Cytotoxic Triterpenoids from the Stalks of Microtropis triflora.

Bioassay-guided phytochemical investigation of the stalks of Microtropis triflora Merr. & F.L. Freeman led to the isolation of ten triterpenes 1 - 10, including one novel compound 3,24-epoxy-2α,24-dihydroxyfriedelan-29-oic acid (1). Their chemical structures were identified on the basis of spectroscopic analysis, including HR-ESI mass spectrometry, 1D- and 2D-NMR (1 H, 13 C, 1 H,1 H-COSY, HSQC, HMBC, and NOESY), and by comparison with the data reported. The cytotoxicities of compounds 1 - 10 against a panel of cultured human tumor cell lines (Bcap37, SMMC7721, HeLa, CNE) were evaluated. The new compound 1 showed moderate anti-tumor activities with IC50 values of 39.22, 29.24, 23.28, and 68.81 µm/ml, respectively. These results might be helpful for explaining the use of M. triflora in traditional medicine. Triterpenes are characteristic of Microtropis genus and could be useful as potential chemotaxonomic markers.

An Unusual Tetrahydrofuran Lignan from the Roots of Zanthoxylum planispinum and the Potential Anti-inflammatory Effects.

An unusual tetrahydrofuran lignin, zanthplanispine (1), together with 14 known lignans (2 - 15) were isolated from the AcOEt-soluble fraction from the MeOH extract of Z. planispinum roots. The structures of 1 was elucidated on the basis of 1D- and 2D-NMR experiments as well as HR-ESI-MS analysis. The known compounds were identified by the comparison of their NMR data with previously reported in the literatures. Bioassay showed that compounds 1 - 4 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS) stimulated RAW 264.7 cells. In particular, compound 1 showed significant inhibitory activity with an IC50 value of 36.8 µm.

Complete NMR assignment of retinal and its related compounds.

Complete and unambiguous (1)H and (13)C NMR chemical shift assignments for all-trans-retinal, 13-cis-retinal, 11-cis-retinal and 9-cis-retinal (1-4) have been established by means of two-dimensional COSY, HSQC, HMBC and NOESY spectroscopic experiments.

Structure characterization of novel heteropolysaccharides from Pteridium revolutum with antioxidant and antiglycated activities.

This study aims to analysis the structures of polysaccharides isolated from Pteridium revolutum and their antioxidant and antiglycated activities. Three novel water-soluble heteropolysaccharides, named PRP0, PRP1, and PRP2, were isolated from P. revolutum. The average molecular weight was determined by high performance gel permeation chromatography analysis as 1.04 × 106, 8.39 × 105, and 7.37 × 105 Da, respectively. Their structures were characterized using physicochemical and spectroscopic methods. The antioxidant and antiglycated activities were assayed in vitro. PRP0, PRP1, and PRP2 consist of l-Ara, l-Rha, d-Man, d-Xyl, d-Fuc, d-Gal, and d-Glc in different proportions. PRP1 mainly has a backbone of (1 â†’ 3,6)-linked d-Man and (1 â†’ 3)-linked d-Gal on main chain. PRP2 is mainly composed of (1 â†’ 2,4)-linked d-Man and (1 â†’ 3)-linked d-Gal on main chain. All polysaccharides have strong scavenging power on 2,2-difenil-1-picril-hidrazil and hydroxyl radicals and significantly antiglycated activity in Bovine serum albumin-Glucose model, which showing that the polysaccharides have potential application value on the functional food.

[A novel C27-steroidal glycoside sulfate from Liriope graminifolia].

An unusual novel C27-steroidal glycoside sulfate was isolated from the underground organs of Liriope graminifolia (Linn.) Baker with three known compounds. Their chemical structures were determined by spectral analysis, including HR-MS, 1D and 2D NMR as (25S)-ruscogenin 1-sulfate-3-O-alpha-L-rhamnopyranoside (1), (25S)-ruscogenin 1-O-beta-D-xylopyranosyl-3-O-alpha-L-rhamnopyranoside (2), hesperidin (3), and 4', 7-dihydroxy-5-methoxyflavanone (4). Compound 1 has cytotoxic activities against K562 and HL60 cells with IC50 values of 18.6 microg x mL(-1) and 16.5 microg x mL(-1), respectively.

