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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Comparative analysis of cyclotide-producing plant cell suspensions presents opportunities for cyclotide plant molecular farming

    Doffek, BenjaminHuang, YvonneHuang, Yen-HuaChan, Lai Yue...
    10页
    查看更多>>摘要：Cyclotides are a class of ribosomally-synthesized plant peptides that function in plants as a defense against insects and fungal pathogens. Their unique structure comprises a cyclized peptide backbone threaded by three disulfide bonds, that imparts structural stability, a desirable quality for peptide-based therapeutics or insecticides. Producing these peptides synthetically is challenging due to the amount of chemical waste produced and inefficiency of folding certain cyclotides. Thus, it is desirable to develop a means to access cyclotide biosynthesis in their native hosts, cultured in defined conditions, at both laboratory and commercial scale. Here we developed suspension cell cultures from two species previously unexplored for cyclotide production in suspension cells, Clitoria ternatea L., Hybanthus enneaspermus F. Muell., as well as with Oldenlandia affinis (Roem. & Schult.) DC., a species reported previously to accumulate cyclotides in cell suspensions. We assessed the growth rate, cyclotide production and gene expression for the various species. We found that while many cyclotides had reduced expression in Oldenlandia affinis suspension cells when compared to plant organs, those in Clitoria ternatea and Hybanthus enneaspermus maintained or increased expression levels. The cyclotides that continued to be expressed in suspension cultures shared similar sequence and biophysical properties as a group, regardless of phylogenetic origin of the host. Of particular interest was the discovery of inducibility by NaCl of cyclotide expression in O. affinis, cycloviolacin O2 expression in O. affinis, and the scale up of cycloviolacin O2 production in H. enneaspermus. Together the results presented here highlight the utility of plant cell suspensions as modalities to produce macrocyclic peptides.
      原文链接:
    • NSTL
    • Elsevier

    Profiling alkaloids in Aconitum pendulum N. Busch collected from different elevations of Qinghai province using widely targeted metabolomics

    Wang, Jun-JieLou, Hua-YongLiu, YingHan, Hong-Ping...
    10页
    查看更多>>摘要：Aconitum pendulum N. Busch (Ranunculaceae) is rich in alkaloids with anti-inflammatory and analgesic activities. Many studies have focused on the identification or quantification of alkaloid components using low-throughput tests. However, the metabolic differences of plants from environmentally distinct regions remain unclear. The present study profiled alkaloid chemical compounds in the rhizomes of A. pendulum from different regions. A total of 80 chemical compounds were identified using a widely targeted ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) approach. Principal component, hierarchical clustering, and orthogonal partial least squares-discriminant analyses of the chemical compounds indicated that the plants from 6 regions clearly separated into distinct groups. A total of 19 compounds contributed the most to the metabolite differences between collection areas and were identified as potential metabolic markers. The antiinflammatory activities of the A. pendulum extracts were also evaluated and the potential environmental effects on the regulation of metabolite composition and bioactivity were explored. These results improve our understanding of the variation in chemical composition of plants from different regions and will serve as a reference for evaluating the medicinal value of A. pendulum in different environments.
      原文链接:
    • NSTL
    • Elsevier

    Spirornatas A-C from brown alga Turbinaria ornata: Anti-hypertensive spiroketals attenuate angiotensin-I converting enzyme

