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Phytochemistry

Current research reports and chronological list of recent articles..




Phytochemistry is the international scientific journal of pure and applied plant chemistry, plant biochemistry and molecular biology. It is also a is a primary source for papers dealing with plant secondary compounds, especially with regard to their biosynthesis and diverse properties.

The publisher is Elsevier. The copyright and publishing rights of specialized products listed below are in this publishing house. This is also responsible for the content shown.

To search this web page for specific words type "Ctrl" + "F" on your keyboard (Command + "F" on a Mac). Then: type the word you are searching for in the window that pops up!

Additional research articles see Current Chemistry Research Articles. Magazines with similar content (phytochemistry):

 - Phytochemical Analysis.

 - Phytochemistry Letters.

 - Phytochemistry Reviews.



Phytochemistry - Abstracts



Dihydro-β-agarofurans from the roots of the Australian endemic rainforest tree Maytenus bilocularis act as leucine transport inhibitors

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Mario Wibowo, Qian Wang, Jeff Holst, Jonathan M. White, Andreas Hofmann, Rohan A. Davis

Phytochemical studies of the roots of the Australian plant, Maytenus bilocularis, resulted in the identification of six previously undescribed dihydro-β-agarofuran sesquiterpenoids, bilocularins D–I, along with three known natural products, namely 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran, pristimerin, and celastrol. The structures of all compounds were characterized via analysis of 1D/2D NMR and MS data. The absolute configuration of bilocularin D was defined by X-ray crystallography analysis. Bilocularins D and G, 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran, and celastrol inhibited leucine transport in the human prostate cancer cell line LNCaP with IC50 values ranging from 2.5–27.9 μM, which were more potent than the L-type amino acid transporter (LAT) family inhibitor 2-aminobicyclo[2,2,1]-heptane-2-carboxylic acid (BCH). Bilocularins D–F are the first examples of dihydro-β-agarofurans bearing a hydroxyacetate group.

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Datum: 21.02.2018


Purine salvage in plants

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Hiroshi Ashihara, Claudio Stasolla, Tatsuhito Fujimura, Alan Crozier

Purine bases and nucleosides are produced by turnover of nucleotides and nucleic acids as well as from some cellular metabolic pathways. Adenosine released from the S-adenosyl-L-methionine cycle is linked to many methyltransferase reactions, such as the biosynthesis of caffeine and glycine betaine. Adenine is produced by the methionine cycles, which is related to other biosynthesis pathways, such those for the production of ethylene, nicotianamine and polyamines. These purine compounds are recycled for nucleotide biosynthesis by so-called “salvage pathways”. However, the salvage pathways are not merely supplementary routes for nucleotide biosynthesis, but have essential functions in many plant processes. In plants, the major salvage enzymes are adenine phosphoribosyltransferase (EC 2.4.2.7) and adenosine kinase (EC 2.7.1.20). AMP produced by these enzymes is converted to ATP and utilised as an energy source as well as for nucleic acid synthesis. Hypoxanthine, guanine, inosine and guanosine are salvaged to IMP and GMP by hypoxanthine/guanine phosphoribosyltransferase (EC 2.4.2.8) and inosine/guanosine kinase (EC 2.7.1.73). In contrast to de novo purine nucleotide biosynthesis, synthesis by the salvage pathways is extremely favourable, energetically, for cells. In addition, operation of the salvage pathway reduces the intracellular levels of purine bases and nucleosides which inhibit other metabolic reactions. The purine salvage enzymes also catalyse the respective formation of cytokinin ribotides, from cytokinin bases, and cytokinin ribosides. Since cytokinin bases are the active form of cytokinin hormones, these enzymes act to maintain homeostasis of cellular cytokinin bioactivity. This article summarises current knowledge of purine salvage pathways and their possible function in plants and purine salvage activities associated with various physiological phenomena are reviewed.

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Datum: 21.02.2018


Editorial Board/Publication Information

Publication date: February 2018
Source:Phytochemistry, Volume 146










Datum: 21.02.2018


Triterpenoids from the leaves of Ilex chinensis

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Wen-Qi Xia, Ruo-Fei Li, Jia-Bao Liu, Bao-Song Cui, Qi Hou, Hua Sun, Shuai Li

Eleven previously undescribed compounds including two triterpenes, ilexchinenin A and ilexchinenin B, and nine triterpenoid saponins, ilexchinenosides A-I, along with twelve known triterpenoids were isolated from the leaves of Ilex chinensis Sims (Aquifoliaceae). Their structures were elucidated by spectroscopic analysis and comparison with known compounds. Furthermore, eight compounds exhibited significant inhibitory effects on NO production of lipopolysaccharide (LPS)-induced murine macrophages, while nine compounds exhibited potent hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays.

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Datum: 21.02.2018


Protective effects of total alkaloids from Dendrobium crepidatum against LPS-induced acute lung injury in mice and its chemical components

Publication date: May 2018
Source:Phytochemistry, Volume 149

Author(s): Yang Hu, Jie Ren, Lei Wang, Xin Zhao, Mian Zhang, Kuniyoshi Shimizu, Chaofeng Zhang

Dendrobium crepidatum was one of the sources of Herba Dendrobii, a famous and precious traditional Chinese medicine. Indolizine-type alkaloids are the main characteristic ingredients of D. crepidatum, which possesses a variety of changeable skeletons. In the present study, we found that the total alkaloids of D. crepidatum (TAD) can inhibit the production of nitric oxide (NO) in lipopolysaccharide (LPS)-activated macrophages and showed protective effects against LPS-induced acute lung injury (ALI) in mice through downregulating the TLR4-mediated MyD88/MAPK signaling pathway. Further phytochemical study showed that six previously undescribed indolizine-type compounds, including a racemic mixture (dendrocrepidine A-E) were isolated from TAD. Meanwhile, dendrocrepidine F was separated into a pair of enantiomers by a chiral chromatography, and their absolute configurations were assigned by single-crystal X-ray diffraction analysis. The isomer (−)-dendrocrepidine F showed higher anti-inflammatory effects by inhibiting NO production in LPS-treated macrophages with an IC50 value of 13.3 μM. Taken together, indolizine-type alkaloids are the active components of D. crepidatum through downregulating the TLR4-mediated pathway, indicating some kind of therapy of TAD for ALI treatment.

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Datum: 21.02.2018


Morning glory resin glycosides as α-glucosidase inhibitors: In vitro and in silico analysis

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Daniel Rosas-Ramírez, Sonia Escandón-Rivera, Rogelio Pereda-Miranda

Twenty-seven individual resin glycosides from the morning glory family (Convolvulaceae) were evaluated for their α-glucosidase inhibitory potential. Four of these compounds displayed an inhibitory activity comparable to acarbose, which was used as a positive control. Molecular modeling studies performed by docking analysis were accomplished to predict that the active compounds and acarbose bind to the α-1,4-glucosidase enzyme catalytic site of MAL12 from the yeast Saccharomyces cerevisiae through stable hydrogen bonds primarily with the amino acid residues HIS279 and GLN322. Docking studies with the human maltase-glucoamylase (MGAM) also identified binding modes for resin glycosides inside the catalytic site in the proximity of TYR1251. These results postulate that resin glycosides may be a source of phytotherapeutic agents with antihyperglycemic properties for the prophylaxis and treatment of non-insulin-dependent type 2 diabetes mellitus.

