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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 investigation of the whole plants of Lycopodiella cernua resulted in the isolation and identification of three new compounds (1–3), namely lycocernuaside E (1), lycernuic ketone F (2)...

Two new merosesquiterpenes, hippomeroterpenes A and B (1 and 2), and four known compounds langconol B (3), 20-demethoxy-20-methylaminodactyloquinone D (4), smenospongidine (5), and smenospongic acid (6) were isolated from the sponge Hippospongia fistulosa. Their structures were determined by extensive analyses of HR ESI MS and NMR spectral data. At concentration of 100 μM, compounds 1-6 exhibited weak cytotoxic effects on Hep-G2, MCF-7, SK-LU-1, and SK-Mel-2 human cancer cells with percentages of dead cells ranging from 8.3 ± 0.3%–36.3 ± 1.5 %.

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 glycosides, named as saurobaccioside A (1), saurobaccioside B (2), saurobaccioside C (3), together with five known magastigmanes, canangaionoside (4), (6S,9S)-roseoside (5), cucumegastigmane I (6), icariside B5 (7), linarionoside A (8) were isolated from the whole plant of Sauropus bacciformis (L.) Airy Shaw. Their structures were established by extensive spectroscopic analysis (UV, IR, HR-ESI-MS and NMR) and by comparison of the spectral data with those reported in the literature. The absolute configurations of compounds 2 and 3 were elucidated by experimental CD spectra. Compounds 1-8 were screened their cytotoxic activities towards CAL27 and MDAMB231 cancer cell lines. Compound 1 exhibited significant cytotoxic activity towards CAL27 and MDAMB231 cell lines with IC50 values of 3.21 ± 0.23 and 4.75 ± 0.17 µM, respectively, which were smaller than those of positive control capecitabine (IC50: 8.20 ± 0.75 and 5.20 ± 0.89 µM). Other compounds (2-8) were inactive.

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.

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.

Three new triterpene glycosides, mussapilosides A–C (1-3) together with six known triterpene glycosides, cincholic acid-28-O-β- d -glucopyranosyl ester (4), mussaendoside S (5), quinovic acid 28-O-β- d -glucopyranosyl ester (6), glycoside A (7), glycoside B (8), and quinovic acid 3-O-β- d -glucopyranosyl(1→2)-β- d -glucopyranoside (9) were isolated from the leaves of Mussaenda pilosissima. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR, and HR ESI MS spectra. All these compounds were examined for their inhibitory activity against PTP1B. The results indicated that compounds 2, 6, and 8 exhibited potent inhibitory effects with IC50 values of 3.4 ± 0.2, 4.2 ± 0.2, and 6.4 ± 0.2 μM, respectively. Compound 5 showed the moderate inhibitory effect with IC50 value of 63.0 ± 3.2 μM.

One new iridoid glycoside (1), shanzhiside N-L-phenylalanyl ester along with seven known compounds, mussaenoside (2), shanzhiside methyl ester (3), barlerin (4), mussaendodise G (5), mussaendodise U (6), mussaendodise P (7), and mussaglaoside B (8) have been isolated from Mussaenda pilosissima Valeton. Their chemical structures were elucidated by spectroscopic methods, 1 D-, 2 D-NMR, and mass spectra. Compounds 1-7 showed significant inhibitory activity on LPS-stimulated NO production in BV2 cells with the IC50 values ranging from 43.5 to 65.2 µM.

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.

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.

Polygala aureocauda Dunn. (Polygalaceae) has been widely used in Vietnamese traditional medicine for the treatment of hepatitis, nephritis, sonasthenia, anaemia, back pain, and knee fatigue. Chemical investigation of a methanol extract of P. aureocauda roots resulted in the isolation of four new oleanane triterpenoid saponins (polyaureosides A–D) and two known ones (polygalasaponin XLVIII and arilloside A). Their structures were elucidated by comprehensive spectroscopic methods, including 1D and 2D NMR and mass spectra. Among the isolates, arilloside A showed a modest anti-inflammatory effect through inhibiting NO overproduction in LPS-stimulated RAW264.7 macrophages, with an IC50 value of 47.4 μM.