Structure Characterization, Antioxidant and Immunomodulatory Activities of Polysaccharide from Pteridium aquilinum (L.) Kuhn.

Pteridium aquilinum (L.) Kuhn (Pteridaceae family) has been widely used as a food and medicine in China and Korea. Previous studies indicate that P. aquilinum contains a variety of bioactive chemical components such as flavonoids, phenols, terpenoids, saponins, polysaccharides, and so on. In the present study, a novel polysaccharide (named as PAP-3) with average molecular weight of 2.14 × 105 Da was obtained from P. aquilinum. The structure was studied through physicochemical and spectroscopic analysis. The results indicated that PAP-3 consists of arabinose, rhamnose, fucose, galactose, mannose, and xylose in a molar ratio of 1.58:1.00:3.26:4.57:4.81:3.33. The polysaccharide is mainly composed of (1→2)-linked xylose and (1→3,6)-linked mannose on the main chain, with (1→2)-linked xylose, (1→6)-linked mannose, and (1→6)- and (1→3,6)-linked galactose as side chains. Galactose, fucose, and xylose are located at the end of the side chains. The in vitro immunomodulatory and antioxidant activities were assayed. PAP-3 has strong free-radical scavenging activity on DPPH and ABTS radicals and significant immunomodulatory activity on RAW264.7 cells. These data provide useful information for further study on the polysaccharides of P. aquilinum and their applications in the food and medical industries.

A new rearranged abietane diterpenoid from Clerodendrum kaichianum Hsu.

A new abietane diterpenoid, (3S,16R)-12,16-epoxy-3,6,11,14,17-pentahydroxy-17(15 â†’ 16)-abeo-5,8,11,13-abietatetraen-7-one (1), was isolated from the stems of Clerodendrum kaichianum Hsu, together with four known diterpenoids. The structures of the isolated compounds were assigned on the basis of their NMR spectra including 2D NMR techniques such as COSY, HMQC, and HMBC experiments, and were compared with those of the literature data. This new compound showed significant cytotoxicity against the HL-60 and A-549 tumor cell lines.

A novel cytotoxic flavonoid C-glycoside from premna fulva.

Premna fulva Craib, locally known as "Zhangu" in China, is a kind of traditional medicinal plant. A phytochemical investigation on this plant led to the isolation of a novel flavonoid glycoside along with three known analogues. The chemical structure of the new compound was determined by spectral and chemical analysis as apigenin 8-C-ß-D-xylopyranoside (1). Compound 1 showed weak inhibitory activities in vitro against to four tumor cell lines (HL-60, Bcap37, SMMC7721, and P388) with IC50 values of 12.58, 19.31, 31.02, and 48.19 µg/mL, respectively. The result might be helpful to explain the application of P. fulva in Traditional Chinese Medicine.[Figure: see text].

Isolation of two new C-glucofuranosyl isoflavones from Pueraria lobata (Wild.) Ohwi with HPLC-MS guiding analysis.

A profiling analysis of the total isoflavone extract of the root of Pueraria lobata (Wild.) Ohwi was performed using HPLC coupled with ESI-ion trap mass spectrometry. A total of seven isoflavones were identified according to their retention times, UV, MS data, and comparing with the literature data. Among them, two proposed new compounds were isolated and their structures were determined to be 8-C-alpha-glucofuranosyl-7,4'-dihydroxyisoflavone and 8-C-beta-glucofuranosyl-7,4'-dihydroxyisoflavone, named as neopuerarin A (7) and neopuerarin B (6), on the basis of chemical and spectral analyses.

Natural Bioactive New Withanolides.

