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Thuc Huy Duong, Bui Linh Chi Huynh, Warinthorn Chavasiri, Marylene Chollet-Krugler, Van Kieu Nguyen, Thi Hoai Thu Nguyen, Poul Erik Hansen, Pierre Le Pogam, Holger Thüs, Joël Boustie, Kim Phi Phung Nguyen
Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3...
February 17, 2017: Phytochemistry
Eric Kuhnert, Frank Surup, Sandra Halecker, Marc Stadler
During the course of our screening for new metabolites with chemotaxonomic importance from stromata of fungi from the family Xylariaceae, we characterized several interesting metabolites in the fungus Annulohypoxylon minutellum. Extraction of the fruiting bodies and purification by preparative HPLC resulted in the isolation of five metabolites. The main compound was identified as the known metabolite hinnulin A (5), while four minor compounds were found to represent previously undescribed azaphilones, named minutellins A - D (1-4)...
February 16, 2017: Phytochemistry
Mu-Yuan Yu, Gao-Ting Zhao, Jie-Qing Liu, Afsar Khan, Xing-Rong Peng, Lin Zhou, Jin-Run Dong, Hai-Zhou Li, Ming-Hua Qiu
Twenty withanolides, including previously unknown nicanlodes A-M, were isolated from aerial parts of Nicandra physalodes. Their structural elucidations were unambiguously achieved through interpretation of extensive spectroscopic data (NMR and HRMS) and by comparison with literature data. Nicanlodes A and B have an unusual aromatic amine moiety. The isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines.
February 16, 2017: Phytochemistry
Riccardo Aversano, Felice Contaldi, Maria Grazia Adelfi, Vincenzo D'Amelia, Gianfranco Diretto, Nunziatina De Tommasi, Carmen Vaccaro, Antonio Vassallo, Domenico Carputo
The cultivated potato Solanum tuberosum is unrivalled among crop plants for its wild relatives, which potentially represent an important source of genetic diversity to improve the nutritional value of potato varieties and understand metabolism regulation. The main aim of this research was to profile human health-related metabolites in a number of clones from 13 Solanum species. Results from HPLC-DAD and LC-ESI-MS analyses highlighted a high interspecific variability in the level of metabolites analysed. Ascorbic acid was confirmed to be the most abundant antioxidant in potato and chlorogenic acid the primary polyphenol...
February 16, 2017: Phytochemistry
Hilal Top, Nazli Boke Sarikahya, Ayse Nalbantsoy, Suheyla Kirmizigul
Phytochemical investigations on n-butanol extract of Cephalaria balansae Raus. (Caprifoliaceae) led to the isolation of four previously undescribed triterpenoid saponins based on hederagenin type aglycone, namely, balansoides A-D, along with ten known compounds. Their structures were proposed based on 1D and 2D NMR spectroscopic data, HRESIMS analysis and chemical evidence as 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-galactopyranosyl-(1 → 6)-β-D-glucopyranosyl ester and 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester...
February 16, 2017: Phytochemistry
Jinkun Xu, Ying Ai, Jianhui Wang, Jingwei Xu, Yongkang Zhang, Dong Yang
S-limonene synthase is a model monoterpene synthase that cyclizes geranyl pyrophosphate (GPP) to form S-limonene. It is a relatively specific enzyme as the majority of its products are composed of limonene. In this study, we converted it to pinene or phellandrene synthases after introducing N345A/L423A/S454A or N345I mutations. Further studies on N345 suggest the polarity of this residue plays a critical role in limonene production by stabilizing the terpinyl cation intermediate. If it is mutated to a non-polar residue, further cyclization or hydride shifts occurs so the carbocation migrates towards the pyrophosphate, leading to the production of pinene or phellandrene...
February 15, 2017: Phytochemistry
Tatsiana V Charnikhova, Katharina Gaus, Alexandre Lumbroso, Mark Sanders, Jean-Paul Vincken, Alain De Mesmaeker, Carolien P Ruyter-Spira, Claudio Screpanti, Harro J Bouwmeester
In the root exudate and root extracts of maize hybrid cv NK Falkone seven putative strigolactones were detected using UPLC-TQ-MS-MS. All seven compounds displayed MS-MS-fragmentation common for strigolactones and particularly the presence of a fragment of m/z 97 Da, which may indicate the presence of the so-called D-ring, suggests they are strigolactones. The levels of all these putative strigolactones increased upon phosphate starvation and decreased upon fluridone (carotenoid biosynthesis inhibitor) treatment, both of which are a common response for strigolactones...
February 15, 2017: Phytochemistry
Chuan-Pu Shen, Jian-Guang Luo, Ming-Hua Yang, Ling-Yi Kong
Eight lindenane dimers, chololactones A-H, along with two known compounds, were isolated from the roots of Chloranthus holostegius. Their structures were elucidated using 1D/2D NMR and HRESIMS, and their absolute configurations were determined using the ECD exciton chirality method. All isolates were tested for inhibitory effects on the NO production of the liposaccharide (LPS)-induced RAW 264.7 macrophages, and showed moderate activity with IC50 values at 3.5-35.4 μM.
