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Alexander E Wilson, Sheng Wu, Li Tian
UDP-dependent glycosyltransferases (UGTs) convert aglycones into more stable, bioactive, and structurally diverse glycosylated derivatives. Pomegranate (Punica granatum L.) produces various glycosylated phenolic metabolites, e.g. hydrolyzable tannins (HTs), anthocyanins, and flavonoids, and constitutes an excellent system for investigating the corresponding UGT activities. Here we report the cloning and functional characterization of a pomegranate UGT, PgUGT95B2, which is highly active towards flavones and flavonols and can glycosylate at more than one position in the substrate molecule...
November 9, 2018: Phytochemistry
Srichanadan Padhi, Marco Masi, Alessio Cimmino, Angela Tuzi, Subhrakanta Jena, Kumananda Tayung, Antonio Evidente
An undescribed substituted dihydroxanthene-1,9-dione, named funiculosone, was isolated together with its two analogues identified as mangrovamide J and ravenelin, from the culture filtrates of Talaromyces funiculosus (Thom) Samson, Yilmaz, Frisvad & Seifert (Trichocomaceae), an endolichenic fungus isolated from lichen thallus of Diorygma hieroglyphicum (Pers.) Staiger & Kalb (Graphidaceae), in India. Funiculosone was characterized, essentially by spectroscopic methods, as 4,8,9a-trihydroxy-3,4a-dimethyl-4a,9a-dihydro-4H-xanthene-1,9-dione...
November 9, 2018: Phytochemistry
Trine Bundgaard Andersen, Silas Anselm Rasmussen, Søren Brøgger Christensen, Henrik Toft Simonsen
The genus Thapsia produces a wide variety of sesquiterpenoids. The Mediterranean plant Thapsia laciniata Rouy is known to have a product profile that differs from several other species in the genus. Thus, the biosynthesis of sesquiterpenoids in Thapsia laciniata Rouy was investigated. Here we describe three terpene synthases, TlTPS820, TlTPS509 and TlTPS18983. TlTPS18983 is a multi-product enzyme with farnesene as the major product, while TlTPS509 produces guaiol and bulnesol along with other major and several minor unknown products...
November 5, 2018: Phytochemistry
Luigi Lucini, Giuseppe Colla, Maria Begoña Miras Moreno, Letizia Bernardo, Mariateresa Cardarelli, Valeria Terzi, Paolo Bonini, Youssef Rouphael
Root exudation patterns are linked to, among other things, plant growth, plant-microbe interaction and the priming effect. In this work, two complementary metabolomic approaches (both liquid and gas chromatography coupled to mass spectrometry) were applied to investigate the modulation of root exudation imposed by two beneficial fungi (substrate treatment of Trichoderma atroviride AT10, substrate application of Rhizoglomus irregulare BEG72 and seed treatment with T. atroviride AT10) on wheat (Triticum aestivum L...
November 5, 2018: Phytochemistry
Yangyang Xiao, Ling Lv, Ping Gou, Haihui Xie
Eight previously undescribed acyl atractyligenin and carboxyatractyligenin glycosides were isolated from whole Antennaria rosea subsp. confinis (Greene) R. J. Bayer (Compositae) [syn. Leontopodium leontopodioides (Willd.) Beauv. (Asteraceae)] plants and their structures were determined by spectroscopic and chemical methods. The compounds were trivially named leontopodiosides F-M. Seven of the compounds showed potent in vitro inhibitory activity toward pancreatic lipase with IC50 values ranging from 3.4 to 52...
November 5, 2018: Phytochemistry
Vedanjali Gogineni, Manal A Nael, Francisco León, Marvin J Núñez, Stephen J Cutler
Calea urticifolia (Mill.) DC. (Compositae) is a medicinal plant found in El Salvador. Calea is used in folkloric medicine as a psychoactive principle with calming effect, as well as in the treatment of diarrhea and fever. Three undescribed bisabolenes, named caleanolenes A-C, as well as, three known sesquiterpene lactones 2,3-epoxyjuanislamin, calealactone B, calein C, and the flavonoid acacetin, were isolated from the chloroform extract of the leaves of C. urticifolia. The chemical structures of the isolated compounds were determined on the basis of HRMS, IR, CD, and from 1D and 2D NMR spectroscopic studies...
