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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



LC-MS guided isolation of sinodamines A and B: Chimonanthine-type alkaloids from the endangered ornamental plant Sinocalycanthus chinensis

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Guang-Lei Ma, Juan Xiong, Ezzat E.A. Osman, Ting Huang, Guo-Xun Yang, Jin-Feng Hu
Two previously undescribed chimonanthine-type [sinodamines A and B] and five related known dimeric tryptamine-derived alkaloids were isolated and characterized from the leaves of the endangered ornamental plant Sinocalycanthus chinensis under the guidance of LC-MS detection and dereplication analyses, along with conventional isolation procedures. Their structures were established on the basis of spectroscopic methods and chemical transformations. Sinodamine A can be regarded as the naturally occurring N-oxide derivative of its pseudo-mesomer sinodamine B. An acid-catalyzed Meisenheimer rearrangement from sinodamine A to its oxazine-form with a final equilibrium of 1:2 was observed by monitoring their NMR spectra. (−)-Folicanthine showed significant cytotoxicity against human lung carcinoma A549 and colorectal carcinoma HT29 cells, with IC50 values of 7.76 and 6.16 μM, respectively.

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Datum: 23.05.2018


Use of fatty acids in the chemotaxonomy of the family Selenastraceae (Sphaeropleales, Chlorophyceae)

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Cilene Cristina Mori, Inessa Lacativa Bagatini, Thais Garcia da Silva, Christopher Charles Parrish, Armando Augusto Henriques Vieira
The family Selenastraceae includes many species of freshwater green microalgae with morphological characteristics that are so subtly different that it is difficult to discriminate species within it. Therefore, the use of the diacritical characteristics of traditional morphological taxonomy may be ineffective at differentiating among many species of the family. Chemotaxonomy based on fatty acid methyl ester (FAME) can help resolve uncertainties not completely addressed by other approaches, such as molecular studies of some species within the Selenastraceae. Here, we first tested three techniques for the analysis of microalgal FAME to choose the one that would provide the best profiles for chemotaxonomy: 1) direct transesterification (DT) of the biomass followed by gas chromatography coupled to mass spectrometry analysis (GC-MS); 2) extraction using chloroform and methanol, followed by transesterification (T) and then analysis by gas chromatography/flame ionization detector (GC-FID); and 3) extraction with chloroform and methanol and then separation into lipid classes using thin-layer chromatography (TLC) using the Iatroscan-Chromarod system. The tests were conducted on 12 strains (11 species) of Selenastraceae and one outgroup strain. The fatty acid profiles produced by the DT-GC-MS technique yielded the best results for the chemotaxonomy of the Selenastraceae species using 12 FAME. The proportion of the variance in the fatty acid profiles obtained with DT-GC-MS analysis explained by species was 85%, whereas the differences explained by strains was 92%. Therefore, DT-GC-MS was used to analyze other microalgae strains, totaling 15 species of 8 genera of green coccoid microalgae, including the recently described Curvastrum. The results with all strains showed that fatty acid profiles obtained by DT-GC-MS were significantly different (p < 0.001) among strains and among species. The variance in fatty acids profiles explained by separation into strains was 97%, whereas the separation into species explained 93% of the variance. Statistical analyses showed that, for our dataset, the C18 fatty acids 18:3ω3 and 18:4ω6 were indicative of the Selenastraceae. Therefore, fatty acid profiles are a useful auxiliary chemotaxonomic tool for species identification in Selenastraceae.

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Datum: 23.05.2018


Diterpenes from buds of Wikstroemia chamaedaphne showing anti-hepatitis B virus activities

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Shi-Fei Li, Ying-Ying Jiao, Zhi-Qiang Zhang, Jian-Bin Chao, Jie Jia, Xun-Long Shi, Li-Wei Zhang
Phytochemical study of the buds of Wikstroemia chamaedaphne Meisn. led to the isolation of seven previously undescribed diterpenes, including one tigliane diterpene (wikstchalide A), two daphnane diterpenes (wikstroelides W-X), and four lathyrane diterpenes (laurifoliosides A-B and 2-epi-laurifoliosides A-B), along with four known diterpenes. The structures of these compounds were established by extensive spectroscopic evidence and electronic circular dichroism (ECD) calculations. Wikstchalide A possesses a 5,6-epoxy ring in the tigliane skeleton. Two compounds exhibited potential anti-hepatitis B virus activities, with IC50 values of 46.5 and 88.3 μg/mL against hepatitis B virus (HBV) surface antigen (HBsAg), and six compounds showed certain inhibitory effects on HBV-DNA replication with the inhibition ratios ranging from 2.0% to 33.0% at the concentrations ranging from 0.39 to 6.25 μg/mL.

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Datum: 23.05.2018


Characterization of anthocyanins in the hybrid progenies derived from Iris dichotoma and I. domestica by HPLC-DAD-ESI/MS analysis

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Wenji Xu, Gangjun Luo, Fengyang Yu, Qingxiang Jia, Yang Zheng, Xiaoying Bi, Jiajun Lei
Iris dichotoma with different flower colors and I. domestica are beardless wild irises belonging to the family Iridaceae that bloom in the summer and have long flowering periods. In this study, we collected three accessions of I. dichotoma with violet, yellow, and white flowers, respectively, in China, and crossed them with I. domestica individuals. The flower color of the hybrids derived from these crosses was categorized into eight groups: violet, purple, brown, orange, red, pink, yellow, and white. From this population, 45 individuals were selected for analysis, and their fully expanded inner and outer perianths were harvested for extraction of anthocyanins. Using high-performance liquid chromatography-mass spectrometry (HPLC-MS) analysis, 29 anthocyanins were identified by comparing MS and UV–visible spectra and elution order based on published data and guidelines. The 29 anthocyanins were classified into six groups: non-acylated glycosides (3RG, 3RG5G), acetylglycosides (3acRG5G), p-coumaroylglycosides (3pCRG, 3pCRG5G), caffeoylglycosides (3CRG5G), feruloylglycosides (3feRG, 3feRG5G), and acetyl-(p-coumaroyl) glycosides (3ac-pCRG5G). Acylated anthocyanin contents were considerably higher than non-acylated anthocyanin contents in the individuals evaluated, regardless of flower color, except in the yellow-flowered I. dichotoma and its yellow-flowered progeny. We found ten anthocyanins derived from pelargonidin, including pelargonidin 3-O-(caffeoyl)rutinoside-5-O-glucoside (Pg3CRG5G), pelargonidin 3-O-(feruloyl)rutinoside-5-O-glucoside (Pg3feRG5G), and pelargonidin 3-O-(feruloyl)rutinoside (Pg3feRG), that have not yet been reported in other Iris species. Moreover, delphinidin 3-O-(feruloyl) rutinoside-5-O-glucoside (Dp3feRG5G), and delphinidin 3-O-(feruloyl)rutinoside (Dp3feRG) were also characterized for the first time in Iris. Two to five major anthocyanins were detected in the petals of the violet and purple groups, whereas those of the brown group contained three to six anthocyanins. Petals of the orange, red, and pink groups contained two to four major anthocyanins. The total variance explained by the first two principal components (PC) in a PC analysis of the intensities of the compound peaks detected in individuals representing the eight color groups was 44.7%. Individuals were classified into 10 types (A-I to A-X) according to their anthocyanidin composition in the flower petals. Knowledge of the types of anthocyanins determining flower petal color will aid comprehensive understanding of flower color characteristics in hybrid progeny and will contribute to the development of breeding Iris cultivars of diverse flower colors.

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Datum: 23.05.2018


Dinardokanshones C–E, isonardoeudesmols A–D and nardoeudesmol D from Nardostachys jatamansi DC.

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Hong-Hua Wu, Xu Deng, Hu Zhang, Ying-Peng Chen, Shu-Song Ying, Yi-Jing Wu, Yan-Ting Liu, Yan Zhu, Xiu-Mei Gao, Yan-Tong Xu, Li Li
Dinardokanshones C–E, three sesquiterpenoid dimers comprising an unusual nornardosinane-type sesquiterpenoid core and an aristolane-type sesquiterpenoid unit conjugated by an extra pyran or furan ring, together with monomeric sesquiterpenoids isonardoeudesmols A–D and nardoeudesmol D, were isolated from the underground parts of Nardostachys jatamansi DC. Structures of the eight compounds were elucidated by analysis of the extensive spectroscopic data, and their absolute configurations were established by analysis of NOESY and X-ray diffraction data, combined with computational electronic circular dichroism (ECD) calculations. The results of SERT activity assay revealed that isonardoeudesmol D and nardoeudesmol D significantly inhibited SERT activity, while dinardokanshones D–E and isonardoeudesmols B–C significantly enhanced SERT activity, among which dinardokanshone D exhibited the strongest effect.

