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Journal of Natural Products

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https://www.readbyqxmd.com/read/28445069/targeted-dereplication-of-microbial-natural-products-by-high-resolution-ms-and-predicted-lc-retention-time
#1
Justine Chervin, Marc Stierhof, Ming Him Tong, Doe Peace, Kine Østnes Hansen, Dagmar Solveig Urgast, Jeanette Hammer Andersen, Yi Yu, Rainer Ebel, Kwaku Kyeremeh, Veronica Paget, Gabriela Cimpan, Albert Van Wyk, Hai Deng, Marcel Jaspars, Jioji N Tabudravu
A new strategy for the identification of known compounds in Streptomyces extracts that can be applied in the discovery of natural products is presented. The strategy incorporates screening a database of 5555 natural products including 5098 structures from Streptomyces sp., using a high-throughput LCMS data processing algorithm that utilizes HRMS data and predicted LC retention times (tR) as filters for rapid identification of known compounds in the natural product extract. The database, named StrepDB, contains for each compound the structure, molecular formula, molecular mass, and predicted LC retention time...
April 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28445065/neomacrophorin-x-a-4-4-3-propellane-type-meroterpenoid-from-trichoderma-sp-1212-03
#2
Kazuaki Kusakabe, Yuna Honmura, Shota Uesugi, Akio Tonouchi, Hayato Maeda, Ken-Ichi Kimura, Hiroyuki Koshino, Masaru Hashimoto
Neomacrophorin X (1) was isolated from Trichoderma sp. 1212-03. Heteronuclear multiple bond correlation (HMBC) spectral analysis indicated a unique [4.4.3]propellane framework, which was verified by the (1)H and (13)C chemical shift calculations based on density functional theory (DFT) and subsequent comparison with experimental data obtained in CDCl3. The DFT-based electronic circular dichroism (ECD) calculations were effective in not only determining the absolute configuration but also confirming the relative structure...
April 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28445049/inflammation-modulatory-phorbol-esters-from-the-seeds-of-aquilaria-malaccensis
#3
Vitthal D Wagh, Michal Korinek, I-Wen Lo, Yu-Ming Hsu, Shu-Li Chen, Hsue-Yin Hsu, Tsong-Long Hwang, Yang-Chang Wu, Bing-Hung Chen, Yuan-Bin Cheng, Fang-Rong Chang
The tree Aquilaria malaccensis is a valuable source of agarwood, which is used in herbal medicinal preparations. Phytochemical research on A. malaccensis seeds has led to the isolation of four new phorbol esters (1-4), two known phorbol esters (5, isolated from Nature for the first time, and 6), and two known glycerides (7 and 8). The structures of these isolates were elucidated by means of spectroscopic data interpretation. The inflammation-modulatory activities of the isolates on elastase release and superoxide anion generation in human neutrophils were evaluated...
April 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28445040/chemoenzymatic-total-synthesis-of-the-proposed-structures-of-putaminoxins-b-and-d
#4
Carolin Bisterfeld, Claudia Holec, Dietrich Böse, Patrick Marx, Jörg Pietruszka
Different enzymatic and nonenzymatic approaches were tested and compared to afford enantiopure homoallylic and allylic alcohols as building blocks in a total synthesis showcase. Thereby, highly enantioselective alcohol dehydrogenases and the P450 BM3 monooxygenase variant A74G L188Q were compared to classical asymmetric reagent-controlled allyl additions. Thus, the first total syntheses of the proposed structures for putaminoxins B/D and their respective enantiomers were accomplished. Detailed spectroscopic analysis of the newly synthesized compounds unraveled a discrepancy with respect to the reported structures of putaminoxins B/D...
April 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28445039/tricyclic-polyprenylated-acylphloroglucinols-from-st-john-s-wort-hypericum-perforatum
#5
Yi Guo, Na Zhang, Chunmei Chen, Jinfeng Huang, Xiao-Nian Li, Junjun Liu, Hucheng Zhu, Qingyi Tong, Jinwen Zhang, Zengwei Luo, Yongbo Xue, Yonghui Zhang
The new polyprenylated acylphloroglucinol derivatives 1-15 and the known furohyperforin (16) were isolated from the stems and leaves of Hypericum perforatum. Their structures were determined by analyses of NMR and HRESIMS data. Their absolute configurations were elucidated by a combination of electronic circular dichroism (ECD) and Rh2(OCOCF3)4-induced ECD, as well as X-ray diffraction crystallography. The new hyperforatin F (9) contains a unique acetyl functionality at C-1 of the bicyclo[3.3.1]nonane core...