November 3, 2018: Phytochemistry
Carolina Elejalde-Palmett, Kévin Billet, Arnaud Lanoue, Johan-Owen De Craene, Gaëlle Glévarec, Olivier Pichon, Marc Clastre, Vincent Courdavault, Benoit St-Pierre, Nathalie Giglioli-Guivarc'h, Thomas Dugé de Bernonville, Sébastien Besseau
The UDP-glycosyltransferase UGT88F subfamily has been described first in Malus x domestica with the characterization of UGT88F1. Up to now UGT88F1 was one of the most active UGT glycosylating dihydrochalcones in vitro. The involvement of UGT88F1 in phloridzin (phloretin 2'-O-glucoside) synthesis, the main apple tree dihydrochalcone, was further confirmed in planta. Since the characterization of UGT88F1, this new UGT subfamily has been poorly studied probably because it seemed restricted to Maloideae. In the present study, we investigate the apple tree genome to identify and biochemically characterize the whole UGT88F subfamily...
November 3, 2018: Phytochemistry
Mikhail S Drenichev, Mark Bennett, Roman A Novikov, John Mansfield, Nick Smirnoff, Murray Grant, Sergey N Mikhailov
Our understanding of how, and the extent to which, phytopathogens reconfigure host metabolic pathways to enhance virulence is remarkably limited. Here we investigate the dynamics of the natural disaccharide nucleoside, 3'-O-β-D-ribofuranosyladenosine, in leaves of Arabidopsis thaliana infected with virulent Pseudomonas syringae pv. tomato strain DC3000. 3'-O-β-D-ribofuranosyladenosine is a plant derived molecule that rapidly accumulates following delivery of P. syringae type III effectors to represent a major component of the infected leaf metabolome...
November 3, 2018: Phytochemistry
Arsenij Kokorin, Christoph Weise, Simko Sama, Alexander Weng
Ribosome-inactivating proteins (RIPs) are enzymes with N-glycosylase activity that remove adenine bases from the ribosomal RNA. In theory, one single RIP molecule internalized into a cell is sufficient to induce cell death. For this reason, RIPs are of high potential as toxic payload for anti-tumor therapy. A considerable number of RIPs are synthesized by plants that belong to the carnation family (Caryophyllaceae). Prominent examples are the RIPs saporin from Saponaria officinalis L. or dianthin from Dianthus caryophyllus L...
November 3, 2018: Phytochemistry
G N Veremeichik, V P Grigorchuk, S A Silanteva, Y N Shkryl, D V Bulgakov, E V Brodovskaya, V P Bulgakov
Calcium-dependent protein kinases (CDPKs) represent a class within a multigene family that plays an important role in biotic and abiotic plant stress responses and is involved in the regulation of secondary metabolite biosynthesis. Our previous study showed that overexpression of the mutant constitutively active Ca2+ independent form of the AtCPK1 gene (AtCPK1-Ca) significantly increased the biosynthesis of anthraquinones and stilbenes in Rubia cordifolia L. and Vitis amurensis Rupr. transgenic cell cultures, respectively...
November 2, 2018: Phytochemistry
Ivan R Chechetkin, Alexander S Blufard, Andrey Y Yarin, Evgenia O Fedina, Bulat I Khairutdinov, Alexander N Grechkin
Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species...
October 31, 2018: Phytochemistry
Chun-Li Xia, Gui-Hua Tang, Yan-Qiong Guo, You-Kai Xu, Zhi-Shu Huang, Sheng Yin
Mulberry Diels-Alder-type adducts (MDAAs) are a group of structurally unique natural products biosynthetically derived from the intermolecular [4 + 2] cycloaddition of a dehydroprenylphenol and a chalcone. In the current study, ten MDAAs, including an undescribed one, inethermulberrofuran C, were isolated from the root bark of Morus alba. The anti-Alzheimer's disease (anti-AD) properties of these isolates were systematically screened for a series of potential targets (Aβ self-aggregation, tau aggregation, and ChEs) as well as the anti-neuroinflammatory and neuroprotective activities...
October 31, 2018: Phytochemistry
XingRong Peng, Lei Li, JinRun Dong, ShuangYang Lu, Jing Lu, XiaoNian Li, Lin Zhou, MingHua Qiu
Twelve previously undescribed lanostane-type triterpenoids, including three triterpenoids with a γ-lactone ring, namely applanlactones A‒C, four highly oxygenated lanostane triterpenoids, namely methyl applaniate A and applanoic acids B‒D, as well as five C21 nortriterpenoids, applanones A‒E were isolated from the fruiting bodies of Ganoderma applanatum (Pers.) Pat.. Their structures were elucidated by 1D, 2D NMR and MS spectra, as well as X-ray crystallographic analyses. Meanwhile, applanlactone A, methyl applaniate A and applanoic acid B showed inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-β1 (TGF-β1) in vitro...
October 31, 2018: Phytochemistry
Shaowei Han, Chao Wang, Baosong Cui, Hua Sun, Jianjun Zhang, Shuai Li
Ten previously undescribed glucosyloxybenzyl succinate derivatives, pleionosides A-J, and fifteen known compounds were isolated from the pseudobulbs of Pleione bulbocodioides (Franch.) Rolfe. Their structures were elucidated by a combination of MS and NMR data, physical and chemical methods and a comparison with known compounds. Furthermore, three compounds exhibited potent hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays, with cell survival rates of 31...