February 15, 2017: Phytochemistry
Yuki Yoneda, Hiroshi Nakashima, Juro Miyasaka, Katsuaki Ohdoi, Hiroshi Shimizu
Stevia rebaudiana (Bertoni) Bertoni is a plant that biosynthesizes a group of natural sweeteners that are up to approximately 400 times sweeter than sucrose. The sweetening components of S. rebaudiana are steviol glycosides (SGs) that partially share their biosynthesis pathway with gibberellins (GAs). However, the molecular mechanisms through which SGs levels can be improved have not been studied. Therefore, transcription levels of several SG biosynthesis-related genes were analyzed under several light treatments involved in GA biosynthesis...
February 15, 2017: Phytochemistry
Bin Li, Zulfiqar Ali, Michael Chan, Juan Li, Mei Wang, Naohito Abe, Can-Rong Wu, Ikhlas A Khan, Wei Wang, Shun-Xiang Li
Two 9,10-dihydrophenanthrenes trivially named phocantol and phocantone, two diterpenoid glycosidesnamed phocantoside A and phocantoside B were isolated from the ethanol extract of the air-dried whole plant of Pholidota cantonensis Rolfe, together with seventeen known compounds. The structures of the four compounds were identified as 1-hydroxy-2,7-dimethoxy-9,10-dihydrophenanthro-[4,5-bcd]furan, 5-hydroxy-2,7-dimethoxy-9,10-dihydro-1,4-phenanthrenedione, (8R,13E)-ent-labd-13-ene-3α,8,15-triol 15-O-β-D-gluco-pyranoside and (5S,8R,9S,10R)-cis-cleroda-3,13(E)-diene-15,18-diol 15-O-β-D-glucopyranosyl-18-O-β-D-glucopyranoside by chemical and spectroscopic methods, including 1D and 2D NMR...
February 15, 2017: Phytochemistry
Dong Young Lee, Hyun Woo Kim, Heejung Yang, Sang Hyun Sung
Nine hydrolyzable tannins, including three previously unknown and six artifacts, were isolated, together with thirty-nine known ones, from the fruits of Terminalia chebula Retz. (Combretaceae). They were identified as 1,2,3-tri-O-galloyl-6-O-cinnamoyl-β-d-glucose, 1,2,3,6-tetra-O-galloyl-4-O-cinnamoyl-β-d-glucose, 4-O-(2″,4″-di-O-galloyl-α-l-rhamnosyl)ellagic acid, 1'-O-methyl neochebulanin, dimethyl neochebulinate, 6'-O-methyl neochebulagate, dimethyl neochebulagate, dimethyl 4'-epi-neochebulagate, and methyl chebulagate by the spectroscopic interpretation...
February 14, 2017: Phytochemistry
Takahiro Matsumoto, Seikou Nakamura, Souichi Nakashima, Tomoe Ohta, Keiko Ogawa, Masashi Fukaya, Junko Tsukioka, Tomohiro Hasei, Tetsushi Watanabe, Hisashi Matsuda
Six neolignan glucosides, named isodonosides I-VI, and a megastigmane glucoside named isodonmegastigmane I, were isolated together with 15 known compounds from the methanolic extract of aerial parts of Isodon japonicus cultivated in Tokushima, Japan. The chemical structures of the compounds were elucidated based on their MS and NMR spectroscopic analysis. The absolute configurations of the neolignan and megastigmane glucosides were determined by derivatizations, by ECD (electronic circular dicroism) Cotton effect approximation, and by the modified Mosher's method...
February 13, 2017: Phytochemistry
Jesica A Dimmer, Susana C Núñez Montoya, Caterine S Mendoza, José L Cabrera
Seven anthraquinones were isolated from aerial parts of Heterophyllaea lycioides (Rusby) Sandwith (Rubiaceae), including three derivatives that have not been described before: a hetero-bianthraquinone identified as (R)-2-hydroxymethyl-2'methyl-1,1',6,6'-tetrahydroxy-5,5' bianthraquinone (lycionine), and two mono-chlorinated derivatives related to soranjidiol. One of them is a homo-bianthraquinone: (R)-7-chloro-2,2'-dimethyl-1,1',6,6'-tetrahydroxy-5,5' bianthraquinone (7-chlorobisoranjidiol), whereas the second halogenated derivative corresponds to a monomeric structure: 5-chloro-1,6-dihydroxy-2-methyl anthraquinone (5-chlorosoranjidiol)...
February 10, 2017: Phytochemistry
André Cruz, Sara Domingos, Eugenia Gallardo, Ana Martinho
Until the mid-60s, only the Mazatecs, an indigenous group from Oaxaca, Mexico, used Salvia Divinorum (S. divinorum) due to its hallucinogen properties. Later it was found that the hallucinogen effects of this plant were caused by the presence of a neoclerodane diterpene Salvinorin A (salvinorin A), which is a highly selective agonist of kappa-opioid receptor (KOR) that cause more intense hallucinations than the common hallucinogens as lysergic acid, mushrooms, ecstasy and others. In fact, smoking of only 200-500 μg of S...
