Search

Twelve new compounds, aspergorakhins A–L (1–12) coupled with one known xanthone leptosphaerin D (13), were isolated from the extract of soil-derived fungus Aspergillus gorakhpurensis F07ZB1707. Their structures were elucidated by spectroscopic data analysis including UV, IR, NMR, and HRESIMS. The absolute configurations of 5 and 8–11 were identified using ECD and OR calculations. All compounds were tested by enzyme inhibitory activity assay in vitro. Aspergorakhin A (1) showed selective activities against PTP1B and SHP1 over TCPTP with IC50 values 0.57, 1.19, and 22.97 μM, respectively. Compounds 1 and 2 exhibited modest cytotoxicity against tumor cell lines A549, HeLa, Bel-7402, and SMMC-7721 with IC50 values in the range of 6.75–83.4 μM.

Seven undescribed sesquiterpene lactone dimers (SLDs) (carpeabrodilactones A-G), one known SLD, and six known sesquiterpenes were isolated from the fruit of Carpesium abrotanoides L. Carpeabrodilactone A was a dimeric carabrane featuring a rare C-13-C-13' linkage. Carpeabrodilactones B and C are the first two SLDs to be described possessing a carabranolide unit and a guaianolide unit connected by an O-ether linkage. The structures of the SLDs were assigned based on HRESIMS, NMR analysis

The genus Saussurea (Asteraceae) contains about 400 species distributed around Asia and Europe and used in the traditional medicines of many cultures. The main compounds isolated from Saussurea species are terpenoids, in particular, sesquiterpenoids are dominant. This review lists 404 chemical constituents as well as their biological activity (111 references).

Two tetranortriterpenoids with new skeletons, xylomexicanins I and J (1 and 2), were isolated during the investigation of chemical constituents from seeds of the Chinese mangrove, Xylocarpus granatum. Xylomexicanin I (1) is an unprecedented limonoid with bridged B- and C-rings. A biosynthesis pathway for 1 from xylomexicanin F is proposed.

The genus Ajuga, a member of the Lamiaceae family, is comprised of more than 300 species of annual and perennial herbaceous flowering plants mainly distributed throughout the temperate regions of Asia, Europe, Australia, North America and Africa. These plants are used as folk medicines effective for rheumatic fevers, dysentery, malaria, hypertension, diabetes and gastrointestinal disorders, as well as anthelmintic, astringent, febrifuge diuretic, antifungal and anti-inflammatory agents. A variety of constituents has been isolated from these plants. This review summarizes the phytochemical progress of the genus Ajuga and lists the compounds isolated up to 2014.

The marine mangrove Xylocarpus granatum is used as a folk medicine and is rich in bioactive limonoids. The quantitative determination of the chemical composition and distribution of limonoids in different parts of X. granatum fruit (fruit peel, seed coat, seed kernels, seed, and fruit) is significant for authentication and quality control purposes. However, the quantitative determination of limonoids in X. granatum has not yet been reported. In this study, a chemometric-assisted liquid chromatography–tandem mass spectrometry (LC–MS/MS) method was developed and validated for the simultaneous determination of 17 limonoids to reveal the chemical composition and distribution in different parts of X. granatum fruit. Ultrasonic-assisted extraction, optimized by response surface methodology (RSM), was more accurate than the general one-variable-at-a-time method. The overall distribution of 17 limonoids in different parts of X. granatum fruit had the following order: seed kernels > seed > fruit, and 13 limonoids showed a rank order of seed kernels > seed > fruit > fruit peel > seed coat. Furthermore, principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) were used to analyze the LC–MS/MS data and provide a chemometric model for easy visualization and interpretation to classify the different parts of X. granatum fruit. In addition, the study indicated that the chemometric-assisted strategy, consisting of RSM, PCA, and OPLS-DA for the development, optimization, and data analysis of multicomponent quantitation by LC–MS/MS, is effective and feasible. This study provided the chemical composition and distribution evidence for the authentication and quality control of X. granatum fruit.