    Chakraborty, KajalDhara, Shubhajit
    10页
    查看更多>>摘要：Bioactive compounds with angiotensin-I converting enzyme attenuation potential are deemed as therapeutic agents for hypertension owing to their capacity to suppress the conversion of angiotensin-I into the vasoconstrictor angiotensin-II. In an aim to develop natural angiotensin-I converting enzyme (ACE-I) inhibitors from marine algae, three 6, 6-spiroketals, spirornatas A-C were isolated from the organic extract of the spiny brown marine macroalga Turbinaria ornata (Turner) (family Sargassaceae). Spirornata A exhibited comparatively greater ACE-I attenuation potential (IC50 4.5 mu M) than those displayed by other studied spiroketals (IC50 4.7-4.9 mu M), and its activity was comparable to the ACE inhibitory agent captopril (IC50 4.3 mu M). Greater antioxidant properties of spirornata A against oxidants (IC50 1.1-1.3 mM) also substantiated its potential attenuation property against ACE-I. Structure-activity correlation studies showed that electronic properties (topological polar surface area, 71) and balanced hydrophilic-lipophilic parameters (partition coefficient of logarithmic octanolwater similar to 3.2) of spirornata A appeared to play pivotal roles in the inhibition of the targeted enzyme. Predicted drug-likeness and other physicochemical parameters appeared to attribute to the acceptable oral bioavailability of spiroketal derivatives. Additionally, the least binding energy of spirornata A with ACE-I (-10.5 kcal/mol) coupled with the maximum number of hydrogen-bonding interactions with allosteric sites of the zinc-dependent dicarboxypeptidyl peptidase could recognize its potential therapeutic application against hypertensive diseases.
      原文链接:
    • NSTL
    • Elsevier

    Hypoglycemic flavonoids from Selaginella tamariscina (P.Beauv.) Spring

    Long, Hong-PingLiu, JianXu, Ping-ShengXu, Kang-Ping...
    8页
    查看更多>>摘要：Six flavonoids, namely, three undescribed biflavonoids, one undescribed 8-aryl flavonoid, and two known compounds, were isolated from Selaginella tamariscina (P.Beauv.) Spring. The structures and absolute configu-rations of those undescribed compounds were established by NMR spectroscopy data, HRESIMS analyses and electronic circular dichroism (ECD) analyses. In addition, all the isolates were evaluated for their hypoglycemic activity in HepG2 cells. Involvenflavone H, I, and J significantly increased glucose consumption in both normal and insulin-resistant HepG2 cells. Interestingly, these three compounds can effectively upregulate the protein expression of glucokinase (GCK) and adenylate cyclases (ADCYs). These results suggested that involvenflavone H, I, and J (especially involvenflavone J) may have potent hypoglycemic activity, which also provided promising molecular targets for the treatment of diabetes.
      原文链接:
    • NSTL
    • Elsevier

    Global metabolome analysis of Dunaliella tertiolecta, Phaeobacter italicus R11 Co-cultures using thermal desorption- Comprehensive two-dimensional gas chromatography- Time-of-flight mass spectrometry (TD-GCxGC-TOFMS)

    Campos, O. Rene ArredondoBannon, Catherine C.de la Mata, A. PaulinaCase, Rebecca J....
    8页
    查看更多>>摘要：Dunaliella tertiolecta is a marine microalgae that has been studied extensively as a potential carbon-neutral biofuel source (Tang et al., 2011). Microalgae oil contains high quantities of energy-rich fatty acids and lipids, but is not yet commercially viable as an alternative fuel. Carefully optimised growth conditions, and more recently, algal-bacterial co-cultures have been explored as a way of improving the yield of D. tertiolecta micro algae oils. The relationship between the host microalgae and bacterial co-cultures is currently poorly understood. Here, a complete workflow is proposed to analyse the global metabolomic profile of co-cultured D. tertiolectra and Phaeobacter italicus R11, which will enable researchers to explore the chemical nature of this relationship in more detail. To the best of the authors' knowledge this study is one of the first of its kind, in which a pipeline for an entirely untargeted analysis of the algal metabolome is proposed using a practical sample preparation, introduction, and data analysis routine.
      原文链接:
    • NSTL
    • Elsevier

    Anti-inflammatory and cytotoxic specialised metabolites from the leaves of Glandularia x hybrida

