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Nampoina Andriamisaina, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Thomas Paululat, Frédéric Lirussi, Marie-Aleth Lacaille-Dubois
The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside...
February 8, 2019: Phytochemistry
Xiaorui Fan, Lihua Yang, Zihan Liu, Limei Lin, Chun Li, Shanshan Guo, Zhimin Wang, Zhuju Wang, Feng Sui
Five undescribed diterpenoid alkaloids tanguticulines A-E and two undescribed amide compounds 5-methoxy-N-Salicylanthranilic acid methyl ester and 3, 5-dimethoxy-4- hydroxycinnamamide-4-O-β-D-glucopyranoside, were isolated from the whole plant of Aconitum tanguticum (Maxim.) Stapf. Their structures were assigned by detailed analysis of MS and NMR spectroscopic data. Compounds 1 and 5 were evaluated for their antivirus activities against influenza a (H1N1) virus in vitro. Both of them showed obvious inhibitory effect on the cytopathic changes induced by H1N1, with IC50 values of 2...
February 5, 2019: Phytochemistry
Ulschan Bathe, Alain Tissier
In plant terpene biosynthesis, oxidation of the hydrocarbon backbone produced by terpene synthases is typically carried out by cytochrome P450 oxygenases (CYPs). The modifications introduced by CYPs include hydroxylations, sequential oxidations at one position and ring rearrangements and closures. These reactions significantly expand the structural diversity of terpenoids, but also provide anchoring points for further decorations by various transferases. In recent years, there has been a significant increase in reports of CYPs involved in plant terpene pathways...
February 5, 2019: Phytochemistry
Luani R de O Piva, Kolby J Jardine, Bruno O Gimenez, Ricardo O Perdiz, Valdiek S Menezes, Flávia M Durgante, Leticia O Cobello, Niro Higuchi, Jeffrey Q Chambers
Volatile terpenoid resins represent a diverse group of plant defense chemicals involved in defense against herbivory, abiotic stress, and communication. However, their composition in tropical forests remains poorly characterized. As a part of tree identification, the 'smell' of damaged trunks is widely used, but is highly subjective. Here, we analyzed trunk volatile monoterpene emissions from 15 species of the genus Protium in the central Amazon. By normalizing the abundances of 28 monoterpenes, 9 monoterpene 'fingerprint' patterns emerged, characterized by a distinct dominant monoterpene...
January 31, 2019: Phytochemistry
Chongzhi Sun, Yang Wu, Bei Jiang, Ying Peng, Mengyue Wang, Jiaxun Li, Xiaobo Li
Two previously undescribed oleanane-type triterpene saponins named liangwanosides III-IV, and one undescribed eudesmane glycoside named liangwanoside A were obtained from the leaves of Metapanax delavayi, a Chinese folk medicine especially for tea used in Yunnan, together with four known compounds. The structures of the undescribed compounds were determined by detailed spectroscopic (1D/2D NMR), HR-ESI-MS data analysis and chemical evidence. The activity against human benign prostate hyperplasia was evaluated with BPH-1 cell line...
January 31, 2019: Phytochemistry
Xu-Yan Wang, Chuang-Jun Li, Jie Ma, Chuan Li, Fang-You Chen, Nan Wang, Cang-Jie Shen, Dong-Ming Zhang
Ten undescribed 9,19-cycloartane type triterpenoid glycosides (cimdahxynoside A-J) and five known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, chemical method and X-ray Single-crystal diffraction analysis. Cimdahxynoside A represented the first X-ray crystallography of 9,19-cycloartane type triterpenoid diglycoside. The cytotoxicity of all compounds were tested against five human cancer cell lines...
January 29, 2019: Phytochemistry
Giuseppe Mannino, Carla Gentile, Massimo E Maffei
The genus Pistacia (Anacardiaceae family) is represented by several species, of which only P. vera L. produces edible seeds (pistachio). Despite the different flavor and taste, a correct identification of pistachio varieties based on the sole phenotypic character is sometimes hard to achieve. Here we used a combination of chemical partitioning and molecular fingerprinting for the unequivocal identification of commercial pistachio seed varieties (Bronte, Kern, Kerman, Larnaka, Mateur and Mawardi) of different geographical origin...
January 25, 2019: Phytochemistry
Karen J Marsh, Isha Saraf, Charles H Hocart, Kara Youngentob, Inder-Pal Singh, William J Foley
A group of plant specialised metabolites (PSMs) collectively known as unsubstituted B-ring flavanones (UBFs) have previously been found in the foliage of some species from the genus Eucalyptus L'Hér. (Myrtaceae), specifically from the subgenus Eucalyptus (monocalypts). Captive feeding studies using artificial diets suggest that these compounds may potentially influence the feeding preferences of marsupial folivores, such as koalas. Understanding natural variation in the composition and concentration of UBFs in eucalypt foliage is a first step to deciding whether, through their effects on herbivory, they might have broader effects on ecosystem dynamics...