Six known quassinoids were isolated from the bark of Ailanthus altissima. Their structures were elucidated by spectroscopic methods. Compounds 1–6 were screened for their antitumor activities evaluated by MTT assay.

Alantolactone (AL), an active sesquiterpene originating from Inula helenium, is a potential anticancer and anti-inflammatory agent. However so far, studies on AL metabolism have not been reported. In the present study, we have investigated for the first time the in vivo and in vitro metabolites of AL using ultra performance liquid chromatography combined with time of flight mass spectrometry (UPLC-TOF-MS/MS). A unique on-line information-dependent acquisition (IDA) method multiple mass defect filter (MMDF) combined with dynamic background subtraction (DBS) was applied to trace all of the probable metabolites of AL. Five MMDF templates were set according to the core structure of AL and the general metabolite biotransformation patterns, and other five sulfur-containing dimer filter templates were first established on the basis of structural elucidation of AL metabolites obtained from rat intestinal bacteria biotransformation. As a result, 44 metabolites were characterized: 41 metabolites from rat urine, bile and feces after oral administration of AL, and 13 metabolites from AL biotransformation by rat intestinal bacteria. Particularly, 26 metabolites were identified as novel sulfur-containing products. The results indicated that addition of double bond at Δ((11,13)) and oxidization were the main metabolic reactions of AL. A new metabolism pathway to produce addition products of H2S to AL and further generate a series of sulfur-containing dimers of AL was revealed. This study significantly enriched our knowledge about AL metabolism, which will lead to a better understanding of the safety and efficacy of AL. At the same time, the established methodology can be widely applied for the structural determination of the metabolites of other sesquiterpene containing α-methylene-γ-lactone moiety.

A new limonoid, named granaxylocartin A (1), was isolated from the seeds of Xylocarpus granatum, and the structure was elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H–1H COSY, HSQC, HMBC, and NOESY).

Vincristine sulfate (VCR), a commonly used chemotherapeutic agent, kills cancer cells as well as the normal cells for its cytotoxicity. But it is still unclear whether it can exert therapeutic effect on untreated cancer cells by changing the supernatant of cancer cells. Here, we explored the subsequent cascade effects of the supernatant of cancer cells that were transiently treated with VCR on untreated tumor cells and its responsible mechanisms. VCR and three different hepatocellular carcinoma (HCC) cell lines were used for an experiment. The experiment was conducted in vitro to eliminate the body's internal factors and the effects of the immune system. The results suggested that drug-free tumor supernatant (TSN) could promote the differentiation, repress the transcription of liver cancer stem cell's markers and the proliferation in SMMC-7721, Bel-7402 and Huh7 cells. Furthermore, we found that the TSN could abolish YAP1 transcriptional activity to inhibit the proliferation and increase the transcriptional activity of HNF4α to promote the differentiation in SMMC-7721 and Bel-7402 cells. In conclusion, the TSN could inhibit the proliferation and induce differentiation in different HCC cells.

The Chloranthaceae is a small family with only four genera (Ascarina, Chloranthus, Hedyosmum, Sarcandra), of which nearly 70 species are distributed around the world. Chemical constituents in Chloranthaceae plants, especially sesquiterpenes, have attracted a great deal of attention in recent 5 years. Many characteristic constituents of this family may be responsible for anti-microbial, anti-tumor and other activities. In order to provide information for the future research, the structures and biological activities of the known constituents from the plants of Chloranthaceae have been reviewed in this article.

