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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Agrocinopine C, a Ti-plasmid-coded enzyme-product, is a 2-O, 6-O linked phosphodiester of D-Glucose and sucrose

    Asenstorfer, Robert E.Ryder, Maarten H.Jones, Graham P.
    8页
    查看更多>>摘要：Agrocinopine C is a small molecule found in crown gall tumours induced by pathogenic Agrobacterium radiobacter carrying the tumour-inducing plasmid pTi Bo542. This phosphodiester opine was isolated (at 0.02 g/100 g fresh wt.) from sunflower (Helianthus annuus L.) galls. It is structurally related to agrocinopine A and is a glucose-2phosphodiester linked to the C6-hydroxy-methyl group of the glucose moiety of sucrose. Sugar-2-phosphates are uncommon in plant tissues, whether transformed by Agrobacterium or not. 1H and 31P NMR signal multiplicity indicates five-fold anomeric complexity of agrocinopine C in solution, implying that the permeases taking up these sucrose-phosphodiesters could recognise any one of the five anomers. Data suggests that the open chain aldehyde forms of the 2-phosphorylated opines agrocinopine C and agrocinopine A and the corresponding phosphorylated glucose-2-phosphoramidate component of the antibiotic agrocin 84 play a central role in agrocin's selective toxicity to certain strains of Agrobacterium after uptake via Ti plasmid-encoded permeases.
      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

    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

    Endophytic fungus Cladosporium tenuissimum DF11, an efficient inducer of tanshinone biosynthesis in Salvia miltiorrhiza roots

    Chen, HaiminChen, JialingQi, YaoChu, Siyuan...
    10页
    查看更多>>摘要：Salvia miltiorrhiza is a traditional medicinal plant mainly used for cardiovascular and cerebrovascular disease treatment. Tanshinones are the main bioactive constituents of S. miltiorrhiza, which mainly accumulate around its root periderm tissue. Endophytic fungi are important bioelicitors or probiotics that can promote the accumulation of secondary metabolites and sustainable cultivation of medicinal plants. Among them, endophytic Cladosporium spp., possessing a variety of biotransformation and metabolic abilities, is an ideal elicitor source. Here, we used a gnotobiotic system to investigate the effects of the endophytic fungus Cladosporium tenuissimum DF11 on tanshinone biosynthesis in S. miltiorrhiza roots. The results showed that C. tenuissimum DF11 mainly colonizes the intercellular space of the root tissues and promotes tanshinone biosynthesis and accumulation in S. miltiorrhiza roots by upregulating the expression of the genes encoding for key enzymes HMGR, DXS, DXR, GGPPS, CPS, KSL and CYP76AH1 of the tanshinone biosynthesis pathway. The expression levels of almost all genes encoding for key enzymes reached the response peak in the first or second week after DF11 colonization. Taken together, the endophytic fungus C. tenuissimum DF11 could promote secondary metabolite accumulation in S. miltiorrhiza roots. These results indicate that DF11 will be a potential biofertilizer fungus to regulate and stabilize the quality of cultivated S. miltiorrhiza medicinal materials.
      原文链接:
    • NSTL
    • Elsevier

    Isolation and structural elucidation of bioactive obovatol dimeric neolignans from the bark of Magnolia officinalis var. biloba

    Xu, KailingMa, JieLi, ChuanLi, Chuangjun...
    6页
    查看更多>>摘要：(+)/(-)-Diobolignans A-F, six pairs of enantiomeric obovatol dimeric neolignans, were isolated from the bark of Magnolia officinalis var. biloba. (+)/(-)-Diobolignans A to C possessed a dioxane ring between the benzene ring and the propyl side chain, while (+)/(-)-diobolignans D to F possessed a furan ring. Meanwhile, (+)/(-)-diobolignans B and C, as well as (+)/(-)-diobolignans E and F, were two epimeric pairs of enantiomers, respectively. Their structures were determined by extensive analyses of HRESIMS, UV, IR, NMR and electronic circular dichroism (ECD) calculations. The bioassay showed (+)-diobolignan A displayed cytotoxic activities against human cancer cell lines HGC27 and HT29 with the IC50 values of 9.43 and 9.45 mu M, respectively. In addition, (-)-diobolignan A and (+/-)-diobolignan E showed neuroprotective effect on glutamic acid-induced cellular damage in SK-N-SH cell.
      原文链接:
    • NSTL
    • Elsevier

    Cytotoxic and alpha-glucosidase inhibitory metabolites from twigs and leaves of Phyllanthus mirabilis, a species endemic to limestone mountains