January 22, 2019: Phytochemistry
Yu Tang, Na Li, Yike Zou, Yanran Ai, Guang-Lei Ma, Ezzat E A Osman, Juan Xiong, Junmin Li, Ze-Xin Jin, Jin-Feng Hu
Lycopodium alkaloids (LAs) are the characteristic metabolites of club mosses. Chemical differences often exist in different specimens of a single plant species collected from different geographic origins. In this study, a preliminary LC-MS detection and dereplication analyses of alkaloidal constituents of Lycopodium cernuum var. sikkimense (Müll. Hal.) C.B. Clarke (LCVS2) collected from Fujian province led to the isolation and characterization of three undescribed LAs, lycocernuskines A-C, and six known cernuane-type LAs...
January 22, 2019: Phytochemistry
Yan-Zhen Zheng, Geng Deng, Rui Guo, Zhong-Min Fu, Da-Fu Chen
Flavonoids widely found in natural foods are characterized by acting as antioxidants compounds. There are close relationship between the antiradical activities and structural properties of flavonoids. In this work, density functional theory (DFT) methods were applied to investigate the influence of the H5⋯OC4 intramolecular hydrogen-bond (IHB) on the antiradical activity of flavonoid based on three prevalently accepted radical scavenging mechanisms: hydrogen atom transfer (HAT), single electron transfer-proton transfer (SET-PT) and sequential proton-loss electron-transfer (SPLET)...
January 19, 2019: Phytochemistry
Chen-Xi Li, Xiao-Yu Song, Wen-Yu Zhao, Guo-Dong Yao, Bin Lin, Xiao-Xiao Huang, Ling-Zhi Li, Shao-Jiang Song
Five pairs of enantiomeric lignanamides including nine undescribed compounds along with a known one were obtained from Solanum nigrum L. (Solanaceae). Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses and quantum chemical calculations of electronic circular dichroism (ECD) curves. Additionally, all isolates were evaluated for their neuroprotective activity against MPP+ (1-methyl-4-phenylpyridinium)-induced SH-SY5Y cells injury. Among them, cannabisin F showed the most significant neuroprotective effects at different concentrations (12...
January 17, 2019: Phytochemistry
Taewoong Rho, Min Sik Choi, Mila Jung, Hyun Woo Kil, Yong Deog Hong, Kee Dong Yoon
Thirty-three phenolic compounds were identified from the extract of fermented tea (Camellia sinensis L.), including three undescribed flavonoids, namely quamoreokchaside I-II and kamoreokchaside I, along with thirty known compounds. All isolates were tested to evaluate their inhibitory effects against amyloid-beta (Aβ) aggregation through thioflavin-T (ThT) fluorescence-based assay and transmission electron microscopy (TEM). Among the isolates, three tea polyphenols, including (-)-catechin gallate (CG), (-)-epicatechin gallate (ECG), and (-)-epigallocatechin gallate (EGCG), significantly decreased Aβ aggregation at a concentration of 10 μg ml-1 , compared to the positive control, Aβ alone...
January 17, 2019: Phytochemistry
Zhu-Jun Fang, Tian Zhang, Shi-Xin Chen, Yan-Lan Wang, Chang-Xin Zhou, Jian-Xia Mo, Yong-Jiang Wu, You-Kai Xu, Li-Gen Lin, Li-She Gan
Five undescribed cycloartane triterpenoids, including two cycloartane trinor-triterpenoids, were isolated from a 70% ethanol extract of the whole plant of Actaea vaginata (Ranunculaceae), together with thirteen known cycloartane triterpenoids. Their structures were determined by spectroscopic techniques and quantum chemical calculations for intramolecular noncovalent interactions with reduced density gradient method. All compounds were evaluated for their anti-inflammatory effects by a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW264...
January 11, 2019: Phytochemistry
Sheng-Zhuo Huang, Fan-Dong Kong, Gao Chen, Xiang-Hai Cai, Li-Man Zhou, Qing-Yun Ma, Qi Wang, Wen-Li Mei, Hao-Fu Dai, You-Xing Zhao
Twelve undescribed compounds including six phenanthrene derivatives (parviphenanthrines A-F), two stilbene derivatives (parvistilbines A-B), three esters (parviesters A-C), and one sesquiterpenoid (parvidiol A) were isolated from the roots of Stemona parviflora, together with twenty-two known ones. The structures of the undescribed compounds were elucidated based on the analyses of their spectroscopic data. The absolute configuration of parviphenanthrine A was determined by the quantum ECD calculations. Parviphenanthrines A and E, stemanthrene A, stilbostenin E, 4-hydroxy-benzenepropanol-α-benzoate, and (E)-4-hydroxycinnamic acid methyl ester showed nematocidal activity against Meloidogyne incognita with IC50 values of 14...