April 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28443671/total-synthesis-of-tanshinone-i
#6
Nan Wu, Wei-Cong Ma, Sheng-Jun Mao, Yong Wu, Hui Jin
A novel total synthesis of tanshinone I (1) via the intermediate 3-hydroxy-8-methyl-1,4-phenanthrenedione (8) is described. The low overall yields and the use of expensive reagents in the synthesis process were minimized by the use of the Diels-Alder reaction to directly construct the 1,4-phenanthrenedione scaffold, providing tanshinone I (1) in only three steps.
April 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28429944/biotechnological-production-of-dimethoxyflavonoids-using-a-fusion-flavonoid-o-methyltransferase-possessing-both-3-and-7-o-methyltransferase-activities
#7
Danbi Lee, Hye Lin Park, Sang-Won Lee, Seong Hee Bhoo, Man-Ho Cho
Although they are less abundant in nature, methoxyflavonoids have distinct physicochemical and pharmacological properties compared to common nonmethylated flavonoids. Thus, enzymatic conversion and biotransformation using genetically engineered microorganisms of flavonoids have been attempted for the efficient production of methoxyflavonoids. Because of their regiospecificity, more than two flavonoid O-methyltransferases (FOMTs) and enzyme reactions are required to biosynthesize di(or poly)-methoxyflavonoids...
April 21, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28429937/total-synthesis-of-two-glycosylated-stilbenes-oxyresveratrol-2-o-%C3%AE-d-glucopyranoside-and-2-3-5-4-tetrahydroxystilbene-2-o-%C3%AE-d-glucopyranoside
#8
Sunil Kumar, Hsueh-Yun Lee, Jing-Ping Liou
Glycosylated stilbenes are biologically active secondary metabolites of plants and have the potential to alleviate a broad range of human diseases. However, some of these compounds are not naturally abundant, and thus the synthesis of such molecules is desirable. This paper reports the first synthesis of oxyresveratrol 2-O-β-d-glucopyranoside (1) and 2,3,5,4'-tetrahydroxystilbene 2-O-β-d-glucopyranoside (1'), which are stilbene glycosides obtained from the rhizomes of Schoenocaulon officinale and Polygonum multiflorum, respectively...
April 21, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28425292/lactone-derivatives-produced-by-a-phaeoacremonium-sp-an-endophytic-fungus-from-senna-spectabilis
#9
Geraldo H Silva, Maria L Zeraik, Camila M de Oliveira, Helder L Teles, Henrique C Trevisan, Ludwig H Pfenning, Camila P Nicolli, Maria C M Young, Yvonne P Mascarenhas, Lucas M Abreu, Amanda C Saraiva, Alexandra I Medeiros, Vanderlan da S Bolzani, Angela R Araujo
Three new isoaigialones, A, B, and C (1-3), along with aigialone (4), were isolated from the crude EtOAc extract of a Phaeoacremonium sp., an endophytic fungus obtained from the leaves of Senna spectabilis. The structures of these compounds were elucidated based on the analysis of spectroscopic data. Compounds 2 and 4 were active against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum. This is the first report of metabolites produced by an Phaeoacremonium sp., associated with S...
