A New Flavan-4-ol Glycoside from Pronephrium triphyllum

Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by analyses of spectral data and physicochemical properties.Results Six compounds were isolated and identified as shelincaoide A(1),n-butyl-β-D-fructopyranoside(2),triphyllin A(3),6,7-di-hydroxycoumarin(4),daucosterol(5),and β-sitosterol(6),respectively.Conclusion Compound 1 is found to be a new compound.Compounds 2 and 4 are firstly isolated from the plants in Pronephrium Presl.and all compounds except 3 are obtained from the species for the first time.

A New Flavan-3-ol Glucoside from Daphniphyllum oldhami

A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscopie analysis and comparison with related compounds.

Effects of Terpinen-4-ol on Four Metabolic Enzymes and Polyphenol Oxidase (PPO) in Mythimna separta Walker

To study insecticidal mechanism of terpinen-4-ol, a main insecticidal composition in the essential oil of Sabina vulgaris, the 5th instar larvae of Mythimna separta, were investigated with terpinen-4-ol by topical application. The activities of phosphatase, glutathione S-transferase （GSTs）, cytochrome P450 （P450）, and polyphenol oxidase （PPO） of tested insects were determined in all poisoning stages, including exciting stage, convulsing stage, paralysis stage, and recover stage. The result showed that the activities of both acid phosphatase （ACP） and alkaline phosphatase （AKP） in treated insects were induced by terpinen-4-ol, but ACP was inhibited in paralysis stage. The activities of GSTs were inhibited in exciting stage, convulsing stage, and paralysis stage, but gradually recovered in recover stage. O-demethylase activity of cytochrome P450 was inhibited by terpinen-4-ol, and the inhibition rate in all poisoning stages were 26.27, 46.03, 80.24, and 90.22%, respectively. PPO activities were strongly inhibited by terpinen-4-ol both in vitro and in vivo. In conclusion, the activities of P450, GSTs, and PPO could have relation with toxicity of terpinen-4-ol against larvae of the Mythimna separta, but recover stage of the poisoning insects might be related to GSTs induced. As a new insecticide or synergist, terpinen- 4-ol has a potential value in field of insecticide resistance management.

Inhibition of Na^+,K^+-ATPase in Housefly (Musca domestica L.) by Terpinen-4-ol and Its Ester Derivatives

To reveal the insecticidal mechanism of terpinen-4-ol, the activity of Na＋,K＋-ATPase in insects tested were determined in vivo and in vitro. The results showed that terpinen-4-ol and its ester derivatives had strong contact activity to housefly and the contact toxicities of its derivatives except Z3 were all superior or equivalent to terpinen-4-ol. All the 7 compounds had strong inhibition towards activity of Na＋,K＋-ATPase. With poisoning symptom exacerbating, the inhibition rates were gradually increased. In vitro, the IC50 of terpinen-4-ol, Z1, Z2, Z4, Z5, and Z6 was 155.89, 197.98, 96.02, 121.36, 124.85, and 153.74 μg mL% respectively. There was well correlation between the LDs0 of terpinen-4-ol derivatives to housefly and the IC50 of terpinen-4-ol derivatives to Na＋,K＋-ATPase in housefly. In conclusion, Na＋,K＋-ATPase was likely the target of terpinen-4-ol against insects.

Influence of Location of Production, Season and Genotype on Caffeine and Flavan-3-ols in Young Green Tea （Camellia sinensis） Leaves in Kenya

Although tea is grown in agro-ecological regions widely varying in environmental factors affecting yield and quality, planters usually import genetic materials across the different growing regions assuming genotypes with good quality attributes in one location maintain their status in all regions. However, tea quality has not been replicated in new production regions. Black tea quality is influenced by the green leaf quality precursors including caffeine, total polyphenols and individual flavan-3-ols which are precursors of theaflavins and thearubigins, key plain black tea quality parameters. Factors influencing levels of the precursors compounds have not been quantified for popular Kenyan tea cultivars. The influence of geographical production location and seasons on levels and ratios of the quality precursors for 10 black tea popular clones grown in three locations in Kenya under uniform agronomic inputs were monitored. Caffeine varied significantly （P _〈 0.05） with clones and location but not with season. The flavan-3-ols and their ratios all varied （P 〈 0.05） with clones and site but not with season, with significant interactions （P 〈 0.05） between locations and clones, and locations and seasons. These results explain the observed variations in plain black tea quality due to clones and location of production. Thus, farmers in different locations are unlikely to produce black tea of same quality. It is therefore necessary to evaluate new tea genotypes in intended growing areas to establish cultivars suitable for producing high quality plain black teas in the locations. Seasonal variations in plain black tea in Kenya are unlikely to vary significantly due to flavan-3-ols.

