Zeylleucapenoids A-D, Highly Oxygenated Diterpenoids with Anti-Inflammatory Activity from Leucas zeylanica (L.) R. Br.

Four previously undescribed highly oxygenated diterpenoids (1-4), zeylleucapenoids A-D, characterized by halimane and labdane skeletons, were isolated from the aerial parts of Leucas zeylanica. Their structures were elucidated primarily via NMR experiments. The absolute configuration of 1 was established using theoretical ECD calculations and X-ray crystallographic analysis, whereas those for 2-4 were assigned using theoretical ORD calculations. Zeylleucapenoids A-D were tested for anti-inflammatory activity against nitric oxide (NO) production in RAW264.7 macrophages, of which only 4 showed significant efficacy with an IC50 value of 38.45 µM. Further, active compound 4 was also evaluated for the inhibition of the release of pro-inflammatory cytokines TNF-α and IL-6 and was found to have a dose-dependent inhibitory effect, while it showed nontoxic activity for zebrafish embryos. A subsequent Western blotting experiment revealed that 4 inhibited the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Furthermore, molecular docking analysis indicated that the possible mechanism of action for 4 may be bind to targets via hydrogen and hydrophobic bond interactions.

[Chemical constituents with α-glucosidase inhibitory activities from seeds of Morinda citrifolia (Noni)].

The present study investigated the chemical constituents and inhibitory activities against α-glucosidase from the seeds of Morinda citrifolia(Noni) by the chromatographic technique and semi-preparative HPLC.Fifteen compounds were isolated from the ethyl acetate extract of the seeds, and their structures were identified on the basis of physiochemical characteristics and spectroscopic data as(9S,2E,4Z,7Z)-9-hydroxydeca-2,4,7-trienoic acid(1), azelaic acid(2), scopoletin(3), ursolic acid(4), quercetin(5), cyclo-(L-Leu-L-Ile)(6), cyclo-(L-Phe-L-Ile)(7), cyclo-(L-Phe-L-Val)(8), cyclo-(L-Leu-L-Val)(9), cyclo-(L-Phe-L-Leu)(10), caffeic acid(11), 3,4-dihydroxycinnamaldehyde(12), p-hydroxybenzoic acid(13), p-hydroxy-cinnamic acid(14), and p-hydroxyphenethyl alcohol(15).Among them, compound 1 was a new fatty acid and compounds 7-10 and 12 were isolated from Morinda plant in the Rubiaceae family for the first time.Compounds 1, 2 and 4-15 were isolated from the seeds of M.citrifolia(Noni) for the first time.All isolated compounds were evaluated for the inhibitory activities against α-glucosidase and compounds 3-5 showed potential inhibitory activity with IC_(50) values of 160, 133, and 120 µmol·L~(-1), respectively.

Ba3Sb2(PO4)4 and Cd3Sb2(PO4)4(H2O)2: Two New Antimonous Phosphates with Distinct [Sb(PO4)2] Structure Types and Enhanced Birefringence.

Two new antimonous phosphates, namely Ba3Sb2(PO4)4 and Cd3Sb2(PO4)4(H2O)2, have been successfully prepared through mild hydrothermal reactions. Ba3Sb2(PO4)4 features a 1D [Sb(PO4)2]3- chain structure separated by Ba2+ cations while Cd3Sb2(PO4)4(H2O)2 presents a 2D [Sb(PO4)2]3- layered structure with Cd2+ located at the interlayer space. The [Sb(PO4)2]3- chain in Ba3Sb2(PO4)4 is the first example of 1D antimonous phosphate structure, and Cd3Sb2(PO4)4(H2O)2 represents the first d10 transition metal antimonous phosphate. Based on UV-vis-NIR spectra, both Ba3Sb2(PO4)4 and Cd3Sb2(PO4)4(H2O)2 can display large optical band gaps (4.30 and 4.36 eV, respectively). But their transparent ranges are quite different because of the coordination water of Cd3Sb2(PO4)4(H2O)2 (500-2000 and 500-1300 nm for Ba and Cd compounds). The anhydrous Ba3Sb2(PO4)4 shows high thermal stability in the nitrogen atmosphere (900 °C). Because of the incorporation of the lone pair cation of Sb(III), the birefringence of Ba3Sb2(PO4)4 and Cd3Sb2(PO4)4(H2O)2 has been enhanced to 0.086 and 0.053 at 532 nm, respectively.

