Three new methylated Δ8-pregnene steroids from the Polyalthia laui-derived fungus Stemphylium sp. AZGP4-2.

Three new methylated Δ8-pregnene steroids, stemphylisteroids A-C (1-3) were isolated from the medicinal plant Polyalthia laui-derived fungus Stemphylium sp. AZGP4-2. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. The absolute configuration of 1 was determined by X-ray crystallographic analysis. Compound 1 show antibacterial activity against Escherichia coli with the MIC value of 6.25 µg/mL, and 2 exhibited a broad spectrum of antibacterial activities against six pathogenic bacteria with the MIC values ranging from 12.5 to 50 µg/mL. The discovery of three methylated Δ8-pregnene steroids 1-3 are a further addition to diverse and complex array of methylated steroids.

Four New Chromone Derivatives from Colletotrichum gloeosporioides.

Four previously unreported chromones, 5-hydroxy-2-(hydroxymethyl)-8-methoxy-4H-chromen-4-one (1), (5R,7S)-5,7-dihydroxy-2-propyl-5,6,7,8-tetrahydro-4H-chromen-4-one (2), (5R,7S)-5,7-dihydroxy-2-methyl-5,6,7,8-tetrahydro-4H-chromen-4-one (3), and (5R,7S)-5,7-dihydroxy-2-[(E)-prop-1-en-1-yl]-5,6,7,8-tetrahydro-4H-chromen-4-one (4), as well as one known analogue 5-hydroxy-2-methyl-4H-chromen-4-one (5) were isolated from the fermentation broth of the endophytic fungus Colletotrichum gloeosporioides derived from the mangrove Ceriops tagal. Their structures were elucidated based on extensive spectroscopic analyses. The absolute configurations of 2-4 were determined by comparison the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 2 showed cytotoxic activity against A549 cell line with the IC50 value of 0.094 mm.

A conceptual framework to untangle the concept of urban ecosystem services.

Urban ecosystem service (UES) is becoming an influential concept to guide the planning, design, and management of urban landscapes towards urban sustainability. However, its use is hindered by definitional ambiguity, and the conceptual bases underpinning its application remain weak. This is exemplified by two different but equally valid interpretations of UES: "urban ecosystem services", referring to ecosystem services from analogs of natural and semi-natural ecosystems within urban boundaries, and "urban ecosystem services", a much broader term that includes the former group as well as urban services in a city. While we recognize that a single definition of UES is not possible nor necessary as its application is context-dependent, it is nevertheless useful to clarify the relationships between these interpretations to promote consistent use, and importantly, explore how a broader interpretation of UES might advance its applications in areas that have been neglected. We developed a conceptual framework that links UES to natural and human-derived capital to explain the relationships between the dual meanings of UES and proposed three normative propositions to guide its application: (1) integrate holistically multiple components of natural capital to provide UES, (2) reduce dependence on non-renewable abiotic resources and human-derived capital, and (3) enhance UES through technology. The framework we developed helps to resolve the current ambiguity in the meanings of UES, highlights the need to recognise neglected aspects of natural capital important for UES, and can be used to clarify relationships with related concepts conveying dependence of human well-being on nature.

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.

Eudesmanolides and Other Constituents from the Flowers of Wedelia trilobata.

Two eudesmane sesquiterpene lactones, wedetrilides B (1) and C (2), along with five known analogues (3 - 8), an ent-kaurane diterpenoid (9), a steroid (10), as well as cinnamic acid derivatives (11 - 13), were isolated from the flowers of Wedelia trilobata. Their structures were elucidated on the basis of extensive spectroscopic analyses and by comparison of their NMR data with those of related compounds. Furthermore, the structures of 1 and 3 - 5 were confirmed by X-ray single-crystal diffraction analyses. Compounds 4 and 5 exhibited weak cytotoxic activities against the MCF-7, HeLa, and A549 cell lines. Compounds 3 - 5 were also evaluated for their inhibitory effects against HIV lytic replication.

Bioactive Phenolic and Isocoumarin Glycosides from the Stems of Homalium paniculiflorum.

Two new phenolic glycosides (1 and 2) and two new isocoumarin glycosides (3 and 4), along with 14 known compounds (5-18), were isolated from the stems of Homalium paniculiflorum. Their structures were established on the basis of extensive spectroscopic analyses and chemical methods. All new compounds were evaluated for their anti-inflammatory activities via examining the inhibitory activity on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in mouse macrophage RAW 264.7 cells in vitro. Compounds 1 and 4 exhibited inhibitory activities with IC50 values of 30.23 ± 1.23 µM and 19.36 ± 0.19 µM, respectively.

Guaiane-Type Sesquiterpenoids from Fissistigma oldhamii Inhibit the Proliferation of Synoviocytes.

