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Kojiro Takanashi, Yasuyuki Yamada, Takayuki Sasaki, Yoko Yamamoto, Fumihiko Sato, Kazufumi Yazaki
Plants produce a large variety of alkaloids, which have diverse chemical structures and biological activities. Many of these alkaloids accumulate in vacuoles. Although some membrane proteins on tonoplasts have been identified as alkaloid uptake transporters, few have been characterized to date, and relatively little is known about the mechanisms underlying alkaloid transport and accumulation in plant cells. Berberine is a model alkaloid. Although all genes involved in berberine biosynthesis, as well as the master regulator, have been identified, the gene responsible for the final accumulation of berberine at tonoplasts has not been determined...
March 16, 2017: Phytochemistry
Valentino Giacomuzzi, Luca Cappellin, Iuliia Khomenko, Franco Biasioli, Alan L Knight, Sergio Angeli
This study investigated the diel emission of volatile organic compounds (VOCs) from intact apple (Malus x domestica Borkh., cv. Golden Delicious) and grape (Vitis vinifera L., cv. Pinot Noir) foliage. Volatiles were monitored continuously for 48 h by proton transfer reaction - time of flight - mass spectrometry (PTR-ToF-MS). In addition, volatiles were collected by closed-loop-stripping-analysis (CLSA) and characterized by gas chromatography-mass spectrometry (GC-MS) after 1 h and again 24 and 48 h later...
March 11, 2017: Phytochemistry
Ashish B Deshpande, Hemangi G Chidley, Pranjali S Oak, Keshav H Pujari, Ashok P Giri, Vidya S Gupta
Uniqueness and diversity of mango flavour across various cultivars are well known. Among various flavour metabolites lactones form an important class of aroma volatiles in certain mango varieties due to their ripening specific appearance and lower odour detection threshold. In spite of their biological and biochemical importance, lactone biosynthetic pathway in plants remains elusive. Present study encompasses quantitative real-time analysis of 9-lipoxygenase (Mi9LOX), epoxide hydrolase 2 (MiEH2), peroxygenase, hydroperoxide lyase and acyl-CoA-oxidase genes during various developmental and ripening stages in fruit of Alphonso, Pairi and Kent cultivars with high, low and no lactone content and explains their variable lactone content...
March 10, 2017: Phytochemistry
Ruijie He, Yanjun Zhang, Liangdeng Wu, Hui Nie, Yan Huang, Buming Liu, Shengping Deng, Ruiyun Yang, Shuai Huang, Zhijie Nong, Jun Li, Haiyan Chen
Two pairs of rare benzofuran glucoside epimers, indicuses A and B and indicuses C and D, three biogenetically related compounds indicuses E-G, and one coumarin indicus H, as well as 11 known compounds, were isolated from the bark of Streblus indicus (Bur.) Corner. The structures of indicuses A-H were elucidated by NMR and MS data, as well as by CD. (S)-Marmesinin exhibited moderate antimicrobial activity in vitro against Bacillus subtilis and Saccharomyces cerevisiae. 7,8-Dihydroxy-3-(3-methyl-2-butenyl) coumarin, umbelliferone, and scopoletin displayed strong cytotoxic activity in vitro against human bladder carcinoma cell line EJ...
March 8, 2017: Phytochemistry
Emmy Tuenter, Kenn Foubert, Dan Staerk, Sandra Apers, Luc Pieters
Seven cyclopeptide alkaloids were isolated from the stem bark of Ziziphus nummularia and Ziziphus spina-christi. Three previously undescribed compounds were identified: nummularine-U, spinanine-B and spinanine-C, together with the known compounds mauritine-F, nummularine-D, nummularine-E and amphibine-D. For their purification either semi-preparative HPLC with DAD and ESIMS detection or HPLC-PDA-(HRMS)-SPE-NMR was applied, together with conventional separation methods. Their structures were elucidated by spectroscopic means...
March 8, 2017: Phytochemistry
Jin-Qian Yu, Ming-Bao Lin, An-Jun Deng, Qi Hou, Jin-Ye Bai, Zhi-Hong Li, Lin Ma, Zhi-Hui Zhang, Shao-Peng Yuan, Ren-Tao Jiang, Hai-Lin Qin
Nine 14,15-secopregnane-type C21-steriosides, stauntosides U, V, V1-V3, W and C1-C3, as well as two known C21-steriosides, were isolated from the roots of Cynanchum stauntonii. Stauntosides U, V and V1-V3 share the same basic structural features of 8α:14α,14:16,15:20,18:20-tetraepoxy-14,15-secopregn-6-ene-3β,5α,9α-triol, with the numbering system following that of C21-pregnanes. The aglycones of stauntosides U, V and V1-V3 are classified into two subcategories, the 5,9-dihydroxy groups and 5α:9α-peroxy bridge, according to the oxidative states of the two hydroxy groups at the C-5 and C-9 positions...