3,4- seco-Norclerodane Diterpenoids from the Roots of Polyalthia laui.

Ten new clerodane diterpenoids, polylauioids A-J (1-10), and five known analogues (11-15) were isolated from the roots of Polyalthia laui. Among the new compounds, 3 and 8 are artifacts. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. The absolute configurations of 4, 5, and 7 were defined based on single-crystal X-ray diffraction and electronic circular dichroism data. Compounds 1 and 2 represent the first examples of rearranged 3,4- seco-norclerodane diterpenoids, and a putative biosynthesis pathway for these compounds is proposed. Compounds 1, 4, 6, 7, 9, and 10 showed anti-HIV activities with EC50 values ranging from 12.2 to 35.2 µM.

[Studies on chemical constituents from Psychotria straminea].

The chemical consituents from Psychotria straminea were separated and purified by column chromatographies on silica gel, Sephadex LH-20, ODS and RP-HPLC. The strictures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data in literature. Sixteen compounds were isolated and elucidated as tectochrysin (1), apigenin (2), kaempferol (3), luteolin (4), diosmetin (5), quercetin (6), kaempferol-4'-O-methylether (7), rhamnetin (8), 7-hydroxycoumarin (9), 7-methoxycoumarin (10), scopoletin (11), lupeol (12), 30-oxo-lupeol (13), lupenyl acetate (14), α-amyrin (15), and ursolic acid (16). This is the first study on the chemical composition of P. Straminea, and all compounds were isolated from P. straminea for the first time. In addition to compounds 6 and 9, the other compounds were isolated from the genus Psychotria for the first time.

[Studies on non-alkaloid constituents from Ochrosia elliptica].

The chemical consituents from Ochrosia elliptica were separated and purified by column chromatographies on silica gel, Sephadex LH-20, ODS and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data in the literature. 18 compounds were isolated and elucidated as (+) -pinoresinol(1), (+) -medioresinol (2), (+) -lariciresinol (3), (+) -5'-methoxy lariciresinol(4), (+) -isolariciresinol (5), syringaresinol(6), episyringaresinol (7), ciwujiatone (8), zhebeiresinol (9), 7-hydroxycoumarin (10), 7-methoxycoumarin (11), scopoletin(12), isofraxidin(13), caffeic acid ethyl ester (14), ferulic acid (15), p-hydroxybenzaldehyde (16), vanillin (17), and vanillic acid(18). All compounds were isolated from the genus Ochrosia for the first time.

Two new lanostane triterpenoids from the branches and leaves of Polyalthia oblique.

Two new lanostane triterpenoids, 20-hydroxyeuphorbol-7-one (1) and 15α-hydroxyeuphorbol-7,11-dione (2), together with four known triterpenoids, euphorbol-7-one (3), friedelin (4), stigmast-4-ene-6α-ol-3-one (5), stigmasta-4-en-3,6-dione (6), were isolated from ethanol extract of the branches and leaves of Polyalthia obliqua. The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic analysis and comparisons with related known compounds. Antibacterial activities of two new compounds and four known compounds were tested.

Deep understanding of the interaction between thienorphine and UDP-glucuronosyltransferase (UGT) isoforms.

Thienorphine has been demonstrated to be a potent, long-acting partial opioid agonist. It is being developed as a good candidate to treat opioid dependence. The thienorphine's glucuronide was detected after thienorphine was incubated with human liver microsomes (HLMs). Recombinant UGT isoforms screening experiment and enzyme kinetic study showed that UGT1A1 completely contributed to the glucuronidation of thienorphine. Among the tested UGT isoforms, UGT1A3 and UGT2B7 were inhibited by thienorphine, with other UGT isoforms negligibly influenced. The inhibition type is competitive, and inhibition kinetic parameters (K(i)) were 1.65 and 5.27 µM for UGT1A3 and UGT2B7, respectively. However, due to low plasma concentration of thienorphine, in vivo drug-drug interaction might not occur.