    Mohamed, Nesma M.Ahmed, Mai A. M.Khan, Shabana, IFronczek, Frank R....
    10页
    查看更多>>摘要：In our ongoing effort to investigate active specialised metabolites from genus Glandularia, phytochemical studies on the ethanolic extract of Glandularia x hybrida (Groenl. & Rumpler) G.L. Nesom & Pruski leaves resulted in the isolation of three undescribed compounds, a dibenzylbutyrolactolic lignan and two echinocystic acid based triterpenoid saponins, in addition to two known compounds. Interestingly, this study reports isolation of chemosystematically valuable specialised metabolites for the first time from the genus under investigation. Additionally, the isolated metabolites were evaluated for their iNOS inhibition and cytotoxic activities using a combination of in silico and in vitro studies. The pharmacokinetics properties (ADMET) of some of the isolated compounds were determined using pkCSM-pharmacokinetics server. Molecular docking analysis showed that saponin compound possesses higher negative score (-9.59 kcal/mol) than the lignan compound (-6.56 kcal/ mol). The isolated compounds also showed iNOS inhibition activity with IC50 values ranging between 6.6 and 49.7 mu M and significant cytotoxic activity against a series of cell lines including SK-MEL, KB, BT-549, SK-OV-3, LLC-PK1 and VERO cells. Hence, this study reveals that specialised metabolites from G. hybrida plant are of significant anti-inflammatory and cytotoxicity potentials.
      原文链接:
    • NSTL
    • Elsevier

    Occurrence and chemotaxonomical analysis of amatoxins in Lepiota spp. (Agaricales)

    Sarawi, SepasShi, Yan-NiLotz-Winter, HermineReschke, Kai...
    8页
    查看更多>>摘要：About 95% of fatal mushroom poisonings worldwide are caused by amatoxins and phallotoxins mostly produced by species of Amanita, Galerina, and Lepiota. The genus Lepiota is supposed to include a high number of species producing amatoxins. In this study, we investigated 16 species of Lepiota based on 48 recently collected specimens for the presence of amatoxins by liquid chromatography coupled to a diode-array detector and mass spectrometry (UHPLC-QTOF-MS/MS). By comparing the retention times, UV absorptions, and diagnostic MS fragment ions with data obtained from the benchmark species Amanita phalloides, we detected alpha-amanitin and gamma-amanitin in Lepiota subincarnata, alpha-amanitin and amaninamide in Lepiota brunneoincarnata, and beta-amanitin and alpha-amanitin in Lepiota elaiophylla. Phallotoxins have not been detected any of these species. Two possibly undescribed amatoxin derivatives were found in Lepiota boudieri and L. elaiophylla, as well as one further nonamatoxin compound in one specimen of L. cf. boudieri. These compounds might be used to differentiate L. elaiophylla from L. xanthophylla and species within the L. boudieri species complex. No amatoxins were detected in L. aspera, L. castanea, L. clypeolaria, L. cristata, L. erminea, L. felina, L. fuscovinacea, L. lilacea, L. magnispora, L. oreadiformis, L. pseudolilacea, L. sp. (SeSa 5), and L. subalba. By combining the occurrence data of amatoxins with a phylogenetic analysis, a monophyletic group of amatoxin containing species of Lepiota is evident. These chemotaxonomic results highlight the relevance of systematic relationships for the occurrence of amatoxins and expand our knowledge about the toxicity of species of Lepiota.
      原文链接:
    • NSTL
    • Elsevier

    Comprehensive evaluation of Bletilla striata and its substitutes by combining phenotypic characteristic, chemical composition, and anti-melanogenic activity

    Wang, RongbinQin, YadongZhou, JuanjuanWang, Juan...
    11页
    查看更多>>摘要：Bletilla striata is a precious traditional Chinese medical herb with a wide range of applications in pharmacological and cosmetic fields. Because of the shortage of resources, Bletilla ochracea and Bletilla formosanare are also used as the substitutes. To distinguish the differences and homologies, the typical morphologic and microscopic characteristics of them were compared, and a UPLC fingerprint analysis coupled with chemometric methods were developed for characterization and quality evaluation of Bletillae Rhizoma. Gastrodin, protocatechuic acid, gymnoside V, blestrianol A, coelonin, gymnosides IX and batatasin II were identified as the potential chemical markers for comprehensive quality evaluation by ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The anti-melanogenic activities of the three species were also compared for the first time in vivo using the zebrafish model, the results suggested that B. striata and its two substitutes had obvious anti-melanogenic activities, and they were not-toxic at depigmenting doses. Molecular docking studies revealed batatasin III, blestrianol A, coelonin, and gastrodin were possible multitarget compounds associated with melanogenesis suppression, which are important for their potential future medical application.
      原文链接:
    • NSTL
    • Elsevier