March 8, 2017: Phytochemistry
Lars Dreßler, Florian Michel, Iris Thondorf, Johanna Mansfeld, Ralph Golbik, Renate Ulbrich-Hofmann
Plant phospholipases D (PLD) are typically characterized by a C2 domain with at least two Ca(2+) binding sites. In vitro, the predominantly expressed α-type PLDs need 20-100 mM CaCl2 for optimum activity, whereas the essential activator of β- or γ-type PLDs, phosphatidylinositol 4,5-bisphosphate (PIP2), plays a secondary role. In the present paper, we have studied the interplay between PIP2 and metal ion activation of the well-known α-type PLD from cabbage (PLDα). With mixed micelles containing phosphatidyl-p-nitrophenol as substrate, PIP2-concentrations in the nanomolar range are able to activate the enzyme in addition to the essential Ca(2+) activation...
March 7, 2017: Phytochemistry
Nikolaj L Hansen, Jakob N Nissen, Björn Hamberger
The medicinal plant Tripterygium wilfordii (Celastraceae) contains a pair of class II diterpene synthases (diTPS) of specialized labdane-type metabolism that, despite remarkably close homology, form strikingly different products. TwTPS21 catalyzes bicyclization of the linear C20 precursor geranylgeranyl diphosphate to ent-copal-8-ol diphosphate, while TwTPS14 forms kolavenyl diphosphate. To determine the amino acid signature controlling the functional divergence of the homologues, we modeled their structures based on an existing crystal structure of the Arabidopsis ent-copalyl diphosphate synthase, archetypal of diTPSs in general metabolism of gibberellin phytohormones...
March 6, 2017: Phytochemistry
Margarita M Del M Bravetti, Raquel V Vico, Maria C Carpinella, Carlos C Ferrayoli, Sara M Palacios
Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses...
March 6, 2017: Phytochemistry
Alen Bozicevic, Maria De Mieri, Angela Di Benedetto, Matthias Hamburger
Phytochemical profiling of Ziziphus spina-christi leaves led to the characterization of 10 dammarane-type saponins and 12 phenolic compounds. Isolation was achieved by gel chromatography on Sephadex LH20, open column chromatography on silica gel, and semi-preparative HPLC with PDA and ELSD detectors. Structural characterization was performed by extensive 1D and 2D NMR, mass spectrometry, and by GC-MS of sugar derivatives. A biosynthetic pathway leading to three previously undescribed sapogenins is proposed...
March 5, 2017: Phytochemistry
Xiaojie Liu, Peter G L Klinkhamer, Klaas Vrieling
Plant specialised metabolites (SMs) are very diverse in terms of both their number and chemical structures with more than 200,000 estimated compounds. This chemical diversity occurs not only among different groups of compounds but also within the groups themselves. In the context of plant-insect interactions, the chemical diversity within a class of structurally related metabolites is generally also related to their bioactivity. In this study, we tested firstly whether individual SMs within the group of pyrrolizidine alkaloids (PAs) differ in their effects on insect herbivores (western flower thrips, Frankliniella occidentalis)...
March 4, 2017: Phytochemistry
Mei-Ping Xie, Lan Li, Hua Sun, An-Qi Lu, Bo Zhang, Jian-Gong Shi, Dan Zhang, Su-Juan Wang
Five previously undescribed hemiterpene glycosides, cibotiumbarosides E-I, and two known hemiterpene glucosides, were isolated from the rhizome of Cibotium barometz (L.) J. Sm. The structures of cibotiumbarosides E-I were established by 1D and 2D NMR spectroscopic analyses and HRMS. The absolute configuration of the aglycone of cibotiumbaroside E was assigned by calculated ECD with the TDDFT method. Cibotiumbarosides F and I both exhibited remarkable hepatoprotective activity against APAP-induced acute liver damage in vitro, which were more effective than the positive control, bicyclol...
March 2, 2017: Phytochemistry
Michael B Wilson, Alison D Pawlus, Doug Brinkman, Gary Gardner, Adrian D Hegeman, Marla Spivak, Jerry D Cohen
Honey bees, Apis mellifera, collect antimicrobial plant resins from the environment and deposit them in their nests as propolis. This behavior is of practical concern to beekeepers since the presence of propolis in the hive has a variety of benefits, including the suppression of disease symptoms. To connect the benefits that bees derive from propolis with particular resinous plants, we determined the identity and botanical origin of propolis compounds active against bee pathogens using bioassay-guided fractionation against the bacterium Paenibacillus larvae, the causative agent of American foulbrood...