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Datum: 21.02.2018


Bioactive steroidal alkaloids from the fruits of Solanum nigrum

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Xin-Yue Gu, Xiao-Fei Shen, Lun Wang, Zhou-Wei Wu, Fu Li, Bin Chen, Guo-Lin Zhang, Ming-Kui Wang

The investigation of the fruits of Solanum nigrum led to the isolation of four previously undescribed steroidal alkaloids, named solanine A, 7α-OH khasianine, 7α-OH solamargine and 7α-OH solasonine, together with six known ones. The structures of the isolated compounds were elucidated unambiguously by spectroscopic data analyses and chemical methods. Solanine A represents an unusual steroidal alkaloid with an unprecedented 6/5/6/5/5/6 hexacyclic ring system, and its structure was confirmed by X-ray single crystal diffraction analysis. Compounds 24 were rare naturally occurring steroidal alkaloid glycosides bearing a hydroxyl group at C-7 position. Solanine A showed the most potent inhibitory activity against the LPS-induced NO production in murine RAW264.7 macrophages with an IC50 value of 3.85 ± 0.71 μM and significant cytotoxicity against MGC803, HepG2 and SW480 cancer cell lines with IC50 values of 6.00 ± 0.52 μM, 9.25 ± 0.49 μM and 6.23 ± 0.26 μM, respectively.

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Datum: 21.02.2018


Bioactive halogenated dihydroisocoumarins produced by the endophytic fungus Lachnum palmae isolated from Przewalskia tangutica

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Min Zhao, Lv-Yi Yuan, Da-Le Guo, Ye Ye, Zhuo-Ma Da-Wa, Xiao-Ling Wang, Feng-Wei Ma, Lei Chen, Yu-Cheng Gu, Li-Sheng Ding, Yan Zhou

Guided by the UPLC-ESIMS profile, seven previously undescribed halogenated dihydroisocoumarins, palmaerones A-G, along with eleven known dihydroisocoumarins, were isolated from Lachnum palmae, an endophytic fungus from Przewalskia tangutica by exposure to a histone deacetylase inhibitor SAHA. Structures of the isolates were elucidated by analysis of their NMR, MS and optical rotation values. The antimicrobial, anti-inflammatory and cytotoxic activities of palmaerones A-G were evaluated. Palmaerones A-G showed antimicrobial activities against the strains (C. neoformans, Penicillium sp., C. albicans, B. subtilis and S. aureus), and palmaerone E exhibited potential antimicrobial activities against all the test strains with the MIC value in the range of 10–55 μg/mL. Palmaerones A and E exhibited moderate inhibitory effects on NO production in LPS-induced RAW 264.7 cells, with the IC50 values of 26.3 and 38.7 μM, respectively and no obvious toxicities were observed at 50 μM. Palmaerone E showed weak cytotoxicity against HepG2 with the IC50 value of 42.8 μM. This work provides an effective strategy for expanding natural product resource.

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Datum: 21.02.2018


Resin glycosides from the seeds of Ipomoea muricata and their multidrug resistance reversal activities

Publication date: May 2018
Source:Phytochemistry, Volume 149

Author(s): Wen-qiong Wang, Shan-shan Liu, Wei-bin Song, Jun Li, Li-jiang Xuan

Resin glycosides represent an important chemotaxonomic marker of the Convolvulaceae family and possess multidrug resistance (MDR) reversal activity. In our recent study, nine previously undescribed resin glycosides, Calonyctins B–J, were isolated from the seeds of Ipomoea muricata. Their structures with the absolute configuration were established on the basis of comprehensive spectroscopic analysis and chemical methods. Among these, Calonyctins F–I possessed a skeleton in which the aglycone moiety and the oligosaccharide core were linked by a 3-hydroxy-2-methylbutanoic acid moiety to form a 25-membered macrocyclic structure. Calonyctins E, J, and muricatic acid C methyl ester were non-cytotoxic but enhanced the cytotoxicity of vincristine by 2.5–407.1 fold at 25 μM in KB/VCR cells. Calonyctin E was the most active one.

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Datum: 21.02.2018


Editorial Board/Publication Information

Publication date: March 2018
Source:Phytochemistry, Volume 147










Datum: 21.02.2018


Synthesis and mode of action studies of N-[(-)-jasmonyl]-S-tyrosin and ester seiridin jasmonate

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Pierluigi Reveglia, Andrea Chini, Alessandro Mandoli, Marco Masi, Alessio Cimmino, Gennaro Pescitelli, Antonio Evidente

Recent analyses on fungal jasmonic acid (JA)-containing metabolites suggest a mode-of-action of these naturally occurring compounds as inactive storage pools of JA. Plants and/or fungi can catabolize JA into the bioactive jasmonyl-isoleucine (JA-Ile) that in turn activates the JA-Ile-pathway in planta. To extend our knowledge on JA-derivates related to natural occurring JA conjugates, N-[(-)-jasmonyl]-S-tyrosin (JA-Tyr) and the ester JA-Sei between JA and seiridin, a fungal disubstituted furanone, were synthesized. The classical procedures for ester synthesis were applied for compound JA-Sei, while N-[(-)-jasmonyl]-S-tyrosin was synthesized with an optimized procedure. JA-Tyr and JA-Sei were characterized by spectroscopic method (essentially 1D and 2D NMR spectroscopy and ESI-MS) and their stereochemical composition was determined by means of HPLC and circular dichroism analysis. Finally, the activity of these JA-derivates was analyzed in planta. JA-Tyr and JA-Sei trigger JA-regulated plant responses, such as protein degradation and growth inhibition. These effects require the conversion of JA into JA-Ile and its recognition by the plant JA-Ile perception complex COI1-JAZ. Overall, these data suggest a mode-of-action of JA-Tyr and JA-Sei as inactive pool of JA that can be transformed into the bioactive JA-Ile to induce the canonical JA-Ile-pathway.

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Datum: 21.02.2018


Phytochemical analysis of salal berry (Gaultheria shallon Pursh.), a traditionally-consumed fruit from western North America with exceptionally high proanthocyanidin content

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Andrew Ferguson, Elisabete Carvalho, Geraldine Gourlay, Vincent Walker, Stefan Martens, Juha-Pekka Salminen, C. Peter Constabel

Salal (Gaultheria shallon Pursh.) is a wild perennial shrub of the Ericaceae and common in coastal forests of western North America, and its berries were an important traditional food for First Nations in British Columbia. Salal berries were investigated for phytochemical content and antioxidant capacity over the course of fruit development. The proanthocyanidin content was extremely high in young berries (280.7 mg/g dry wt) but dropped during development to 52.8 mg/g dry wt. By contrast, anthocyanins accumulated only at the late berry stages. Total antioxidant capacity, as measured by the 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method, reflected both proanthocyanidin and anthocyanin content, and in mature berries reached 36 mmol Trolox equivalents/100 g dry wt. More detailed phytochemical analysis determined that delphinidin 3-O-galactoside is the dominant anthocyanin, and that the berries are also rich in procyanidins, including procyanidin A2 which has been implicated in anti-adhesion activity for uropathogenic E. coli. Proanthocyanidins were 60% prodelphinidin, and overall concentrations were higher than reported for many Vaccinium species including blueberry, lingonberry, and cranberry. Overall, the phenolic profile of salal berries indicates that these fruit contain a diversity of health-promoting phenolics.

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Datum: 21.02.2018


Seco-labdane diterpenoids from the leaves of Callicarpa nudiflora showing nitric oxide inhibitory activity

Publication date: May 2018
Source:Phytochemistry, Volume 149

Author(s): Xiaocong Sun, Feng Liu, Xueyuan Yang, Jinghan Wang, Bangjian Dong, Chunfeng Xie, Da-Qing Jin, Jie Zhang, Dongho Lee, Yasushi Ohizumi, Jing Xu, Yuanqiang Guo

Nine previously undescribed seco-labdane diterpenoids, nudiflopenes A−I, were isolated from the leaves of Callicarpa nudiflora. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by the modified Mosher's method and experimental and calculated electronic circular dichroism spectra. Nudiflopenes A−I belong to the class of seco-labdane diterpenoids. All of the isolates showed inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production in murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.