[Composition and antitumor activities of essential oil from the fruits of Dasymaschalon trichophorum].

OBJECTIVE: To study the chemical components and antitumor activities of essential oil from the fruits of Dasymaschalon trichophorum. METHODS: The essential oil from the fruits of Dasymaschalon trichophorum was extracted by steam-stilling and analyzed by GC-MS. The inhibitory effect of extract of Dasymaschalon trichophorum on SPCA-1,BEL-7402, SGC-7901 and K-562 cell proliferation was assayed using the MTU. RESULTS: GC-MS result showed that there were 55 peaks and 30 compounds were identified which weighed 74.98%. The major components were nerolidol (19.887%), caryophyllene (16.714%) and beta-myrcene (9.29%). The essential oil exhibited strong antitumor activity against SPCA-1 human tumor cell line with IC50 value of 6.61 microg/mL. CONCLUSION: This experiment provides scientific foundation for further utilization of Dasymaschalon trichophorum.

Identification of CYP isoforms involved in the metabolism of thymol and carvacrol in human liver microsomes (HLMs).

Carvacrol and thymol are phenolic compounds with similar structures isolated from many aromatic plants, and have been demonstrated to exert multiple pharmacological effects. The metabolic and pharmacokinetic behaviour of thymol and carvacrol has received much attention. Carvacrol and thymol have been demonstrated to undergo phase I metabolism such as hydroxylation reaction. However, drug-metabolizing enzymes involved in this process remain unclear. Given that cytochrome P450s (CYPs) are involved in most phase I metabolism, the aim of the present study was to investigate the role of CYPs in the metabolism of thymol and carvacrol. After incubation with human liver microsomes (HLMs) in the presence of NADPH, a new metabolite and two metabolites were detected for thymol and carvacrol, respectively. A combination of chemical inhibition studies and assays with recombinant CYP isoforms demonstrated that CYP2A6 was the predominant drug-metabolizing enzyme involved in the metabolism of thymol and carvacrol. All these results remind the researchers that special attention should be paid on pharmacokinetic and clinical outcomes when thymol or carvacrol was co-administrated with other compounds mainly undergoing CYP2A6-mediated metabolism.

A new isoflavone from the fruits of Ficus auriculata and its antibacterial activity.

A new isoflavone (Z)-5,7,4'-trihydroxy-3'-[3-hydroxy-3-methyl-1-butenyl] isoflavone (1) together with seven known isoflavones (2-8) were isolated from the fruits of the Ficus auriculata. Their structures were established on the basis of 1 D, 2 D-NMR spectroscopic data and HR-ESI-MS analysis. All compounds were evaluated for their antibacterial activities against five pathogenic bacteria in vitro. Compounds 3 and 4 exhibited significant antibacterial activities against five pathogenic bacteria with the MIC values ranging from 1.25 to 20 µg/mL.[Formula: see text].

Callnudoids A-H: Highly modified labdane diterpenoids with anti-inflammation from the leaves of Callicarpa nudiflora.

Eight undescribed 3,4-seco-norlabdane diterpenoids, callnudoids A-H, as well as two known analogues were isolated from the leaves of Callicarpa nudiflora. The structures were elucidated using spectroscopic methods and were compared with published NMR spectroscopic data. The absolute configurations of callnudoids D and E were defined based on ECD data or single-crystal X-ray diffraction. Callnudoids A-C are the highly modified labdane diterpenoids featuring rearranged 3,4-seco-ring and the formation of an undescribed cyclohexene moiety via C2-C18 cyclization. They only contain 15 carbon atoms on the carbon skeleton. Callnudoid D represents the unusual 3,4-seco-15,16-norlabdane diterpenoid with C13-C17 cyclization, and a putative biosynthesis pathway for callnudoids A, B, D, and E was proposed. All compounds were evaluated for their anti-inflammatory activities by inhibiting the lipopolysaccharide (LPS)-induced nitric oxide (NO) released in RAW264.7 cells; callnudoids A-E and H, and methylcallicarpate obviously inhibited pro-inflammatory cytokines TNF-α and IL-1ß in a dose-dependent manner.