March 1, 2017: Phytochemistry
Aldo Tava, Elisa Biazzi, Mariella Mella, Paolo Quadrelli, Pinarosa Avato
Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and (1)H and (13)C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10 h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3β,22β,24-trihydroxyolean-18(19)-en and named soyasapogenol H...
February 28, 2017: Phytochemistry
André Matagne, Laetitia Bolle, Rachida El Mahyaoui, Danielle Baeyens-Volant, Mohamed Azarkan
Crude pineapple proteases extract (aka stem bromelain; EC is an important proteolytic mixture that contains enzymes belonging to the cysteine proteases of the papain family. Numerous studies have been reported aiming at the fractionation and characterization of the many molecular species present in the extract, but more efforts are still required to obtain sufficient quantities of the various purified protease forms for detailed physicochemical, enzymatic and structural characterization. In this work, we describe an efficient strategy towards the purification of at least eight enzymatic forms...
February 23, 2017: Phytochemistry
Mi Zhang, Chenxing Zhao, Weifeng Dai, Jing He, Shiyun Jiao, Baocai Li
Nineteen ent-kaurane diterpenes were isolated and identified from the barks of Gochnatia decora (Kurz) A. L. Cabrera (Compositae), which has been used as an ethnic medicine for treating cough, asthma and wounds in southwestern China. Among them, six compounds are previously undescribed ent-kaurenoic acids, and a known compound, 7β,15β-dihydroxy-ent-kaur-16-en-19-oic acid, was obtained for the first time from nature. Based on its traditional effects in Chinese folk, the potential anti-inflammatory activities of its methanol extracts (ME) and isolated diterpenes were evaluated by the tests of the xylene-induced ear swelling in mice, lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage cellular RAW 264...
February 21, 2017: Phytochemistry
Angela Mari, Alexandru Ciocarlan, Nicola Aiello, Fabrizio Scartezzini, Cosimo Pizza, Michele D'Ambrosio
The traditional use of extracts of Euphrasia rostkoviana to relieve ocular inflammation or infections is well documented and supported by clinical studies. Various classes of chemical compounds such as iridoids, phenylethanoids, flavonoids and hydroxycinnamic acids have been reported. The present work aims to assess the chemical diversity among seven populations of Euphrasia rostkoviana found in northern Italy. A meticulous separation of components led to the isolation and structural characterization of two previously unrecorded phenylethanoids methoxycrassifolioside and deoxycrassifolioside and one previously undescribed terpene glucoside (1E,6E)-8-hydroxy-3,7-dimethyl-octa-1,6-dienyl 1-O-β-D-glucopyranoside...
February 20, 2017: Phytochemistry
Patima Phainuphong, Vatcharin Rukachaisirikul, Kwanruthai Tadpetch, Yaowapa Sukpondma, Saowanit Saithong, Souwalak Phongpaichit, Sita Preedanon, Jariya Sakayaroj
Chromatographic separation of the broth extract of the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178 resulted in isolation of four γ-butenolide-furanone dimers, aspersclerotiorones A-D, a furanone derivative, aspersclerotiorone E, and two γ-butenolide derivatives, aspersclerotiorones F and G, together with six known compounds, penicillic acid, dihydropenicillic acid, 5,6-dihydro-6-hydroxypenicillic acid, 6-methoxy-5,6-dihydropenicillic acid, coculnol and (4R,5R)-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-en-1-one...
February 19, 2017: Phytochemistry
Thuc Huy Duong, Bui Linh Chi Huynh, Warinthorn Chavasiri, Marylene Chollet-Krugler, Van Kieu Nguyen, Thi Hoai Thu Nguyen, Poul Erik Hansen, Pierre Le Pogam, Holger Thüs, Joël Boustie, Kim Phi Phung Nguyen
Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3...
February 17, 2017: Phytochemistry
Eric Kuhnert, Frank Surup, Sandra Halecker, Marc Stadler
During the course of our screening for new metabolites with chemotaxonomic importance from stromata of fungi from the family Xylariaceae, we characterized several interesting metabolites in the fungus Annulohypoxylon minutellum. Extraction of the fruiting bodies and purification by preparative HPLC resulted in the isolation of five metabolites. The main compound was identified as the known metabolite hinnulin A (5), while four minor compounds were found to represent previously undescribed azaphilones, named minutellins A - D (1-4)...
February 16, 2017: Phytochemistry
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