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Datum: 23.05.2018


Biotransformation of cyclocanthogenol by the endophytic fungus Alternaria eureka 1E1BL1

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Güner Ekiz, Seda Duman, Erdal Bedir
The microbial transformation of cyclocanthogenol (CCG), Astragalus sp. originated sapogenin, by the endophytic fungus Alternaria eureka 1E1BL1 isolated from Astragalus angustifolius was investigated. Hydroxylation, oxidation, epoxidation, O-methylation, ring-expansion and methyl migration reactions were observed on the triterpenoid skeleton. As a result, eight metabolites were isolated and the structures of the previously undescribed compounds were established by 1-D, 2-D NMR and HR-MS analyses.

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Datum: 23.05.2018


Graphical Contents List

Publication date: June 2018
Source:Phytochemistry, Volume 150




Datum: 23.05.2018


Biotransformation of ruscogenins by Cunninghamella blakesleeana NRRL 1369 and neoruscogenin by endophytic fungus Neosartorya hiratsukae

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Özge Özçinar, Özgür Tağ, Hasan Yusufoglu, Bijen Kivçak, Erdal Bedir
Biotransformation of steroidal ruscogenins (neoruscogenin and ruscogenin) was carried out with Cunninghamella blakesleeana NRRL 1369 and endophytic fungus Neosartorya hiratsukae yielding mainly P450 monooxygenase products together with a glycosylated compound. Fermentation of ruscogenins (75:25, neoruscogenin-ruscogenin mixture) with C. blakesleeana yielded 8 previously undescribed hydroxylated compounds. Furthermore, microbial transformation of neoruscogenin by endophytic fungus N. hiratsukae afforded three previously undescribed neoruscogenin derivatives. While hydroxylation at C-7, C-12, C-14, C-21 with further oxidation at C-1 and C-7 were observed with C. blakesleeana, N. hiratsukae biotransformation provided C-7 and C-12 hydroxylated compounds along with C-12 oxidized and C-1(O) glycosylated derivatives. The structures of the metabolites were elucidated by 1-D (1H, 13C and DEPT135) and 2-D NMR (COSY, HMBC, HMQC, NOESY, ROESY) as well as HR-MS analyses.

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Datum: 23.05.2018


Lanostane-type C31 triterpenoid derivatives from the fruiting bodies of cultivated Fomitopsis palustris

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Jinzhi Zhao, Yun Yang, Mengyao Yu, Ke Yao, Xia Luo, Huayi Qi, Guolin Zhang, Yinggang Luo
Fifteen undescribed and five known lanostane-type C31 triterpenoid derivatives were isolated from the aqueous EtOH extract of the fruiting bodies of cultivated Fomitopsis palustris. Their structures were identified from the spectroscopic data and chemical degradation studies. The structures of palustrisoic acids A and H were confirmed by X-ray crystallography. Polyporenic acid B showed strong cytotoxicity against the HCT116, A549, and HepG2 cell lines with IC50 values of 8.4, 12.1, and 12.2 μM, respectively. Palustrisolides A, C, and G displayed weak cytotoxicity.

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Datum: 23.05.2018


Coriariin M, a trimeric hydrolysable tannin with dehydrodigalloyl and valoneoyl groups as linking units, and accompanying dimeric hydrolysable tannins from Coriaria japonica

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Yuuki Shimozu, Takayasu Hirai, Tsutomu Hatano
Three oligomeric hydrolysable tannins, coriariins K, L, and M, which were previously undescribed, together with five known hydrolysable tannins were isolated from dried leaves of Coriaria japonica. Their structures were determined based on 1D and 2D NMR spectroscopy, HR-ESI-MS, and ECD spectroscopy experiments. Among the isolated compounds, coriariin M has a unique trimer structure where both dehydrodigalloyl and valoneoyl group linkages were found between the hydrolysable tannin monomers. Dimeric hydrolysable tannins coriariins K and L, having a dehydrodigalloyl group as the linking unit, were structurally related to coriariin A, the main hydrolysable tannin of this plant species. Additionally, the complexation of the eight hydrolysable tannins isolated in this study with bovine serum albumin (BSA) to form water-soluble macromolecules was analyzed using native polyacrylamide gel electrophoresis (PAGE). A comparison of the behaviors of the oligomeric hydrolysable tannins suggested the participation of the hexahydroxydiphenoyl group and the importance of the molecular sizes of the hydrolysable tannins in the formation of macromolecules.

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Datum: 23.05.2018


Editorial Board/Publication Information

Publication date: June 2018
Source:Phytochemistry, Volume 150




Datum: 23.05.2018


Triterpenoid saponins from Scabiosa stellata collected in North-eastern Algeria

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Meryem Lehbili, Abdulmagid Alabdul Magid, Ahmed Kabouche, Laurence Voutquenne-Nazabadioko, Hamid Morjani, Dominique Harakat, Zahia Kabouche
Eight undescribed triterpenoid saponins, scabiostellatosides A-H, together with three known compounds were isolated from the whole plant of Scabiosa stellata L. Their structures were established by spectroscopic analyses (1D, 2D-NMR and HRESIMS) and chemical methods. Scabiostellatosides A-H were evaluated for their cytotoxicity against human fibrosarcoma cell line (HT1080). Scabiostellatoside F, a heptasaccharide derivative of oleanolic acid, exhibited moderate cytotoxicity against HT1080 cell line with IC50 value of 12.0 μM.

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Datum: 23.05.2018


Radial distribution of wood extractives in European larch Larix decidua by TOF-SIMS imaging

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Tingting Fu, Nicolas Elie, Alain Brunelle
Wood extractives in the xylem of European larch Larix decidua were mapped by time-of-flight secondary ion mass spectrometry (TOF-SIMS) imaging, which allows the radial distribution of both mineral and lipophilic extractives in the xylem to be scrutinized with high spatial resolution for the first time. Results show that all the components are inhomogeneously distributed across the annual ring. Mineral nutrients including Na+, K+, Ca+, and Cl ions exhibit no preferential localization between earlywood and latewood, whereas PO3 ion is exclusively present in the ray cells, indicating it may be related to acid phosphatase. Lipophilic extractives were found to be more abundant in the inner secondary xylem. Ion images with 400 nm spatial resolution reveal that fatty acids, triglycerides and phytosterols are co-localized principally in the earlywood within the first annual ring. Resin acids prove to be the main components in the resin canal of the secondary xylem and are distributed in the outer of it.

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Datum: 23.05.2018


Bioactive carbazole and quinoline alkaloids from Clausena dunniana

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Nankai Cao, Yuemei Chen, Xiaoli Ma, Kewu Zeng, Mingbo Zhao, Pengfei Tu, Jun Li, Yong Jiang
Nine undescribed carbazole and quinoline alkaloids, named dunnines A–E, and 14 known analogues were isolated from the leaves and stems of Clausena dunniana. Their structures were elucidated on the basis of comprehensive analysis of NMR and HRMS spectroscopic data, and the absolute configurations were assigned via comparison of their specific rotations and calculated and experimental ECD data. (±)-Dunnines A–C and (±)-clausenawalline A are four pairs of biscarbazole atropisomers and (±)-dunnine D is a pair of dihydropyranocarbazole enantiomers. They were separated by chiral HPLC to obtain the optically pure compounds. Three compounds showed weak inhibitory effects on nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells (IC50 > 50 μM); five compounds could significantly promote insulin secretion in HIT-T15 cell line (1.9–3.1-fold of the control, p < 0.01) at 40 μM, and nine compounds could inhibit the apoptosis of PC12 cell induced by 6-hydroxydopamine with IC50 values in the range of 10.9–47.2 μM.

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Datum: 23.05.2018


Bioactive norditerpenoids from Cephalotaxus fortunei var. alpina and C. lanceolata

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Ling Ni, Xiu-Hong Zhong, Xiao-Jiao Chen, Bing-Jie Zhang, Mei-Fen Bao, Xiang-Hai Cai
Twenty-eight naturally occurring Cephalotaxus tropone analogues, including 19 previously undescribed ones, were identified from Cephalotaxus fortunei Hook. var. alpina H. L. Li and C. lanceolata K. M. Feng. The presence of the C20 cephinoids A−E revealed that these tropones were assigned to the norditerpenoids and were perhaps derived from labdane-type diterpenoids. These norditerpenoids showed excellent cytotoxicity against human cancer cells (IC50, 20–0.1 μM) in vitro. The SAR (structure-activity relationship) analysis disclosed that the tropone moiety and the lactone ring were crucial structural features for the observed activities. Further SAR analyses led to a new candidate, cephinoid H, which demonstrated an inhibition of 49.0% by administration to zebrafish at a dose of 60.0 ng/mL, compared to cisplatin (DDP, 22.4%) at 15.0 μg/mL. These compounds might affect the NF-κB signaling pathway rather than binding to microtubules. Additionally, the isolated norditerpenoids showed almost equal anti-inflammatory activities compared to the positive control, MG132.

