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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    13,13a-seco-protoberberines from the tubers of Corydalis yanhusuo and their anti-inflammatory activity

    Xia, Gui-YangFang, Dong-JieWang, Ling-YanXia, Huan...
    9页
    查看更多>>摘要：Six undescribed protoberberine derivatives including two pairs of enantiomers, named yanhusanines G-L, along with fifteen reported protoberberine alkaloids, were isolated from the tubers of Corydalis yanhusuo. Among them, yanhusanines H-L feature a unique 13,13a-seco skeleton which is rare in nature. Their structural elucidations were achieved by extensive spectroscopic analysis and quantum chemistry calculations. A biogenetic route for yanhusanines H-L was proposed. Bioassay results showed that yanhusanine J exhibited potent inhibitory effect against the nitric oxide (NO) production in lipopolysaccharide (LPS) induced RAW 264.7 cells (IC50 = 2.25 +/- 1.32 mu M). Western blot analysis demonstrated that yanhusanine J exerted its anti-inflammatory effect via suppressing the nuclear factor kappa B (NF-kappa B) pathway, together with the decrease of the inflammatory factors TNF-alpha, IL-6 and IL-1 beta. Furthermore, molecular simulation docking indicated that yanhusanine J had strong interaction with the active site of the inducible nitric oxide synthase (iNOS) protein.
      原文链接:
    • NSTL
    • Elsevier

    Changes in glycosyl inositol phosphoceramides during the cell cycle of the red alga Galdieria sulphuraria

    Vitova, MiladaCizkova, MariaNahlik, VitRezanka, Tomas...
    10页
    查看更多>>摘要：Sphingolipids are significant component of plant-cell plasma membranes, as well as algal membranes, and mediate various biological processes. One of these processes is the change in lipid content during the cell cycle. This change is key to understanding cell viability and proliferation. There are relatively few papers describing highly glycosylated glycosyl inositol phosphorylceramide (GIPC) due to problems associated with the extractability of GIPCs and their analysis, especially in algae. After alkaline hydrolysis of total lipids from the red alga Galdieria sulphuraria, GIPCs were measured by highresolution tandem mass spectrometry and fragmentation of precursor ions in an Orbitrap mass spectrometer in order to elucidate the structures of molecular species. Fragmentation experiments such as tandem mass spectrometry in the negative ion mode were performed to determine both the ceramide group and polar head structures. Measurement of mass spectra in the negative regime was possible because the phosphate group stabilizes negative molecular ions [M-H]-. Analysis: of GIPCs at various stages of the cell cycle provided information on their abundance. It was found that, depending on the phases of the cell cycle, in particular during division, the uptake of all three components of GIPC, i.e., long-chain amino alcohols, fatty acids, and polar heads, changes. Structural modifications of the polar headgroup significantly increased the number of molecular species. Analysis demonstrated a convex characteristic for molecular species with only one saccharide (hexose or hexuronic acid) as the polar head. For two carbohydrates, the course of Hex-HexA was linear, while for HexA-HexA it was concave. The same was true for GIPC with three and four monosaccharides.
      原文链接:
    • NSTL
    • Elsevier

    Molecular differentiation of Panax notoginseng grown under different conditions by internal extractive electrospray ionization mass spectrometry and multivariate analysis

    Zhang, XiaopingQiu, Zi-DongLiu, MingxingXu, Jiaquan...
    9页
    查看更多>>摘要：Panax notoginseng is a highly valuable and widely used herb in traditional Chinese medicine. The quality and efficacy of Panax notoginseng grown under different conditions can greatly vary due to the differences in chemical composition. The analysis of chemical composition in Panax notoginseng typically involves various experimental steps including extraction, chromatographic separation and characterization, which can be time-and labor-consuming. Therefore, the efficient quality assessment and control of Panax notoginseng requires the develop-ment of more rapid methods for the chemical characterization and classification of Panax notoginseng. In this study, a method based on internal extractive electrospray ionization mass spectrometry (iEESI-MS) was devel-oped to characterize chemical components of Panax notoginseng samples under different growth conditions (e.g., place of origin, soil quality, growth season) at the speed of 0.5 min per sample, without sample pretreatment and chromatographic separation. A total of 35 chemical components, including sugars, saponins, organic acids, etc., were identified in Panax notoginseng samples. Clear separation was observed in the multivariate analysis of the iEESI-MS data from Panax notoginseng samples grown under different conditions. The difference in the content of sucrose, fructose, Rg1, Rf, Rb1, Noto-R1, malonyl-Rb1, malonyl-Rg1, malonyl-Rf, Rd, Re, linoleic acid, palmitic acid and malic acid can be used as key characteristic indicators to discriminate origin, commercial specifications, and cultivation conditions of Panax notoginseng samples. The results of our study indicate the high power of iEESI-MS for the rapid molecular characterization and classification of Panax notoginseng under different growth conditions, which can be used for the quality assessment of traditional herbal medicines as well as in pharma-ceutical and clinical analysis.
      原文链接:
    • NSTL
    • Elsevier