Withanolides are a group of highly oxygenated steroids derived from a C28 ergostane skeleton, and have attracted significant scientific interest due to their complex structural features and multiple bioactivities. More than 170 new natural withanolides were isolated and identified in the last 5 years. This review provides a comprehensive summary of the structural, biological and pharmacological activities of these new compounds.

A novel polysaccharide from Dendrobium devonianum serves as a TLR4 agonist for activating macrophages.

Dendrobium devonianum has been used as herbal medicines and nutraceutical products since ancient time in China. However, its chemical composition and pharmacological mechanisms are not fully known. In present studies, by chemical purification and characteristic identification, we discovered a novel polysaccharide from D. devonianum, which was designated as DvP-1 with molecular weights of 9.52 × 104 Da. DvP-1 is a homogeneous heteropolysaccharide consisting of D-mannose and d-glucose in the molar ration of 10.11: 1. The main glycosidic linkages were ß-1, 4-Manp, which were substituted with acetyl groups at the O-2, O-3 and/or O-6 positions. DvP-1 was found to directly stimulate the activation of macrophages in vitro, as evidenced by inducing morphologic change, thereby promoting the production of cytokines TNF-α, IL-6 and NO, and enhancing the pinocytic activity of macrophages. By establishing a zebrafish model, we also found that DvP-1 could alleviate vinorelbine-induced decrease of macrophages in vivo. Further findings indicated that DvP-1 activated macrophages through several toll-like receptors (TLRs), but mainly through TLR4. DvP-1 served as a TLR4 agonist and induced ERK, JNK, p38, and IκB-α phosphorylation, suggesting the activation of MAPK and NFκB signaling pathways downstream of TLR4. These findings could help us further understand the immunomodulating effects of D. devonianum in Chinese medicines or health foods for immunocompromised persons. They also show the medicinal value of DvP-1 for the treatment of cancer and infectious diseases caused by TLR4 dysfunction.

A new triterpenoidal ester from Celastrus rosthornianus.

3-O-Palmitate of 1beta, 3beta, 11beta-trihydroxy-olean-12-ene (1),was isolated from the stalks of Celastrus rosthornianus. The structure was elucidated by MS, 1D- and 2D-NMR experiments as well as by chemical degradation.

New Bioactive Metabolites from the Marine-derived Fungi Aspergillus.

Recently, the marine-derived Aspergillus present as producers of a large number of structurally novel secondary metabolites. Some of these metabolites have shown antitumor, antimicrobial, anti-inflammatory, antioxidant and enzymatic activities, and may be promising resources for new therapeutic drugs. This review sums up 232 new bioactive metabolites from the marine-derived Aspergillus with classification through their biological activities and chemical structures in 2006-2016. Besides, structure-activity relationships of some compounds are explored.

New Analogues of Aporphine Alkaloids.

Aporphine alkaloids, characterized by a heterocyclic aromatic basic skeleton, are known from different organisms and exhibit various biological activities: anti-tumor, anti-viral, anti-microbial, anti-inflammatory etc. The review gives information which provides an overview of the latest progress in the structural diversity and the biological activity of the aporphine alkaloids with their derivatives isolated from natural resource in recent years. Additionally, the synthetic approaches of aporphine alkaloids have also been reviewed.

Aporphine Alkaloids from Illigera aromatica from Guangxi Province, China.

Three undescribed aporphine alkaloids laurodionine B (1), illigerine A (2), and N-formyl-laurolitsine (3) were isolated from the methanolic extracts of the Chinese medicinal plant, Illigera aromatica, together with three known analogues (4-6). The chemical structures of 1-6 were identified by spectroscopic methods including 1D and 2D NMR (1H, 13C, COSY, HSQC, and HMBC) and high resolution mass spectrometry (HRESIMS). Compounds 1-3 showed moderate inhibitory activities in vitro against two cultured tumor cell lines, Hela and SMMC7721, with IC50 values of 32.42-62.90 µM. Only compound 1 had in vitro cytotoxic activity against Bcap37 cells, with the IC50 value of 90.61 µM.