    Phukhatmuen, PiyapornPornpongrungrueng, PimwadeeKanokmedhakul, SomdejSomteds, Apisara...
    10页
    查看更多>>摘要：The first investigation of Phyllanthus mirabilis Mull.Arg. led to the isolation of six undescribed compounds including two tyramine derivatives: phyllatyramines A and B; three butenolide analogues, phyllantenolide, phyllantenocoside-O-gallate and epi-phyllantenocoside-O-gallate; and a flavanonol gallate, (-)-taxifolin-3-Ogallate; as well as two first isolated natural products, phyllatyramine C and phyllantenocoside; together with twenty-three known compounds. Their structures were elucidated by spectroscopic means. ECD spectra of all isolated butenolides were compared and assigned the configurations. Phyllatyramine A displayed weak cytotoxicity against the KB cell line, while phyllatyramines B and C showed weak cytotoxicity against KB and HeLa cell lines. In addition, phyllatyramine B and (-)-taxifolin-3-O-gallate showed more potent alpha-glucosidase inhibitory activity than the standard acarbose 3.4 and 5.8 fold, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Sesquiterpenes from Kadsura coccinea attenuate rheumatoid arthritis-related inflammation by inhibiting the NF-kappa B and JAK2/STAT3 signal pathways

    Yang, YupeiLiu, YongbeiYu, HuangheXie, Qingling...
    9页
    查看更多>>摘要：The roots of Kadsura coccinea is commonly used in Tujia ethnomedicine, named "heilaohu", having the effect of treating rheumatic arthritis (RA). Chemical investigation on the ethanol extract of heilaohu led to the isolation of one undescribed cuparane sesquiterpenoid, heilaohusesquiterpenoid A, one undescribed carotane sesquiterpenoids, heilaohusesquiterpenoid B, and eighteen sesquiterpene derivatives. Their structures were subsequently determined based on their 1D and 2D-NMR, HR-ESI-MS, and ECD spectroscopic data. Gaultheriadiolide was the most cytotoxic compound against the proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells with an IC50 value of 9.37 mu M. In the same line, nine compounds exhibited significant inhibition effects against TNF-alpha and IL-6 release in the LPS-induced RAW264.7 cells with IC50 values ranging between 1.03 and 10.99 mu M. The potential molecular mechanisms of the active compounds against RA were established through pharmacological network analysis based on the initial screening results. Experimental validation showed that gaultheriadiolide suppressed inflammation by inhibiting the NF-kappa B and JAK2/STAT3 pathways. This study enriches the structural diversity of sesquiterpenes in K. coccinea and lays a foundation for further anti-RA and antiinflammatory studies.
      原文链接:
    • NSTL
    • Elsevier

    Structures of ganorbifates C-I, seven previously undescribed lanostanoids from the mushroom Ganoderma orbiforme, and insights of computed biosynthesis with DFT

    Yin, XiaYu, ChaoTuong, Thi M. L.Kou, Rong-Wei...
    8页
    查看更多>>摘要：Ganorbifates C-I, seven undescribed biosynthetically related polyoxygenated 3,4-seco-27-norlanostanoid congeners, were isolated from the edible mushroom, Ganoderma orbiforme. Ganorbifate C features a unique cyclo-butene ring constructed at C19/C11, and both D and E incorporate an unusual cyclopropane ring formed by C -19/C-9 linkage. Their structures, including the absolute configurations, were determined by spectroscopic methods and ECD calculations. The proposed Norrish-Yang cyclization-based key biosynthetic pathway for ganorbifates C-E is revealed by density functional theory (DFT) calculations. The computational studies uncover the formation of both cyclobutene and cyclopropane rings in the isolates and the stereoselectivity centers of these steps are consistent with those in the natural products. All compounds exhibited NO generation inhibition in LPS-induced BV-2 microglial cells, among them ganorbifate C was the most promising one with the IC50 values of 4.37 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Structure and activity of a novel robust peroxidase from Alkanna frigida cell culture

    Asl, Saeed SoleimaniKarkhane, Ali AsgharAmirzakaria, Javad ZamaniNoghabi, Kambiz Akbari...
    10页
    查看更多>>摘要：Demands for peroxidases (POX)s with diverse physicochemical properties have steadily grown as more applications of POXs are demonstrated. Plants are among the best sources of versatile POXs, and plant biotechnology, as an agricultural hassle-free technology, promises to circumvent the limitations of natural resource exploitation and to address the demands. Following this trend, it was shown that POX production steadily increased during the 31-day subculture of Alkanna frigida (from Boraginaceae) callus on Murashige-Skoog medium containing 2,4dichlorophenoxyacetic acid (10-6 M) and kinetin (10-5 M). The purified cationic enzyme (POXalf) maintained its optimal activity over pH 4-7 for 2 years. It was resistant to H2O2 high concentrations (IC50 = 543.7 mM) and showed high specific activity in the reaction with phenol (4320.5 AU mg-1 > 20-fold of HRP AU). Furthermore, the specificity constant ratio of guaiacol to phenol indicated a 100 times faster reaction of POXalf with guaiacol. However, in contrast to HRP, it had little effect on diazo derivatives of aniline and meta-diaminobenzene. Based on the resulting primary structure from the tandem mass analysis, the POXalf 3D structure was constructed via homology modelling. Despite the high topological similarity between the HRP and POXalf structures, there were important differences between the active site pockets that could explain the observed differences in the corresponding substrate spectra and the specific activities. Considering the dynamics of POXalf production, its inactivity towards IAA and its high affinity for guaiacol, POXalf may have associated roles with A. frigida cell wall construction and monolignol metabolism.
      原文链接:
    • NSTL
    • Elsevier