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Datum: 23.05.2018


Impact of drought and salt stress on the biosynthesis of alkaloids in Chelidonium majus L.

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Mahdi Yahyazadeh, Rieke Meinen, Robert Hänsch, Sara Abouzeid, Dirk Selmar
When plants are exposed to various stress situations, their alkaloid concentration frequently is enhanced. This well-known phenomenon is presumably due to a passively enhanced rate of biosynthesis, caused by greatly elevated concentrations of NADPH in stressed plants. Here, we used Chelidonium majus L. plants, which accumulate high concentrations of dihydrocoptisine in their leaves, to study the impact of drought and salt stress on the biosynthesis and accumulation of alkaloids. In comparison to well-watered controls, in the transcriptome of the gene encoding the key enzyme in alkaloid biosynthesis, stylopine synthase, is enhanced in stressed C. majus plants. If we presuppose that increased transcript levels correlate with increased enzymatic activity of the gene products, these data indicate, for the first time, that stress-related increases in alkaloid concentration might not only be caused by the well-known stress-related passive shift, but may also be due to an enhancement of enzymatic capacity.

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Datum: 23.05.2018


Hebecarposides A−K, antiproliferative lanostane-type triterpene glycosides from the leaves of Lyonia ovalifolia var. hebecarpa

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Yang Teng, Hanqi Zhang, Junfei Zhou, Guanqun Zhan, Guangmin Yao
Eleven previously undescribed lanostane-type triterpene glycosides, hebecarposides A−K, were isolated from the leaves of Lyonia ovalifolia var. hebecarpa (Ericaceae), along with two known analogues, lyonifolosides L and O. The structures of hebecarposides A−K were established by extensive spectroscopic analysis and chemical methods, and the absolute configuration of C-24 in hebecarposides A and E was determined to be S and R, respectively, by a Mo2(OAc)4−induced electronic circular dichroism method. This is the first report of the presence of lanostane-type triterpene glycosides in L. ovalifolia var. hebecarpa. All compounds were evaluated for their antiproliferative activities against five cancer cell lines, SMMC-7721, HL-60, SW480, MCF-7, and A-549, and a normal epithelial cell line BEAS-2B, and none of them showed general cytotoxity to the normal cell line BEAS-2B. Interestingly, hebecarposides C, D, G, and K selectively inhibited the proliferation of HL-60 and SMMC-7721 cell lines, and hebecarposides C and D showed significant anti-proliferative activities against A-549 cell lines than the positive control, cis-platin. In addition, hebecarposides C and H exhibited more potent anti-proliferative activities against MCF-7 than cis-platin.

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Datum: 23.05.2018


High correlation of chemical composition with genotype in cryptic species of the liverwort Aneura pinguis

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Rafał Wawrzyniak, Wiesław Wasiak, Beata Jasiewicz, Agnieszka Ludwiczuk, Alina Bączkiewicz, Katarzyna Buczkowska
Chemical constituents of cryptic species detected within the liverwort Aneura pinguis were identified using headspace solid-phase microextraction gas chromatography–mass spectrometry (HS-SPME-GC-MS). Fibre coating with divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) was used. A total of 48 samples of A. pinguis were analysed. The studied plants were identified genetically based on barcode DNA sequences and represented three cryptic species (A, B and F) of A. pinguis. Cryptic species A and B are genetically diverse; both represent three evolutionary lineages: A1, A2, A3 and B1, B2, B3, respectively. The cryptic species F that was recently detected is not diverse. The most characteristic compounds in analysed samples were sesquiterpene hydrocarbons (up to 17.7% for A1; 15.7% for A2; 20.6% for A3; 7.7% for B1; 2.0% for B2; 3.7% for B3; 10.2% for F), oxygenated sesquiterpenoids (up to 68.0% for A1; 54.7% for A2; 52.6% for A3; 63.5% for B1; 88.7% for B2; 82.7% for B3; 78.8% for F), and linear aliphatic hydrocarbons (up to 14.8% for A1; 1.1% for A2; 12.1% for A3; 6.9 for B1; 5.2% for B2; 1.1% for B3; 7.0% for F). The dominant compound in the studied samples was pinguisone. The second dominant compound present in the tested plant material was deoxopinguisone, except for lineage B2, where only a small relative concentration of this compound was found. A high content of deoxopinguisone in cryptic species A (lineages A1, A2 and A3) was accompanied by the presence of isopinguisone and methyl norpinguisonate, whereas these two compounds were not detected in cryptic species B (lineages B1 and B3) and F. The chemical compounds detected in the studied samples of A. pinguis were subjected to multivariate statistical analysis. The results showed that the chemical composition depends mainly on the genotype of the plant and slightly on the habitat. However, there was no clear correlation between the volatile compounds and the date of collection of the studied plants.

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Datum: 23.05.2018


Outside Front Cover

Publication date: June 2018
Source:Phytochemistry, Volume 150




Datum: 23.05.2018


Alkaloid diversity in the leaves of Australian Flindersia (Rutaceae) species driven by adaptation to aridity

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Luke P. Robertson, Casey R. Hall, Paul I. Forster, Anthony R. Carroll
The genus Flindersia (Rutaceae) comprises 17 species of mostly Australian endemic trees. Although most species are restricted to rainforests, four have evolved to grow in semi-arid and arid environments. In this study, the leaf alkaloid diversity of rainforest and semi-arid/arid zone adapted Australian Flindersia were compared by LC/MS-MS and NMR spectroscopy. Contrary to expectations, Flindersia alkaloid diversity was strongly correlated with environmental aridity, where species predominating in drier regions produced more alkaloids than their wet rainforest congenerics. Rainforest species were also more chemically similar to each other than were the four semi-arid/arid zone species. There was a significant relationship between the presence of alkaloid structural classes and phylogenetic distance, suggesting that alkaloid profiles are influenced by both genetic and environmental factors. The results suggest that the radiation of Flindersia species out of the rainforest and into drier environments has promoted the evolution of unique alkaloid diversity. Plants growing in arid and semi-arid regions of Australia may represent an untapped source of undescribed specialised metabolites.

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Datum: 23.05.2018


Morphology of glandular trichomes of Japanese catnip (Schizonepeta tenuifolia Briquet) and developmental dynamics of their secretory activity

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Chanchan Liu, Narayanan Srividya, Amber N. Parrish, Wei Yue, Mingqiu Shan, Qinan Wu, B. Markus Lange
Schizonepeta tenuifolia Briquet, commonly known as Japanese catnip, is used for the treatment of colds, headaches, fevers, and skin rashes in traditional Asian medicine (China, Japan and Korea). The volatile oil and its constituents have various demonstrated biological activities, but there is currently limited information regarding the site of biosynthesis. Light microscopy and scanning electron microscopy indicated the presence of three distinct glandular trichome types which, based on their morphological features, are referred to as peltate, capitate and digitiform glandular trichomes. Laser scanning microscopy and 3D reconstruction demonstrated that terpenoid-producing peltate glandular trichomes contain a disk of twelve secretory cells. The oil of peltate glandular trichomes, collected by laser microdissection or using custom-made micropipettes, was demonstrated to contain (−)-pulegone, (+)-menthone and (+)-limonene as major constituents. Digitiform and capitate glandular trichomes did not contain appreciable levels of terpenoid volatiles. The yield of distilled oil from spikes was significantly (44%) higher than that from leaves, while the composition of oils was very similar. Oils collected directly from leaf peltate glandular trichomes over the course of a growing season contained primarily (−)-pulegone (>80% at 32 days after germination) in young plants, while (+)-menthone began to accumulate later (>75% at 80 days after germination), at the expense of (−)-pulegone (the levels of (+)-limonene remained fairly stable at 3–5%). The current study establishes the morphological and chemical characteristics of glandular trichome types of S. tenuifolia, and also provides the basis for unraveling the biosynthesis of essential oil in this popular medicinal plant.