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.

Chemical investigation of the marine-derived fungal isolate Penicillium sp. SF-5497 resulted in the isolation of two new preaustinoid-related meroterpenoids, named preaustinoid A6 (1) and preaustinoid A7 (2), along with three known metabolites (3–5). Their structures were elucidated by extensive spectroscopic analyses, such as 1D and 2D NMR and MS data. Among these, compounds 1 and 3 inhibited PTP1B activity in a dose-dependent manner, with IC50 values of 17.6 and 58.4 µM, respectively. Furthermore, kinetic analyses indicated that compound 1 inhibited PTP1B in a noncompetitive manner, with the Ki value of 17.0 µM.

Three new muurolane type sesquiterpene glycosides, named balanoindicosides A − C (1 − 3), were isolated from the whole plant of Balanophora fungosa subsp. indica using various chromatographic methods. Their structures were determined by extensive analysis of HR-ESI-MS and NMR spectroscopy. The stereochemistry of muurolane sesquiterpene backbone was demonstrated by NOESY analysis. Configuration of C-12 in compounds 2 and 3 could be distinguished by chemical shift value of C-14. Compounds 1-3 exhibited weak cytotoxic activity towards HepG-2, HL-60, LU-1, and MCF-7 cell lines.

Chemical investigation of the leaves and stems of Dioscorea bulbifera resulted in isolation of 10 compounds, including three new norclerodane diterpenoids, diosbulbiferins A (1) and B (2) and diosbulbiferinoside A (3), and one new natural congener, diosbulbiferin C (4), along with one new tetrahydrophenanthrene, diosbulbinone (8). Their structures were elucidated by comprehensive analyses of spectroscopic methods, including NMR and mass spectra. The absolute configurations of compounds 1-3 and 8 were deduced by time-dependent density functional theory (TD-DFT) electronic circular dichroism (ECD) spectroscopic analyses. In addition, cytotoxic effects against MCF-7, HepG2, and SK-Mel-2 cancer cells and in vitro anti-inflammatory effects of the isolated compounds in LPS-stimulated BV2 microglial cells were also reported.

A prenylated flavonoid, cudraflavanone B, is isolated from Cudrania tricuspidata. In this study, we investigated its anti-inflammatory and anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced RAW264.7 and BV2 cells. In our initial study of the anti-inflammatory effects of cudraflavanone B the production of nitric oxide and prostaglandin E2 was attenuated in LPS-stimulated RAW264.7 and BV2 cells. These inhibitory effects were related to the downregulation of inducible nitric oxide synthase and cyclooxygenase-2. In addition, cudraflavanone B suppressed the production of pro-inflammatory cytokines such as interleukin-6 and tumor necrosis factor-α in LPS-induced RAW264.7 and BV2 cells. Moreover, the evaluation of the molecular mechanisms underlying the anti-inflammatory effects of cudraflavanone B revealed that the compound attenuated the nuclear factor-kappa B signaling pathway in LPS-induced RAW264.7 and BV2 cells. In addition, cudraflavanone B inhibited the phosphorylation of extracellular signal-regulated kinase mitogen-activated protein kinase signaling pathways in these LPS-stimulated cells. Thus, cudraflavanone B suppressed nuclear factor-κB, and extracellular signal-regulated kinase mitogen-activated protein kinase mediated inflammatory pathways, demonstrating its potential in the treatment of neuroinflammatory conditions.

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.

A comprehensive phytochemical investigation of the dichloromethane-soluble fraction of Physalis angulata led to the isolation of eight compounds (1–8) including two new withanolides named physagulin P and Q (compounds 5 and 8). Their chemical structures were established using two-dimensional nuclear magnetic resonance (spectroscopy. The cytotoxic activity of these metabolites was investigated against A549, HeLa, and PANC-1 cancer cell lines. Among them, compound 1 showed significant cytotoxic activity against A549 cells with a half-maximal inhibitory concentration (IC50) value of 8.27 μM, while compound 7 showed the most potent activity against PANC-1 cells with an IC50 value of 3.18 μM.