A novel, simple and efficient sample preparation procedure was established for the fast extraction and preconcentration of six trace components, daphnetin, scopoletin, umbelliferone, daphnoretin, isopimpinellin and ebracteolata compound B, in a traditional Chinese drug Langdu preparation using a combination of microwave-assisted extraction (MAE) and ionic liquid-based dispersive liquid–liquid microextraction (IL-based DLLME) coupled with high-performance liquid chromatography (HPLC). Several important parameters affecting extraction performance, such as microwave power, temperature and irradiation time; type and volume of extraction solvent; type and volume of dispersion solvent; centrifugation speed and time; pH of sample solution and salt concentration, were evaluated. Under optimal experimental conditions, the method exhibited a good performance in terms of linearity with correlation coefficients over 0.9993 and limits of detection (LODs) within the range 0.28–0.56 ng mL−1. The present method was applied to determine the above six analytes in a Langdu preparation named the ‘Jieheling’ tablet and the extraction recoveries obtained were in the range of 80.1–92.9%. The results indicated that the proposed method is an accurate, rapid and reliable technique, which gives excellent enrichment factors (EFs) and LODs for the extraction and preconcentration of trace analytes from a complex matrix.

Eupatorium (family: Compositae), which comprises nearly 1200 species, is distributed throughout tropical America, Europe, Africa, and Asia. Up to now, the reported constituents from the genus Eupatorium involve flavonoids, terpenoids, pyrrolizidine alkaloids, phenylpropanoids, quinonoids, essential oils, and some others, altogether more than 300 compounds. Studies have shown that Eupatorium and its active principles possess a wide range of pharmacological activities, such as cytotoxic, antifungal, insecticidal, antibacterial, anti-inflammatory, and antinociceptive activities. Currently, effective monomeric compounds or active parts have been screened for pharmacological activities from Eupatorium in vivo and in vitro. Increasing amount of data supports application and exploitation for new drug development.

Two minor taxane glycosides were isolated for the first time from the needles of Taxus canadensis. Their structures were characterized as 2α,5α-diacetoxy-10β-(6′-O-acetyl-β-d-glucopyranosyl)oxy-14β-[(2′R,3′S)-3′-hydroxy-2′-methylbutanoyl]oxytaxa-4(20),11-diene (1) and 2α,14β-diacetoxy-10β-(β-d-glucopyranosyl)oxytaxa-4(20),11-dien-5β-ol (2) on the basis of 1D and 2D NMR data analysis and confirmed by high-resolution fast atom bombardment mass spectrometry.

Ailanthone is isolated from the bark of Ailanthus altissima (Mill.) Swingle (Simaroubaceae). The mechanism that underlies the activity of ailanthone on MCF-7 cells was investigated by MTT assay. Breast cancer MCF-7 cells were treated with 0.5, 1.0, 2.0, 4.0 and 8.0 µg/ml ailanthone for 24, 48 and 72 h. The inhibition of proliferation induced by treatment with ailanthone was assessed by MTT assay. Apoptosis and cell cycle distribution in MCF-7 cells with the same doses of ailanthone for 48 h were determined by flow cytometry. Expression of apoptosis-associated genes and proteins were analyzed by reverse transcription-polymerase chain reaction (RT-PCR) and western blot analysis, respectively. The results revealed that ailanthone inhibited MCF-7 cell proliferation. Flow cytometry assay demonstrated that ailanthone induced apoptosis and G0/G1 cell cycle arrest in MCF-7 cells. Western blotting and RT-PCR assays demonstrated that upregulation of pro-apoptotic caspase-3 and Bcl-associated X, and downregulation of anti-apoptotic apoptosis regulator B-cell lymphoma-2 in MCF-7 cells may be associated with the induction of apoptosis and inhibition of proliferation. To the best of our knowledge, the present study is the first to investigate the antitumor activity of ailanthone from A. altissima on MCF-7 cells and to attempt to elucidate the underlying mechanism. The present study revealed the presence of ailanthone-mediated antitumor effects, indicating that ailanthone may be a novel phytomedicine with potential use in breast cancer therapy.

Two new eudesmanolides, 3β-acetoxy-1β,4α-dihydroxy-11αH-eudesman-12,6α-olide (1) and 3β-acetoxy-1β-hydroxy-11αH-eudesman-4(15)-en-12,6α-olide (2), were isolated from the flowers of Achillea millefolium, their structures were established on the basis of spectral analysis.