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Datum: 23.05.2018


Profiling of phenolic compounds and antioxidant properties of European varieties and cultivars of Vicia faba L. pods

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Inês M. Valente, Margarida R.G. Maia, Nertila Malushi, Hugo M. Oliveira, Lumturi Papa, José A. Rodrigues, António J.M. Fonseca, Ana R.J. Cabrita
Vicia faba L. pods are a by-product generated from the industrial processing of beans for human and animal consumption. As phenolic compounds may play important roles in health, the present work envisaged the phenolic characterization of seven European varieties and cultivars of V. faba (major and minor) pods and the assessment of their antioxidant activity. The V. faba methanolic extracts were characterized by HPLC-DAD-MS/MS for identification of polyphenolic compounds. The total phenolic content and antioxidant capacity of the extracts were evaluated by colorimetric methods (Folin-Ciocalteu, DPPH scavenging capacity assay, and FRAP assay). Main compounds identified by HPLC-DAD-MS/MS were derivatives of caffeic acid, coumaric acid and kaempferol. The broad bean Jögeva variety presented the highest content of free and esterified phenolics (26.3 and 26.7 mg 100 g−1 dry weight, respectively), followed by the horse bean varieties Bauska and Lielplatones. These results were corroborated by the analysis of total phenolic content, DPPH scavenging capacity and FRAP. This study confirmed the rich phenolic content of V. faba pods suggesting to be an interesting novel source for animal nutrition, promoting product quality and consumers' health.

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Datum: 23.05.2018


Discrimination of different geographic varieties of Gymnema sylvestre, an anti-sweet plant used for the treatment of type 2 diabetes

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Ha Thanh Tung Pham, Minh Chau Hoang, Thi Kim Quy Ha, Lan Huong Dang, Van On Tran, Thi Bich Thu Nguyen, Chul Ho Lee, Won Keun Oh
Gymnema sylvestre (Retz.) R.Br. ex Sm. (Asclepiadaceae) is a well-known Ayurvedic anti-sweet plant for the treatment of type 2 diabetes mellitus. Although it was previously proposed that G. sylvestre exhibits chemical variation based on geography, most research on G. sylvestre has used material originating from India. Morphological and anatomical descriptions, ITS1-5.8S-ITS2 DNA sequencing, and acid hydrolysis analyses showed that G. sylvestre samples from Vietnam are distinguishable from those of Indian origin and thus suggest a dissimilarity among G. sylvestre samples with different geographic distributions. An LC-MS-guided strategy targeting 3β-glucuronide oleane-triterpenes in the Vietnamese G. sylvestre variety led to the isolation of four known compounds and nine previously undescribed compounds, named gymnemosides ND1-ND9. None of the isolated compounds were reported in the Indian sample, further supporting the geo-diversity of G. sylvestre. Three compounds, gymnemosides ND7-9, exerted significant stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells and thus have potential as lead molecules for anti-diabetes agents.

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Datum: 23.05.2018


1H-NMR and UPLC-MS metabolomics: Functional tools for exploring chemotypic variation in Sceletium tortuosum from two provinces in South Africa

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Jianping Zhao, Ikhlas A. Khan, Sandra Combrinck, Maxleene Sandasi, Weiyang Chen, Alvaro M. Viljoen
Sceletium tortuosum (Aizoaceae) is widely recognised for the treatment of stress, anxiety and depression, as well as for obsessive compulsive disorders. A comprehensive intraspecies chemotypic variation study, using samples harvested from two distinct regions of South Africa, was done using both proton nuclear magnetic resonance (1H-NMR) spectroscopy of methanol extracts (N = 145) and ultra performance liquid chromatography-mass spectrometry (UPLC-MS) of acid/base extracts (N = 289). Chemometric analysis of the 1H-NMR data indicated two main clusters that were region-specific (Northern Cape and Western Cape provinces). Two dimensional (2D) NMR was used to identify analytes that contributed to the clustering as revealed by the S-plot. The sceletium alkaloids, pinitol and two alkylamines, herein reported for the first time from S. tortuosum, were identified as markers that distinguished the two groups. Relative quantification of the marker analytes conducted by qNMR indicated that samples from the Northern Cape generally contained higher concentrations of all the markers than samples from the Western Cape. Quantitative analysis of the four mesembrine alkaloids using a validated UPLC-photo diode array (PDA) detection method confirmed the results of qNMR with regard to the total alkaloid concentrations. Samples from the Northern Cape Province were found to contain, on average, very high total alkaloids, ranging from 4938.0 to 9376.8 mg/kg dry w. Regarding the Western Cape samples, the total yields of the four mesembrine alkaloids were substantially lower (averages 16.4–4143.2 mg/kg). Hierarchical cluster analysis of the UPLC-MS data, based on the alkaloid chemistry, revealed three branches, with one branch comprising samples primarily from the Northern Cape that seemed somewhat chemically conserved, while the other two branches represented mainly samples from the Western Cape. The construction of an orthogonal projections to latent structures-discriminant analysis model and subsequent loadings plot, allowed alkaloid markers to be identified for each cluster. The diverse sceletium alkaloid chemistry of samples from the three clusters may facilitate the recognition of alkaloid profiles, rather than individual compounds, that exert targeted effects on various brain receptors involved in stress, anxiety or depression.

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Datum: 23.05.2018


Seasonality effect on the composition of oxindole alkaloids from distinct organs of Uncaria tomentosa from the Caribbean region of Costa Rica

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Silvana Alvarenga-Venutolo, Catalina Rosales-López, Luis Sánchez-Chinchilla, Rodrigo Muñoz-Arrieta, Francisco Aguilar-Cascante
Uncaria tomentosa (Willd.) D.C. (Rubiaceae), commonly known as “Uña de Gato” or “Cat's Claw”, is a tropical vine from the rainforest used in traditional medicine and spread through Central and South America, including Costa Rica. There is an increasing demand for medicinal extracts with biological activity attributed mainly to oxindole alkaloids (OA), where the ratio between tetracyclic (TOA) and pentacyclic oxindole alkaloids (POA) determines its feasibility for medicinal applications. The ratio is affected by distinct factors including the dynamics of environmental conditions during seasons. The purpose of the study was to assess the seasonality effect in oxindole alkaloids content in relation to plant organs from U. tomentosa grown in the Caribbean region of Costa Rica. Young leaves followed by mature leaves presented the highest amount of total OA during seasons; for these, isoryncophylline, pteropodine and isomitraphylline, were the predominant OA. The POA/TOA ratio of both leaf materials was nearly 1:1 (3.2 mg g‐1: 3.1 mg g‐1). Bark and root material showed a pentacyclic chemotype in all seasons with a ratio of 6:1 (6.7 mg g‐1: 1.3 mg g‐1) with pteropodine and isomitraphylline as the predominant POA. The POA content presented seasonality with a significant increase from rainy to dry season in young leaves, bark and roots. In contrast, TOA amount remained virtually unchanged in all plant parts. Humidity and temperature between the studied seasons were constant except for precipitation, reflecting that differences of water content had an effect in the POA amounts. Further studies of abiotic factors, like water stress, could explain the variation of POA content due to seasonality.

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Datum: 23.05.2018


Trijugin- and mexicanolide-type limonoids from the fruits of Heynea trijuga that reverse multidrug resistance in MCF-7/DOX cells

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Fa-Liang An, Dong-Mei Sun, Rui-Zhi Wang, Ming-Hua Yang, Jun Luo, Ling-Yi Kong
Eleven previously undescribed limonoids, trichisins A-K, including eight structural analogues A-H of trijugin and three H-J mexicanolide derivatives, together with two known mexicanolide derivatives were isolated from the fruits of Heynea trijuga Roxb. ex Sims. The structure determination was based on extensive physical data analyses (NMR, MS), and their basic skeletons and the absolute configurations of trichisins A, B, E, K and trichiconnarone A were assigned via X-ray crystallographic analysis (Cu Kα radiation). The hemiketal motifs in trijugins A, B, and E-G are rare in limonoids. Bioactivity screenings suggested that the trijugin H and mexicanolide-type trichiconnarones A and B limonoids were effective in reversing resistance in MCF-7/DOX cells at a nontoxic concentration of 50 μM with IC50 values of 12.45, 10.86, and 14.96 μM, respectively.

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Datum: 23.05.2018


Cytotoxic garcimultiflorones K–Q, lavandulyl benzophenones from Garcinia multiflora branches

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Zhao-Quan Wang, Xing-Yu Li, Dong-Bao Hu, Chun-Lin Long
Seven undescribed lavandulyl benzophenones garcimultiflorones KQ, and fourteen known compounds were isolated from the CHCl3 soluble fraction of 95% EtOH extract of Garcinia multiflora branches. Their structures and absolute configurations were determined by spectroscopic techniques including NMR spectroscopy, MS analysis, and ECD calculations. Seven isolated compounds expect for garcimultiflorone L and garcimultiflorone O exhibited cytotoxic activities in vitro against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480). It is worth mentioning that garcimultiflorone Q exhibited most significant cytotoxicities against five cancer cell lines with IC50 values ranging from 3.07–12.56 μM.