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Datum: 21.02.2018


Specialized metabolites from Ageratina adenophora and their inhibitory activities against pathogenic fungi

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Guowei Zheng, Shihong Luo, Shifei Li, Juan Hua, Weiqi Li, Shenghong Li

The Asteraceae plant Ageratina adenophora (also called Eupatorium adenophorum) has became the most destructive invasive species in China, especially the southwestern region, and is gravely threatening the native biodiversity. Its high reproductive capacity is partly due to the developed root system. From the roots of A. adenophora, ten compounds including three previously undescribed benzofuran derivatives (7-hydroxy-dehydrotremetone, 7,10,11-trihydroxy dehydrotremetone, 10-oxo-7-hydroxy-nordehydrotremetone), a previously undescribed chromene derivative (5-β-glucosyl-7-demethoxy-encecalin) and a previously undescribed monoterpene glucoside (8-hydroxy-8-β-glucosyl-2-carene) were isolated and identified. The previously undescribed structures were established by spectroscopic studies including 1D and 2D-NMR and HR-MS analyses. Antifungal activity of six compounds against one strain of pathogenic fungus of A. adenophora, Alternaria alternata, and other four strains of agricultural pathogenic fungi, Colletotrichum gloeosporioides, C. musae, Rhizoctonia solani and Fusarium oxysporum f. sp. niveum were investigated. The most abundant compound we isolated from A. adenophora roots was 7-hydroxy-dehydrotremetone, which showed significant broad-spectral inhibitory activity against the growth of all tested fungal strains, with diameter of inhibitory zones ranging from 13.90 ± 1.05 mm to 17.28 ± 0.46 mm at 50 μg/disk (nystatin: 24.76 ± 1.19 mm to 36.64 ± 0.85 mm). Encecalin also showed weak inhibitory activity against F. oxysporum f. sp. niveum, while other compounds were not active. Our results suggested that 7-hydroxy-dehydrotremetone might function as a constitutive defense compound in the roots of A. adenophora against pathogenic fungi.

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Datum: 21.02.2018


Terpenoids from the mushroom-associated fungus Montagnula donacina

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Zhen-Zhu Zhao, Kuan Zhao, He-Ping Chen, Xue Bai, Ling Zhang, Ji-Kai Liu

Molecular identification suggested an edible mushroom, which was previously named as Craterellus odoratus should be revised as Montagnula donacina. A chemical re-investigation of the culture broth of this fungus resulted in the isolation of four rare tetracyclic bergamotane-type sesquiterpenoids, namely donacinolides A and B, donacinoic acids A and B, and three cadinane-type ones, namely donacinols A–C and a meroterpenoid (Z)-4-hydroxy-3-(3-hydroxy-3-methylbut-1-en-1-yl)benzoic acid. Their structures were established via extensive spectroscopic methods, single crystal X-ray diffraction analysis, and computational methods. (Z)-4-Hydroxy-3-(3-hydroxy-3-methylbut-1-en-1-yl)benzoic acid showed antibacterial activity against Staphylococcus aureus.

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Datum: 21.02.2018


Anti-inflammatory steroidal glycosides from the berries of Solanum nigrum L. (European black nightshade)

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Limin Xiang, Yihai Wang, Xiaomin Yi, Xiangjiu He

Seven previously undescribed steroidal glycosides, along with three known congeners were isolated from the unripe berries of Solanum nigrum L. (Solanaceae). Their structures were elucidated on basis of 1D and 2D NMR, HR-ESI-MS spectroscopic data and GC analysis after acid hydrolysis. The potential inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide in RAW 264.7 cell line and the anti-proliferative activities against five cancer cell lines (HL-60, U-937, Jurkat, K562 and HepG2) were evaluated. Seven compounds exhibited inhibition activities on NO production with IC50 values ranging from 11.33 to 49.35 μM. Structure-activity relationships of the isolated compounds were also discussed.

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Datum: 21.02.2018


Anti-inflammatory flavone and chalcone derivatives from the roots of Pongamia pinnata (L.) Pierre

Publication date: May 2018
Source:Phytochemistry, Volume 149

Author(s): Ran Wen, Hai-Ning Lv, Yong Jiang, Peng-Fei Tu

A phytochemical study on the roots of Pongamia pinnata (L.) Pierre yielded 52 flavonoids, including four previously undescribed flavone and four previously undescribed chalcone derivatives. The structures of the isolated compounds were determined on the basis of the 1D, 2D NMR, and mass spectroscopic data. The absolute configurations of the compounds were assigned via the specific rotation, Mosher's method, as well as the electronic circular dichroism (ECD) spectra. All the isolates were evaluated for their inhibitory effects on NO production in LPS-stimulated BV-2 microglial cells. Ten compounds showed significant inhibitory effects against NO production, comparable to the positive control, dexamethasone.

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Datum: 21.02.2018


Jatrophane diterpenoids with multidrug-resistance modulating activity from the latex of Euphorbia nicaeensis

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Gordana Krstić, Milka Jadranin, Nina M. Todorović, Milica Pešić, Tijana Stanković, Ivana S. Aljančić, Vele V. Tešević

Seven previously undescribed jatrophane diterpenoids, nicaeenin A–G, with eight known jatrophane diterpenoids, namely euphodendrophanes A–C, F, N, O, Q, S, were isolated from latex of Euphorbia nicaeensis collected in Serbia. The chemical structures of the compounds were determined by spectroscopic analysis including 1D and 2D NMR and HRESIMS experiments. All but one of the previously undescribed jatrophanes, showed significant potential to inhibit P-glycoprotein (P-gp) activity in two MDR cancer cells (NCI-H460/R and DLD1-TxR). The most powerful were nicaeenin F and nicaeenin G. Moreover nicaeenin G significantly stronger sensitized NCI-H460/R cells to DOX than Dex-VER.

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Datum: 21.02.2018


Sesquiterpenoids from Artemisia vestita

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Shuai-Hua Tian, Chen Zhang, Ke-Wu Zeng, Ming-Bo Zhao, Yong Jiang, Peng-Fei Tu

Eleven previously undescribed sesquiterpenoids, arvestolides D–J, arvestonates A–C, and arvestonol were isolated from the aerial parts of Artemisia vestita W. Their structures were elucidated by extensive analysis of HRMS, UV, IR, and NMR spectroscopic data, and the absolute configurations were determined by single crystal X-ray diffraction, empirical rules, and comparison of calculated and experimental ECD data. Arvestolides H and I showed inhibitory effects on nitric oxide production in BV-2 cells induced by lipopolysaccharide with IC50 values of 43.2 and 39.9 μM, respectively.