    Effect of light intensity on steviol glycosides production in leaves of Stevia rebaudiana plants

    Vives Hernandez, KarelMoreno-Romero, JordiHernandez de la Torre, MarthaPerez Manriquez, Claudia...
    10页
    查看更多>>摘要：Stevia rebaudiana leaf extracts contain stevioside and rebaudioside A, two steviol glycosides (SGs) used as natural sweeteners because of their non-toxic, thermally stable and non-caloric properties. Indeed, leaf extracts can be up to 300 times sweeter than sucrose. Stevioside and rebaudioside A have organoleptic differences, the first one having an undesirable bitterness and the second one a higher sweetener capacity. Selection of the S. rebaudiana varieties and the best environmental conditions that elicit higher SGs content and the appropriate composition is an important goal. In this study we quantified and compared the amount of stevioside and rebaudioside A in two of the most used S. rebaudiana cultivars, Morita II and Criolla. Our results show a strong differential ratio of stevioside and rebaudioside A accumulated in the leaf between these cultivars. The Criolla cultivar showed about 3 times more stevioside per mg of dry weight than Morita II, whereas the Morita II accumulated almost 10 times more rebaudioside A than that produced in Criolla. We observed an enhanced expression in Morita II of three genes (SrKA13H, SrUGT74G1 and SrUGT76G1) known to encode three enzymes that participate in SGs biosynthesis, likely contributing to the differences in the stevioside and rebaudioside A accumulation. Not only genetic variation can affect SGs composition, but also environmental factors and crop management. Numerous studies have shown that the light regime in which S. rebaudiana cultivars grow can affect SGs accumulation. However, the optimal light regime to increase total SGs content is currently controversial. By applying various light intensities, we detected an increase of expression of these three biosynthetic genes at higher light intensity, accompanied by higher levels of stevioside and rebaudioside A, demonstrating that light intensity influences the synthesis of SGs.
      原文链接:
    • NSTL
    • Elsevier

    Isolation, absolute configurations and bioactivities of pestaphilones A-I: Undescribed methylated side chain containing-azaphilones from Pestalotiopsis oxyanthi

    Deng, MengyiQiao, YubenShi, ZhengyiWang, Jianping...
    10页
    查看更多>>摘要：Nine undescribed side chain containing azaphilones, pestaphilones A-I, were isolated from the Anoectochilus roxburghii endophytic fungus Pestalotiopsis oxyanthi. The structures of these isolates were identified by spectroscopic data, electronic circular dichroism (ECD) calculations and comparisons, quantum-chemical C-13 NMR calculations with DP4+ probability analysis, Rh-2(OCOCF3)(4)-induced ECD, acetonide formation, selective oxidation reaction and X-ray crystallographic data. Structurally, pestaphilones A-I were the first azaphilones characteristically formed via a methyl group at C-9 in the C-7 side chain. More importantly, a selective oxidation reaction was firstly set up to resolve the absolute configuration of flexible side chain containing azaphilones, and an acetonide formation based Rh-2(OCOCF3)(4)-induced ECD experiment was performed to identify the configurations of the oxygenated pyranoquinone core in the azaphilones. In bioassay, pestaphilones A-F displayed potential immunosuppressive activity in concanavalin A (Con A)-induced T lymphocyte proliferation, with IC50 values ranging from (9.36 +/- 1.14) mu M to (35.21 +/- 3.25) mu M.
      原文链接:
    • NSTL
    • Elsevier

    Isoquinoline alkaloid dimers with dopamine D1 receptor activities from Menispermum dauricum DC

    Wei, Hong-LiHan, YangZhou, HanHou, Tao...
    9页
    查看更多>>摘要：A phytochemical investigation on chemical constituents from the rhizomes of Menispermum dauricum DC. identified eight undescribed dimeric alkaloids with structurally diverse monomeric isoquinoline. Alkaloid structures were elucidated by a combination of spectroscopic data analyses and time-dependent density functional theory (TDDFT) ECD calculation. The isolates were evaluated for inhibitory effect on dopamine D1 receptor and compound 1 exhibited potent D1 receptor antagonistic activity with an IC50 value of 8.4 +/- 2.0 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Polyhydroxylated bergamotane-type sesquiterpenoids from cultures of Paraconiothyrium sporulosum YK-03 and their absolute configurations