October 29, 2018: Phytochemistry
Arnon Chukaew, Saowanit Saithong, Sasitorn Chusri, Surasuk Limsuwan, Ramida Watanapokasin, Supayang P Voravuthikunchai, Suda Chakthong
Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xanthones were elucidated based on spectroscopic methods. 5-Hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone were also confirmed by X-ray diffraction data. In addition, the isolated compounds were determined for antibacterial, antioxidant and cytotoxic activities...
October 24, 2018: Phytochemistry
Jin-Pyo An, Lan Huong Dang, Thi Kim Quy Ha, Ha Thanh Tung Pham, Ba-Wool Lee, Chul Ho Lee, Won Keun Oh
A library of extracted natural materials (Korea Bioactive Natural Material Bank) have been screened to discover candidates for the treatment of non-alcoholic liver disease (NAFLD), and the 70% ethanol extract of Sicyos angulatus was found to inhibit hepatic lipid accumulation. Bioassay-guided fractionation of this bioactive extract yielded five previously undescribed flavonoid glycosides and one previously undescribed flavonolignan glycoside along with seven known flavonoid glycosides. The chemical structures of these compounds were elucidated by a combination of extensive spectroscopic analysis, including MS, NMR and UV techniques...
October 24, 2018: Phytochemistry
Kai Guo, Yan-Chun Liu, Yan Liu, Shi-Hong Luo, Wen-Yuan Li, Xiao-Nian Li, Sheng-Hong Li
Twenty-four diterpenoids of abietane family, including thirteen undescribed compounds and eleven known ones, were isolated from the leaves of Leucosceptrum canum. Their structures were elucidated by comprehensive spectroscopic analyses (including 1D and 2D-NMR and HRMS), and in the case of 15-hydroxy-abieta-8,11,13-trien-3-one by single-crystal X-ray diffraction. Their frameworks are highly diversified, involving normal abietane, 9,10-epoxy-9,10-seco-abietane, 18(4 → 3)-abeo-abietane, 3,4-seco-18(4 → 3)-abeo-abietane, and 16-nor-abietane...
October 23, 2018: Phytochemistry
Md Nur Ahad Shah, Shatil Arabia, Tahmina Islam, Ajit Ghosh
SUN (Sad1/UNC-84) domain-containing proteins are highly conserved throughout evolution. They are localized to the inner membrane of the nuclear envelope and are involved in nuclear migration and nucleoskeleton formation. In the present study, a genome-wide investigation was performed in three dicotyledonous (Arabidopsis thaliana, Glycine max and Medicago truncatula) and three monocotyledonous (Oryza sativa, Zea mays and Sorghum bicolor) plants. A total of 56 SUN proteins encoded by 30 genes were identified...
October 22, 2018: Phytochemistry
Wuttichai Jaidee, Raymond J Andersen, Brian O Patrick, Stephen G Pyne, Chatchai Muanprasat, Suparerk Borwornpinyo, Surat Laphookhieo
Eight previously undescribed compounds, including four alkaloids and five styryllactones together with 36 known compounds were isolated from the twig and leaf extracts of Goniothalamus cheliensis. Their structures were elucidated by extensive analysis of their spectroscopic data. The absolute configuration of (-)-(4S,5S,6R,7S,8S)-goniochelienlactone and (-)-(4S,5S,6R,7S,8S)-7-acetylgoniochelienlactone were established from single crystal X-ray analysis using Cu Kα radiation. The absolute configurations of the other related compounds were identified by comparisons of their ECD spectra with those of related known compounds...
October 20, 2018: Phytochemistry
Jiayin Yue, Yuanyuan Sun, Jing Xu, Jiaqing Cao, Gang Chen, Huixing Zhang, Xiaoshu Zhang, Yuqing Zhao
Momordica charantia L. (Cucurbitaceae) is a popular vegetable and traditional folk medicine, that has been used for hundreds of years. In this study, three undescribed cucurbitane-type triterpene glycosides furpyronecucurbitane A, goyaglycoside I and charantagenin F along with nine known compounds were isolated from the immature fruit of Momordica charantia L. Their structures were identified on the basis of extensive 1D, 2D NMR and HRESIMS spectroscopy analysis. All isolated compounds were examined for their anti-hepatic fibrosis activity against murine hepatic stellate cells (t-HSC/Cl-6) and anti-hepatoma activity against two kinds of liver cancer cell lines (HepG2 and Hep3B)...
October 20, 2018: Phytochemistry
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