Two new polyacetylene glycosides from rhizomes of Atractylodes lancea / 中草药

Objective: To investigate the chemical components from the 80% EtOH extract of Atractylodes lancea, as well as the inhibitory activities of the isolated compounds on LPS-induced NO production of microglia BV2 cells. Methods: The n-BuOH-soluble fraction of the crude extract was successively chromatographed with Diaion HP-20, Sephadex LH-20, and preparative HPLC C18-column. At last, the planar and stereochemical structures of these obtained compounds were established on the basis of extensive spectroscopic data (HRESIMS, NMR, and ECD, etc). Results: Ten glycosides were isolated from the n-BuOH-soluble fraction of the 80% EtOH extract of A. lancea, including (2E,8R)-decene-4,6-diyne-1,8-diol-1-O-β-D- apiofuranosyl-(1→6)-β-D-glucopyranoside (1), (8S)-decane-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside (2), (2E,8R)-decene-4,6- diyne-1,8-diol-8-O-β-D-glucopyranoside (3), (2E,8S)-decene-4,6-diyne-1,8-diol-8-O-β-D-glucopyranoside (4), (2E,8E)-2,8- decadiene-4,6-diyne-1,10-diol-1-O-β-D-glucopyranoside (5), (7R,8S)-3',9,9'-trihydroxyl-3-methoxyl-1'-propanol-7,8-dihydrobenzo- funanneoligan-4-O-β-D-glucopyranoside (6), (7'R*,8S*,8'S*)-lyoniresinol 9'-O-β-D-glucopyranoside (7), (7S,8R)-4,9,9'-trihydroxy- 3'-methoxy-8-O-4'-neolignan 7-O-β-D-glucopyranoside (8), methyl salicylate 2-O-α-L-xylopyranosyl-(1→6)-β-D-glucopyranoside (9), and phenylmethanol 7-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (10). Conclusion: Compounds 1 and 2 are named atractyeneyneglycoside A and atractyeneyneglycoside B, while compounds 6, 8-10 are first isolated from the rhizomes of A. lancea. At the concentration of 10 μmol/L, compound 10 exhibited the strongest inhibitory effects on LPS-induced NO production of microglia BV2 cells with the value of 31.18%, while compounds 1 and 2 just showed weaker inhibitory effects with values of 22.01% and 14.09%, respectively.

Anti-inflammatory and Immunosuppressive Effects of Panax notoginseng

Here, we designed to examine the anti-inflammatory effects on RAW264.7 cells and the immunosuppressive effects by evaluating interleukin-2 (IL-2) production in Jurkat T cells using a MeOH extract of Panax notoginseng roots. The results showed that the MeOH extract inhibited the synthesis of nitric oxide (NO) in a dose-dependent manner (IC₅₀ value of 7.08 µg/mL) and displayed effects on T cell activation at a concentration of 400 µg/mL. In efforts to identify the potent compounds, bioactivity-guided fractionation of the MeOH extract and chemical investigation of its active CH₂Cl₂-, EtOAc-, and butanol-soluble fractions led to the successful isolation and identification of eleven compounds, including two polyacetylenes (1, 2), a steroid saponin (3), seven dammarane-type ginsenosides (4 – 10), and an oleanane-type ginsenoside (11). Among them, compound 11 was isolated from this plant for the first time. Compound 2 exhibited potent inhibitory effects on NO synthesis and an immunosuppressive effect with IC₅₀ values of 2.28 and 65.57 µM, respectively.

Rapid analysis on chemical constituents in roots of Codonopsis tangshen by UPLC coupled with Q-Exactive quadrupole-orbitrap mass spectrometry / 中草药

Objective: The chemical constituents from the roots of Codonopsis tangshen were isolated and identified using ultra-high performance liquid chromatography coupled with Q-Exactive quadrupole-orbitrap MS spectrometry in positive and negative ion modes. Methods: The 50% methanol extract from the roots of C. tangshen was isolated on an Acquity UPLC BEH C18 column (100 mm × 2.1 mm, 1.7 μm). The mobile phase was acetonitrile and water containing 0.1% formic acid by gradient elution. The constituents in the roots of C. tangshen were rapidly isolated and identified by HRMS in the positive and negative ion mode using both full scan and two stage threshold-triggered mass modes. Results: A total of 36 compounds from the roots of C. tangshen were identified, including 7 alkaloids, 7 phenylpropanoids, 3 polyacetylenes, 6 hexanol glycosides and hexylene glycosides, 8 organic acids, 3 amino acids, 1 nucleoside, and 1 sesquiterpenoid. Among them, nine compounds were unambiguously identified comparing with the reference standards. Nineteen chemical components were reported in this plant for the first time. One of them is potential new compound. Conclusion: Chemical components in the roots of C. tangshen were isolated and identified rapidly with UPLC-Q-Exactive quadrupole-orbitrap MS technology to provide the theory basis for the study on the quality control and pharmacodynamic material.

Quantitative analysis of eight polyacetylenes derived from Bupleuri Radix by ultra-performance liquid chromatography coupled with photodiode array detector / 中国中药杂志

To establish quantitative methods for determination of polyacetylenes in Bupleuri Radix, an ultra-performance liquid chromatography method coupled with photodiode array detector (UPLC-PDA) was developed. The analysis was performed on a Waters BEH C₁₈ column (2.1 mm×100 mm, 1.7 μm) using a gradient system of methanol and water. The flow rate was 0.3 mL•min⁻¹ and the detection wavelength was 315 nm. Eight polyacetylenes were prepared using traditional extraction and isolation method, of which compounds 7 and 8 were two new polyacetylenes. All calibration curves showed good linearity (r>0.999 0) within the concentration range. Both the intra- and inter-day precisions for eight analytes were less than 1.9%, respectively, with the mean recovery at the range of 93.21%-108.4%. Meanwhile, 17 bupleurum samples were examined with this process. The results showed a variety either the chemotaxonomic or content of polyacetylenes. The method indicated good linearity, limit of detection and quantification, precision, accuracy and recovery. The developed method allows quantitative assessment and quality control of polyacetylenes, and might be a good alternative according to detection levels in polyacetylenes from Bupleurum Radix.

