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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    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

    Dammarane-type saponins with proprotein convertase subtilisin/kexin type 9 inhibitory activity from Gynostemma pentaphyllum

    Huang, Ya-PingWang, Yun-ShanLiu, Bi-WenSong, Zhe...
    11页
    查看更多>>摘要：Seven undescribed dammarane-type saponins, gypenosides LXXXI-LXXXVII, together with four known compounds, were isolated from the whole herb of Gynostemma pentaphyllum. The chemical structures of these undescribed compounds were elucidated on the basis of physical and spectroscopic analysis and comparison with literature data. All the isolates were evaluated for their proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitory activities in HepG2 cells. Among them, gypenosides LXXXII-LXXXVII, gynosaponin II, IV and VI suppressed the expression of PCSK9 in LPDS-induced HepG2 cells at 20 mu M; gypenosides LXXXII, LXXXV and LXXXVII showed inhibitory activities against PCSK9 at 10 mu M; notably, gypenoside LXXXII still exhibited inhibitory activity against PCSK9 at 5 mu M.
      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

    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

    Bioactive cytochalasans from the fungus Arthrinium arundinis DJ-13

    Shu, YanWang, Jia-PengLi, Bing-XianGan, Jun-Li...
    8页
    查看更多>>摘要：The investigation of the metabolites from Arthrinium arundinis DJ-13 grown in solid medium revealed six undescribed cytochalasans, arundisins A-F and twelve known compounds. Their structures were initially investigated in detail by spectroscopic analyses and were further confirmed by X-crystallography and ECD experiments. In the in vitro bioassays, arundisins A and B showed cytotoxic activity against the MCF-7 breast cancer cell line with IC50 values of 18.82 +/- 0.36 and 15.20 +/- 0.42 mu M, respectively. Arundisin F exhibited potent antibacterial activity against Escherichia coli with MIC of 8.00 mu g/mL (kanamycin, 2.00 mu g/mL), and arundisin D displayed gently antibacterial activity against Candida albicans with MIC of 32.00 mu g/mL (Nystatin, 1.00 mu g/mL).
      原文链接:
    • NSTL
    • Elsevier

    Squamins C-F, four cyclopeptides from the seeds of Annona globiflora

    Sosa-Rueda, JavierDominguez-Melendez, VanihaminOrtiz-Celiseo, AraceliLopez-Fentanes, Fernando C....
    7页
    查看更多>>摘要：Four cyclic octapeptides, squamins C-F, were isolated from the seeds of Annona globiflora Schltdl. These compounds share part of their amino acid sequence, -Pro-Met(O)-Tyr-Gly-Thr-, with previously reported squamins A and B. Their structures were determined using NMR spectroscopic techniques together with quantum mechanical calculations (QM-NMR), ESI-HRMS data and a modified version of Marfey's chromatographic method. All compounds showed cytotoxic activity against DU-145 (human prostate cancer) and HeLa (human cervical carcinoma) cell lines. Clearly, A. globiflora is an important source of bioactive molecules, which could promote the sustainable exploitation of this undervalued specie.
      原文链接:
    • NSTL
    • Elsevier

    Sesquiterpenoids and furan derivatives from the Orychophragmus violaceus (L.) OE Schulz endophytic fungus Irpex lacteus OV38

    Jia, Ai-QunLuo, Huai-ZhiJiang, HuanSun, Bing...
    9页
    查看更多>>摘要：Nine undescribed compounds, including six tremulane-type sesquiterpenoids, irpexolaceus A-F, one phenolic bisabolane-type sesquiterpenoid, irpexolaceus G, and two furan derivatives, irpexonjust A-B, as well as eight known analogs, were isolated from an endophytic fungus (Irpex lacteus OV38) of Orychophragmus violaceus (L.) O. E. Schulz, a Chinese medicinal and edible plant. The structures of these natural compounds were elucidated based on NMR, HRESIMS, single-crystal X-ray diffraction, and ECD spectroscopic data. Among the tested isolates (50 mu g/mL), the inhibitory effects of irpexolaceus A, C, D, F, and G, irpexonjust B, and irpexlacte B against NO release from LPS-induced RAW 264.7 cells were higher than 45%, while irpexlacte C (42.6%), irpexolaceus B (39.6%), irpexonjust A (43.7%), and irpexolaceus E (33.6%) exhibited weaker inhibitory effects on the release of NO.
      原文链接:
    • NSTL
    • Elsevier

    Jellynolide A, pokepola esters, and sponalisolides from the aquaculture sponge Spongia officinalis L

    Jin, TianyunLi, PinglinWang, CiliTang, Xuli...
    11页
    查看更多>>摘要：Jellynolide A, an unreported bicyclic diterpenoid with an unprecedented penta-substituted carbon skeleton which implied an irregular biogenic pathway, together with four pairs of rare phosphate triesters, (+/-)-pokepola ester B-E, one undescribed related racemic furanoterpenoid, (+/-)-sponalisolide C, one undescribed furanoterpenoid, (-)-sponalisolide D, and two known (+/-)-sponalisolide B and dendrolasin carboxylic acid were isolated from the aquaculture Spongia officinalis L. Their structures were elucidated by comprehensive spectroscopic analysis, quantum chemical calculation of NMR parameters, and electronic circular dichroism (ECD). The plausible biosynthetic pathway of jellynolide A was proposed. (+/-)-Pokepola ester C exhibited significant inhibition against Wnt, HIF1 signaling pathways. (+)-Pokepola ester B and (-)-pokepola ester D showed moderate cytotoxicity activities.
      原文链接:
    • NSTL
    • Elsevier