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Datum: 21.02.2018


Outside Front Cover

Publication date: March 2018
Source:Phytochemistry, Volume 147










Datum: 21.02.2018


Relationship between chemotypic and genetic diversity of natural populations of Artemisia herba-alba Asso growing wild in Tunisia

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Faten Younsi, Najoua Rahali, Sameh Mehdi, Mohamed Boussaid, Chokri Messaoud

A total of 80 individuals collected from eight populations growing wild in different geographic zones were considered to assess the intraspecific variability of essential oil composition, genetic diversity and population structure of Artemisia herba-alba. The essential oil composition varied significantly between populations. Essential oil profiles were classified into four chemotypes (trans-sabinyl acetate, α-thujone/trans-sabinyl acetate, camphor and α-thujone/camphor/β-thujone). Despite significant correlation between the amount of some essential oil compounds and a set of climatic data, the global chemical divergence among populations was not related to their bioclimatic and geographic appurtenances. A high level of genetic diversity within populations was revealed either with RAPD and ISSR markers (Na = 1.67, PPL = 66.5%, H = 0.26, I = 0.38 and Na = 1.7, PPL = 69.8%, H = 0.26, I = 0.38, respectively). The level of genetic diversity varied across populations and chemotypes. Populations from the α-thujone/trans-sabinyl acetate chemotype exhibited the highest genetic diversity as revealed by the RAPD markers. However, populations from α-thujone/camphor/β-thujone chemotype showed the important genetic variation determined by ISSR markers. A significant genetic differentiation among populations and among chemotypes was detected. The combined analysis showed a significant correlation (r = 0.484, p = .032) between the chemical and molecular markers. The PCA, performed on percentages of major oil compounds and the frequencies of polymorphic RAPD and ISSR bands, divided populations according to their chemotypic classification. Taking into consideration the current situation of A. herba-alba populations and their endangered habitats, these results are of value in order to ensure the in-situ and ex-situ conservation of this medicinal species.

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Datum: 21.02.2018


Graphical Contents List

Publication date: March 2018
Source:Phytochemistry, Volume 147










Datum: 21.02.2018


Saponins from seeds of Genus Camellia: Phytochemistry and bioactivity

Publication date: May 2018
Source:Phytochemistry, Volume 149

Author(s): Na Guo, Tuantuan Tong, Ning Ren, Youying Tu, Bo Li

Camellia seeds have been traditionally used as oil raw materials in Asia, and are known for a wide spectrum of applications. Oleanane-type triterpene saponins are the major specialised metabolites in Camellia seeds, and more than seventy saponins have been isolated and characterized. These natural compounds have caught much attention due to their various biological and pharmacological activities, including modulation of gastrointestinal system, anti-cancer, anti-inflammation, anti-microorganism, antioxidation, neuroprotection, hypolipidemic effects, foaming and detergence, as well as helping the accumulation of pollutants by plants. These compounds have a promising application in medicine, agriculture, industry and environmental protection. The present paper summarized the information from current publications on Camellia seed saponins, with a focus on the advances made in chemical structures, determination methods, bioactivities and toxicity. We hope this article will stimulate further investigations on these compounds.

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Datum: 21.02.2018


Phytochemistry and pharmacology of the genus Leonurus: The herb to benefit the mothers and more

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Rui-Han Zhang, Zhi-Ke Liu, Da-Song Yang, Xing-Jie Zhang, Han-Dong Sun, Wei-Lie Xiao

Plants belonging to the genus Leonurus, also named motherwort, are traditionally used for anti-gynecological disorder in East Asia, and for sedative in Europe. Chemical investigation of the genus Leonurus not only enriched the natural products library, but also enlarged the pharmacological application of this traditional herb. In this review, we systematically summarized the structures of 259 compounds isolated from the genus Leonurus, featured with 147 labdane diterpenoids. The reported bioactivity studies up to 2017 are presented in the second part, with the main focus on the isolated compounds and also concerning the extracts. In addition to the traditional uterine contraction and sedative activity, recently the cardiovascular protection effect of leonurine has drawn most attention. Other than that, neuroprotection, anti-inflammation, anti-cancer, anti-platelet aggregation and many other activities have been assigned to various compounds from the genus Leonurus. Among 70 bioactivity references cited in this review, 57% of them were concentrated on two alkaloids (leonurine and stachydrine), whereas only 20% are about the 147 diterpenoids. Anti-inflammation is the major bioactivity discovered so far for the labdane diterpenoids from the genus Leonurus, whose further therapeutic potential still remains for exploration.

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Datum: 21.02.2018


CRISPR/Cas9-mediated efficient targeted mutagenesis of RAS in Salvia miltiorrhiza

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Zheng Zhou, Hexin Tan, Qing Li, Junfeng Chen, Shouhong Gao, Yun Wang, Wansheng Chen, Lei Zhang

The CRISPR (Clustered Regularly Interspaced Short Palindromic Repeats)/Cas9 (CRISPR-associated) system is a powerful genome editing tool that has been used in many species. In this study, we focused on the phenolic acid metabolic pathway in the traditional Chinese medicinal herb Salvia miltiorrhiza, using the CRISPR/Cas9 system to edit the rosmarinic acid synthase gene (SmRAS) in the water-soluble phenolic acid biosynthetic pathway. The single guide RNA (sgRNA) was designed to precisely edit the most important SmRAS gene, which was selected from 11 family members through a bioinformatics analysis. The sequencing results showed that the genomes of 50% of the transgenic regenerated hairy roots had been successfully edited. Five biallelic mutants, two heterozygous mutants and one homozygous mutant were obtained from 16 independent transgenic hairy root lines when the sgRNA was driven by the Arabidopsis U6 promoter, while no mutants were obtained from 13 independent transgenic hairy root lines when the sgRNA was driven by the rice U3 promoter. Subsequently, expression and metabolomics analysis showed that the contents of phenolic acids, including rosmarinic acid (RA) and lithospermic acid B, and the RAS expression level were decreased in the successfully edited hairy root lines, particularly in the homozygous mutants. In addition, the level of the RA precursor 3,4-dihydroxyphenyllactic acid clearly increased. These results indicated that the CRISPR/Cas9 system can be utilized to identify important genes in a gene family with the assistance of bioinformatics analysis and that this new technology is an efficient and specific tool for genome editing in S. miltiorrhiza. This new system presents a promising potential method to regulate plant metabolic networks and improve the quality of traditional Chinese medicinal herbs.

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Datum: 21.02.2018


Potato native and wound periderms are differently affected by down-regulation of FHT, a suberin feruloyl transferase

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Liqing Jin, Qing Cai, Wenlin Huang, Keyvan Dastmalchi, Joan Rigau, Marisa Molinas, Mercè Figueras, Olga Serra, Ruth E. Stark

Potato native and wound healing periderms contain an external multilayered phellem tissue (potato skin) consisting of dead cells whose cell walls are impregnated with suberin polymers. The phellem provides physical and chemical barriers to tuber dehydration, heat transfer, and pathogenic infection. Previous RNAi-mediated gene silencing studies in native periderm have demonstrated a role for a feruloyl transferase (FHT) in suberin biosynthesis and revealed how its down-regulation affects both chemical composition and physiology. To complement these prior analyses and to investigate the impact of FHT deficiency in wound periderms, a bottom-up methodology has been used to analyze soluble tissue extracts and solid polymers concurrently. Multivariate statistical analysis of LC-MS and GC-MS data, augmented by solid-state NMR and thioacidolysis, yields two types of new insights: the chemical compounds responsible for contrasting metabolic profiles of native and wound periderms, and the impact of FHT deficiency in each of these plant tissues. In the current report, we confirm a role for FHT in developing wound periderm and highlight its distinctive features as compared to the corresponding native potato periderm.