New alkaloids from the noni juice with potential α-glucosidase inhibitory activity.

Four new alkaloids, nonialkaloids A-D (1-4) and six known analogues (5-10) were isolated from the noni juice. Among the new compounds, 1 and 2 are indole alkaloids with a seven-membered fused N-heterocyclic ring, 3 and 4 are quaternary ammonium derivatives. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or the modified Mosher's method. All the isolates were tested for α-glucosidase inhibitory activities. Compounds 1 and 3 displayed potent inhibitory activity against α-glucosidase with the IC50 values of 413.7 and 364.4 µM, respectively.

[Pollution Characteristics of Heavy Metals in PM2.5 Near Highway].

In this study, we evaluate the pollution characteristics of heavy metals in particulate matter with diameters less than 2.5 µm (PM2.5) near highways. Three rounds of cluster sampling of PM2.5 were conducted on three highways, Changzhang, Changtong, and Wenhou, in peri-urban areas near Nanchang from March to August 2018. The sampling sites included service areas, toll stations, tunnels, and areas near the highway. The concentrations of six heavy metals including Cu, Zn, Pb, Cd, Cr, and Ni in PM2.5 were analyzed using inductively coupled plasma mass spectrometry (ICP-MS). The pollution and distribution of heavy metals in PM2.5 near the highway were analyzed, and that pollution characteristics and the level of possible ecological jeopardy were assessed by using the Geoaccumulation Index and Potential Risk Index methods. No significant difference was observed in PM2.5 or in heavy metals in PM2.5 along highways with different traffic flow, but they differed significantly in among highway settings in the following order:super-long tunnels > long tunnels and area near the highway > service areas and toll stations. The heavy metal concentration in highways decreased in the following order:Zn (3.8 µg·m-3) > Pb (10.2×10-2 µg·m-3) > Cr (6.8×10-2 µg·m-3) > Cu (3.5×10-2 µg·m-3) > Ni (1.5×10-2 µg·m-3) > Cd (0.1×10-2 µg·m-3). In accordance with the influence of temperature and precipitation, PM2.5 and heavy metals in PM2.5 showed significant variations among the monitoring months. The PM2.5 concentration had a significant negative correlation with atmospheric temperature. We observed that PM2.5 concentration was significantly lower from May to August than from March to April. The Zn concentration in PM2.5 was more significant from May to August than from March to April. Pearson analysis showed a significant positive correlation between Zn in PM2.5 with atmospheric temperature because elevated temperatures could aggravate wear and tear and metallic corrosion, which then prompts the emission of Zn. According to the Geoaccumulation Index and Potential Ecological Jeopardy Index, the level of pollution associated with heavy metals of PM2.5 manifested in the following order:Zn and Cd > Pb > Cu > Ni and Cr. The pollution and degree of jeopardy associated with Zn and Cd were the most severe in the assessment criteria; therefore, the pollution by these elements and the sources of traffic should be noted in air pollution control plans. Super long tunnels, long tunnels, and areas near highways showed greater levels of pollution and higher potential ecological jeopardy than service areas and toll stations. The degree of pollution in densely populated service areas and toll stations was consistent across partially urban areas.

A new12-membered lactone from the stems of Ficus auriculata.

A new lactone ficusine D (1), together with six known compounds (2-7) were isolated from the stems of the Ficus auriculata. The new compound 1 was a rare 12-membered lactone containing a quinone ring skeleton. The structure of the 1 was elucidated by comprehensive spectroscopic data. The relative and absolute configurations of 1 were elucidated by the ROESY analysis and biogenesis pathway. All compounds were evaluated for their antibacterial activities against six pathogenic bacteria in vitro. Compounds 6 and 7 exhibited potent antibacterial activities against Bacillus cereus with the MIC values of 2.5 and 5 µM, respectively.

Impact of inhalational anesthetics on postoperative cognitive function: Study protocol of a systematic review and meta-analysis.