    Pei, Yue-HuZhang, Li-HuaWu, Xi-LeWu, Hong-Hua...
    8页
    查看更多>>摘要：Eight undescribed polyhydroxylated bergamotane-type sesquiterpenoids with bicyclic, tricyclic and tetracyclic systems, namely sporulamides A-D, sporulosoic acids A-B and sporuloketals A-B, along with three known analogs were isolated from cultures of the marine mud-associated fungus Paraconiothyrium sporulosum YK-03. The chemical structures of these sesquiterpenoids were elucidated by the extensive spectroscopic techniques of NMR and HR-ESI-MS. Assisted by the X-ray crystallography analysis and electronic circular dichroism (ECD) spectroscopic calculation and comparison, their absolute configurations were established. Sporuloketals A-B represent two rare tetracyclic bergamotanes. It's the first time that ECD empirical rules have been successfully verified and applied for determining the absolute configurations of these bergamotane-type sesquiterpenoids.
      原文链接:
    • NSTL
    • Elsevier

    Metabolite profiles of brown planthopper-susceptible and resistant rice (Oryza sativa) varieties associated with infestation and mechanical stimuli

    Uawisetwathana, UmapornJamboonsri, WatchareewanBamrungthai, JakrinJitthiang, Prapatsorn...
    10页
    查看更多>>摘要：Understanding brown planthopper (BPH) resistance mechanism will expedite selective breeding of better BPH resistant lines of rice (Oryza sativa). Metabolic responses during BPH infestation derived from wound stress imposed by insect feeding, comparing with mechanical piercing will provide an insight into resistance mechanism in rice. Therefore, this study aimed to compare the metabolic responses of needle piercing treatment and BPH feeding treatment in BPH-susceptible (KD) and BPH-resistant (RH) varieties at four different time points (0, 6, 24 and 96 h) using liquid chromatography-high resolution mass spectrometry (LC-HRMS). Phenotypes of RH were not different among the treatments, whereas KD exhibited hopperburn symptom at 96 h post-BPH infestation. Principal component and cluster analyses revealed that metabolite profiles between KD and RH were different in response to both insect and mechanical stimuli. Metabolite profiles of RH under BPH and mechanical treatments at 24 and 96 h were different from the untreated, whereas metabolite profiles of KD after BPH infestation at 24 and 96 h were distinct from needle piercing and no treatment, suggesting that the resistant variety has an ability to adapt and defend both mechanical and insect stimuli. Metabolomics result showed that BPH infestation perturbed purine salvage biosynthesis (e.g., inosine, hypoxanthine) in both varieties, amino acid biosynthesis (e.g., phenylalanine, tryptophan) in KD, while the infestation perturbed lysine metabolism (pipe colic acid) and phenylpropanoid pathway (2-anisic acid) only in RH. BPH and mechanical stimuli perturbed phenylamide only in RH, but not in KD. These findings revealed that different rice varieties utilize different metabolites in response to insect and mechanical stimuli, resulting in different degrees of resistance.
      原文链接:
    • NSTL
    • Elsevier

    Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

    Vrabec, RudolfMarikova, JanaLocarek, MiroslavKorabecny, Jan...
    13页
    查看更多>>摘要：One undescribed indole alkaloid together with twenty-two known compounds have been isolated from aerial parts of Vinca minor L. (Apocynaceae). The chemical structures of the isolated alkaloids were determined by a combination of MS, HRMS, 1D, and 2D NMR techniques, and by comparison with literature data. The NMR data of several alkaloids have been revised, corrected, and missing data have been supplemented. Alkaloids isolated in sufficient quantity were screened for their in vitro acetylcholinesterase (AChE; E.C. 3.1.1.7) and butyrylcholinesterase (BuChE; E.C. 3.1.1.8) inhibitory activity. Selected compounds were also evaluated for prolyl oligopeptidase (POP; E.C. 3.4.21.26), and glycogen synthase 3 beta-kinase (GSK-3 beta; E.C. 2.7.11.26) inhibition potential. Significant hBuChE inhibition activity has been shown by (- )-2-ethyl-3[2-(3-ethylpiperidinyl)-ethyl]-1Hindole with an IC50 value of 0.65 +/- 0.16 mu M. This compound was further studied by enzyme kinetics, along with in silico techniques, to reveal the mode of inhibition. This compound is also predicted to cross the blood-brain barrier (BBB) through passive diffusion.
      原文链接:
    • NSTL
    • Elsevier

    Potential inhibitors of microglial activation from the roots of Vernicia montana Lour

    Wang, YingjieChen, GangMeng, QingqiYao, Xiaohu...
    9页
    查看更多>>摘要：During our continuous investigation of natural, herbal inhibitors of microglial over-activation in the Euphorbiaceae family, two plants of the Vernicia genus showed remarkable inhibitory effects on nitric oxide (NO) production in over-activated microglia. In this study, bioactivity-guided phytochemical research on the active fraction of the roots of V. montana was carried out. As a result, seven undescribed terpenoids and lignans, together with thirty-one known components, were isolated and identified using comprehensive spectral analysis. All the identified compounds were evaluated for their inhibitory effects on NO production in lipopolysaccharidestimulated BV-2 cells. Combined with our previous research on the Vernicia genus, the effective material basis of different plants and medicinal components was analyzed systematically.
      原文链接:
    • NSTL
    • Elsevier