Six previously reported taxanes with alkaloid side chains were isolated from the methanol extract of the needles of Taxus canadensis. The structures were established on the basis of 1D and 2D NMR spectroscopic data. The identification of different alkaloid side chains in these taxanes by Matrix Assisted Laser Desorption Mass Spectrometry (MALDI-MS) was discussed.

Dichrocephala integrifolia (Asteraceae) is a small herb widely distributed in many countries in Asia, Africa, and the Middle East. Many species of the genus Dichrocephala are used as folk medicines for ulcer, fever, hypertension, and pneumonia. In addition, the leaves of D. integrifolia are used for treating malaria and hepatitis. The composition of the essential oil from the leaves and flowers of D. integrifolia has been reported [1, 2]. There are also some studies on the aerial parts of D. integrifolia, and some of its compounds show inhibitory effects on NO production and induced NO synthase inhibitory activities [3]. In our continuing studies on bioactive compounds from plants [5–9], we investigated the aerial parts of Dichrocephala integrifolia. A review of the literature shows that several chemical compounds have been isolated from this plant, including diterpene lactones, sesquiterpene lactones, sterols, dicaffeoylquinic acid, and flavonoids [3, 4]. In continuation of our investigation on this plant, eight compounds were isolated and elucidated here. The dried and chopped aerial parts of Dichrocephala integrifolia (6 kg) were extracted three times with EtOH (24 L) and successively fractionated into petroleum ether, CH2Cl2, EtOAc, and n-BuOH fractions. The four fractions were subjected to all kinds of column chromatography and Prep-TLC to obtain eight compounds characterized as 3-O-methyleupatorin (1), quercetin-3-O-glucoside (2), N-benzoylphenylalaninyl-N-benzoylphenylalaninate (3), aurantiamide acetate (4), 2-hydroxyolean-12-ene-23,28-dioic acid-3-O--D-glucopyranoside (5), 3,4-dicaffeoylquinic acid (6), dichrocephol B (7), and dichrocephol C (8) by analyzing their spectral data and by comparing with published data in the literature. Compound 1, yellow needle crystals (acetone), characterized as 3-O-methyleupatorin [10].

The genus Neolitsea (Lauraceae) contains over 85 species distributed around the world. These plants have been found to be rich in sesquiterpenes, triterpenes, steroids, and alkaloids. This review summarizes the phytochemical progress and list of all the constituents isolated from the genus Neolitsea over the past few decades. Some biological activities of compounds isolated from this genus are also included.

Structural modifications were performed on isoalantolactone in an effort to find compounds with potential anticancer activity. Seven previously unknown adducts of active methylene compounds with isoalantolactone were synthesized by the Michael reaction. Moreover, four derivatives of aryl-substituted isoalantolactone were prepared by the Heck reaction. All synthetic products were evaluated for toxic activities against three different hepatoma cell lines, Bel-7402, SMMC-7721, and Hep G2. Products prepared through the Heck reaction and 3a,b show potential antiproliferative activity against the Hep G2 cell.