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Datum: 23.05.2018


Caudatan A, an undescribed human kidney-type glutaminase inhibitor with tetracyclic flavan from Ohwia caudata

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Yiwei Sun, Xiaohe Feng, Xuanli Liu, Cheng Qian, Xin Che, Fei Cao, Sanshan Jin, Dali Meng
Human kidney-type glutaminase (KGA) is an important target that is often over expressed in many cancer cells but very few effective inhibitors of this enzyme have yet reached clinical trials. Caudatan A and caudatan B, two undescribed tetracyclic flavans with an unusual ether bond between the C-4 and C-2′ were isolated from the roots of Ohwia caudata (Thunb.) H.Ohashi. Caudatan A exhibited stronger inhibitory activity and caudatan B showed moderate effect from the results of inhibitory activities evaluations on KGA. The molecular docking and primary structure-activity relationship analysis revealed that the less steric hindrance at ring A was necessary to the effect. Therefore, combined its better solubility than that of bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl)ethyl sulfide (BPTES), caudatan A might be the potential candidate as the inhibitor of KGA for further studies.

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Datum: 23.05.2018


Flavonoid alkaloids from Scutellaria moniliorrhiza with anti-inflammatory activities and inhibitory activities against aldose reductase

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Qing-Tong Han, Yan Ren, Gui-Sheng Li, Kang-Lin Xiang, Sheng-Jun Dai
Four undescribed flavonoid alkaloids, as two pairs of enantiomers, were initially isolated as a racemate from the whole plant of Scutellaria moniliorrhiza. By means of chiral HPLC, four isomers, named scumonilines A-D, were successfully separated, and their chemical structures including absolute configurations were established by mass as well as NMR spectroscopy and CD technique. In vitro, four flavonoid alkaloids showed anti-inflammatory activities, with IC50 values against the release of β-glucuronidase from polymorphonuclear leukocytes of rats being in the range 5.16–5.85 μΜ. Moreover, four compounds were evaluated for their inhibitory activities against aldose reductase, and gave IC50 values in the range 2.29–3.03 μΜ.

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Datum: 23.05.2018


Ilicicolinic acids and ilicicolinal derivatives from the fungus Neonectria discophora SNB-CN63 isolated from the nest of the termite Nasutitermes corniger found in French Guiana show antimicrobial activity

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Jonathan Sorres, Abir Sabri, Orianne Brel, Didier Stien, Véronique Eparvier
The fungus Neonectria discophora SNB-CN63 has been isolated from the nest of the termite Nasutitermes corniger found in French Guiana. From the ethyl acetate extract of fungal culture, bioassay guided fractionation led to the isolation of fourteen ilicicolinic acids and ilicicolinal derivatives. Their structures were elucidated by analyses of 1D and 2D NMR and MS spectroscopic data. All metabolites were tested against several microbial pathogens and six displayed antimicrobial activities with MIC <16 μg/mL on T. rubrum, Staphylococcus aureus and methicillin-resistant S. aureus. Based on their structural similarities, a common biosynthetic pathway is proposed for all isolated metabolites.

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Datum: 23.05.2018


Glycosides of naphthohydroquinones and anthraquinones isolated from the aerial parts of Morinda parvifolia Bartl. ex DC (Rubiaceae) increase p53 mRNA expression in A2780 cells

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Xianming Su, Jian Zhang, Changkang Li, Fenghua Li, Hongqing Wang, Haifeng Gu, Baoming Li, Ruoyun Chen, Jie Kang
Eight previously undescribed naphthohydroquinone glycosides, namely morindaparvins H–O, together with four known anthraquinone glycosides were isolated from the n-BuOH extract of the aerial parts of Morinda parvifolia Bartl. ex DC (Rubiaceae).The structures of morindaparvins H–O were elucidated on the basis of spectroscopic analysis. To our knowledge, this is the first isolation of quinone glycosides from the plant M. parvifolia. The results showed that all 12 compounds at the concentration of 50 μM significantly increased p53 mRNA expression in A2780 cells compared with the blank control group.

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Datum: 23.05.2018


Increased cytotoxic potential of infrequent triterpenoid saponins of Cephalaria taurica obtained through alkaline hydrolysis

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Ozgur Ozer, Nazli Boke Sarikahya, Ayse Nalbantsoy, Suheyla Kirmizigul
Phytochemical investigations of the aerial parts of the plant Cephalaria taurica Szabó. (Caprifoliaceae) have resulted in the isolation of nine oleanane-type triterpenoid saponins, of which two still remain undescribed. The structures of tauricosides A and B were characterized based on NMR analysis, HRESIMS spectrometry, and chemical evaluations. The saponins tauricosides A and B have been rarely reported in the literature due to the presence of eight sugar moieties, and this is also the first report of saponins containing eight sugar moieties in the Caprifoliaceae family.The cytotoxic activities of tauricosides A and B, their undescribed prosapogenins, aglycone hederagenin, and n-butanol extract of C. taurica against the cancerous cells A-549, HeLa, PANC-1, and SH-SY5Y and the noncancerous HEK-293 cells were evaluated by the MTT method. Although tauricosides A and B and the crude n-butanol extract did not exhibit any activity at the tested concentrations on all the tested cells, after alkaline hydrolysis, the cytotoxic activity potential of the compounds was obviously improved. The most active compound, obtained after the alkaline hydrolysis of tauricoside B, showed a significant inhibitory effect, which was higher than that of the standard, commercially available drug doxorubicin, on the cancerous A-549, HeLa, PANC-1, and SH-SY5Y cells with IC50 values of 9.04, 8.75, 6.87, and 4.32 μM, respectively. In addition, prosapogenin, obtained after the alkaline hydrolysis of tauricoside A, exhibited considerable cytotoxic activity on the cancerous A-549, HeLa, PANC-1, and SH-SY5Y cells, with IC50 values of 13.19, 10.32, 11.91, and 7.49 μM, respectively. In conclusion, the alkaline hydrolysis of the saponins (tauricosides A and B) obviously improved their cytotoxic activity potential.

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Datum: 23.05.2018


Lanostane triterpenoids from Tricholoma pardinum with NO production inhibitory and cytotoxic activities

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Shuai-Bing Zhang, Zheng-Hui Li, Marc Stadler, He-Ping Chen, Ying Huang, Xiao-Qing Gan, Tao Feng, Ji-Kai Liu
Eight undescribed lanostane triterpenoids, pardinols A‒H, along with one previously reported lanostane triterpenoid, namely saponaceol B, were isolated from the fruiting bodies of Tricholoma pardinum. Their structures and stereoconfigurations were established via combination of extensive spectroscopic analyses, alkaline methanolysis method and TDDFT/ECD calculations. Pardinols B and E-H exhibited certain inhibition activities of nitric oxide (NO) production with IC50 value ranging from 5.3 to 14.7 μM, as well as cytotoxicities against human cancer cell-lines.

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Datum: 23.05.2018


Pentacyclic triterpenoids from Cyclocarya paliurus and their antioxidant activities in FFA-induced HepG2 steatosis cells

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Hui-Min Yang, Zhi-Qi Yin, Meng-Ge Zhao, Cui-Hua Jiang, Jian Zhang, Ke Pan
Six undescribed pentacyclic triterpenoids including four triterpenoid aglycones, 1β,2a,3β,23-tetrahydroxyurs-12-en-28-ursolic acid, 2a,3a,6β,19α,23-pentahydroxyurs-12-en-28-ursolic acid, 2α,3α,20β,23-tetrahydroxyurs-12-en-28-ursolic acid and 1β,2a,3β,23-tetrahydroxyurs-12,20(30)-dien-28-ursolic acid, and two triterpenoid glucosides, 2a,3a,23-trihydroxy-12,20(30)-dien-28-ursolic acid 28-O-β-d-glucopyranoside and 1-oxo-3β,23-dihydroxyolean-12-en-28-oic acid 28-O-β-d-xylopyranoside, along with 5 known triterpenoids were isolated from a CH3Cl-soluble extract of the leaves of Cyclocarya paliurus. Their structures were established on the basis of chemical and spectroscopic approaches. These compounds were assessed for their antioxidant effects on FFA-induced hepatic steatosis in HepG2 cells. The results revealed that three saponins and two aglycones markedly increased SOD activity and reduced MDA level.