January 8, 2019: Phytochemistry
Jun Zhang, Chen Zhang, Fu-Chun Xu, Quesheng, Qing-Ying Zhang, Peng-Fei Tu, Hong Liang
Eight previously undescribed isoquinoline alkaloids, mucroniferanines H-M, together with 16 known isoquinoline alkaloids, were isolated from Corydalis mucronifera Maxim.. The structures of the previously undescribed compounds were elucidated by interpretation of 1D and 2D NMR spectroscopic and HRMS data, and their absolute configurations were established by computational electronic circular dichroism (ECD) calculations and X-ray diffraction data. Mucroniferanine L is reported as the first natural amide bond linked isoquinoline alkaloid dimer...
January 6, 2019: Phytochemistry
Hui Liu, Rui-Xue Xu, Xiao-Shuang Zhang, Ting-Ting Zhu, Hong-Xiang Lou, Ai-Xia Cheng
Previously it has been shown that the caffeoyl coenzyme A O-methyltransferase (CCoAOMT) type enzyme PaF6OMT, synthesized by the liverwort Plagiochasma appendiculatum Lehm. & Lindenb., (Aytoniaceae), interacts preferentially with 6-OH flavones. To clarify the biochemistry and evolution of liverwort OMTs, a comparison was made between the nucleotide sequence and biological activity of PaF6OMT and those of three of its homologs MpOMT1 (from Marchantia paleacea Bertol., (Marchantiaceae)), MeOMT1 (Marchantia emarginata Reinw et al...
January 6, 2019: Phytochemistry
Joanna Nawrot, Jaromir Budzianowski, Gerard Nowak
Seven germacranolides - balsamin, izospiciformin, stizolin, 9α-hydroxyparthenolide, 8α-E-(4'-hydroxy)-senecioyloxy-9α-hydroxyparthenolide, stizolicin and 11βH,13-dihydrostizolicin, as well as one undescribed phenol glycoside 3-(3,4-dihydroxyphenyl) propyl senecioate 3-O-β-glucopyranoside were isolated from the leaves of Stizolophus balsamita growing in Iran. Three coumarins, scoparone, scopoletin, umbelliferone and two guaianolides, cynaropicrin and desacylcynaropicrin 8α-(Z)-(4'-hydroxy-2'-methyl)butenoate (= cebellin F) were isolated from the leaves of Psephellus sibiricus...
January 6, 2019: Phytochemistry
S Soundappan Mohanraj, Mariyamma Gujjarlapudi, Vadthya Lokya, Nalini Mallikarjuna, Aparna Dutta-Gupta, Kollipara Padmasree
Rhynchosia sublobata, a wild relative of pigeonpea, possesses defensive proteinase/protease inhibitors (PIs). Characterization of trypsin specific PIs (RsPI) separated from seeds by column chromatography using 2-D gel electrophoresis and Edman degradation method identified R. sublobata possessed both Bowman-Birk isoinhibitors (RsBBI) and Kunitz isoinhibitors (RsKI). A quick method was developed to separate RsBBI and RsKI from RsPI based on their differential solubility in TCA and acetate buffer. N-terminus sequencing of RsBBI and RsKI by MALDI-ISD ascertained the presence of Bowman Birk and Kunitz type isoinhibitors in R...
January 6, 2019: Phytochemistry
Milena Masullo, Antonietta Cerulli, Paola Montoro, Cosimo Pizza, Sonia Piacente
Ziziphus jujuba Mill. leaves are receiving a great attention for their ability to improve sleep, exerting beneficial effects for both the heart and the central nervous system. With the aim to obtain a comprehensive analysis of the specialised metabolites occurring in the leaves of Z. jujuba, a LC-ESI/(HR)Orbitrap/MS profile in negative ion mode of the methanol extract was carried out. The LC-MS profile guided the isolation of 42 compounds, of which the structures were elucidated by 1D and 2D-NMR experiments...
January 4, 2019: Phytochemistry
Fuli Ma, Wenkong Yao, Lei Wang, Yuejin Wang
Stilbene phytoalexins derived from grapevine can be rapidly accumulated when exposed to an artificial UV-C treatment. However, the underlying mechanisms involved in this accumulation and translocation are unclear. Here, we describe an investigation of the influence of UV-C treatment on the dynamic subcellular distribution of a member of a stilbene synthase family VpSTS29 derived from Chinese wild Vitis pseudoreticulata W.T. Wang when over-expressed in V. vinifera L. cv. Thompson Seedless. Our results show that VpSTS29-GFP was accumulated at a relatively high level in roots and mature leaves of transgenic grape lines, and was predominantly distributed in the cytoplasm...
January 3, 2019: Phytochemistry
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