A new fatty acid ester of triterpenoid from Celastrus rosthornianus with anti-tumor activitives.

The methanol extract of the stalks of Celastrus rosthornianus Loes. afforded a new fatty acid ester of triterpene: 1beta,3beta-dihydroxy-olean-9(11),12-dienyl-3-palmitate (1), and three known compounds beta-amyrin palmitate (2), 3beta-hydroxy-11-oxo-olean-12-enyl-3-palmitate (3) and lupeol palmitate (4). Their structures were established by HRMS, 1D and 2D NMR experiments, as well as, by chemical degradation. The new compound showed cytotoxicity against human cervical squamous carcinoma (Hela) cells.

[Study on triterpenes of Microtropis tiflora].

OBJECTIVE: To study the chemical constituents of Microtropis triflora. METHOD: The compounds were isolated by chromatography on silica gel and Sephadex LH-20. There structures were elucidatedby by chemical methods and spectral analysis. RESULT: Five triterpenoids were isolated and elucidated as friedelin (1), 3-oxo-28-friedelanoic acid (2), 29-hydroxy-3-friedelanone (3), salaspermic acid (4), orthosphenic acid (5). CONCLUSION: Compounds 1-5 are all isolated from M. triflora for the first time.

[Antitumor effects of novel triterpene from Celastrus hypoleucus on human colorectal cancer cell line RKO in vitro].

OBJECTIVE: To investigate the effects of novel triterpene (12-oleanene-3beta, 6alpha-diol) from Celastrus hypoleucus on the proliferation and apoptosis of human colorectal cancer cell line RKO. METHOD: The inhibitory effect of the novel triterpene on RKO cell proliferation was assayed by MTT dye reduction. The morphology of apoptotic cells was observed with AO/EB double fluorescence staining and HE staining, DNA fragment with electrophoresis on agarose gels, sub-diploid peak and cell cycle with flow cytometer (FCM). RESULT: Novel triterpene (12-oleanene-3beta, 6alpha-diol) from C. hypoleucus significantly inhibited proliferation of RKO cells in dose-dependent and time-dependent manner, the IC50 was (12.20 +/- 0.79) microg x mL(-1) at 48 h. Typical apoptotic changes were observed in RKO cells under the fluorescence microscope and the light microscope. DNA ladder was detected on agarose gels at concentrations from 10 microg x mL(-1) to 20 microg x mL(-1) at 48 h. With FCM methods, dose-dependent apoptosis-induced effect was observed in RKO cell line after treatment of triterpene for 48 h, and the apoptotic rates were increased from(2.93 +/- 0.84) % to (50.79 +/- 6.61) % at concentrations from 2.5 microg x mL(-1) to 20 microg x mL(-1). DNA histograms data from FCM analysis showed that the number of cells was obviously reduced during G0-G1 phase and G2-M phase, but not during S phase for RKO cell line after treatment with various concentrations of the triterpene for 48 hours. CONCLUSION: Novel triterpene (12-oleanene-3beta, 6alpha-diol) from C. hypoleucus can induce apoptosis and has inhibition effect on the proliferation in RKO cell line.

Isolation and absolute configurations of diastereomers of 8α-hydroxy-T-muurolol and (1α,6ß,7ß)-cadinane-4-en-8α,10α-diol from Chimonanthus salicifolius.

Phytochemical investigation of the aerial parts of Chimonanthus salicifolius resulted in the isolation of two sesquiterpenoids, 8α-hydroxy-T-muurolol and (1α,6ß,7ß)-cadinane-4-en-8α,10α-diol, together with 13 known compounds. The 15 structures were established by means of 1D and 2D NMR spectroscopy. The relative and absolute configurations of 8α-hydroxy-T-muurolol and 8α,11-elemodiol were achieved by NOESY experiments and X-ray crystallography using CuKα radiation. 8α-hydroxy-T-muurolol and (1α,6ß,7ß)-cadinane-4-en-8α,10α-diol showed immunosuppressive activities in a dose-dependent manner.