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Datum: 23.05.2018


Bisindole alkaloids from Tabernaemontana corymbosa

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Bing-Jie Zhang, Jing-Song Lu, Mei-Fen Bao, Xiu-Hong Zhong, Ling Ni, Jing Wu, Xiang-Hai Cai
Continued study in bioactive monoterpenoid alkaloids led to the isolation of nine undescribed alkaloids, taberyunines A-I, together with 32 known ones from the aerial parts of Tabernaemontana corymbosa Roxb. ex Wall (Apocynaceae). Among the undescribed alkaloids, taberyunines A-G and H-I were assigned to Aspidosperma-Aspidosperma and Vobasinyl-Ibogan type bisindoles, respectively. Their structures were determined by NMR spectra, MS data and X-ray diffraction. Taberyunine B showed significant cytotoxicity against three cancer cell lines.

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Datum: 23.05.2018


Erythrosaponins A–J, triterpene saponins from the roots and stem bark of Gardenia erythroclada

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Sutin Kaennakam, Thammarat Aree, Jantana Yahuafai, Pongpun Siripong, Santi Tip-pyang
Ten undescribed triterpene saponins, named erythrosaponins A–J, along with one known analogue were isolated from the roots and stem bark of Gardenia erythroclada. Their structures were determined on the basis of extensive 1D and 2D NMR analyses. Absolute structure of erythrosaponin A was unequivocally affirmed by single-crystal X-ray crystallography. All isolated compounds were evaluated for their cytotoxicity against cancer cell lines (KB and HeLa S-3) and their anti-inflammatory activity based on the inhibition of NO production in RAW264.7 cells. Erythrosaponin D showed moderate cytotoxicity against KB and HeLa S-3 cells with IC50 values of 25.8 and 29.5 μM, respectively. Erythrosaponins D, F, G, I and J showed moderate anti-inflammatory with IC50 values in the range of 63.0–81.4 μM.

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Datum: 23.05.2018


Estrogenic properties of coumarins and meroterpene from the fruits of Cullen corylifolium: Experimental and computational studies

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Tiehua Zhang, Shuning Zhong, Ligang Hou, Tiezhu Li, XiaoJia Xing, Tianzhu Guan, Jie Zhang, Yongjun Wang
Coumarins and meroterpene from the fruits of Cullen corylifolium were evaluated for their ability to bind and activate human estrogen receptor α (hERα) by a combination of in vitro studies and molecular dynamics simulations. The recombinant hERα ligand binding domain (hERα-LBD) was produced in BL21 (DE3)pLysS and the fluorescence polarization (FP) assay was performed to determine the binding affinities of coumarins and meroterpene with receptor protein. These compounds displayed distinct binding potency toward hERα-LBD, generally increased with their increasing molecular length and Connolly solvent-excluded volume (CSEV). In an estrogen response element-luciferase (ERE-Luc) reporter gene assay, coumarins and meroterpene acted as agonists of human estrogen receptor α. Subsequently, molecular docking was conducted to elucidate the molecular mechanism behind their agonistic activities. Coumarins and meroterpene adopted an agonist conformation within the cavity of hERα-LBD. The hydrophobic and hydrogen-bonding interactions were dominant forces to stabilize their binding. The structure-activity relationship analysis suggested that the presence of hydroxyl groups and prenyl group were crucial for possessing estrogenic activities. Comparison of the calculated binding energies with the determined binding affinities yielded a good correlation (R2 = 0.9727). In conclusion, molecular modeling techniques can potentially be applied for in silico screening of selective estrogen receptor modulators (SERMs) from undescribed compounds.

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Datum: 23.05.2018


Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Karolina Kubiasová, Václav Mik, Jaroslav Nisler, Martin Hönig, Alexandra Husičková, Lukáš Spíchal, Zuzana Pěkná, Olga Šamajová, Karel Doležal, Ondřej Plíhal, Eva Benková, Miroslav Strnad, Lucie Plíhalová
Isoprenoid cytokinins play a number of crucial roles in the regulation of plant growth and development. To study cytokinin receptor properties in plants, we designed and prepared fluorescent derivatives of 6-[(3-methylbut-2-en-1-yl)amino]purine (N6-isopentenyladenine, iP) with several fluorescent labels attached to the C2 or N9 atom of the purine moiety via a 2- or 6-carbon linker. The fluorescent labels included dansyl (DS), fluorescein (FC), 7-nitrobenzofurazan (NBD), rhodamine B (RhoB), coumarin (Cou), 7-(diethylamino)coumarin (DEAC) and cyanine 5 dye (Cy5). All prepared compounds were screened for affinity for the Arabidopsis thaliana cytokinin receptor (CRE1/AHK4). Although the attachment of the fluorescent labels to iP via the linkers mostly disrupted binding to the receptor, several fluorescent derivatives interacted well. For this reason, three derivatives, two rhodamine B and one 4-chloro-7-nitrobenzofurazan labeled iP were tested for their interaction with CRE1/AHK4 and Zea mays cytokinin receptors in detail. We further showed that the three derivatives were able to activate transcription of cytokinin response regulator ARR5 in Arabidopsis seedlings. The activity of fluorescently labeled cytokinins was compared with corresponding 6-dimethylaminopurine fluorescently labeled negative controls. Selected rhodamine B C2-labeled compounds 17, 18 and 4-chloro-7-nitrobenzofurazan N9-labeled compound 28 and their respective negative controls (19, 20 and 29, respectively) were used for in planta staining experiments in Arabidopsis thaliana cell suspension culture using live cell confocal microscopy.

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Datum: 23.05.2018


Phytochemical profiles, phototoxic and antioxidant properties of eleven Hypericum species – A comparative study

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Edoardo Napoli, Laura Siracusa, Giuseppe Ruberto, Alessandra Carrubba, Silvia Lazzara, Antonio Speciale, Francesco Cimino, Antonella Saija, Mariateresa Cristani
Hypericum is one out of the nine genera belonging to the botanical family Clusiaceae Lindl (syn. Hypericaceae Juss.; APG III, 2009). The genus contains 484 species spread worldwide, one of which, Hypericum perforatum, is largely used in folk medicine. The aim of this study was to evaluate the chemical composition, along with the antioxidant and phototoxic activity, of 11 Hypericum species grown in Sicily (H. perforatum L., H. aegypticum L., H. androsaemum L., H. calycinum L., H. hircinum L., H. hirsutum L., H. montanum L., H. patulum Thunb., H. perfoliatum L., H. pubescens Boiss., H. tetrapterum Fr.).Samples of flowering tops collected from these Hypericum species were extracted and analysed by high performance liquid chromatography with diode-array detection and mass spectrometry (HPLC-DAD-MS) to determine their content of main polyphenols, acylphloroglucinols, and naphthodianthrones. The extracts were also subjected to a photocytotoxic assay using murine fibroblast (NIH/3T3), and their antioxidant activity evaluated by means of Folin-Ciocalteau, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, and oxygen radical antioxidant capacity assays.Phytochemical analysis allowed us to identify and quantify 20 metabolites, each of them possessing a well-known biological activity. Furthermore, all examined species showed a good cytotoxic and antioxidant/radical scavenging activity. These results indicate that in addition to the well-known H. perforatum, at least other three species (H. tetrapterum, H. pubescens, and H. montanum) represent potential sources of biologically active compounds, and at least other two species (H. perfoliatum and H. tetrapterum), due to their phototoxicity are candidates for application in photodynamic therapy.

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Datum: 23.05.2018


Bisabolane, cyclonerane, and harziane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum cf44-2

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Yin-Ping Song, Xiang-Hong Liu, Zhen-Zhen Shi, Feng-Ping Miao, Sheng-Tao Fang, Nai-Yun Ji
Three undescribed bisabolane derivatives, trichaspin, trichaspsides A and B, three undescribed cyclonerane sesquiterpenes, 9-cycloneren-3,7,11-triol, 11-cycloneren-3,7,10-triol, and 7,10-epoxycycloneran-3,11,12-triol, and one undescribed harziane diterpene, 11-hydroxy-9-harzien-3-one, were obtained from the culture of Trichoderma asperellum cf44-2, an endophyte of the marine brown alga Sargassum sp. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and MS data, and their absolute configurations were established by ECD or specific optical rotation data. Trichaspin features an unprecedented ethylated bisabolane skeleton, while trichaspsides A and B represent the first aminoglycosides of bisabolane and norbisabolane sesquiterpenes, respectively. Nine of the compounds were evaluated for inhibition of five marine-derived pathogenic bacteria and toxicity to a marine zooplankton.