April 20, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28422509/%C3%AE-glucosidase-inhibitors-from-salvia-circinata
#10
Laura Flores-Bocanegra, Martin González-Andrade, Robert Bye, Edelmira Linares, Rachel Mata
A dried infusion prepared from the aerial parts of Salvia circinata did not provoke acute toxicity in mice (LD50 > 5 g/kg). This infusion showed poor hypoglycemic and antihyperglycemic effects (100-570 mg/kg) when tested in normal and hyperglycemic mice using acute and oral glucose tolerance tests, respectively. However, this infusion possessed antihyperglycemic action in vivo during an oral sucrose tolerance test (31.6-316 mg/kg), suggesting the presence of α-glucosidase inhibitors in S. circinata. Fractionation of a nonpolar extract of the aerial parts of the plant yielded a new biflavone (1) and four new neoclerodane diterpenoid glucosides (2-5) along with the known compounds amarisolide (6), pedalitin (7), apigenin-7-O-β-d-glucoside (8), and the flavone 2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-one (9)...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28422496/the-combined-use-of-proteomics-and-transcriptomics-reveals-a-complex-secondary-metabolite-network-in-peperomia-obtusifolia
#11
Andrea N L Batista, José Roberto A Dos Santos-Pinto, João M Batista, Tatiana M Souza-Moreira, Mariana M Santoni, Cleslei F Zanelli, Massuo J Kato, Silvia N López, Mario S Palma, Maysa Furlan
Peperomia obtusifolia, an ornamental plant from the Piperaceae family, accumulates a series of secondary metabolites with interesting biological properties. From a biosynthesis standpoint, this species produces several benzopyrans derived from orsellinic acid, which is a polyketide typically found in fungi. Additionally, the chiral benzopyrans were reported as racemic and/or as diastereomeric mixtures, which raises questions about the level of enzymatic control in the cyclization step for the formation of the 3,4-dihydro-2H-pyran moiety...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28422495/cochliotoxin-a-dihydropyranopyran-4-5-dione-and-its-analogues-produced-by-cochliobolus-australiensis-display-phytotoxic-activity-against-buffelgrass-cenchrus-ciliaris
#12
Marco Masi, Susan Meyer, Suzette Clement, Alessio Cimmino, Massimo Cristofaro, Antonio Evidente
Buffelgrass (Pennisetum ciliare or Cenchrus ciliaris) is a perennial grass that has become highly invasive in the Sonoran Desert of southern Arizona. In the search for novel control strategies against this weed, strains of the foliar fungal pathogen Cochliobolus australiensis from buffelgrass have been screened for their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides in an integrated pest management strategy. A new phytotoxin, named cochliotoxin, was isolated from liquid culture of this fungus together with radicinin, radicinol, and their 3-epimers...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28422493/triazolide-strigolactone-mimics-influence-root-development-in-arabidopsis
#13
Marcela Dvorakova, Petr Soudek, Tomas Vanek
Strigolactones are the most recently recognized class of phytohormones, which are also known to establish plant symbiosis with arbuscular mycorhizal fungi or induce germination of parasitic plants. Their relatively complex structures and low stability urgently calls for simple derivatives with maintained biological function. We have prepared a series of triazolide strigolactone mimics and studied their ability to affect root development of Arabidopsis thaliana. The strigolactone mimics significantly induced root elongation and lateral root formation while resembling the effect of the reference compound GR24...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28421773/exploring-jolkinol-d-derivatives-to-overcome-multidrug-resistance-in-cancer
#14
Mariana A Reis, Omar B Ahmed, Gabriella Spengler, Joseph Molnár, Hermann Lage, Maria-José U Ferreira
Macrocyclic monoacyl lathyrane derivatives bearing a benzoyl moiety were previously found to be strong ABCB1 modulators. To explore the effects of different substituents of the aromatic moiety, 14 new compounds (1.1-1.7, 1.10, and 2.1-2.4) were prepared from jolkinol D (1), obtained from Euphorbia piscatoria, and from jolkinodiol (2), its hydrolysis derivative. Compounds 1.8 and 1.9, having aliphatic moieties, were also obtained. The reversal of ABCB1-mediated MDR was evaluated through functional and chemosensitivity assays on the human ABCB1-gene-transfected L5178Y mouse T-lymphoma cell line...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28421764/total-synthesis-of-the-claimed-structure-of-%C3%A2-hyptinin-and-structural-revision-of-natural-hyptinin
#15
Kazuto Maeda, Toshiyuki Hamada, Satoaki Onitsuka, Hiroaki Okamura
A total synthesis of (±)-hyptinin was achieved via a convergent route using the key phosphonate, cyclic ketone, and aryl Grignard components. The (1)H and (13)C NMR spectra of natural hyptinin did not agree with those of the synthesized compound. In particular, there were considerable differences between the signals assigned to the protons and carbons surrounding the lactone carbonyl group for the natural and synthesized compounds. The NMR data strongly suggested that the naturally occurring compound, hyptinin, was a structural isomer of the synthesized compound...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28421754/orbicularisine-a-spiro-indolothiazine-isolated-from-gills-of-the-tropical-bivalve-codakia-orbicularis
#16
Francesca Goudou, Philippe Petit, Céline Moriou, Olivier Gros, Ali Al-Mourabit
A novel spiro-indolofuranone fused to a thiazine skeleton, orbicularisine (1), was isolated from gills of the mollusk Codakia orbicularis. The isolation and structure elucidation using spectroscopic evidence including mass and NMR spectroscopy are described. The final structure of 1 was supported by key HMBC correlation.