Five new isomalabaricane analogues, named rhabdastrellins G - K (1–5), and three known compounds including jaspolide C (6), globostelletin C (7), and globostelletin D (8) were isolated from the sponge Rhabdastrella providentiae collected in the Eastern Sea of Vietnam. Their chemical structures were determined by HR-ESI-MS, NMR spectroscopy, experimental and calculated circular dichroism spectra. The isolated secondary metabolites were evaluated for their cytotoxicity toward HepG2, LU-1, MCF-7, HL-60, and SK-Mel2 human cancer cell lines. New isomalabaricane analogues 1-3 exhibited significant cytotoxicity with IC50 values ranging from 11.2 ± 1.4 to 84.8 ± 6.7 μM. Interestingly, the 20(22)Z stereoisomer (2) exhibited dramatic increase of cytotoxic activity in comparison with 20(22)E isomer (1).

Five new secondary metabolites, modiolides D-G (1−4) and 1-(2,5-dihydroxyphenyl)-3-methoxy-butan-1-one (8), one new natural product, 1-(2,5-dihydroxyphenyl)-3-hydroxybutan-1-one (7), along with three known compounds, modiolides A (5) and B (6), and 1-(2,5-dihydroxyphenyl)-2-buten-1-one (9) were isolated from a fermentation culture of the marine endophytic fungus Paraconiothyrium sp. VK-13. Their chemical structures were elucidated by the NMR and MS spectroscopic analysis as well as the modified Mosher’s method. Compounds 7 and 9 inhibited the overproduction of proinflammatory mediators NO and PGE2 in LPS-stimulated RAW264.7 cells, with IC50 values ranging from 3.9 to 12.5 µM. The inhibitory effects of 7 and 9 on the release of NO and PGE2 were correlated with their significant suppression of iNOS and COX-2 protein expression, respectively. Furthermore, both compounds 7 and 9 inhibited the mRNA expression of proinflammatory cytokines, including TNF-α, IL-1β, IL-6, and IL-12, with IC50 values in a range of 2.4−12.5 µM.

Context: Cudrania tricuspidata Bureau (Moraceae) is an important source of traditional Korean and Chinese medicines used to treat neuritis and inflammation. Objective: The anti-neuroinflammatory effects of cudraflavanone A isolated from a chloroform fraction of C. tricuspidata were investigated in LPS-induced BV2 cells. Materials and methods: Cudraflavanone A was isolated from the root of C. tricuspidata, and its structure was determined by MS and NMR data. Cytotoxicity of the compound was examined by MTT assay, indicating no cytotoxicity at 5–40 μM of cudraflavanone A. NO concentration was measured by the Griess reaction, and the levels of PGE2, cytokines and COX-2 enzyme activity were measured by each ELISA kit. The mRNA levels of cytokines were analysed by quantitative-PCR. The expression of iNOS, COX-2, HO-1, NF-κB, MAPKs and Nrf2 was detected by Western blot. Results: Cudraflavanone A had no major effect on cell viability at 40 μM indicating 91.5% viability. It reduced the production of NO (IC50 = 22.2 μM), PGE2 (IC50 = 20.6 μM), IL-1β (IC50 = 24.7 μM) and TNF-α (IC50 = 33.0 μM) in LPS-stimulated BV2 cells. It also suppressed iNOS protein, IL-1β and TNF-α mRNA expression. These effects were associated with the inactivation of NF-κB, JNK and p38 MAPK pathways. This compound mediated its anti-neuroinflammatory effects by inducing HO-1 protein expression via increased nuclear translocation of Nrf2. Discussion and conclusions: The present study suggests a potent effect of cudraflavanone A to prevent neuroinflammatory diseases. Further investigation is necessary to elucidate specific molecular mechanism of cudraflavanone A.