Torreya nucifera is an evergreen coniferous tree, widely distributed in Japan, Korea, and People's Republic of China. Its seeds exhibit significant insecticidal activity. The fruits of this evergreen are widely used in folk medicine for the treatment of tapeworm infestation in Korea and to induce abortion in Japan, but most chemical studies of T. nucifera have focused on its leaves and wood. A number of sesquiterpenoids, labdane and abietane diterpenoids, ligans, and flavonoids were identified as active secondary metabolites [1–8]. T. nucifera is a Taxaceae plant endemic to Korea, Japan, and China. In order to compare its constituents with those of Taxus spp. and to understand their taxonomic relationship, we investigated the chemical composition of Torreya nucifera. Five diterpenoids were isolated for the first time from the pulp of the title plant, including one labdane diterpenoid, two abietane diterpenoids, and two pimarane-type diterpenoids. Their structures were established on the basis of 1D and 2D NMR spectrascopic analysis. We report herein the isolation and structure characterization of these diterpenoids and detailed the 1H and 13C NMR data of compounds 1–5. Melting points were measured with an MRK micro-melting point apparatus and were uncorrected. Column chromatographic separations were carried out using silica gel (300–400 mesh, Qingdao Haiyang Chemical Group Corporation, Qingdao, P. R. China). Na2SO4 was the drying agent used in all workup procedures. Solvents and reagents of analytic grade (reagent grade used without further purification) were purchased from commercial sources. TLC was performed on precoated silica gel F254 glass-backed plates without activation. Fractions were monitored by TLC with visualization under UV light (254 and 365 nm) and by dipping the plates into a solution of 10% (v/v) H2SO4 in EtOH followed by heating on a hot plate for 5 min. Analytical HPLC was performed on a Waters 2695 separation module coupled to a 2996 photodiode array detector. Preparative HPLC was carried out on a Waters Delta Prep 3000 instrument coupled to a UV 2487 dual absorbance detector. Analytical HPLC was performed using two Whatman partisil 10 ODS-2 analytical columns (4.6 250 mm) in series. Preparative HPLC was performed using a partisil 10 ODS-2 MAG-20 preparative column (9.4 250 mm). The products were eluted with a 50 min linear gradient of acetonitrile (25 to 100%) in water at a flow rate of 3 mL/min (preparative HPLC). Positive ion fast atom bombardment mass spectra (FAB-MS) was obtained with a Vacuum Generators ZAB-HS instrument. All NMR spectra were recorded on a Varian Unity INOVA 600 or 500 NMR spectrometer equipped with a 5 mm probe at ambient temperature in CDCl3 solution. The 1H and 13C chemical shifts were referenced relative to TMS residue. Typical one-dimensional (1D) 1H and 13C spectra were acquired under standard condition on a Varian Unity INOVA 500/600 spectrometer operating at 499.861/599.913 and 125.690/150.848 MHz, respectively. 1H and 13C chemical shifts are expressed in the scale as parts per million (ppm).

Radix Ophiopogonis and Radix Liriopes are two widely used herbal medicines and functional foods with similar pharmacological activities and clinical efficacies. In order to figure out whether phytoequivalence of species leads to therapeutic equivalence and consistency, in this study, a novel sensitive and selective high performance liquid chromatography-tandem mass spectrometric method (HPLC-MS/MS) has been developed for the simultaneous analysis of 11 bioactive components (6 steroidal saponins and 5 flavonoids) and then was applied for comparing in Radix Ophiopogonis and Radix Liriopes from different habitats. Separation was performed using a C18 analytical column with gradient elution of acetonitrile and 0.3‰ acetic acid (v/v) at a flow rate of 0.8 mL/min. Multiple-reaction monitoring (MRM) scanning was employed with switching electrospray ion source polarity between positive and negative modes in a single run. All calibration curves showed good linearity (r2 > 0.9915) within the test ranges. The intra-day and inter-day precision for 11 analytes were less than 3.7% and 4.2%, respectively. The recoveries were between 95.3% and 106.7%. Fifty-three batches of commercial samples from different sources were analyzed using the developed method. Hierarchical clustering analysis (HCA) and content analysis were performed to differentiate and classify the samples. The results demonstrated that steroidal saponins were the major components in both Liriopes species, and a low content of flavonoids could become an important symbol of distinction between Ophiopogonis and Liriopes. The developed method could successfully differentiate between Ophiopogonis and Liriopes.