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Datum: 21.02.2018


Differentiation analysis of boron isotopic fractionation in different forms within plant organ samples

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Aide Sun, Qingcai Xu, Gangjian Wei, Huayu Zhu, Xuefei Chen

As a critical micronutrient, boron (B) plays an important role in plant growth and embryonic development. To further understand the effects of B uptake, transportation and isotopic fractionation, the contents and isotopic compositions of hydro-soluble B in the sap and structural B fixed in the cell within individual plant tissues were investigated. The B isotope ratio was determined by multi-collector inductively coupled plasma mass spectrometry. The δ11B values in hydro-soluble and structural B in the investigated plant samples ranged from −1.57‰ to +11.30‰ and from +6.57‰ to +16.64‰, respectively. Different fractionation factors of the B isotopes, in the range of 0.9954–1.0150, were observed in these samples, indicating that in most plant tissues, the heavy isotope (11B) was preferentially enriched in structural B, which was fixed into the cell. However, there was a reversal in the fractionation of B isotopic compositions in the fruit samples compared with the other plant tissue samples. It is more powerful to examine the molecular mechanisms of B transport, uptake and utilization than the use of limited plant organ samples containing a mixture of hydro-soluble and structural B within different intra-plant compartments and in inter-plant interactions. These isotopic shifts, which may be used as important isotopic indicators, contribute to the surface processes interactions in the plant–soil system and the knowledge of the molecular mechanisms of B in the uptake and absorption by different plant species in nature.

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Datum: 21.02.2018


Anthocyanins in perilla plants and dried leaves

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Yumi Fujiwara, Miya Kono, Airi Ito, Michiho Ito

High-quality perilla leaves are purple on upper and lower surfaces and have a good aroma. The Japanese Pharmacopoeia specifies the content of essential oils in perilla leaves but not that of anthocyanins. Several reports have described the chemical species of anthocyanins in red perilla, but a complete analysis of anthocyanins in perilla has not been reported. In this study, the anthocyanins in the leaves of cultivated and wild species of perilla and those in commercially available perilla herbs were studied. Red perilla and most P. citriodora strains accumulate cyanidin derivatives that differ in the acyl group on the glucose moiety at the 3-O- and 5-O-positions of the anthocyanins. Several strains of P. citriodora contain cyanidin derivatives that are different from those in red perilla and most P. citriodora species. Green perilla and wild species other than P. citriodora do not contain foliar anthocyanins. The anthocyanins in commercially available perilla herbs and natural dyes made from red perilla were in agreement with those in fresh red perilla leaves and most P. citriodora samples. The amounts and types of anthocyanins were not associated with place of cultivation, although some changes occurred due to degradation during storage. These results provide clues regarding the biosynthesis of anthocyanins in perilla and the evolution of red perilla. The characteristics and stability of anthocyanins are discussed.

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Datum: 21.02.2018


Changes in isovitexin-O-glycosylation during the development of young barley plants

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Dominic Brauch, Andrea Porzel, Erika Schumann, Klaus Pillen, Hans-Peter Mock

Phenylpropanoids are a class of plant natural products that have many biological functions, including stress defence. In barley, phenylpropanoids have been described as having protective properties against excess UV-B radiation and have been linked to resistance to pathogens. Although the phenylpropanoid composition of barley has recently been addressed in more detail, the biosynthesis and regulation of this pathway have not been fully established. Barley introgression lines, such as the S42IL-population offer a set of genetically diverse plants that enable the correlation of metabolic data to distinct genetic regions on the barley genome and, subsequently, identification of relevant genes. The phenylpropanoid profiles of the first and third leaf of barley seedlings in Scarlett and four members of the S42IL-population were obtained by LC-MS. Comparison of the leaf profiles revealed a change in the glycosylation pattern of the flavone-6-C-glucoside isovitexin in the elite cultivar Scarlett. The change was characterized by the stepwise decrease in isovitexin-7-O-glucoside (saponarin) and an increase in isovitexin-2″-O-β-D-glucoside content. The lines S42IL-101-, -177 and -178 were completely devoid of isovitexin-2″-O-β-D-glucoside. Parallel glucosyltransferase assays were consistent with the observed metabolic patterns. The genetic region responsible for this metabolic effect was located on chromosome 1H between 0.21 and 15.08 cM, encompassing 505 gene candidates in the genome of the sequenced cultivar Morex. Only one of these genes displayed sequence similarity with glucosyltransferases of plant secondary metabolism that possessed the characteristic PSPG motif.

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Datum: 21.02.2018


Diterpenoid fingerprints in pine foliage across an environmental and chemotypic matrix: Isoabienol content is a key trait differentiating chemotypes

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Astrid Kännaste, Lauri Laanisto, Leila Pazouki, Lucian Copolovici, Marina Suhorutšenko, Muhammad Azeem, Lauri Toom, Anna-Karin Borg-Karlson, Ülo Niinemets

Diterpenoids constitute an important part of oleoresin in conifer needles, but the environmental and genetic controls on diterpenoid composition are poorly known. We studied the presence of diterpenoids in four pine populations spanning an extensive range of nitrogen (N) availability. In most samples, isoabienol was the main diterpenoid. Additionally, low contents of (Z)-biformene, abietadiene isomers, manoyl oxide isomers, labda-7,13,14-triene and labda-7,14-dien-13-ol were quantified in pine needles. According to the occurrence and content of diterpenoids it was possible to distinguish ‘non diterpenoid pines’, ‘high isoabienol pines’, ‘manoyl oxide – isoabienol pines’ and ‘other diterpenoid pines’. ‘Non diterpenoid pines’, ‘high isoabienol pines’ and ‘other diterpenoid pines’ were characteristic to the dry forest, yet the majority of pines (>80%) of the bog Laeva represented ‘high isoabienol pines’. ‘Manoyl oxide – isoabienol pines’ were present only in the wet sites. Additionally, orthogonal partial least-squares analysis showed, that in the bogs foliar nitrogen content per dry mass (N M ) correlated to diterpenoids. Significant correlations existed between abietadienes, isoabienol and foliar N M in ‘manoyl oxide – isoabienol pines’, and chemotypic variation was also associated by population genetic distance estimated by nuclear microsatellite markers. Previously, the presence of low and high Δ-3-carene pines has been demonstrated, but the results of the current study indicate that also diterpenoids form an independent axis of chemotypic differentiation. Further studies are needed to understand whether the enhanced abundance of diterpenoids in wetter sites reflects a phenotypic or genotypic response.

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Datum: 21.02.2018


Triterpenoid saponins from the pulp of Sapindus mukorossi and their antifungal activities

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Qingwen Hu, Ying-Ying Chen, Qi-Yang Jiao, Afsar Khan, Feng Li, De-Feng Han, Gui-Dong Cao, Hong-Xiang Lou

Under the guidance of anti-fungal bioassay, four previously undescribed oleanane-type and one lupane-type triterpenoid saponins, along with twelve known analogues, were isolated from the extract of Sapindus mukorossi pulps. Their structures were determined on the basis of spectroscopic analysis and chemical methods. In vitro biotests, oleanolic acid 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside showed inhibitory activity against Trichophyton rubrum with MIC80 value of 8 μg/mL, while oleanolic acid 3-O-α-L-arabinopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside exhibited inhibitory activity against both Trichophyton rubrum and Candida albicans with MIC80 values of 8 μg/mL.