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28418248/total-synthesis-configuration-assignment-and-cytotoxic-activity-evaluation-of-protulactone-a
#17
Martin Markovič, Peter Koóš, Tomáš Čarný, Saskia Sokoliová, Nikola Boháčiková, Ján Moncol, Tibor Gracza
The first total synthesis and absolute configuration assignment of protulactone A (1) has been achieved. Four stereoisomers, 1a, ent-1a, 1b, and ent-1b, of this natural polyketide were prepared by chiral pool synthesis starting from l- and d-arabinose, respectively. The absolute and relative configurations of all isomers were assigned by single-crystal X-ray analysis. Target compounds were screened for their in vitro cytotoxicity toward certain human tumor cells (NCI60 cancer cell line panel).
April 18, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28418245/geranylpyrrol-a-and-piericidin-f-from-streptomyces-sp-chq-64-%C3%AE-rdmf
#18
Xiaoning Han, Zengzhi Liu, Zhenzhen Zhang, Xiaomin Zhang, Tianjiao Zhu, Qianqun Gu, Wenli Li, Qian Che, Dehai Li
Two new compounds, geranylpyrrol A (1) and piericidin F (2), were isolated from a reedsmycins nonproducing mutant strain of Streptomyces sp. CHQ-64. Their structures, including absolute configurations, were elucidated by extensive NMR, MS, NOESY, and ECD analyses. Geranylpyrrol A (1) is an unusual naturally occurring 2,3,4-trisubstituted pyrrole, and piericidin F (2) showed cytotoxicity against HeLa, NB4, A549, and H1975 cell lines with IC50 values of 0.003, 0.037, 0.56, and 0.49 μM, respectively.
April 18, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28414230/computer-aided-13-c-nmr-chemical-profiling-of-crude-natural-extracts-without-fractionation
#19
Ali Bakiri, Jane Hubert, Romain Reynaud, Sylvie Lanthony, Dominique Harakat, Jean-Hugues Renault, Jean-Marc Nuzillard
A computer-aided, (13)C NMR-based dereplication method is presented for the chemical profiling of natural extracts without any fractionation. An algorithm was developed in order to compare the (13)C NMR chemical shifts obtained from a single routine spectrum with a set of predicted NMR data stored in a natural metabolite database. The algorithm evaluates the quality of the matching between experimental and predicted data by calculating a score function and returns the list of metabolites that are most likely to be present in the studied extract...
April 17, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28409637/halogenated-compounds-from-directed-fermentation-of-penicillium-concentricum-an-endophytic-fungus-of-the-liverwort-trichocolea-tomentella
#20
Tehane Ali, Masanori Inagaki, Hee-Byung Chai, Thomas Wieboldt, Chad Rapplye, L Harinantenaina Rakotondraibe
One new chlorinated xanthone, 6-chloro-3,8-dihydroxy-1-methylxanthone (1), a new 2-bromo-gentisyl alcohol (2), and a mixture of 6-epimers of 6-dehydroxy-6-bromogabosine C (3a and 3b), together with 19 previously identified compounds, epoxydon (4), norlichexanthone (5), 2-chlorogentisyl alcohol (6), hydroxychlorogentisyl quinone (7), 6-dehydroxy-6α-chlorogabosine C (8a), 6-dehydroxy-6β-chlorogabosine C (8b), gentisyl alcohol (9), gentisyl quinone (10), (R,S)-1-phenyl-1,2-ethanediol (11), dehydrodechlorogriseofulvin (12), dechlorogriseofulvin (13), dehydrogriseofulvin (14), griseofulvin (15), ethylene glycol benzoate (16), alternariol (17), griseoxanthone C (18), drimiopsin H (19), griseophenone C (20), and griseophenone B (21), were isolated from cultures of Penicillium concentricum, a fungal endophyte of the liverwort Trichocolea tomentella...
April 14, 2017: Journal of Natural Products
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