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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...
May 18, 2018: Phytochemistry
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...
May 18, 2018: Phytochemistry
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 (1 H-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 1 H-NMR data indicated two main clusters that were region-specific (Northern Cape and Western Cape provinces)...
May 17, 2018: Phytochemistry
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...
May 17, 2018: Phytochemistry
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...
May 15, 2018: Phytochemistry
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...
May 15, 2018: Phytochemistry
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...
May 15, 2018: Phytochemistry
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)...
May 14, 2018: Phytochemistry
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...
May 12, 2018: Phytochemistry
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...
May 11, 2018: Phytochemistry
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...
May 11, 2018: Phytochemistry
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...
May 11, 2018: Phytochemistry
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...
May 11, 2018: Phytochemistry
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...
May 11, 2018: Phytochemistry
Zhao-Quan Wang, Xing-Yu Li, Dong-Bao Hu, Chun-Lin Long
Seven undescribed lavandulyl benzophenones garcimultiflorones K-Q, 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)...
May 5, 2018: Phytochemistry
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...
May 4, 2018: Phytochemistry
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...
May 4, 2018: Phytochemistry
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...
May 4, 2018: Phytochemistry
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...
May 3, 2018: Phytochemistry
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...
May 3, 2018: Phytochemistry
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