Mechanism of Cinnamomum camphora essential oil for analgesia based on gas chromatography-mass spectrometry integrated network pharmacology

This study aims to explore the analgesic ingredients and mechanism of Cinnamomum camphora essential oil(CCEO).The constituents in CCEO were characterized qualitatively by gas chromatography-mass spectrometry.Targets related to active ingredients were collected by PubChem and Swiss Target Prediction.Targets related to pain were screened by TTD and OMIM database,and compound-target network was established by Cytoscape software.Gene ontology(GO)function and Kyoto encyclopedia of genes and genomes(KEGG)pathway enrichment analysis of targets were carried out by DAVID database.Protein-protein interaction(PPI)network was established and analyzed by STRING database.Molecular docking method was used to verify the interaction between main components and relevant core targets.A total of 13 compounds were identified in CCEO,and 58 related targets were predicted.GO function enrichment analysis revealed that the selected targets were mainly involved in biological processes such as chemical synaptic transmission and molecular function such as neurotransmitter receptor activity;24 signal pathways were screened by KEGG pathway enrichment analysis,including neuroactive ligand-receptor interaction,retrograde endocannabinoid signaling and calcium signaling pathway.Docking results showed that the main constituents had certain affinities with the key targets.The active ingredients in CCEO regulated multiple signaling pathways to ameliorate pain through AR,ACHE,ESR1,GABRG2,PTGS2 and PPARγ.

A Novel Phenylpropanoid-substituted Catechin Glycoside and a New Dihydrochalcone from Sarcandra glabra

A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analyses and chiroptical methods.

苍术聚炔类化学成分研究

目的研究苍术中聚炔类化学成分。方法采用开放ODS柱色谱及制备液相色谱等分离技术,根据化合物的理化性质和光谱数据鉴定其结构。结果从苍术80%乙醇提取物部分共分离7个聚炔类成分,分别鉴定为12,14-diacetate-2E,8E,10E-trien-4,6-diyn-1-ol(1),(2Z,4E,10E)-dodeca-2,4,10-trien-6,8-diynyl acetate(2),(5E,11E)-trideca-1,5,11-trien-7,9-diyne-3,4-diyl diacetate(3),1-(2-Furvl)-(E)-nonene-3,5-diyne-l,2-diacetate(4),atractulodin(5),(4E,6E,12E)-tetradecatriene-8,10-diyne-1,3-diol-diacetate(6),atractylodinol(7)。结论化合物1,2鉴定为苍术新的聚炔类成分。

Dietary flavonoid intake and risk of stomach and colorectal cancer

Stomach and colorectal cancers are common cancers and leading causes of cancer deaths.Because the alimentary tract can interact directly with dietary components,stomach and colorectal cancer may be closely related to dietary intake.We systematically searched published literature written in English via PubMed by searching for terms related to stomach and colorectal cancer risk and dietary flavonoids up to June 30,2012.Twenty-three studies out of 209 identified articles were finally selected for the analysis.Log point effect estimates and the corresponding standard errors were calculated using covariate-adjusted point effect estimates and 95%CIs from the selected studies.Total dietary flavonoid intake was not associated with a reduced risk of colorectal or stomach cancer [odds ratio(OR)(95%CI) = 1.00(0.90-1.11) and 1.07(0.70-1.61),respectively].Among flavonoid subclasses,the intake of flavonols,flavan-3-ols,anthocyanidins,and proanthocyanidins showed a significant inverse association with colorectal cancer risk [OR(95%CI) = 0.71(0.63-0.81),0.88(0.79-0.97),0.68(0.56-0.82),and 0.72(0.61-0.85),respectively].A significant association was found only between flavonols and stomach cancer risk based on a limited number of selected studies [OR(95%CI) = 0.68(0.46-0.99)].In the summary estimates from casecontrol studies,all flavonoid subclasses except flavones and flavanones were inversely associated with colorectal cancer risk,whereas neither total flavonoids nor any subclasses of flavonoids were associated with colorectal cancer risk in the summary estimates based on the cohort studies.The significant association between flavonoid subclasses and cancer risk might be closely related to bias derived from the case-control design.There was no clear evidence that dietary flavonoids are associated with reduced risk of stomach and colorectal cancer.