    Serratene triterpenoids from Lycopodium cernuum L. as alpha-glucosidase inhibitors: Identification, structure-activity relationship and molecular docking studies

    Wei, Guo-ZhuZhang, Pu-ZhaoLiu, Bing-RuiZheng, Hai-Rong...
    11页
    查看更多>>摘要：Phytochemical investigation of Lycopodium cernuum L. afforded seven undescribed serratene triterpenoids named 3 beta, 21 beta-dihydroxyserra-14-en-24-oic acid-3 beta-(5'-hydroxybenzoate) (1), 3 beta, 21 beta, 24-trihydroxyserrat-14-en-3 beta- (5'-hydroxyl benzoate) (2), 3 beta, 14 alpha, 15 alpha, 21 beta-tetrahydroxyserratane-24-methyl ester (3), 3 beta, 14 alpha, 21 beta-trihy-droxyserratane-15 alpha-(4'-methoxy-5'-hydroxybenzoate)-24-methyl ester (4), 3 beta, 14 alpha, 21 beta-trihydroxyserratane-15 alpha-(4'-methoxy-5'-hydroxybenzoate) (5), 3 beta-hydroxy-21 beta-acetate-16-oxoserrat-14-en-24-oic acid (6), 3 beta, 21 beta-dihydroxy-16 alpha, 29-epoxyserrat-14-en-24-methyl ester (7), together with eleven known compounds (8-18), whose chemical structures were elucidated through spectroscopic analysis of HRESIMS, 1D NMR, 2D NMR and comparison between the literature. All compounds were evaluated for their a-glucosidase inhibitory activity for the first time. The results showed that compounds 1, 2, 4, 5, 6, 10, 13, 15, and 16 were among the most potent alpha-glucosidase inhibitors, with IC50 values ranging from 23.22 +/- 0.64 to 50.65 +/- 0.82 mu M. Structure-activity relationship (SAR) studies indicated that the combined properties of the 5-hydroxybenzoate moiety at C-3, beta-OH at C-21, COOH-at C-24, and Delta(14,15) groups enabled an increase in the alpha-glucosidase inhibitory effect. In addition, molecular docking studies showed that the potential inhibitors mainly interact with key amino acid residues in the active site of alpha-glucosidase through hydrogen bonds and hydrophobic forces.
      原文链接:
    • NSTL
    • Elsevier

    A/D-rings-seco limonoids from the fruits of Aglaia edulis and their bioactivities

    Sun, YujinCui, LetianSun, YunpengLi, Qiurong...
    9页
    查看更多>>摘要：Agledulines A-K, eleven previously undescribed limonoids, including eight biogenic A/D-rings-seco limonoid analogs (agledulines A-H), one D-ring-seco limonoid (agleduline I) and two A-ring-seco limonoids with a rare Delta(4,28) moiety (agledulines J-K), together with twelve reported limonoids, were isolated from the fruits of Aglaia edulis. Their structures were determined by NMR data, HRESIMS, X-ray diffraction, ECD spectra and the CD exciton chirality method. Observably, the absolute configurations of agleduline A, agleduline C and nymania 2 were unambiguously elucidated by single-crystal X-ray diffraction analyses. The biological evaluation showed that agleduline C exhibited significant cytotoxic activities with IC50 values of 10.05 mu M, and 11 alpha-acetoxygedunin showed notable anti-inflammatory activity (IC50: 4.70 mu M). In addition, agleduline I and 11 alpha-acetoxygedunin reversed the multidrug resistance with IC50 values of 5.05 and 1.49 mu M (RI: 4.64 and 15.77) in the MCF-7/Dox cells.
      原文链接:
    • NSTL
    • Elsevier