This study was performed to examine the anticancer and anti-metastatic effects of 4-parvifuran (PVN), a novel flavonoid isolated from the heartwood of Dalbergia odorifera, and to study its underlying signaling pathway in human osteosarcoma cells. In the present study, PVN was found to inhibit cell proliferation in a concentration- and time-dependent manner in the human osteosarcoma cell lines studied (MG-63 and U-2 OS) and induce apoptosis, as evidenced by Annexin V+ and TUNEL+ cells. Cleaved poly (ADP-ribose) polymerase (PARP) and caspase-3 were up-regulated while anti-apoptotic proteins including Bcl-2, Bcl-xL, and survivin were down-regulated after treatment with PVN. Matrigel cell migration assay, invasion assay, and soft agar assay were used to show that PVN effectively suppressed cell migration and invasion and colony formation in osteosarcoma cells. Protein and mRNA levels of MMP-2 and MMP-9 were reduced by PVN in a concentration-dependent manner. Furthermore, PVN inhibited Janus kinase 2 (JAK2)/signal transducers and activators of transcription 3 (STAT3), mitogen-activated protein kinases (MAPKs) including JNK, ERK, p38 kinase, and cAMP response element-binding protein (CREB). Therefore, this is the first study to demonstrate that PVN might be a novel anticancer and anti-metastatic agent for the treatment of osteosarcoma through the inhibition of JAK2/STAT3, MAPKs, and CREB signaling pathways.

Chemical investigation of an acidic methanol extract of the whole plants of Datura metel resulted in the isolation of two new guainane sesquiterpenes, 1β,5α,7β-guaiane-4β,10α,11-triol ( 1 ) and 1α,5α,7α-11-guaiene-2α,3β,4α,10α,13-pentaol ( 2 ), along with eight known compounds: pterodontriol B ( 3 ), disciferitriol ( 4 ), scopolamine ( 5 ), kaempferol 3- O -β- d -glucosyl(1 → 2)-β- d -galactoside 7- O -β- d -glucoside ( 6 ), kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-glucopyranoside-7-O-α-rhamnopyranoside ( 7 ), pinoresinol 4′′- O - β - d -glucopyranoside ( 8 ), (7 R ,8 S ,7′ S ,8′ R )-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxy-lignan-4- O -β- d -glucopyranoside ( 9 ), and (7 S ,8 R ,7′ S ,8′ S )-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4- O -β- d -glucopyranoside ( 10 ). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. Compounds 2 - 4 and 6 - 10 were shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.

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.

In our search for cytotoxic constituents from Vietnamese plants, the methanolic extract of Isotrema tadungense was found to exhibit significant cytotoxic effect. Subsequent phytochemical investigation of ethyl acetate fractions of this plant led to isolation of 11 compounds including one new arylbenzofuran rhamnoside namely aristolochiaside (1), two aristololactams (2 and 3), three lignanamides (4–6) and five phenolic amides (7–11). Their structures were elucidated by 1 D and 2 D NMR and HR-QTOF-MS experiments. Among the isolated compounds, aristolochiaside (1), aristolactam AIIIa (2) and N-trans-sinapoyltyramine (10) exhibited strong and selective cytotoxicity on the HeLa human cancer cell line with IC50 values of 7.59 ± 1.03, 8.51 ± 1.73 and 9.77 ± 1.25 μM, respectively.

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.

After the chemical investigation of the ethyl acetate extract of the marine-derived fungal strain Penicillium sp. SF-5629, the isolation and structural elucidation of eight secondary metabolites, including (3R,4S)-6,8-dihydroxy-3,4,7-trimethylisocoumarin (1), (3S,4S)-sclerotinin A (2), penicitrinone A (3), citrinin H1 (4), emodin (5), ω-hydroxyemodin (6), 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (7), and 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (8) were carried out. Evaluation of the anti-inflammatory activity of these metabolites showed that 4 inhibited nitric oxide and prostaglandin E2 production in lipopolysaccharide-stimulated BV2 microglia, with IC50 values of 8.1 ± 1.9 and 8.0 ± 2.8 μM, respectively. The inhibitory function of 4 was confirmed based on decreases in inducible nitric oxide synthesis and cyclooxygenase-2 gene expression. In addition, 4 was found to suppress the phosphorylation of inhibitor kappa B-α, interrupt the nuclear translocation of nuclear factor kappa B, and decrease the activation of p38 mitogen-activated protein kinase.