A series of new taxanes, 1-93, have been isolated, together with 37 known taxoids including Taxol(®) (paclitaxel) and cephalomannine, from the Canadian yew, Taxus canadensis (Taxaceae) in the past 30 years. These new taxoids possess various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, and 6/12 ring systems and six new taxanes with four novel skeletons, i.e., a taxane with a 6/6/8/6 ring system, a taxane with a [3.3.3] propellane skeleton, three taxanes with [3.3.3] [3.4.5] dipropellane sytems, as well as a novel taxane with a unique 5/5/4/6/6/6 hexacyclic skeleton, containing a unique [3.3.2] propellane, were isolated for the first time from natural sources. It should be emphasized that 13-acetyl-9-dihydrobaccatin III, a very useful starting material for the semisynthesis of Taxol(®) and Taxotere(®) , represents the most abundant taxane in the needles of this yew tree. These findings establish the above mentioned yew tree as significantly different from the remaining species. On the other hand, some chemical modifications on the taxanes isolated from this plant were carried out.

A new thiophene acetylene, named 2,2-dimethyl-4-[5′-(prop-1-ynyl)-2,2′-bithiophen-5-yl]-1,3-dioxolane (1), was isolated from the roots of Echinops spinosus, and the structure was elucidated on the basis of oneand two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H–1H COSY, HSQC, and HMBC).

A novel bidihydroflavone was isolated from the whole plant of Chromolaena odorata. The structure was characterized as 6-methylenebis(5,7-dihydroxy-4′-methoxyflavanone) (1) on the basis of spectroscopic methods.

A new taraxastane-type triterpene, named 3β-hydroxy-20-taraxasten-22-one palmitate (1), along with a known compound, taraxasterol palmitate (2), was isolated from the flowers of Inula cappa, and the structure was elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H–1H COSY, HSQC, HMBC, and NOESY).

Two new non-taxoids, named (Z)-2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)acetic acid (1) and (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic anhydride (2), were isolated from the leaves of Taxus cuspidata, and the structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H–1H COSY, HSQC, HMBC, and NOESY).

A monoterpene and a pair of epi-isomers of norsesquiterpenoids were isolated from the flowers of Achillea millefolium, and their structures were established as 1-hydroxy-2R,3R-isopyliden-hex-5-en-4-one (1), isololiolide (2), and 6-epiloliolide (3) on the basis of spectral analysis.

A new taxane was isolated from the needles of the Japanese yew, Taxus cuspidata. Its structure was established as 2α,7β,9α-triacetoxy-5α,10β-dihydroxy-taxa-4(20),11-dien-13-one (1) on the basis of spectrascopic data, including 1D and 2D NMR data.

Torreyanoxane, a novel 3,4-secoglutinane triterpenoid, was isolated from the pulp of Torreya nucifera. The structure was determined on the basis of spectroscopic methods.

A taxane with an amino-side chain on C-5 was identified for the first time from rooted cuttings of the Canadian yew, Taxus canadensis. The structure was characterized as 2α,10β,13α-triacetoxy-5α-[3'-(N-formyl-Nmethylamino)-3'-phenylpropanoyloxy]taxa-4(20),12-dien-9α-ol (1) on the basis of 1D and 2D NMR data and HR-FAB-MS analyses. The spectra revealed that in CDCl3 solution 1 was composed of two rotamers (1a and 1b) in a ratio of approximately 1:1.

A new natural product, 8,8'-bi-3-O-methylquercetin (9), and eight known flavonoids were isolated from the flowers of Achillea millefolium. Their structures were established on the basis of spectral evidence. All the spectral data of these compounds were reassigned after interpretation of their 2D NMR spectroscopic data. Compounds 2, 5, and 7 exhibited antiproliferative activity against human breast cancer cell line MCF7WT. In addition, 2 and 5 showed antiproliferative activity against human prostatic cancer cell line PC-3, while the other compounds did not show inhibitory effects in two human tumor cell lines tested.

A new glyceride, 1,3-di-(16'-acetoxy-palmitoyl)-glycerol (1), and a known ceramide, (2S,3S,4R,8E)-2-[(2'R)-hydroxypalmitoylamino]-8-tetracosene-1,3,4-triol (2), were isolated from the seeds of Xylocarpus granatum K.D.Koenig (Meliaceae). Their structures were established on the basis of spectral evidence.

