and two flavone glycosides, acacetin-7- O -β- d -glucopyranoside ( 3 ) and acacetin-7- O -α- l -rhamopyranoside ( 4 ), were isolated from the methanol extract of Chrysanthemum morifolium flowers by a bioassay-guided fractionation. Compound 1 showed strong inhibitory effects against α-glucosidase and lipase activities, with IC 50 values of 229.3 and 161.0 μM, respectively. The flavone glycosides 3 and 4 inhibited both α-glucosidase and α-amylase, while flavanone 2 was only effective against α-amylase.

Six iridoid derivatives (1–6), including two new compounds myrmecodoides A and B (1 and 2), were isolated from the ant-plant Myrmecodia tuberosa. Their structures were determined on the basis of spectroscopic data (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY and HR-ESI-MS) and by comparison with the literature values. Among isolates, 3 and 4 exhibit weak antibacterial effect against Staphylococcus aureus subsp. aureus with MIC value of 100.0 μg/mL.

Phytochemical study of the ethanol extract of Sarcandra glabra resulted in the isolation of two new sesquiterpenes, glabranols A (1) and B (2). Their structures were elucidated as 8alpha,9alpha,15-trihydroxylinden-4,7(11)-dien-12,8beta-olide (1) and 1beta,4alpha,7beta,11-tetrahydroxyeudesmane (2), by spectroscopic methods including 1D- and 2D-NMR and FTICR-MS.