Two new naphtoquinones (smenocerones A and B, 1 and 2) and four known sesquiterpene cyclopentenones (dactylospongenones A-D, 3-6) were isolated from sponge Smenospongia cerebriformis living in the Eastern Sea of Vietnam. Their chemical structures were determined by high resolution electrospray ionization (HR-ESI)-MS, NMR spectroscopic analysis, and in comparison with the reported data. The chiroptical properties of compounds 3-6 were examined by experiment and theoretical calculation of circular dichroism (CD) spectra to prove their absolute configurations. Compound 2 significantly exhibited cytotoxic activity towards lung carcinoma (LU-1), hepatocellular carcinoma (HepG-2), promyelocytic leukemia (HL-60), breast carcinoma (MCF-7), and melanoma (SK-Mel-2) human cancer cells with IC50 values of 5.5±0.8, 3.2±0.2, 4.0±0.7, 4.1±0.8, and 5.7±1.1 µg/mL, respectively.

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.

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.

Although the heartwood of Dalbergia odorifera T. Chen (Leguminosae) is an important source of traditional Korean and Chinese medicines, the effects of novel compound methoxydalbergione (4-MD) isolated from Dalbergia odorifera was not reported. Herein, we investigated the effects of the 4-MD in vitro and in vivo against osteosarcoma cells and its molecular mechanisms. 4-MD inhibited the proliferation of osteosarcoma cells and induced apoptosis as evidenced by Annexin V + and TUNEL + cells. This apoptosis was accompanied by upregulation of apoptotic proteins (procaspase-3 and PARP), but downregulation of anti-apoptotic proteins (Bcl-2, Bcl-xL, and Survivin). 4-MD inhibited phosphorylation of JAK2 and STAT3 with the inactivation of mitogen-activated protein kinases (MAPKs) and CREB, and the upregulation of PTEN in osteosarcoma cells. Importantly, 4-MD reduced colony formation in soft agar and inhibited tumor growth in mice xenograft model in association with the reduced expression of PCNA, Ki67, p-STAT3, and Survivin. Taken together, the present study for the first time demonstrates that 4-MD exerts in vitro and in vivo anti-proliferative effects against osteosarcoma cells through the inhibition of the JAK2/STAT3 pathway, and suggest the potential for therapeutic application of 4-MD in the treatment of osteosarcoma.

Two new lignans (7S,7'R,8S,8'R)-3,3'-dimethoxy-7,7'-epoxylignan-4,4',9-triol 4-O-β-D-glucopyranoside (1) and 9-O-formylaviculin (2) together with other thirteen known secondary metabolites were isolated from the leaves of Antidesma hainanensis. Their chemical structures were determined using NMR, electrospray ionization (ESI)-MS, circular dichroism (CD) spectroscopic methods, and as well as by comparison with those reported in the literature. Neuro-inflammatory activity of isolated compounds was evaluated by their inhibition on nitric oxide (NO) production in activated BV2 microglial cells. At concentration of 40 µM, compounds 1-3, 5, 7, 8, 9, 14, and 15 exhibited inhibitory effects over 50%, suggesting that they could be potential candidate drugs for the cure of neuro-inflammation. In addition, compounds 1, 8, 14, and 15 significantly inhibited 16.23, 27.76, 21.23, and 29.44% NO production at diluted concentration as low as 2.5 µM.