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Datum: 23.05.2018


Cytotoxic and other withanolides from aeroponically grown Physalis philadelphica

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Ya-Ming Xu, E.M. Kithsiri Wijeratne, Alan D. Brooks, Poonam Tewary, Li-Jiang Xuan, Wen-Qiong Wang, Thomas J. Sayers, A.A. Leslie Gunatilaka
Eleven withanolides including six previously undescribed compounds, 16β-hydroxyixocarpanolide, 24,25-dihydroexodeconolide C, 16,17-dehydro-24-epi-dioscorolide A, 17-epi-philadelphicalactone A, 16-deoxyphiladelphicalactone C, and 4-deoxyixocarpalactone A were isolated from aeroponically grown Physalis philadelphica. Structures of these withanolides were elucidated by the analysis of their spectroscopic (HRMS, 1D and 2D NMR, ECD) data and comparison with published data for related withanolides. Cytotoxic activity of all isolated compounds was evaluated against a panel of five human tumor cell lines (LNCaP, ACHN, UO-31, M14 and SK-MEL-28), and normal (HFF) cells. Of these, 17-epi-philadelphicalactone A, withaphysacarpin, philadelphicalactone C, and ixocarpalactone A exhibited cytotoxicity against ACHN, UO-31, M14 and SK-MEL-28, but showed no toxicity to HFF cells.

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Datum: 23.05.2018


Metabolomic analysis applied to chemosystematics and evolution of megadiverse Brazilian Vernonieae (Asteraceae)

Publication date: June 2018
Source:Phytochemistry, Volume 150
Author(s): Marília Elias Gallon, Marcelo Monge, Rosana Casoti, Fernando Batista Da Costa, João Semir, Leonardo Gobbo-Neto
Vernonia sensu lato is the largest and most complex genus of the tribe Vernonieae (Asteraceae). The tribe is chemically characterized by the presence of sesquiterpene lactones and flavonoids. Over the years, several taxonomic classifications have been proposed for Vernonia s.l. and for the tribe; however, there has been no consensus among the researches. According to traditional classification, Vernonia s.l. comprises more than 1000 species divided into sections, subsections and series (sensu Bentham). In a more recent classification, these species have been segregated into other genera and some subtribes were proposed, while the genus Vernonia sensu stricto was restricted to 22 species distributed mainly in North America (sensu Robinson). In this study, species from the subtribes Vernoniinae, Lepidaploinae and Rolandrinae were analyzed by UHPLC-UV-HRMS followed by multivariate statistical analysis. Data mining was performed using unsupervised (HCA and PCA) and supervised methods (OPLS-DA). The HCA showed the segregation of the species into four main groups. Comparing the HCA with taxonomical classifications of Vernonieae, we observed that the groups of the dendogram, based on metabolic profiling, were in accordance with the generic classification proposed by Robinson and with previous phylogenetic studies. The species of the genera Stenocephalum, Stilpnopappus, Strophopappus and Rolandra (Group 1) were revealed to be more related to the species of the genus Vernonanthura (Group 2), while the genera Cyrtocymura, Chrysolaena and Echinocoryne (Group 3) were chemically more similar to the genera Lessingianthus and Lepidaploa (Group 4). These findings indicated that the subtribes Vernoniinae and Lepidaploinae are non-chemically homogeneous groups and highlighted the application of untargeted metabolomic tools for taxonomy and as indicators of species evolution. Discriminant compounds for the groups obtained by OPLS-DA were determined. Groups 1 and 2 were characterized by the presence of 3′,4′-dimethoxyluteolin, glaucolide A and 8-tigloyloxyglaucolide A. The species of Groups 3 and 4 were characterized by the presence of putative acacetin 7-O-rutinoside and glaucolide B. Therefore, untargeted metabolomic approach combined with multivariate statistical analysis, as proposed herein, allowed the identification of potential chemotaxonomic markers, helping in the taxonomic classifications.

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Datum: 23.05.2018


Terpenoid glycosides from the root's barks of Eriocoelum microspermum Radlk. ex Engl.

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): David Pertuit, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Clément Delaude, Marie-Aleth Lacaille-Dubois
Eight undescribed triterpenoid saponins together with a known one, and two undescribed sesquiterpene glycosides were isolated from root's barks of Eriocoelum microspermum. Their structures were elucidated by spectroscopic methods including 1D and 2D experiments in combinaison with mass spectrometry as 3-O-α-L-rhamnopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 4)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 1-O-{β-D-xylopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 6)}-[β-D-xylopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(2E,6E)-farnes-1-ol, 1-O-{β-D-glucopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 6)}-[β-D-xylopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(2E,6E)-farnes-1-ol. These results represent a contribution to the chemotaxonomy of the genus Eriocoelum highlighting farnesol glycosides as chemotaxonomic markers of the subfamily of Sapindoideae in the family of Sapindaceae.

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Datum: 23.05.2018


Peniciphenalenins A−F from the culture of a marine-associated fungus Penicillium sp. ZZ901

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Qiao Li, Rongyao Zhu, Wenwen Yi, Weiyun Chai, Zhizhen Zhang, Xiao-Yuan Lian
Marine-derived fungi of the genus Penicillium represent a huge potential for synthesizing the secondary metabolites with structural and bioactive uniqueness and diversity. In this study, six previously undescribed compounds peniciphenalenins A−F and four known compounds (+)-sclerodin, (+)-scleroderolide, (+)-sclerodione, and physcion were isolated from the culture of a marine-derived fungus Penicillium sp. ZZ901. Structures of the isolated compounds were elucidated by a combination of extensive NMR spectroscopic analysis, HRESIMS data, optical rotation value, ECD calculation, and single crystal X-ray diffraction. Peniciphenalenins A−C are the second examples of the type of neoherqueinones. The possible biosynthetic route of nine phenalenone derivatives has been suggested. The known (+)-scleroderolide showed both antiproliferative activity against glioma cells with IC50 values of 23.24–37.26 μM and antibacterial activity in suppressing the growth of methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 7.0 and 9.0 μg/mL, respectively.

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Datum: 23.05.2018


γ-Pyrone compounds: flavonoids and maltol glucoside derivatives from Herniaria glabra L. collected in the Ternopil region of the Ukraine

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Solomiia Kozachok, Łukasz Pecio, Joanna Kolodziejczyk-Czepas, Svitlana Marchyshyn, Pawel Nowak, Jarosław Mołdoch, Wiesław Oleszek
The phytochemical investigation of the whole plant extracts of Herniaria glabra L. (Caryophyllaceae) led to the identification and isolation of four known flavonoids, one known and three undescribed maltol derivatives, and benzyl β-gentiobioside. The structures were established by extensive 1D and 2D NMR spectroscopic analyses, as well as HRESIMS data. For the first time in Herniaria genus, as well as in Caryophylaceae family the presence of apiorutin {quercetin 3-O-[(D-apio-β-d-furanosyl-(1 → 2)-O-[-α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside]} and licoagroside B {maltol 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-d-glucopyranoside} were revealed. Additionally, antioxidant actions of apiorutin, rutin, narcissin (isorhamentin 3-O-β-d-rutinoside) and licoagroside B were assessed in human blood plasma, exposed to the peroxynitrite-induced oxidative stress in vitro. The isolates partly reduced oxidative (oxidation of thiol groups) and nitrative (tyrosine nitration) damage to blood plasma proteins, decreased plasma lipid peroxidation as well as enhanced the non-enzymatic antioxidant capacity of blood plasma. No cytotoxicity of the examined substances towards peripheral blood mononuclear cells was found.

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Datum: 23.05.2018


Identification of UDP glucosyltransferases from the aluminum-resistant tree Eucalyptus camaldulensis forming β-glucogallin, the precursor of hydrolyzable tannins

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Ko Tahara, Mitsuru Nishiguchi, Andrej Frolov, Juliane Mittasch, Carsten Milkowski
In the highly aluminum-resistant tree Eucalyptus camaldulensis, hydrolyzable tannins are proposed to play a role in internal detoxification of aluminum, which is a major factor inhibiting plant growth on acid soils. To understand and modulate the molecular mechanisms of aluminum detoxification by hydrolyzable tannins, the biosynthetic genes need to be identified. In this study, we identified and characterized genes encoding UDP-glucose:gallate glucosyltransferase, which catalyzes the formation of 1-O-galloyl-β-d-glucose (β-glucogallin), the precursor of hydrolyzable tannins. By homology-based cloning, seven full-length candidate cDNAs were isolated from E. camaldulensis and expressed in Escherichia coli as recombinant N-terminal His-tagged proteins. Phylogenetic analysis classified four of these as UDP glycosyltransferase (UGT) 84A subfamily proteins (UGT84A25a, -b, UGT84A26a, -b) and the other three as UGT84J subfamily proteins (UGT84J3, -4, -5). In vitro enzyme assays showed that the UGT84A proteins catalyzed esterification of UDP–glucose and gallic acid to form 1-O-galloyl-β-d-glucose, whereas the UGT84J proteins were inactive. Further analyses with UGT84A25a and −26a indicated that they also formed 1-O-glucose esters of other structurally related hydroxybenzoic and hydroxycinnamic acids with a preference for hydroxybenzoic acids. The UGT84A genes were expressed in leaves, stems, and roots of E. camaldulensis, regardless of aluminum stress. Taken together, our results suggest that the UGT84A subfamily enzymes of E. camaldulensis are responsible for constitutive production of 1-O-galloyl-β-d-glucose, which is the first step of hydrolyzable tannin biosynthesis.

