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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    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

    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

    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

    The GH3 amidosynthetases family and their role in metabolic crosstalk modulation of plant signaling compounds

    Wojtaczka, PatrycjaCiarkowska, AnnaStarzynska, EwelinaOstrowski, Maciej...
    16页
    查看更多>>摘要：The Gretchen Hagen 3 (GH3) genes encoding proteins belonging to the ANL superfamily are widespread in the plant kingdom. The ANL superfamily consists of three groups of adenylating enzymes: aryl- and acyl-CoA synthetases, firefly luciferase, and amino acid-activating adenylation domains of the nonribosomal peptide synthetases (NRPS). GH3s are cytosolic, acidic amidosynthetases of the firefly luciferase group that conjugate auxins, jasmonates, and benzoate derivatives to a wide group of amino acids. In contrast to auxins, which amide conjugates mainly serve as a storage pool of inactive phytohormone or are involved in the hormone degradation process, conjugation of jasmonic acid (JA) results in biologically active phytohormone jasmonyl-isoleucine (JAIle). Moreover, GH3s modulate salicylic acid (SA) concentration by conjugation of its precursor, isochorismate. GH3s, as regulators of the phytohormone level, are crucial for normal plant development as well as plant defense response to different abiotic and biotic stress factors. Surprisingly, recent studies indicate that FIN219/JAR1/ GH3.11, one of the GH3 proteins, may act not only as an enzyme but is also able to interact with tau-class glutathione S-transferase (GSTU) and constitutive photomorphogenic 1 (COP1) proteins and regulate light and stress signaling pathways. The aim of this work is to summarize our current knowledge of the GH3 family.
      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

    Pregnane glycosides from Adonis amurensis and their bioactivity

    Yan, YueZhou, DiLi, XuezhengFeng, Yuan...
    9页
    查看更多>>摘要：Seven undescribed pregnane glycosides named amurensides A-G and two known aglycones were isolated from the whole herb of Adonis amurensis Regel & Radde. Their structures were established based on 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and acid hydrolysis. The cytotoxicity of all compounds against three tumor cell lines (HepG2, Caco-2, and A549) were evaluated. Among them, amurensides A-C and E showed moderate inhibitory effects on the growth of HepG2 cells, with IC50 values ranging from 15.6 to 48.7 mu M (sorafenib, 7.5 +/- 1.9 mu M). Amurensides A, D and F displayed inhibitory effects on the growth of A549 cells with IC50 values of 18.8 +/- 1.2, 12.4 +/- 0.6, and 30.4 +/- 0.1 mu M (cis-platinum, 6.1 +/- 0.1 mu M), 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

    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

    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

    Psilostachyins as trypanocidal compounds: Bioguided fractionation of Ambrosia tenuifolia chemically modified extract

    Adessi, Tonino G.Ana, YamileStempin, Cinthia C.Garcia, Monica C....
    9页
    查看更多>>摘要：This work focusses on the chemical diversification of an Ambrosia tenuifolia extract and its bioguided fractionation, aiming to unveil the chemical entity responsible for the trypanocidal activity. Besides, a revision of the phytochemical study of this species, based on previous reports of the antiparasitic psilostachyins A and C as main compounds, was conducted. To improve the biological properties of a plant extract through a simple chemical reaction, the oxidative diversification of the dichloromethane extract of this plant species was carried out. A bioguided fractionation of a chemically modified extract was performed by evaluating the inhibitory activity against Trypanosoma cruei trypomastigotes. This experiment led to the isolation of one of the most active compounds. In general terms, epoxidized metabolites were obtained as a result of the oxidation of the major metabolite of the species. The trypanocidal activity of some tested metabolites overperformed the reference drug, benznidazole, displaying no cytotoxicity at trypanocidal concentrations. Key structure-activity relationships were obtained for designing previously undescribed antiparasitic sesquiterpene lactones.
      原文链接:
    • NSTL
    • Elsevier