A Nitrile Glucoside and Biflavones from the Leaves of Campylospermum excavatum (Ochnaceae)

The study of the MeOH extract of the leaves of Campylospermum excavatum led to the isolation of a nitrile glucoside, named campyloside C ( 1 ) and an original derivative of ochnaflavone, 7‐O‐methylochnaflavone ( 2 ), along with three known biflavonoids, amentoflavone, sequoiaflavone, and sotetsuflavone ( 3 – 5 ). The linkage site of the sub‐units of 2 was confirmed by chemical correlation, after semi‐synthesis of a trimethoxylated derivative of ochnaflavone ( 2a ). The structures of these compounds as well as their relative and absolute configurations were assigned by 1D‐ and 2D‐NMR experiments, HR‐ESI‐MS and Electronic Circular Dichroism (ECD) calculations. A low‐pass J filter HMBC experiment was performed in order to define the configuration of the double bond of 1 . All of the biflavonoids were evaluated against protozoan parasites. Amentoflavone moderately inhibited the promastigote form of Leishmania infantum.     

Frequency and distribution of cyanogenic glycosides in Eucalyptus L'Hérit

In this study approximately 420 of the described species of Eucalyptus were examined for cyanogenesis. Our work has identified an additional 18 cyanogenic species, 12 from living tissues and a further six from herbarium samples. This brings the total of known cyanogenic species to 23, representing approximately 4% of the genus. The taxonomic distribution of the species within the genus is restricted to the subgenus Symphyomyrtus, with only two exceptions. Within Symphyomyrtus, the species are in three closely related sections. The cyanogenic glycoside was found to be predominantly prunasin (1) in the 11 species where this was examined. We conclude that cyanogenesis is plesiomorphic in Symphyomyrtus (i.e. a common basal trait) but has probably arisen independently in the other two subgenera, consistent with recent phylogenetic treatments of the genus. The results of this study have important implications for the selection of trees for plantations to support wildlife, and to preserve genetic diversity.     

Diastereomeric stilbene glucoside dimers from the bark of Norway spruce (Picea abies)

As part of a long-term study of the chemical defenses of Norway spruce (Picea abies) against herbivores and pathogens, a phytochemical survey of the phenolics in the bark was carried out. Eight stilbene glucoside dimers, designated as piceasides A-H (1a-4b), were isolated as four 1:1 mixtures of inseparable diastereomers. Their structures were determined by extensive spectroscopic means including 1D (1H and 13C) and 2D NMR (1H-1H COSY, HSQC, HMBC, ROESY) spectra, and were supported by enzymatic hydrolysis and computational analysis.     

Phenolic and iridoid glycosides from Strychnos axillaris

Five phenolic glycosides 1-5 and an iridoid glucoside 6 were isolated, together with 22 known compounds, from the dried barks and woods of Strychnosaxillaris. Their structures were determined by application of spectroscopic (NMR, MS) and chemical methodologies.     

Grevillosides A-F: glucosides of 5-alkylresorcinol derivatives from leaves of Grevillea robusta

From a MeOH extract of leaves of Grevillea robusta, seven compounds (1-7) were isolated. One known compound (7) was identified with a benzyl glucoside, icariside F₂. The structures of the six of these, named grevillosides A-F (1-6), were elucidated on detailed inspection of one- and two-dimensional NMR spectroscopic data as glucosides of 5-alkylresorcinols.     

竹菌化学成分的研究

从肉座菌科真菌竹菌(Engleromyces goetzei P. Henn.)的乙酸乙酯部分分离到一个新化合物(2S, 3S, 4R, 10E)-2-[(2′R)-2′-hydroxytetracosanoyl amino]-10-octadecene-1,3,4-triol (1)和12个已知化合物,分别为cerebroside A、cerebroside B、cerebroside D、cytochalasin D、expoxycytochalasin D、cytochalasin C、loganin、cerevisterol、ergosta-7,22-dien-3β, 5α, 6α-triol、ergosta-4,6,8 (14), 22-tetraen-3-one、ergosterol peroxide和ergosta-5,7,22-trien-3-ol.利用现代波谱方法(1H-NMR、13C-NMR、2D-NMR和ESI-MS等)及化学方法将化合物1鉴定为一新的神经酰胺.除化合物cytochalasin D 外, 其余的化合物均系首次从该真菌中发现.首次从真菌界分离鉴定了一个环烯醚萜甙类化合物 loganin.     