Repellent,larvicidal and adulticidal activities of essential oil from Dai medicinal plant Zingiber cassumunar against Aedes albopictus

Zingiber cassumunar is an important plant used in traditional medicine and as a natural mosquito re-pellent.However,the compounds responsible for the repellent activity of the plant are still unknown.The aim of the study is to identify the components of Z.cassumunar essential oil that show repellent activity against Aedes albopictus.We also evaluated the larvicidal and adulticidal activities of Z.cassumunar essential oil against Ae.albopictus.In-cage mosquito repellent experiments showed that Z.cassumunar essential oil possessed moderate repellent activity with a minimum effective dose(MED)of 0.16±0.01 mg/cm^(20,compared to reference standard N,N-diethyl-3-methylbenzamide(DEET,0.03±0.01 mg/cm^(20).Bioassay-guided fractionation identified the major active compound of Z.cassumunar essential oil as(-)-terpinen-4-ol(1)(MED:0.19±0 mg/cm^(20).We also found that Z.cassumunar essential oil showed moderate larvicidal activity against first instar larvae of Ae.albopictus with a LC50(50%lethal concentration)of 44.9 mg/L after 24 h.Fumigation bioassays showed that Z.cassumunar essential oil exhibits moderate adulticidal activity against Ae.albopictus with a LC50 of 5.44%,while(-)-terpinen-4-ol showed significant adulticidal activity with a LC50 of 2.10%after 24 h.This study verifies that the Z.cassumunar essential oil has mosquito repellent activity,and that(-)-terpinen-4-ol is mainly responsible for this activity.Furthermore,this study provides scientific support for the folk usage of Z.cassumunar essential oil as mosquito repellent and indicates that Z.cassumunar essential oil and(-)-terpinen-4-ol can be used as plant-derived repellents and insecticides for mosquito control.

A new prenylated arylbenzofuran derivative from Morus alba L.

2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including MS,~1H NMR,^(13)C NMR,DEPT,~1H-~1HCOSY,HMQC and HMBC.

Effect of （＋）-limonene and 1-methoxy-2-propanol on Ips typographus response to pheromone blends

We compared two different strategies to increase the catches oflps typographus （L.）, particularly males, in pheromone-baited traps. The first of these strategies, the barrier approach, used alternating pheromone blends, targeting males and females respectively, in closely-spaced traps forming a barrier around forest stands. The second strategy, the single trap approach, used widely-spaced traps that were all baited with the same lure and intended to trap the highest possible numbers of males without compromising trapping of females. In the blend used for the barrier traps targeting primarily males, with a lower percentage of （4S）-cis-verbenol （cV）, the （-）-α-pinene was replaced step wise with （＋）-limonene at rates of 0%, 1%, 10%, 35%, 60% and 90%. This replacement had no significant effect on the numbers of responding 1. typographus males, but there was a slight effect on the percentage of males caught. In the attractant blend for the barrier traps targeting females, with a higher percentage of cV, the 2-methyl-3-buten-2-ol （MB） was replaced with 1-methoxy-2-propanol （MP） in a similar fashion as for the male-specific blends. The replacement did not significantly affect the catch of females. Thus, it is pos- sible to use the MP in the blend with cV and ipsdienol without significant change in catch efficacy. In the blends for single traps, the （-）-α- pinene was replaced with （＋）-limonene and MB with MP. The replacement of （-）-α-pinene had only a slight effect on the percentage of males, but the results suggest that replacing MB with MP in the blend will not significantly reduce trapping efficacy.