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Datum: 23.05.2018


Biochemical properties of a bacterially-expressed Bowman-Birk inhibitor from Rhynchosia sublobata (Schumach.) Meikle seeds and its activity against gut proteases of Achaea janata

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Soundappan S. Mohanraj, Sarada D. Tetali, Nalini Mallikarjuna, Aparna Dutta-Gupta, Kollipara Padmasree
Crude proteinase inhibitors (CPIs) extracted from the seeds of Rhynchosia sublobata, a wild relative of pigeon pea showed pronounced inhibitory activity on the larval gut trypsin-like proteases of lepidopteran insect pest – Achaea janata. Consequently, a full-length cDNA of Bowman-Birk inhibitor gene (RsBBI1) was cloned from the immature seeds of R. sublobata. It contained an ORF of 360 bp encoding a 119-amino acid polypeptide (13.3 kDa) chain with an N-terminus signal sequence comprising of 22 amino acids. The amino acid sequence and phylogenetic analysis together revealed that RsBBI1 exhibited a close relation with BBIs from soybean and Phaseolus spp. A cDNA sequence corresponding to RsBBI1 mature protein (89 amino acid stretch) was expressed in E. coli. The recombinant rRsBBI1 protein with a molecular mass of 9.97 kDa was purified using trypsin affinity chromatography. The purified rRsBBI1 exhibited non-competitive mode of inhibition of both bovine trypsin (Ki of 358 ± 11 nM) and chymotrypsin (Ki of 446 ± 9 nM). Its inhibitory activity against these proteases was stable at high temperatures (>95 °C) and a wide pH range but sensitive to reduction with dithiothreitol (DTT), indicating the importance of disulphide bridges in exhibiting its activity. Also, rRsBBI1 showed significant inhibitory activity (IC50 = 70 ng) on A. janata larval gut trypsin-like proteases (AjGPs). Conversely, it showed <1% inhibitory activity (IC50 = 8 μg) on H. armigera larval gut trypsin-like proteases (HaGPs) than it has against AjGPs. Besides, in vivo feeding experiments clearly indicated the deleterious effects of rRsBBI1 on larval growth and development in A. janata which suggests it can be further exploited for such properties.

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Datum: 23.05.2018


PepSAVI-MS reveals anticancer and antifungal cycloviolacins in Viola odorata

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Nicole C. Parsley, Christine L. Kirkpatrick, Christopher M. Crittenden, Javad Ghassemi Rad, David W. Hoskin, Jennifer S. Brodbelt, Leslie M. Hicks
Widespread resistance to antimicrobial and cancer therapeutics is evolving in every country worldwide and has a direct impact on global health, agriculture and the economy. The specificity and selectivity of bioactive peptide natural products present a possible stopgap measure to address the ongoing deficit of new therapeutic compounds. PepSAVI-MS (Statistically-guided bioActive Peptides prioritized VIa Mass Spectrometry) is an adaptable method for the analysis of natural product libraries to rapidly identify bioactive peptides. This pipeline was validated via screening of the cyclotide-rich botanical species Viola odorata and identification of the known antimicrobial and anticancer cyclotide cycloviolacin O2. Herein we present and validate novel bioactivities of the anthelmintic V. odorata cyclotide, cycloviolacin O8 (cyO8), including micromolar anticancer activity against PC-3 prostate, MDA-MB-231 breast, and OVCAR-3 ovarian cancer cell lines and antifungal activity against the agricultural pathogen Fusarium graminearum. A reduction/alkylation strategy in tandem with PepSAVI-MS analysis also revealed several previously uncharacterized putatively bioactive cyclotides. Downstream implementation of ultraviolet photodissociation (UVPD) tandem mass spectrometry is demonstrated for cyO8 as a method to address traditionally difficult-to-sequence cyclotide species. This work emphasizes the therapeutic and agricultural potential of natural product bioactive peptides and the necessity of developing robust analytical tools to deconvolute nature's complexity.

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Datum: 23.05.2018


Probing the transcriptome of Aconitum carmichaelii reveals the candidate genes associated with the biosynthesis of the toxic aconitine-type C19-diterpenoid alkaloids

Publication date: August 2018
Source:Phytochemistry, Volume 152
Author(s): Dake Zhao, Yong Shen, Yana Shi, Xingqiao Shi, Qin Qiao, Shuhui Zi, Erqiang Zhao, Diqiu Yu, Edward J. Kennelly
Aconitum carmichaelii has long been used as a traditional Chinese medicine, and its processed lateral roots are known commonly as fuzi. Aconitine-type C19-diterpenoid alkaloids accumulating in the lateral roots are some of the main toxicants of this species, yet their biosynthesis remains largely unresolved. As a first step towards understanding the biosynthesis of aconitine-type C19-diterpenoid alkaloids, we performed de novo transcriptome assembly and analysis of rootstocks and leaf tissues of Aconitum carmichaelii by next-generation sequencing. A total of 525 unigene candidates were identified as involved in the formation of C19-diterpenoid alkaloids, including those encoding enzymes in the early steps of diterpenoid alkaloids scaffold biosynthetic pathway, such as ent-copalyl diphosphate synthases, ent-kaurene synthases, kaurene oxidases, cyclases, and key aminotransferases. Furthermore, candidates responsible for decorating of diterpenoid alkaloid skeletons were discovered from transcriptome sequencing of fuzi, such as monooxygenases, methyltransferase, and BAHD acyltransferases. In addition, 645 differentially expressed genes encoding transcription factors potentially related to diterpenoid alkaloids accumulation underground were documented. Subsequent modular domain structure phylogenetics and differential expression analysis led to the identification of BAHD acyltransferases possibly involved in the formation of acetyl and benzoyl esters of diterpenoid alkaloids, associated with the acute toxicity of fuzi. The transcriptome data provide the foundation for future research into the molecular basis for aconitine-type C19-diterpenoid alkaloids biosynthesis in A. carmichaelii.

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Datum: 23.05.2018


Antimicrobial activity and cytotoxicity of xanthoquinodin analogs from the fungus Cytospora eugeniae BCC42696

Publication date: July 2018
Source:Phytochemistry, Volume 151
Author(s): Karoon Sadorn, Siriporn Saepua, Nattawut Boonyuen, Tanapong Boonruangprapa, Pranee Rachtawee, Pattama Pittayakhajonwut
Eleven previously undescribed compounds, including cytosporanthraxanthone, xanthoquinodins A7–A10, ketoxanthoquinodin A6, xanthoquinodins B6–B8, and spiroxanthoquinodins A and B, and one synthetically known compound, 2-methoxy pinselin, as well as ten known compounds, including xanthoquinodins A4−A6, B4, and B5, chrysophanol, physcion, (4S)-5-hydroxy-4-methoxy-α-tetralone, (4S)-4,8-dihydroxy-α-tetralone (or isosclerone), and gonytolide C were isolated from the fungus Cytospora eugeniae BCC42696. Their chemical structures were determined based on the analysis of NMR spectroscopic and mass spectrometric data. Moreover, the absolute configurations of the unknown compounds were established by using NOESY and NOEDIFF NMR experiments along with CD spectroscopic data. The isolated xanthoquinodins exhibited a broad range of antimalarial, antibacterial, and fungicidal activities as well as cytotoxicity. Xanthoquinodins A6, B4, and B5 showed strong activity to Plasmodium falciparum, K1 strain (IC50 0.52–0.92 μM) and displayed anti-Bacillus cereus (MIC 1.56 μg/mL). Xanthoquinodin A6 also showed anti-Curvularia lunata (MIC 3.13 μg/mL). In addition, xanthoquinodins A4, A6, B4, and B5 and ketoxanthoquinodin A6 showed cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells.

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Datum: 23.05.2018


 


Category: Current Chemistry Research

Last update: 28.03.2018.






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