Three guaiane-type sesquiterpenoids, dysodensiols G-I (1-3), together with five known sesquiterpenoids (4-8) were isolated from the stems of Fissistigma oldhamii (Hemsl.) Merr. Compound 1 represents the first example of an ene(6 → 5)-abeo-14-norguaiane sesquiterpenoid derived from natural products. Their structures were elucidated by a combination of 1D and 2D NMR and MS spectra. The absolute configuration of 2 was determined by an X-ray crystallographic analysis. The inhibitory effect of all compounds on the proliferation of primary synovial cells was evaluated. Compound 3 showed a potent inhibitory effect on the proliferation of synoviocytes with an IC50 value of 1.0 µM.

[Sesquiterpenes from Artabotrys hongkongensis].

The chemical consituents from Artabotrys hongkongensis were separated and purified by column chromatographies with 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 reported in the literature. As a result, 16 sesquiterpenes were isolated and elucidated as blumenol A (1), 4, 5-dihydroblumenol A (2), (6R, 9S)-3-oxo-a-ionol (3), 3-hydroxy-ß-ionone (4), dehydrovomifoliol (5), (3R, 6R, 7E) -3-hydroxy-4, 7-megastigmadien-9-one (6), sarmentol F (7), 10-oxo-isodauc-3-en-15-oic acid (8), fukinone (9), petasitolone (10), ß-eudesmol (11), trans-3ß-(1-hydroxy-1-methylethyl)- 8aß-methyl-5-methylenedecalin-2-one (12), 10-hydroxyaristolan-9-one (13), aristol-8-en-1-one (14), aristolan-9-en-1-one (15), and aristolan-1, 9-diene (16). This is the first study on the chemical consituents of A. hongkongensis, and all compounds were isolated from the genus Artabotrys for the first time.

Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile.

A new enantiomeric pair of spirodiketones, (+)- and (-)-denobilone A (1 and 2), three new phenanthrene derivatives (3-5), and three new biphenanthrenes (22-24), along with 11 known phenanthrene derivatives (6-16), five known bibenzyl derivatives (17-21), and four known biphenanthrenes (25-28), were isolated from Dendrobium nobile. The structures of 1-5 and 22-24 were elucidated using comprehensive spectroscopic methods. (+)-Denobilone and (-)-denobilone A (1 and 2) were isolated as a pair of enantiomers by chiral HPLC. The absolute configurations of (+)- and (-)-denobilone A (1 and 2) were determined by comparing their experimental and calculated electronic circular dichroism spectra. The absolute configuration of denobilone B (3) was determined by X-ray crystallographic analysis. The inhibitory activities of all compounds against nine phytopathogenic fungi and three cancer cell lines were evaluated.

[Studies on alkaloids from Fissistigma oldhamii].

14 alkaloids were obtained from stems and leaves of Fissistigma oldhamii, by silica gel, ODS, Sephadex LH-20 column chromatographies, and semi-preparative HPLC. Using physicochemical and spectral methods, the isolated alkaloids were identified as norcepharadione B(1), asimilobine(2), lanuginosine(3), laurotanine(4), isocorydine(5), anolobine(6), xylopine(7), N-methylbuxifoline(8), aristolactam AIIIa(9), piperumbellactam A(10), goniopedaline(11), aristololactam BIII(12), liriodenine(13), and salutaridine(14), respectively. Compounds 3-5, 8, 10, 11 and 14 were isolated from the genus Fissistigma for the first time.

Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase.

Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 6' position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension.

Lactones from Ficus auriculata and their effects on the proliferation function of primary mouse osteoblasts in vitro.

Bioassay-guided fractionation of the petroleum ether, chloroform and EtOAc extracts of the stems of Ficus auriculata led to the isolation of five new 12-membered lactones (3R,4R)-4-hydroxy-de-O-methyllasiodiplodin (1), 6-oxolasiodiplodin (2) and ficusines A-C (3-5), together with three known related analogues (6-8). The structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configurations of 3 and 8 were established by single crystal X-ray diffraction analysis. Compounds 3-5 represent the first 12-membered lactones with a quinone ring unit. Compounds 6 and 7 exhibited significant proliferation function of primary osteoblasts (OBs) in vitro. Especially, the promotion rate of 6 reached 151.55±1.34% (P<0.001) at the concentration of 100 µM.

Bioactive anthraquinone derivatives from the mangrove-derived fungus Stemphylium sp. 33231.

Four new anthraquinone derivatives (1-4) and four new alterporriol-type anthranoid dimers (14-17), along with 17 analogues, were isolated from the solid rice fermentation of the fungus Stemphylium sp. 33231 obtained from the mangrove Bruguiera sexangula var. rhynchopetala collected from the South China Sea. Their structures were elucidated using comprehensive spectroscopic methods. The absolute configurations of 1, 3, and 4 were determined by single-crystal X-ray diffraction of their derivatives (1a, 3b, and 4a). The absolute configurations of the chiral 17-19 were determined by comparing their CD spectra with 21. The inhibitory activities of most of the compounds against seven terrestrial pathogenic bacteria and two cancer cell lines were evaluated.