Molecular Iodine Promoted Synthesis of New Pyrido[2,3-d]pyrimidin-4-ols

A highly efficient synthesis of novel pyrido[2,3-d]pyrimidin-4-ols was developed via an iodine-catalyzed tandem oxidative cyclization under focused microwave irradiation. Pyrido[2,3-d]pyrimidin-4-ols were obtained from easily available 2-amino-4-aryl-6-arylnicotinamides and benzylic amines with good to excellent yields.

Chemical Composition and Antioxidant Potential of Pistacia lentiscus L. Essential Oil from Oran (Algeria)

Essential oil from the leaves of Pistacia lentiscus L. growing in the Oran region in the west of Algeria was obtained by hydrodistillation with a 1.26 % yield on a dry weight basis. Spectrophotometric analyses were employed to highlight the scavenger capacity of this oil using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. Twenty compounds were identified by GC and CG/MS analyses, and the main part of the compounds of the oil was terpinene-4-ol (41.24%) and α-terpineol (7.31%), α-pinene (9.48%), limonene (09.11%), β-myrcene (10.5%), p-cymene (8.67%) and α-phellandrene (2.20%), β-caryophyllene (12.62%) as major compounds. The DPPH test shows that Pistacia lentiscus essential oil possesses antiradical activity. A linear correlation (correlation coefficient R2 = 0.995, P Pistacia lentiscus essential oil.

新型白念珠菌生物被膜抑制剂IMB-H12的活性和作用机制研究

白念珠菌是真菌感染疾病中的主要病原菌,生物被膜的形成是白念珠菌毒力特征,同时也是重要的耐药机制,开发具有生物被膜抑制活性的抗真菌药物具有重要的意义。本研究对前期获得的新型的具有生物被膜抑制活性的化合物1-(cyclopentylamino)-3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propan-2-ol(简称IMB-H12)进行了深入的研究。IMB-H12对生物被膜的形成具有良好的抑制活性,并且对成熟的生物被膜具有一定的清除作用;初步作用机制研究发现IMB-H12能够抑制酵母-菌丝相的转换、抑制菌丝体的形成,降低白念珠菌的黏附活性和疏水性;IMB-H12能够诱导生物被膜菌细胞壁成分含量的改变,下调多个与黏附和菌丝形成相关的基因的表达。因此,对该化合物的进一步研究,有望发现新型的具有抗真菌活性的先导化合物。

Dietary (poly)phenol intake is associated with cardiometabolic health parameters in adolescents

The protective role of(poly)phenols against metabolic disorders has been extensively studied in adults but not in adolescents.To assess associations of dietary(poly)phenols and their subclasses with cardiometabolic health parameters in adolescents.A cross-sectional study was conducted in 944 individuals aged 11–14 years enrolled in the SI!Program for Secondary Schools trial(NCT03504059).(Poly)phenol intake was assessed using semiquantitative food frequency questionnaires and the Phenol-Explorer database.The measured cardiometabolic parameters were waist circumference(WC)age-sex Z-score,blood pressure(BP)age-sex Z-score,blood glucose(BG),triglycerides(TG),and high-density lipoprotein cholesterol(HDL-c).Multilevel mixedeffect linear regression models were applied to examine the association between(poly)phenol quintiles and cardiometabolic health parameters.Compared to the lowest quintile,adolescents in the highest quintile of total(poly)phenol intake had lower WC Z-scores,mean arterial pressure Z-scores,and HDL-c after multivariable adjustment.The WC Z-scores and HDL-c were lower in the highest quintile of flavonoid intake compared to the lowest quintile.The highest quintile of phenolic acid intake was associated with a lower WC Z-score and TG levels,and the highest quintile of stilbene intake with lower BG and TG,and with higher HDL-c compared to the lowest quintile.A higher intake of(poly)phenols,especially flavonoids,phenolic acids,and stilbenes,was associated with better cardiometabolic parameters in adolescents.