Two new natural taxanes were isolated from the heartwood of Taxus cuspidata. The structures were established as rel-(2α,5α,7β,9α,10β,12α)-7,9-bis(acetyloxy)-2-(benzoyloxy)-11,12-epoxy-1,5-dihydroxy-10-[(hydroxyacetyl)oxy]tax-4(20)-en-13-one (1), and (2α,5α,10β,14β)-taxa-4(20),11-diene-2,5,10,14-tetrol 2-acetate (2) on the basis of spectroscopic analysis.

Eleven taxoids were isolated from needles of the Japanese yew, Taxus cuspidata Sieb. et Zucc., one of them being a new compound whose structure was established as 5α-cinnamoyl-9α,10β,13α-triacetoxy-11(15→1)abeotaxa-4(20),11-dien-15-ol (7-deactoxytaxuspine J) on the basis of a spectroscopic analysis. Its relative stereochemistry is proposed from the results of a NOESY experiment.

Four novel taxane diterpenes were isolated from the needles of the Japanese yew, Taxus cuspidata. Their structures were established as 1-hydroxy taxuspine C, 2α,7β,9α, 10β,13α-pentaacetoxy-5α-cinnamoyloxy-4β,20-epoxy- taxa-11-en-1β-ol, 2α,9α,10β,13α-tetraacetoxy-taxa-4(20), 11-dien-5α-ol and 10-deacetyl taxinine on the basis of spectral analyses.

The inhibitory effect of 13 taxanes isolated from the Chinese yew (Taxus chinensis var. mairei) on the proliferation of human cervical cancer HeLa cells were examined using an MTT assay. Four compounds having a hydrophobic cinnamate side chain showed antiproliferative activity, which may be due to increased cell permeability.

Context The bark of Ailanthus altissima (Mill.) Swingle (Simaroubaceae) is traditionally used to treat ascariasis, diarrhoea, spermatorrhoea, bleeding and gastrointestinal diseases. Objective The objective of this study is to investigate the antitumour activity and mechanism of 2-dihydroailanthone isolated from A. altissima. Materials and methods The U251 cells were treated with 1.00, 4.00 and 8.00 μg/mL of 2-dihydroailanthone for 48 h and the normal cells treated with 20.00 μg/mL of 2-dihydroailanthone were tested as well. Proliferation inhibition of 2-dihydroailanthone on the cells was tested by MTT. Apoptosis and cell-cycle distribution in U251 cells with 1.00, 3.00 and 5.80 μg/mL of 2-dihydroailanthone for 48 h were determined by flow cytometry, respectively. The expression of the apoptosis-related genes and proteins was analysed by RT-PCR and Western blot method, respectively. Results MTT assay revealed that 2-dihydroailanthone inhibited U251 cells proliferation. The cell viability of U251 cells was 62.82, 31.34 and 25.58%, and that of three normal cells was 72.75, 82.74 and 44.92%, respectively. Flow cytometry assay showed that 2-dihydroailanthone induced apoptosis and G0/G1 phase cycle arrest towards U251 cells. The late apoptotic cells were 11.37, 21.73 and 33.83%, and the cells cycle distributed in the G0/G1 accounted for 48.85, 62.77 and 64.40%, respectively. The Western blot and RT-PCR assay showed that up-regulation of pro-apoptotic bax protein and down-regulation of anti-apoptotic bcl-2 protein as well as their mRNA on U251 cells might be related to the apoptosis induction and proliferation inhibition. Conclusion An important bioactive component, 2-dihydroailanthone, has antitumour effects, enlightening a novel source of phytomedicines in tumour therapy.

Two new taxane-glycosides are isolated from the methanolic extract of the needles of T.canadensis.Their structures are evaluated by 1D and 2D NMR data analysis and high-resolution fast atom bombardment mass spectroscopy.