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Datum: 21.02.2018


Abnormal swelling of the peritrophic membrane in Eri silkworm gut caused by MLX56 family defense proteins with chitin-binding and extensin domains

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Kotaro Konno, Sachiko Shimura, Chihiro Ueno, Toru Arakawa, Masatoshi Nakamura

MLX56 family defense proteins, MLX56 and its close homolog LA-b, are chitin-binding defense proteins found in mulberry latex that show strong growth-inhibitions against caterpillars when fed at concentrations as low as 0.01%. MLX56 family proteins contain a unique structure with an extensin domain surrounded by two hevein-like chitin-binding domains, but their defensive modes of action remain unclear. Here, we analyzed the effects of MLX56 family proteins on the peritrophic membrane (PM), a thin and soft membrane consisting of chitin that lines the midgut lumen of insects. We observed an abnormally thick (>1/5 the diameter of midgut) hard gel-like membrane consisted of chitin and MLX56 family proteins, MLX56 and LA-b, in the midgut of the Eri silkworms, Samia ricini, fed a diet containing MLX56 family proteins, MLX56 and LA-b. When polyoxin AL, a chitin-synthesis-inhibitor, was added to the diet containing MLX56 family proteins, the toxicity of MLX56 family proteins disappeared and PM became thinner and fragmented. These results suggest that MLX56 family proteins, through their chitin-binding domains, bind to the chitin framework of PM, then through their extensin-domain (gum arabic-like structure), which functions as swelling agent, expands PM into an abnormally thick membrane that inhibits the growth of insects. This study shows that MLX56 family proteins are plant defense lectins with a totally unique mode of action, and reveals the functions of extensin domains and arabinogalactan proteins as swelling (gel-forming) agents of plants.

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Datum: 21.02.2018


Lipidomic analysis of Botryococcus (Trebouxiophyceae, Chlorophyta) - Identification of lipid classes containing very long chain fatty acids by offline two-dimensional LC-tandem MS

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Tomáš Řezanka, Jaromír Lukavský, Milada Vítová, Linda Nedbalová, Karel Sigler

Very long chain fatty acids (VLCFAs) were identified in four strains of the green alga Botryococcus braunii (Trebouxiophyceae). The algae contained a series of monoenoic fatty acids up to triacontenoic acid and further VLCFAs in amounts around 1% of total fatty acids. The separation of lipid classes using hydrophilic interaction chromatography revealed that the most abundant VLCFAs (28:2, 28:1 and 28:0) were contained in neutral lipids (triacylglycerols and/or diacylglycerols) and in phospholipids (phosphatidic acid and/or phosphatidylcholine). Using non-aqueous reversed-phase liquid chromatography tandem mass spectrometry (NARP-LC/MS2) of the appropriate collected fractions, molecular species of triacylglycerols containing one or two VLCFAs were described and phosphatidylcholines containing VLCFAs were separated for the first time. Because the presence of Botryosphaerella sudetica (Chlorophyceae) as contaminant of Botryococcus braunii strain Droop 1950/807-1 placed some doubts on the results of previous studies, a strain of this green alga of was also analyzed. In contrast to Botryococcus, C16, a substantially lower proportion of C18 polyunsaturated fatty acids and no VLCFAs were detected in Botryosphaerella.

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Datum: 21.02.2018


Cytoprotective dihydronaphthalenones from the wood of Catalpa ovata

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Yun-Seo Kil, Yang Kang So, Min Jung Choi, Ah-Reum Han, Chang Hyun Jin, Eun Kyoung Seo

Three previously undescribed dihydronaphthalenones, 7-hydroxycatalponol, (4S)-3,4-dihydro-4-hydroxy-2-[(2R)-2,3-dihydroxy-3-methylbutylidene]naphthalen-1(2H)-one, and (6S)-5,6-dihydro-6-hydroxy-2,2-dimethyl-2H-benzo[h]chromen-4(3H)-one and one phthalide, (±)-3-(5-hydroxy-5-methyl-2-oxohex-3-en-1-yl)isobenzofuran-1(3H)-one, were isolated from the wood of Catalpa ovata G. Don (Bignoniaceae), together with six known compounds. The structures of the previously undescribed compounds were elucidated by interpretation of 1D and 2D NMR data. The absolute configurations of the dihydronaphthalenones were deduced by analysis of the ECD data and application of Mosher ester methodology. All isolates were investigated for their cytoprotective effects against hydrogen peroxide (H2O2)-induced oxidative damage in HepG2 cells. Moreover, the mRNA expression levels of antioxidant enzymes such as heme oxygenase-1 (HO-1) and NAD(P)H:quinine oxidoreductase 1 (NQO1) in HepG2 cells were examined by RT-PCR analysis. As a result, catalponol and epi-catalponol showed antioxidant activities via directly scavenging of intracellular ROS and inducing the antioxidant enzymes in vitro.

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Datum: 21.02.2018


Daphnane diterpenoids with nitric oxide inhibitory activities and interactions with iNOS from the leaves of Trigonostemon thyrsoideus

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Feng Liu, Xueyuan Yang, Yue Liang, Bangjian Dong, Guochen Su, Muhetaer Tuerhong, Da-Qing Jin, Jing Xu, Yuanqiang Guo

A phytochemical investigation to search for new nitric oxide (NO) inhibitors resulted in the isolation of seven previously undescribed daphnane diterpenoids, thyrsoidpenes A−G, from the leaves of Trigonostemon thyrsoideus. Their structures including absolute configurations were elucidated on the basis of extensive NMR spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Thyrsoidpenes B−G feature rare polycyclic caged structures of daphnane diterpenoid orthoester. The NO inhibitory effects were examined and all of the compounds showed inhibitory activities toward LPS-induced NO production in murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the iNOS protein.

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Datum: 21.02.2018


Cucurbitane-type triterpenes from the tubers of Hemsleya penxianensis and their bioactive activity

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Nailiang Zhu, Zhonghao Sun, Meigeng Hu, Yedan Li, Dawei Zhang, Haifeng Wu, Yu Tian, Pengfei Li, Junshan Yang, Guoxu Ma, Xudong Xu

The tubers of the medicinal plant Hemsleya penxianensis (Cucurbitaceae) yielded 11 cucurbitane-type triterpenes Xuedanencins A-K by silica gel column, ODS column, and pre-HPLC techniques. Their structures were determined by spectroscopic analysis and examined alongside existing data from prior studies. Separated compounds were evaluated for cytotoxic activity against the Hela human cancer cell line and compounds 7 and 8 showed significant cytotoxicity with IC50 values at 1.82 and 2.45 μM, respectively.

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Datum: 21.02.2018


Differential metabolism of L–phenylalanine in the formation of aromatic volatiles in melon (Cucumis melo L.) fruit

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Itay Gonda, Rachel Davidovich-Rikanati, Einat Bar, Shery Lev, Pliaa Jhirad, Yuval Meshulam, Guy Wissotsky, Vitaly Portnoy, Joseph Burger, Arthur A. Schaffer, Yaakov Tadmor, James J. Giovannoni, Zhangjun Fei, Aaron Fait, Nurit Katzir, Efraim Lewinsohn

Studies on the active pathways and the genes involved in the biosynthesis of L-phenylalanine-derived volatiles in fleshy fruits are sparse. Melon fruit rinds converted stable-isotope labeled L-phe into more than 20 volatiles. Phenylpropanes, phenylpropenes and benzenoids are apparently produced via the well-known phenylpropanoid pathway involving phenylalanine ammonia lyase (PAL) and being (E)-cinnamic acid a key intermediate. Phenethyl derivatives seemed to be derived from L-phe via a separate biosynthetic route not involving (E)-cinnamic acid and PAL. To explore for a biosynthetic route to (E)-cinnamaldehyde in melon rinds, soluble protein cell-free extracts were assayed with (E)-cinnamic acid, CoA, ATP, NADPH and MgSO4, producing (E)-cinnamaldehyde in vitro. In this context, we characterized CmCNL, a gene encoding for (E)-cinnamic acid:coenzyme A ligase, inferred to be involved in the biosynthesis of (E)-cinnamaldehyde. Additionally we describe CmBAMT, a SABATH gene family member encoding a benzoic acid:S-adenosyl-L-methionine carboxyl methyltransferase having a role in the accumulation of methyl benzoate. Our approach leads to a more comprehensive understanding of L-phe metabolism into aromatic volatiles in melon fruit.