Identification and biosynthesis of plant papanridins,a group of novel oligomeric flavonoids

The discovery of novel flavonoids and elucidation of their biosynthesis are fundamental to understanding their roles in plants and their benefits for human and animal health.Here,we report a new pathway for polymerization of a group of novel oligomeric flavonoids in plants.We engineered red cells for discovering genes of interest involved in the flavonoid pathway and identified a gene encoding a novel flavanol polymerase(FP)localized in the central vacuole.FP catalyzes the polymerization of flavanols,such as epicatechin and catechin,to produce yellowish dimers or oligomers.Structural elucidation shows that these compounds feature a novel oligomeric flaven–flavan(FF)skeleton linked by interflavan–flaven and interflaven bonds,distinguishing them from proanthocyanidins and dehydrodicatechins.Detailed chemical and physical characterizations further confirmed the novel FFs as flavonoids.Mechanistic investigations demonstrated that FP polymerizes flavan-3-ols and flav-2-en-3-ol carbocation,forming dimeric or oligomeric flaven-4→8-flavans,which we term“papanridins.”Data from transgenic experiments,mutant analysis,metabolic profiling,and phylogenetic analyses show that the biosynthesis of papanridins is prevalent in cacao,grape,blueberry,corn,rice,Arabidopsis,and other species in the plant kingdom.In summary,our study discoveries a group of novel oligomeric flavonoids,namely papanridins,and reveals that a novel FP-mediated polymerization mechanism for the biosynthesis of papanridins in plants.

Tea tree oil,a vibrant source of neuroprotection via neuroinflammation inhibition:a critical insight into repurposing Melaleuca alternifolia by unfolding its characteristics

Over the past few decades,complementary and alternative treatments have become increasingly popular worldwide.The purported therapeutic characteristics of natural products have come under increased scrutiny both in vitro and in vivo as part of efforts to legitimize their usage.One such product is tea tree oil(TTO),a volatile essential oil primarily obtained from the native Australian plant,Melaleuca alternifolia,which has diverse traditional and industrial applications such as topical preparations for the treatment of skin infections.Its anti-inflammatory-linked immunomodulatory actions have also been reported.This systematic review focuses on the anti-inflammatory effects of TTO and its main components that have shown strong immunomodulatory potential.An extensive literature search was performed electronically for data curation on worldwide accepted scientific databases,such as Web of Science,Google Scholar,PubMed,ScienceDirect,Scopus,and esteemed publishers such as Elsevier,Springer,Frontiers,and Taylor&Francis.Considering that the majority of pharmacological studies were conducted on crude oils only,the extracted data were critically analyzed to gain further insight into the prospects of TTO being used as a neuroprotective agent by drug formulation or dietary supplement.In addition,the active constituents contributing to the activity of TTO have not been well justified,and the core mechanisms need to be unveiled especially for anti-inflammatory and immunomodulatory effects leading to neuroprotection.Therefore,this review attempts to correlate the anti-inflammatory and immunomodulatory activity of TTO with its neuroprotective mechanisms.

款冬花中抑制肺癌细胞LA795增殖的活性成分研究

分析研究了款冬花中具有抑制肺癌细胞增殖的活性成分.以小鼠肺腺癌LA795细胞为体外抑瘤筛选模型,利用四甲基偶氮唑盐(MTT)比色法,结合硅胶柱色谱,Sephadex LH-20,PHPLC等手段追踪分离款冬花抗肺癌的活性成分.并通过理化和波谱分析方法鉴定了单体化合物的结构.它们分别是:1,2-di-(3′,4′-dihydroxycinnamoyl)-cychopenta-3-ol,(Ⅰ)、芦丁(Rutin,Ⅱ)、山奈酚(Kaemferol,Ⅲ)、槲皮素(Quercetin,Ⅳ)、异槲皮苷(Isoquercitrin,Ⅴ).其中(Ⅰ)为新化合物,化合物(Ⅴ)为首次从款冬花中分离得到.并采用MTT法对分得的化合物进行抑制LA795细胞株增殖作用的研究,用半数抑制浓度(IC)评价其抗肿瘤活性.结果表明化合物Ⅰ,Ⅲ,Ⅳ对小鼠肺腺癌细胞LA795的增殖都显示出一定的抑制作用.其中化合物Ⅰ和Ⅳ抑瘤作用较显著.IC50分别为125.2和83.2μg/mL.这些化合物抗肺癌细胞增殖活性为款冬花中首次发现.