A new stereoisomer Meso-araguspongine C together with nine reported macrocyclic bis-quinolizidine alkaloids araguspongines A, C, E, L, N−P, petrosin, and petrosin A were isolated from marine sponge Xestospongia muta. Stereochemistry of meso-araguspongine C (2) and araguspongines N-P (3−5) were established by their NMR data and conformational analyses. Both araguspongine C (1) and meso-araguspongine C (2) exhibited great cytotoxic activity towards HepG-2, HL-60, LU-1, MCF-7, and SK-Mel-2 human cancer cells (IC50 in the range of 0.43–1.02 μM). At a concentration of 20 μM, isolated compounds (1−10) also showed modest inhibitory effects (from 7.6 to 40.8%) on the NO production in LPS activated RAW264.7 macrophages.

Three new ent-kaurane diterpenoids, 7β,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7β,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-β-d-glucopyranoside ester (2), 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16β,17-dihydroxy-ent-kaurane (6), 16β,17-dihydroxy-ent-kauran-19-al (7), and 16β,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01±0.01μM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39±0.12μM and 0.32±0.04μM, respectively.

Two new meroterpenoid-type fungal metabolites, furanoaustinol (1) and 7-acetoxydehydroaustinol (2), were isolated from the ethyl acetate extract of a marine-derived fungal strain Penicillium sp. SF-5497, along with eight (3-10) known meroterpenoids. Their structures were elucidated mainly based on the analysis of their NMR (1D and 2D) and MS data. Particularly, the novel meroterpenoid, furanoaustinol (1), belonging to the austin group, was identified to possess an unprecedented hexacyclic ring system. Biological evaluation of these compounds revealed that furanoaustinol (1) weakly inhibited the activity of protein tyrosine phosphatase 1B in a dose-dependent manner with an IC50 value of 77.2 μM. In addition, 7-acetoxydehydroaustinol (2) and four other known meroterpenoids (5, 7, 9, and 10) weakly suppressed the overproduction of nitric oxide in lipopolysaccharide-challenged BV2 microglial cells with IC50 values of 61.0, 30.1, 58.3, 37.6, and 40.2 μM, respectively.

Korea Polar Research Institute, KORDI, Incheon 406-840, KoreaReceived March 3, 2014, Accepted April 14, 2014Chemical investigation on the methanol extract of the starfish Ctenodiscus crispatus resulted in the isolation offive steroids, (22E,24ξ)-26,27-bisnor-24-methyl-5α-cholest-22-en-3β,5,6β,15α,25-pentol 25-O-sulfate (1),(22E,24R,25R)-24-methyl-5α-cholest-22-en-3β,5,6β,15α,25,26-hexol 26-O-sulfate (2), (28R)-24-ethyl-5α-cholesta-3β,5,6β,8,15α,28,29-heptaol-24-sulfate ( 3), (25 S)-5α-cholestane-3β,5,6β,15α,16β,26-hexaol ( 4), andΔ7-sitosterol ( 5). Their structures were identified by extensive spectroscopic analyses, including 1D, 2D NMRand MS and chemical methods. Compound 4 showed cytotoxicity against human hepatoma HepG2 andglioblastoma U87MG cells via inhibition of cell growth and induction of apoptosis. Induction of apoptosis by4 was demonstrated by cell death, DNA fragmentation, increased Bax/Bcl-2 protein ratio and the activation ofcaspase-3, caspase-9 and poly (ADP-ribose) polymerase (PARP).Key Words : Starfish, Steroids, Ctenodiscus crispatus, Anti-proliferation, ApoptosisIntroductionMarine natural products are considered as a rich source ofbioactive substances with high structural diversity. Since thefirst researches on marine natural product reported in 1960s,over 20,000 natural products have been discovered frommarine organisms

Department of Pharmaceutical Engineering, Dongshin University, Naju 520-714, KoreaReceived March 12, 2014, Accepted March 28, 2014Key Words : Curcuma longa, Turmeric, Sesquiterpene, GermacraneCurcuma longa L. (Zingiberaceae), also known as turmeric,has been widely cultivated as a vegetable and spice in Southand Southeastern Asia. In traditional medicine, it has beenused extensively due to various beneficial properties, includ-ing anti-arthritic, reducing cholesterol level, and anti-inflam-mation.