Structural and Functional Analysis of SoPIP2;1 Mutants Adds Insight into Plant Aquaporin Gating

Plant plasma membrane aquaporins facilitate water flux into and out of plant cells, thus coupling their cellular function to basic aspects of plant physiology. Posttranslational modifications of conserved phosphorylation sites, changes in cytoplasmic pH and the binding of Ca²⁺ can regulate water transport activity by gating the plasma membrane aquaporins. A structural mechanism unifying these diverse biochemical signals has emerged for the spinach aquaporin SoPIP2;1, although several questions concerning the opening mechanism remain. Here, we describe the X-ray structures of the S115E and S274E single SoPIP2;1 mutants and the corresponding double mutant. Phosphorylation of these serines is believed to increase water transport activity of SoPIP2;1 by opening the channel. However, all mutants crystallised in a closed conformation, as confirmed by water transport assays, implying that neither substitution fully mimics the phosphorylated state. Nevertheless, a half-turn extension of transmembrane helix 1 occurs upon the substitution of Ser115, which draws the C^α atom of Glu31 10 Å away from its wild-type conformation, thereby disrupting the divalent cation binding site involved in the gating mechanism. Mutation of Ser274 disorders the C-terminus but no other significant conformational changes are observed. Inspection of the hydrogen-bond interactions within loop D suggested that the phosphorylation of Ser188 may also produce an open channel, and this was supported by an increased water transport activity for the S188E mutant and molecular dynamics simulations. These findings add additional insight into the general mechanism of plant aquaporin gating.     

枇杷叶的化学成分

枇杷叶系蔷薇科（Rosaceae）枇杷属植物枇杷[Eriobotrya japonica（Thunb．）Lindl．]的干燥叶,为常用中药,收载于历版《中华人民共和国药典》中。枇杷叶归肺、胃经,具清肺止咳、降逆止呕的作用,用于治疗肺热咳嗽、气逆喘气、胃热呕逆及烦热口渴之症状。目前,已经从枇杷叶中分离出三萜酸、黄酮类、多酚、倍半萜及其苷类等成分,对其药效的研究主要集中在三萜酸的抗炎心、降血糖和抗病毒活性等方面。     

Spectroscopic and in silico study of binding mechanism of cynidine‐3‐O‐glucoside with human serum albumin and glycated human serum albumin

The drug–serum albumin interaction plays a dominant role in drug efficacy and disposition. The glycation of serum albumin that occurs during diabetes may affect its drug‐binding properties in vivo. In order to evaluate the interactivity characteristics of cyanidin‐3‐O‐glucoside (C3G) with human serum albumin (HSA) and glycated human serum albumin (gHSA), this study was undertaken using multiple spectroscopic techniques and molecular modeling analysis. Time‐resolved fluorescence and the thermodynamic parameters indicated that the quenching mechanism was static quenching, and hydrogen bonding and Van der Waals force were the main forces. The protein fluorescence could be quenched by C3G, whereas the polarity of the fluorophore was not obviously changed. C3G significantly altered the secondary structure of the proteins. Furthermore, the interaction force that existed in the HSA–C3G system was greater than that in the gHSA–C3G system. Fluorescence excitation emission matrix spectra, red edge excitation shift, Fourier transform infrared spectroscopy and circular dichroism spectra provided further evidence that glycation could inhibit the binding between C3G and proteins. In addition, molecular modeling analysis supported the experimental results. The results provided more details for the application of C3G in the treatment of diabetes.     

岩芋中的一个新苯丙素苷

从岩芋(Remusatia vivipara)干燥的球茎中分离得到10个化合物,其中一个为新的苯丙素苷,经波谱学分析及酸水解的方法确定该新化合物的结构为Caffeyl alcohol-3-O-β-D-glucopyranoside.已知化合物包括3个苯丙素类(松柏苷,caffeyl alcohol和松柏醇),3个新木脂素[4,7,9,9-tetrahydroxy-3,3-dimethoxy-8-O-4-neolign-7-ene,(7 R,8S)-△~(7')-3,3-dimethoxy-4,7,9,9-tetrahydroxy-8-O-4-neoli-gnan-7-O-β-D-glucopyranoside,以及dehydrodiconiferyl alcohol-4-β-D-glucoside],1个酰胺[(2 E,4 E)-N-isobutyl-2,4-decadienamide],1个甾体皂苷(methyl proto-taccaoside)和1个三萜皂苷(saxifra-gifolin B).所有化合物均为首次从岩芋属植物中分离得到.