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Datum: 21.02.2018


Anti-HIV and cytotoxic biphenyls, benzophenones and xanthones from stems, leaves and twigs of Garcinia speciosa

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Phanruethai Pailee, Chutima Kuhakarn, Chanyapat Sangsuwan, Sakchai Hongthong, Pawinee Piyachaturawat, Kanoknetr Suksen, Surawat Jariyawat, Radeekorn Akkarawongsapat, Jitra Limthongkul, Chanita Napaswad, Palangpon Kongsaeree, Samran Prabpai, Thaworn Jaipetch, Manat Pohmakotr, Patoomratana Tuchinda, Vichai Reutrakul

Eleven previously undescribed compounds, including four benzophenones (garciosones A−D), four xanthones (garciosones E−H) and three biphenyls (garciosines A−C), along with eighteen known compounds were isolated from the stems, leaves and twigs of Garcinia speciosa Wall. (Clusiaceae). Their structures were established by extensive spectroscopic analysis. For garciosines A−C, the structures were confirmed by single crystal X-ray diffraction analysis. Most of the isolated compounds were evaluated for their cytotoxic activity and anti-HIV-1 activity using the syncytium inhibition assay and HIV-1 reverse transcriptase (RT) assay. The known compounds, 4,6,3′,4′-tetrahydroxy-2-methoxybenzophenone and macluraxanthone, displayed significant cytotoxic activity with the ED50 in the range of 1.85–11.76 μM. 1,5-Dihydroxyxanthone exhibited the most potent anti-HIV activity against syncytium formation with EC50 < 17.13 μM (SI > 25.28) and 2-(3,3-dimethylallyl)-1,3,7-trihydroxyxanthone was the most active compound in the HIV-1 reverse transcriptase assay with IC50 value of 58.24 μM. Structure-activity relationship of some isolated compounds were also discussed.

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Datum: 21.02.2018


Rapid structure prediction by HPLC-ESI-MSn of twenty-five polyoxypregnane tetraglycosides from Dregea sinensis with NMR confirmation of eight structures

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Juan Song, Rongji Dai, Yulin Deng, Fang Lv

Dregea sinensis Hemsl is an important herbal medicine in the Dai nationality of China. Its prominent clinical application has generated interest in the polyoxypregnane glycosides of the plant. This paper describes an extension of previous research on the polyoxypregnane di- and triglycosides of D. sinensis, aiming at identifying related tetraglycosides. On the basis of HPLC-ESI-MSn analysis in positive mode, twenty-five previously undescribed polyoxypregnane tetraglycosides were characterized (regarding molecular masses and fragmentation in MSn) from an ethyl acetate fraction that was not previously investigated. Guided by MSn fragmentation and known structures of related di- and triglycosides from D. sinensis, tentative structures were predicted from the MS data. In order to test the predictions, eight of the glycosides were isolated and their structures were elucidated by 1D and 2D NMR methods, confirming the tentative predictions. Finally, the cytotoxicity of the isolates was evaluated on several human cell lines with little effect in general, even though slight inhibitory effects of four polyoxypregnane glycosides were detected at 10 μM against the human leukemia cell line HL-60.

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Datum: 21.02.2018


Oleanane-type triterpenoid saponins from Lysimachia fortunei Maxim

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Shu-Lin Zhang, Zi-Ni Yang, Cui He, Hai-Bing Liao, Heng-Shan Wang, Zhen-Feng Chen, Dong Liang

Six previously undescribed oleanane-type triterpenoid saponins, fortunosides A–F, together with six known ones, were isolated from the aerial parts of Lysimachia fortunei Maxim. Their structures were established by spectroscopic data analyses (1D, 2D-NMR and HRESIMS) and chemical methods. All isolated triterpenoid saponins were evaluated for their cytotoxicity against four human liver cancer cell lines (SMMC-7721, Hep3B, HuH7, and SK-Hep-1). Three saponins with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines, with IC50 values ranging from 4.76 to 15.12 μM.

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Datum: 21.02.2018


Gallocatechin biosynthesis via a flavonoid 3′,5′-hydroxylase is a defense response in Norway spruce against infection by the bark beetle-associated sap-staining fungus Endoconidiophora polonica

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Almuth Hammerbacher, Bettina Raguschke, Louwrance P. Wright, Jonathan Gershenzon

One of the best-studied defense responses to fungal infection in Norway spruce (Picea abies) is the biosynthesis of flavan-3-ols, which accumulate as monomers or polymers known as proanthocyanidins. The individual flavan-3-ol units consist of compounds with a 3′,4′-dihydroxylated B ring [2,3-(trans)-(+)-catechin or 2,3-(cis)-(−)-epicatechin] and compounds with a 3′,4′,5′-trihydroxylated B ring [2,3 (trans)-(+)-gallocatechin or 2,3-(cis)-(−)-epigallocatechin]. While much is known about the biosynthesis and biological activity of catechin in Norway spruce, there is little comparable information about gallocatechin or epigallocatechin. We found that there was a significant increase in the gallocatechin content of Norway spruce bark and wood after inoculation with the bark beetle-associated sap-staining fungus Endoconidiophora polonica. Gallocatechins increased proportionally more than catechins as both monomers and units of polymers. A flavonoid 3′,5′-hydroxylase gene identified in Norway spruce was shown by heterologous expression in Nicotiana benthamiana to be involved in the conversion of 2,3 (trans)-(+)-catechin to 2,3 (trans)-(+)-gallocatechin. The formation of the trihydroxylated B ring in Norway spruce occurs at the level of flavan-3-ols, rather than at the level of dihydroflavonols as in many angiosperms. The transcript abundance of the flavonoid 3′,5′-hydroxylase gene also increased significantly during fungal infection underlining its importance in gallocatechin biosynthesis. Comparisons of the effect of 2,3 (trans)-(+)-catechin and 2,3 (trans)-(+)-gallocatechin on fungal growth revealed that 2,3 (trans)-(+)-catechin is a stronger inhibitor of fungal growth, while 2,3 (trans)-(+)-gallocatechin is a stronger inhibitor of melanin biosynthesis.

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Datum: 21.02.2018


Isolation, purification, structural characterization and immunostimulatory activity of water-soluble polysaccharides from Lepidium meyenii

Publication date: March 2018
Source:Phytochemistry, Volume 147

Author(s): Zhengqi Zha, Su-Yan Wang, Weihua Chu, Yang Lv, Hongjin Kan, Qiuli Chen, Lili Zhong, Long Yue, Jinna Xiao, Ying Wang, Hongping Yin

A water-soluble polysaccharide LMP-1 was isolated and purified by ion-exchange chromatography from maca (Lepidium meyenii Walp.). LMP-1 has a molecular weight of 1.01 × 104 Da, and is composed of glucose and arabinose with a molar ratio of 7.03:1.08. Methylation and the 1D and 2D NMR spectroscopy of LMP-1 revealed that it is mainly composed of →4)-α-D-Glcp-(1→, →6)-α-D-Glcp-(1→, →3)-α-D-Glcp-(1→, and β-D-Araf-(1→, with branching at O-6 of →4,6)-α-D-Glcp-(1 → . LMP-1 showed up-regulation of Toll-like receptor 4 (TLR4) and Toll-like receptor 2 (TLR2). The upstream proteins of Toll-like receptors (TLRs) (CD14 and MD2) and mRNA level of IL-1β also increased. Increased transcription factor nuclear factor-kappa B (NF-κB) p65 was found in the nuclei and cytoplasm in LMP-1-treated RAW264.7 macrophages. These results indicated that LMP-1 activated RAW264.7 macrophages and elicited immunostimulatory activities via the TLRs/NF-κB signalling pathway.