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.

Healing of stoma after magnetic biliary-enteric anastomosis in canine peritonitis models.

OBJECTIVE: To assese the healing of stoma after magnetic anastomosis for the reconstruction of biliary-enteric continuity under severe inflammation. METHODS: Acute bile duct injury was constructed as a bile peritonitis model in mongrel dogs (n=32). Magnetic anastomosis (group A, n=16) and traditional suture anastomosis (group B, n=16) were performed to reconstruct the biliary-enteric continuity in one stage. Half of the dogs in each group were euthanized on the 30th postoperative day, and the other half on the 90th postoperative day to harvest the stoma region. The healing conditions of the stoma after the 2 anastomotic approaches were observed with naked eyes, under light microscope and scanning electron microscope. RESULTS: The stoma leakage rate (50% versus 0% on the 30th postoperative day, 37.5% versus 12.5% on the 90th postoperative day, both P<0.05) and stenosis degree (13.9%±0.3% versus 7.1%±0.3% on the 30th postoperative day, 17.2%±0.4% versus 9.4%±0.4% on the 90th postoperative day, both P<0.01) were significantly higher in group B than in group A. Compared with traditional manual anastomoses, the histological analysis under light and electron microscope showed a more continuous stoma with more regular epithelium proliferation and collagen arrangement, less inflammation in group A. CONCLUSIONS: Magnetic anastomosis stent ensures better healing of the stoma even under the circumstance of severe inflammation.

Five new degraded diterpenoids from Trigonostemon xyphophylloides.

Five new degraded diterpenoids trigoxyphins J-N (1-5), among them trigoxyphins K and L have a novel carbon skeleton, together with four known analogues (6-9) have been obtained from the ethanol extract of the twigs of Trigonostemon xyphophylloides. Compounds 1-5 were evaluated for their cytotoxic activity in vitro against three human tumor cell lines by MTT assay. The results exhibited that Trigoxyphin N (5) showed moderate cytotoxicities against SPC-A-1 and SGC-7901 cancer cell lines.

Genome-wide association study identifies ALDH7A1 as a novel susceptibility gene for osteoporosis.

Osteoporosis is a major public health problem. It is mainly characterized by low bone mineral density (BMD) and/or low-trauma osteoporotic fractures (OF), both of which have strong genetic determination. The specific genes influencing these phenotypic traits, however, are largely unknown. Using the Affymetrix 500K array set, we performed a case-control genome-wide association study (GWAS) in 700 elderly Chinese Han subjects (350 with hip OF and 350 healthy matched controls). A follow-up replication study was conducted to validate our major GWAS findings in an independent Chinese sample containing 390 cases with hip OF and 516 controls. We found that a SNP, rs13182402 within the ALDH7A1 gene on chromosome 5q31, was strongly associated with OF with evidence combined GWAS and replication studies (P = 2.08x10(-9), odds ratio = 2.25). In order to explore the target risk factors and potential mechanism underlying hip OF risk, we further examined this candidate SNP's relevance to hip BMD both in Chinese and Caucasian populations involving 9,962 additional subjects. This SNP was confirmed as consistently associated with hip BMD even across ethnic boundaries, in both Chinese and Caucasians (combined P = 6.39x10(-6)), further attesting to its potential effect on osteoporosis. ALDH7A1 degrades and detoxifies acetaldehyde, which inhibits osteoblast proliferation and results in decreased bone formation. Our findings may provide new insights into the pathogenesis of osteoporosis.

Synthesis of 2-aryl-3,4-dihydroisoquinolin-2-ium bromides and their in vitro acaricidal activity against Psoroptes cuniculi.

By employing sanguinarine, a natural active quaternary isoquinoline alkaloid, as a model molecule, a series of structurally simple quaternary 2-aryl-3,4-dihydroisoquinolin-2-ium compounds were designed and synthesized and evaluated for in vitro acaricidal activity against P. cuniculi. A new approach towards the title compounds was developed with isochroman as starting material. The results showed that 22 of 24 tested compounds displayed the activity in varying degrees at 0.4 mg/mL. Fourteen compounds were significantly more effective than ivermectin, a standard acaricide, and 6-methoxy dihydrosanguinarine, a derivative of sanguinarine (p<0.05). And their comprehensive relative activity was 1.4 to 16.5 times than that of ivermectin and 1.5 to 18.8 times than that of 6-methoxy dihydrosanguinarine. The structure-activity relationship indicated that the introduction of a substituent to N-benzene ring, especially halogen atom and trifluoromethyl group, led to great improvement of the activity. The position of fluorine atom, methyl group and hydroxyl group made very significant effects on the activity. It was concluded that 2-aryl-3,4-dihydroisoquinolin-2-iums are very promising candidates for the development of new isoquinoline acaricidal agents.

[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.