Search

Cephalotaxus mannii Hook. f. is a rare evergreen conifer native listed in the International Union for Conservation of Nature (IUCN) Red List, which is utilized for leukemia treatment. Although endophytic fungi from C. mannii was reported before, their cytotoxic property has not been revealed yet. In the present study, a total of 7 endophytic fungi were isolated from C. mannii collected in Ha Giang province, Vietnam, among which the isolate WQF18 was active against 5 tested pathogens with inhibition zones ranging from 18.0 ± 0.7 to 25.0 ± 0.4 mm. In addition, only ethyl acetate extract of isolate WQF18 showed cytotoxicity on A549 and MCF7 cell lines with IC50 values of 69.6 ± 2.3 µg/mL and 78.6 ± 1.6 µg/mL, respectively. PCR-based molecular screening revealed that the positive hits for both 10-deacetylbaccatin III-10-O-acetyl transferase (dbat) and taxadiene synthase (ts) genes involved in paclitaxel biosynthesis were only observed in the WQF18 isolate. Based on morphological and molecular identification, the WQF18 isolate was identified as Talaromyces wortmannii WQF18. The presence of paclitaxel in T. wortmannii WQF18 was further confirmed by dbat sequence alignment, phenotypic, and HPLC-DAD analysis. To the best of our knowledge, this is the first report demonstrating the paclitaxel-producing capability of endophytic fungi from C. mannii. These findings provide a new platform for deciphering paclitaxel biosynthesis of endophytic fungi from non-Taxus plants and further paclitaxel production.

Cephalotaxus mannii Hook.f is a rare medicinal plant used for the treatment of leukemia, however, its fungal endophytes with antibacterial and anticancer properties have not been exploited yet. In this study, six fungal isolates were recovered from roots of C. mannii collected in Ha Giang province, Vietnam. Among them, ethyl acetate crude extract of strain WQF5 exhibited strong antibacterial activity against 5 tested pathogens with inhibition zones ranging from 13.0 ± 0.5 mm to 20.0 ± 0.4 mm. Sulforhodamine B assay showed that WQF5 extract possessed the most potent cytotoxic activity against lung cancer A549 and breast cancer MCF7 cell lines with IC50 values of 6.9 ± 0.7 µg/mL and 23.1 ± 1.9 µg/mL, respectively. PCR-based molecular marker screening revealed that the positive hits for essential genes encoding 10-deacetylbaccatin III-10-O-acetyltransferase (dbat) and C-13 phenylpropanoyl side chain-CoA acyltransferase (bapt) involved in paclitaxel production were found in the fungal isolate WQF5. In addition, isolate WQF5, identified as Fusarium fujikuroi by morphological and ITS analysis, also produced paclitaxel as shown by HPLC-DAD analysis. This is the first report of bioprospecting endophytic fungi isolated from C. mannii, in which the capability of producing paclitaxel of endophytic fungi was also proved for the first time. These findings addressed a potent candidate for paclitaxel production and provided excellent material for further investigations of how endophytic fungi from non-Taxus plant species synthesize paclitaxel.

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 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 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

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.

The tubers of Dioscorea persimilis have been widely consumed as a food and for the treatment of sonasthenia, intestinal disease, diarrhea, long-term dysentery, spermatorrhea, metritis, kidney failure, back pain, dizziness, and night sweats. The present study describes the isolation of 11 secondary metabolites, including three new phenanthrenes namely diospersimilosides A (1) and B (2) and diosbiphenanthrene (3), and eight known phenolic compounds: 2,4,6,7-tetrahydroxy-9,10-dihydrophenanthrene (4), aerosin (5), gastrodin (6), 2-phenylethyl-β- d -glucopyranoside (7), afzelechin (8), catechin (9), eucomic acid (10), and vanillic acid-4-O-β- d -glucopyranoside (11) from the tubers of D. persimilis. Their chemical structures were elucidated based on comprehensive analyses of the NMR and mass spectra. Evaluation of their cytotoxicity against three human cancer cell lines, including liver (HepG2), breast (MCF7), and melanoma (SK-Mel-2) revealed that the phenanthrene metabolites (3-5) possess cytotoxicity toward all the cell lines, with IC50 values ranging from 8.2–68.4 μM. Our results revealed that the free of the hydroxy groups plays an important role in cytotoxicity of the phenanthrenes and suggests that pohydroxylated dihydrophenanthrene and biphenanthrene metabolites could be considered as promising cytotoxic agents against human cancer cells.

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.

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.

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.

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.

Phytochemical investigation of a methanol extract of

Phytochemical investigation of the whole plants of

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.