BACKGROUND: Conflict findings of the impact of inhalational anesthetics on postoperative cognitive function are reported. No systematic review has been performed to solve the problem. The aim of the study was to assess the effect of different inhalational anesthetics on postoperative cognitive function in a network meta-analysis. METHODS: We will search MEDLINE, EMBASE, the Central Register of Controlled Trials in the Cochrane library, and CINAHL for randomized controlled trials or cohort studies assessing the short-term or long-term cognitive function of elderly patients (over 60 years) receiving major surgeries and inhalational anesthetics (desflurane, isoflurane, sevoflurane, halothane, and nitrous oxide) during surgery. Two reviewers will independently screen study eligibility, extract information from eligible studies, and appraise study quality. The impact of inhalational anesthetics will be assessed through: incidence of postoperative cognitive dysfunction at 1 week, 3 months, 1 year, and over 1 year after surgery; incidence of post-operative delirium; test of postoperative cognitive function. RESULTS: The results of this systematic review and meta-analysis will be published in a peer-reviewed journal. CONCLUSION: To our knowledge, this systematic review will be the first to evaluate existing research on the incidence of postoperative cognitive function after inhalational anesthetics. Our study will assess the effect of different inhalational anesthetics on postoperative cognitive function. ETHICS AND DISSEMINATION: The review will be finished in December 2017, and the result will be published in a peer-reviewed journal or disseminated through conference posters or abstracts. REVIEW REGISTRATION NUMBER: CRD42017056675 (www.crd.york.ac.uk/PROSPERO).

A new biphenyl derivative from the mangrove endophytic fungus Phomopsis longicolla HL-2232.

A new biphenyl derivative 5,5'-dimethoxybiphenyl-2,2'-diol (1), together with five known compounds (2-5), was isolated from the mangrove endophytic fungus Phomopsis longicolla HL-2232. The structures of these compounds were elucidated using comprehensive spectroscopic methods. The absolute configuration of 4 was determined by single-crystal X-ray diffraction for the first time. The inhibitory activities of all compounds against two Vibrio bacteria were evaluated.

New phenylpropanoid and 6H-dibenzo[b,d]pyran-6-one derivatives from the stems of Dasymaschalon rostratum.

Three new phenylpropanoid derivatives, dasymaroacid A (1), dasymaroesters B and C (2 and 3), and one new polyoxygenated 6H-dibenzo[b,d]pyran-6-one derivative dasymarolactone D (4), together with seven known compounds (5-11), were isolated from the stems of Dasymaschalon rostratum Merr. Compounds 1 and 2 are unusual phenylpropanoid derivatives with a polymethyl substituted cyclopentene conjugated diketone as a substituent, and 3 is a unique cinnamic acid detective with a polymethyl substituted cyclohexene conjugated triketone as a substituent. Their structures were elucidated by extensive spectroscopic methods and chemical method, and 4 was further confirmed by the single crystal X-ray diffraction method. Compounds 1-4 and 7 showed weak anti-HIV-1 activities with EC50 values ranged from 16.44 to 25.91µM.

A new norsesquiterpene from the roots of Polyalthia laui.

One new norsesquiterpene polyalone A (1), and one new natural product 9-keto-cyclocolorenone (2), along with three known analogues (3-5) were isolated from the roots of Polyalthia laui. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All compounds were evaluated for their cytotoxic activities and antibacterial activities.

New clerodane diterpenoids from the roots of Polyalthia laui.

Five new clerodane diterpenoids, polylauiester A (1), (4→2)-abeo-2,13-diformyl-cleroda-2,12E-dien-14-oic acid (2) and polylauiamides B-D (3-5), together with 11 known clerodane diterpenoids (6-16), were isolated from the roots of Polyalthia laui. Among them, polylauiester A (1) represents the first example of a novel norclerodane diterpenoid only containing 17 carbon atoms on the carbon skeleton, and polylauiamide B (3) is an unusual diterpenoid with a p-substituted benzene ring as a substituent. Their structures were elucidated by extensive spectroscopic methods, and the relative configuration of polylauiamide B (3) was further confirmed by the single crystal X-ray diffraction method. Biological evaluation of new compounds against human Hela, MCF-7 and A549 human cancer cell lines showed that all compounds displayed weak cytotoxicities against various human cancer cell lines in the range of IC50 at 25.01-39.31µM.