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Datum: 21.02.2018


Filler Advert language

Publication date: March 2018
Source:Phytochemistry, Volume 147










Datum: 21.02.2018


Aims and Scope

Publication date: March 2018
Source:Phytochemistry, Volume 147










Datum: 21.02.2018


Cadopherone and colomitide polyketides from Cadophora wood-rot fungi associated with historic expedition huts in Antarctica

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Yudi Rusman, Benjamin W. Held, Robert A. Blanchette, Yanan He, Christine E. Salomon

Recent investigations of filamentous fungi isolated from coastal areas and historic wooden structures in the Ross Sea and Peninsula regions of Antarctica have identified the genus Cadophora as one of the most abundant fungal groups, comprising more than 30% of culturable fungi at some locations. A methanol extract of Cadophora luteo-olivacea grown on rice media yielded the known polyketides spiciferone A, spiciferol A, dihydrospiciferone A and dihydrospiciferol A. Additionally, nine related hexaketides were identified, including spiciferone F, two isomers of the known fungal bicyclic ketal colomitide B, cadopherones A-D, similin C, and spicifernin B. HPLC and NMR analysis of extracts from other isolates collected in Antarctica suggests that the spiciferones and colomitides are produced by at least two different Cadophora species. Preliminary precursor feeding experiments provided evidence for the biosynthesis of the colomitides from the same polyketide pathway as the spiciferone phytotoxins, possibly via a type III polyketide synthase (PKS). None of the compounds were active in a panel of anti-bacterial, anti-fungal, and mammalian cytotoxicity assays.

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Datum: 21.02.2018


Outside Front Cover

Publication date: February 2018
Source:Phytochemistry, Volume 146










Datum: 21.02.2018


Phenolic metabolites from Hypericum kelleri Bald., an endemic species of Crete (Greece)

Publication date: February 2018
Source:Phytochemistry, Volume 146

Author(s): Angeliki Mathioudaki, Ariola Berzesta, Zacharias Kypriotakis, Helen Skaltsa, Jörg Heilmann

Thirteen compounds were isolated from the aerial parts of Hypericum kelleri Bald., growing as an endemic on the island of Crete (Greece). These compounds comprise four previously unknown prenylated xanthones 1,2-dihydro-3,8-dihydroxy-6-methoxy-1,1,5-tri(3-methylbut-2-enyl)xanthen-2,9-dione (kellerine A), 1,2-dihydro-3,6,8-trihydroxy-1,1,5-tri(3-methylbut-2-enyl)xanthen-2,9-dione (kellerine B), 1,2-dihydro-3,8-dihydroxy-6-methoxy-1,1-bi(3-methylbut-2-enyl)xanthen-2,9-dione (6-methylpatulone), (R/S)-1,3,5-trihydroxy-2-(3-methyl-2-buten-1-yl)-4-[2-(3-methylbut-2-enyl)-3-methylbut-3-enyl]-6-methoxy-9H-xanthen-9-one ((2″R/S)-kellerine C) and the hitherto undescribed depsidone (R/S)-1,3,6-trihydroxy-5-methoxy-2-(3-methyl-2-buten-1-yl)-4-[2-(3-methylbut-2-enyl)-3-methylbut-3-enyl]-11Η-dibenzo[b,e] [1,4]dioxepin-9-one ((2″R/S)-creticine). As known compounds, brevipsidone D, 4-geranyl-2-(2′-isobutyryl)-phloroglucinol, 4-geranyl-2-(2′-methylbutyryl)-phloroglucinol, I3, II8-biapigenin, quercetin, avicularin, pseudohypericin and neochlorogenic acid have been isolated. The structures were elucidated on the basis of their 1D, 2D NMR, CD and MS data. The study confirms the typical occurrence of xanthones in Hypericum section Oligostema (Boiss.) Stef., and is also the first report on the simultaneous isolation of acylphloroglucinols in this section. Furthermore the first evidence of depsidones in the genus Hypericum L. is reported. Cytotoxicity was investigated in HeLa cells for prenylated xanthones and the depsidones. Both triprenylated 1,2-dihydroxanthones (kellerine A and B) showed significant in vitro cytotoxicity with IC50 values of 2.5 ± 0.1 (kellerine A) and 5.9 ± 0.9 (kellerine B) μM, whereas other compounds were less cytotoxic (IC50 > 20 μM).

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Datum: 21.02.2018


Graphical Contents List

Publication date: February 2018
Source:Phytochemistry, Volume 146










Datum: 21.02.2018


Indole diterpenoids from the endophytic fungus Drechmeria sp. as natural antimicrobial agents

Publication date: April 2018
Source:Phytochemistry, Volume 148

Author(s): Jian-Chao Zhao, Ya-Li Wang, Tian-Yuan Zhang, Zhong-Jian Chen, Tian-Mei Yang, Ying-Ying Wu, Cheng-Peng Sun, Xiao-Chi Ma, Yi-Xuan Zhang

A fungal strain, Drechmeria sp., was isolated from the root of Panax notoginseng. Totally, seven new indole diterpenoids, drechmerins A-G (17), were isolated from the fermentation broth of Drechmeria sp. together with four known analogues (811). Their structures were determined on the basis of 1D and 2D NMR and electronic circular dichroism (ECD) spectroscopic analyses as well as theoretical calculations. All the isolated compounds were evaluated for their antimicrobial activities against Candida albicans, Staphylococcus aureus, Bacillus cereus, B. subtillis, Pseudomonas aeruginosa, and Klebsiella pneumonia, respectively. Drechmerin B (2) displayed antimicrobial activity against C. albicans with an MIC value of 12.5 μg/mL. Molecular docking was used to investigate interactions of peptide deformylase with compounds 1–3, 5–7, 9, and 10.

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Datum: 21.02.2018


Phenolic chemistry of the seagrass Zostera noltei Hornem. Part 1: First evidence of three infraspecific flavonoid chemotypes in three distinctive geographical regions

Publication date: February 2018
Source:Phytochemistry, Volume 146

Author(s): Micheline Grignon-Dubois, Bernadette Rezzonico

The flavonoid content of Zostera noltei leaves was investigated over a broad spatial scale using chromatographic and spectroscopic techniques (HPLC-DAD, LC/MS and NMR). Samples were collected at fifteen localities covering Mediterranean Sea and NE Atlantic coast, and representative of three types of coastal ecosystems: mesotidal bays, coastal lagoons, and open-sea. Three geographically distinct flavonoid chemotypes were identified on the basis of their respective major compound. One is characterized by apigenin 7-sulfate (Eastern part of Gulf of Cadiz), one by diosmetin 7-sulfate (French Atlantic coast and Mediterranean Sea), and the third contained similar quantities of the above two compounds (Mauritania and South Portugal). Our results show that metabolomic profiling using a combination of analytical techniques is a tool of choice to characterize chemical phenotype accurately. This work emphasizes for the first time the spatial variability in the flavonoid chemistry of Z. noltei throughout Atlantic and Mediterranean range, and constitutes the first report of chemical races in the Zosteraceae family. This infraspecific chemical differentiation should be considered when dealing with the role of Z. noltei in coastal ecosystems or in the selection of the best population donor for Z. noltei beds restoration. Combined with molecular identification, phenolic fingerprinting might be helpful to elucidate the evolutionary history of Z. noltei.

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Datum: 21.02.2018


 


Category: Current Chemistry Research

Last update: 04.01.2018.






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