Polyacetylenes from capitulum of Coreopsis tinctoria / 中草药

Objective: To study the chemical constituents in the capitulum of Coreopsis tinctoria. Methods: The constituents were separated and purified by AB-8 macroporous resin, silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. The structures were elucidated on the basis of chemical evidences, spectroscopic methods, and optical rotation data. The new compound was evaluated for its inhibitory activity against LPS-activated NO production in BV-2 microglial cells using the Griess assay. Results: Five polyacetylenes were obtained from the fraction of 50% ethanol extract of C. tinctoria identified as (3S)-(6E,12E)-tetradecadiene-8,10-diyne-1-ol-3-O-β-D-glucopyranoside (1),(2S)-(3Z,11E)-decadiene-5,7,9-triyne-1,2-diol (2),(2R)-(3E,5E,11E)-triene-7,9-diyne-1,2-diol (3),(E)-7-phenyl-2-heptene-4,6-diyn-1-ol (4), and (Z)-7-phenyl-2-heptene-4,6-diyn-1-ol (5). Conclusion: Compound 1 is a new polyacetylene glycoside named coreoside E and shows weak anti-inflammatory activity. Compounds 3 and 5 are isolated from the plants of C. tinctoria for the first time.

Chemical constituents from roots of Campanumoea javanica and their antiangiogeneic activities / 中草药

Objective: To study the chemical constituents from the roots of Campanumoea javanica and their antiangiogenesis activities. Methods: The compounds were isolated and purified by various chromatographic techniques and their structures were elucidated by spectral analysis, the antiangiogenic activities of the isolated compounds were evaluated using a zebrafish model. Results: Fourteen compounds were isolated and identified from 90% ethanol extract in ethyl acetate fraction in the roots of C. javanica, including campanumoside (1), lobetyol (2), tetradeca-4E,8E,12E-triene-10-yne-1,6,7-triol (3), 9-(tetrahydropyran-2-yl)-non-trans- 8-ene-4,6-diyn-3-ol (4), 9-(tetrahydropyran-2-yl)-nona-trans,trans-2,8-diene-4,6-diyn-1-ol (5), lobetyolinin (6), (Z)-3-hexenyl-O- α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (7), 3,4-dihydroxybenzoic acid (8), tangshenoside II (9), zanthocapensol (10), ampelopsin (11), agathisflavone (12), β-ecdysterone (13), and α-tocopherolquinone (14). Conclusion: Compound 1 is a new polyacetylene glucoside named campanumoside. Compounds 2-14 are isolated from the plants of Campanumoea Bl. for the first time. Compounds 3 and 4 exhibit the certain antiangiogenic activity in the pharmacological evaluation with a zebrafish model.

Polyacetylene Compound from Cirsium japonicum var. ussuriense Inhibited Caspase-1-mediated IL-1beta Expression

Our previous report showed that polyacetylene compound, 1-Heptadecene-11, 13-diyne-8, 9, 10-triol (PA) from the root of Cirsium japonicum var. ussuriense has anti-inflammatory activity. In this study we investigated the role of the PA as inhibitor of caspase-1, which converts prointerleukin-1beta (proIL-1beta) to active IL-1beta and is activated by inflammasome involved in the inflammatory process. We tested the effect of PA on the production of pro-inflammatory cytokines, IL-1beta in murine macrophage cell line, RAW264.7. PA inhibited lipopolysaccharide (LPS)-induced IL-1beta production by macrophages at a dose dependent manner. PA also suppressed the activation of caspase-1. The mRNA level of ASC (apoptosis-associated spec-like protein containing a CARD), an important adaptor protein of inflammasome, was decreased in the PA treated group. Therefore our results suggest that the anti-inflammatory effect of PA is due to inhibit the caspase-1 activation.

Chemical constituents of Bidens bipinnata / 中草药

Objective To study the chemical constituents of Bidens bipinnata and search for bioactive natural products, which have the anticancer and antiinflammation activities. Methods The six compounds were isolated by a combination of silica gel, reversed phase silica gel column chromatography, and polyamide column chromatography. Their structures were identified by spectral methods. Results Ten compounds were isolated and six structures were identified. They are trideca-2-?-D-glucopyranosyl-1, 13-dihydroxy-3 (E), 11 (E)-en-5, 7, 9-triyne (Ⅰ), trideca -2-?-D-glucopyranosyl-1, 13-dihydroxy-11 (E)-dien-3, 5, 7, 9-tetrayne (Ⅱ), hyperoside (Ⅲ), 6-O-(3″, 6″-diacetyl-?-D-glucopyranosyl)-6, 7, 3′, 4′-(tetrahydroxyaurone) (Ⅳ), 6-O-(6″-acetyl-?-D-glucopyranosyl)-6, 7, 3′, 4′-tetrahydroxyaurone (Ⅴ), 6-O-(4″, 6″-diacetyl-?-D-glucopyranosyl)-6, 7, 3′, 4′-tetrahydroxyaurone (Ⅵ). Conclusion Compound Ⅱ is a novel compound, compound Ⅴ is isolated from this plant for the first time.