Isoalantolactone (IAL) is an active sesquiterpene naturally present in many vegetables, condiments and medicinal plants. In this study, an efficient strategy was developed for the identification of metabolites following the in vivo metabolism and in vitro biotransformation of IAL with rat intestinal bacteria utilizing ultra performance liquid chromatography combined with Triple TOF mass spectrometry (UPLC-Triple TOF-MS/MS). As a result, 46 metabolites including 34 novel sulfur-containing products were identified. The results demonstrated that IAL could undergo general metabolic reactions, including oxidation, hydration, hydrogenation, demethylation, cysteine conjugation and N-acetylcysteine conjugation, but the most noticeable characteristic of IAL metabolism was the H2S addition to the double bond between C-11 and C-13 and subsequent reactions to produce a series of novel sulfur-containing dimers. This is the first study of IAL metabolism in vivo, whose results provide novel and useful data for a better understanding of the safety and efficacy of IAL.

A novel 30-nortriterpenoid saponin, (3β)-3-hydroxy-30-noroleana-12,20(29)-dien-28-oic acid 3-(β-D-glucopyranosiduronic acid 6-methyl ester) (1), and a known compound, (3β)-oleanolic acid 3-(β-D-glucopyranosiduronic acid 6-methyl ester) (2), were isolated from the aerial parts of Wedelia chinensis. The structures were established by their spectral data including 1H- and 13C-NMR, 1H,1H-COSY, HMBC, HSQC, NOESY, and HR-FAB-MS data.

Ten 1,10-secoguaianolides were isolated from the flowers of Achillea millefolium. Their structures were determined on the basis of spectroscopic methods. Three of them (millifolides A-C) including two dimeric sesquiterpenoids exhibit new skeletons. Seco-tanapartholide A exhibited moderate cell growth inhibitory activity against the human cancer cell line MCF7WT (IC50 = 5.51 μm) in vitro.

A novel 6/12-membered bicyclic taxane with a 13,17-ether bridge, named canataxpyran A, was isolated from the needles of Taxus canadensis. The structures were characterized as 7β,9,10β,20-tetracetoxy-13β,17-epoxy-3,8-secotaxa-3E,8E,11-triene-2α,5α-diol (designated as canataxpyran A, 1). This bicyclic taxane gradually decomposed in CDCl3to give the corresponding enones, 10β,20-diacetoxy-13β,17-epoxy-4α,5α-dihydroxy-3,8-secotaxa-2E,7E,11-trien-9-one (canataxpyran B, 2) and 5α,10β,20-triacetoxy-13β,17-epoxy-4α-hydroxy- 3,8-secotaxa-2E,7E,11-trien-9-one (canataxpyran C, 3). Compound 1 is the first example of a natural 3,8-secotaxane with 13,17-oxygen bridge.

Eupatorium (family: Compositae), which comprises nearly 1200 species, is distributed throughout tropical America, Europe, Africa, and Asia. Up to now, the reported constituents from the genus Eupatorium involve flavonoids, terpenoids, pyrrolizidine alkaloids, phenylpropanoids, quinonoids, essential oils, and some others, altogether more than 300 compounds. Studies have shown that Eupatorium and its active principles possess a wide range of pharmacological activities, such as cytotoxic, antifungal, insecticidal, antibacterial, anti-inflammatory, and antinociceptive activities. Currently, effective monomeric compounds or active parts have been screened for pharmacological activities from Eupatorium in vivo and in vitro. Increasing amount of data supports application and exploitation for new drug development.

Two new eudesmanolides, 3β-acetoxy-1β,4α-dihydroxy-11αH-eudesman-12,6α-olide (1) and 3β-acetoxy-1β-hydroxy-11αH-eudesman-4(15)-en-12,6α-olide (2), were isolated from the flowers of Achillea millefolium, their structures were established on the basis of spectral analysis.