February 9, 2017: Phytochemistry
Yolande Despinasse, Sébastien Fiorucci, Serge Antonczak, Sandrine Moja, Aurélie Bony, Florence Nicolè, Sylvie Baudino, Jean-Louis Magnard, Frédéric Jullien
Lavender essential oils (EOs) of higher quality are produced by a few Lavandula angustifolia cultivars and mainly used in the perfume industry. Undesirable compounds such as camphor and borneol are also synthesized by lavender leading to a depreciated EO. Here, we report the cloning of bornyl diphosphate synthase of lavender (LaBPPS), an enzyme that catalyzes the production of bornyl diphosphate (BPP) and then by-products such as borneol or camphor, from an EST library. Compared to the BPPS of Salvia officinalis, the functional characterization of LaBPPS showed several differences in amino acid sequence, and the distribution of catalyzed products...
February 9, 2017: Phytochemistry
Marília Gabriela de Santana Costa, Paulo Mazzafera, Tiago Santana Balbuena
Eucalyptus grandis and Eucalyptus globulus are among the most widely cultivated trees, differing in lignin composition and plantation areas, as E. grandis is mostly cultivated in tropical regions while E. globulus is preferred in temperate areas. As temperature is a key modulator in plant metabolism, a large-scale proteome analysis was carried out to investigate changes in the antioxidant system and the lignification metabolism in plantlets grown at different temperatures. Our strategy allowed the identification of 3111 stem proteins...
February 9, 2017: Phytochemistry
Fumi Tatsuzawa, Natsu Tanikawa, Masayoshi Nakayama
A previously undescribed acylated anthocyanin was extracted from the red-purple flowers of Pueraria lobata with 5% HOAc-H2O, and determined to be petunidin 3-O-(β-glucopyranoside)-5-O-[6-O-(malonyl)-β-glucopyranoside], by chemical and spectroscopic methods. In addition, two known acylated anthocyanins, delphinidin 3-O-(β-glucopyranoside)-5-O-[6-O-(malonyl)-β-glucopyranoside] and malvidin 3-O-(β-glucopyranoside)-5-O-[6-O-(malonyl)-β-glucopyranoside] were identified. Delphinidin 3,5-di-glucoside, petunidin 3,5-di-glucoside, and malvidin 3,5-di-glucoside, have been known as major components of P...
February 8, 2017: Phytochemistry
Zhong-Nan Wu, Yu-Bo Zhang, Neng-Hua Chen, Mo-Jiao Li, Man-Mei Li, Wei Tang, Ling Zhuang, Yao-Lan Li, Guo-Cai Wang
Seven sesquiterpene lactones, 8-O-methacryloylelephanpane, 2,4-bis-O-methyl-8-O-methacryloylelephanpane, 4-O-ethyl-8-O-methacryloylelephanpane, 8-O-methacryloylisoelephanpane, 2-O-demethyltomenphantopin C, molephantin A, molephantin B, along with ten known ones, were isolated from Elephantopus mollis (Asteraceae). Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D and 2D NMR). The isolates were evaluated for their anti-inflammatory activities on LPS-stimulated RAW 264...
February 5, 2017: Phytochemistry
SeonJu Park, Nanyoung Kim, Guijae Yoo, Sang-Nam Kim, Hyun-Jung Kwon, Kiwon Jung, Dong-Chan Oh, Yun-Hee Lee, Seung Hyun Kim
Juglans mandshurica Maxim. (Juglandaceae) is a traditional folk medicine used for treatment of dermatosis and to relieve aches in Korea and China. In this study, eight compounds, along with six known compounds, were isolated from the fruit of J. mandshurica. Among the six known compounds, the absolute configuration of two compounds were determined. The structures of compounds were determined on the basis of extensive spectroscopic methods, including 1D and 2D NMR and CD spectroscopic data. All isolated compounds were tested for their lipolytic activities in differentiated adipocytes using C3H10T1/2 mouse embryonic fibroblasts...
February 5, 2017: Phytochemistry
Lu-Mei Dai, Ri-Zhen Huang, Bin Zhang, Jing Hua, Heng-Shan Wang, Dong Liang
Eleven oleanane-type triterpenoid saponins, foegraecumosides A-K, and eight known ones, were isolated from the aerial parts of Lysimachia foenum-graecum. Their structures were elucidated by spectroscopic data analyses and chemical methods. All isolated saponins were evaluated for their cytotoxicity against four human cancer cell lines (NCI-H460, MGC-803, HepG2, and T24). Seven saponins containing the aglycone cyclamiretin A exhibited moderate cytotoxicity against all tested human cancer cell lines, with IC50 values of 9...
February 4, 2017: Phytochemistry
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