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Acetogenins

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https://www.readbyqxmd.com/read/28416750/annonaceous-acetogenins-mediated-up-regulation-of-notch2-exerts-growth-inhibition-in-human-gastric-cancer-cells-in-vitro
#1
Yan Li, Jianbin Ye, Zhongbiao Chen, Junjie Wen, Fei Li, Pengpeng Su, Yanqing Lin, Bingxin Hu, Danlin Wu, Lijun Ning, Qi Xue, Hongxiang Gu, Yunshan Ning
BACKGROUND: Gastric cancer (GC) is a global health problem because of limited treatments and poor prognosis. Annonaceous acetogenins (ACGs) has been reported to exert anti-tumorigenic effects in cancer, yet the mechanism underlying its effects on GC remains largely unknown. Notch signaling plays a critical role in cell proliferation, differentiation and apoptosis. Therefore, it may contribute to the development of GC. This study aims to explore the role of Notch2 in ACGs' activities in GC cells...
March 28, 2017: Oncotarget
https://www.readbyqxmd.com/read/28415154/annona-species-annonaceae-a-rich-source-of-potential-antitumor-agents
#2
REVIEW
Rosa Tundis, Jianbo Xiao, Monica R Loizzo
Plants have provided the basis of traditional medicine systems throughout the world for thousands of years and continue to yield molecules for new remedies. We analyzed studies published from 2009 to 2016 on the Annona species (Annonaceae), including A. coriacea, A. crassifolia, A. hypoglauca, A. muricata, A. squamosa, A. sylvatica, and A. vepretorum, as sources of potential antitumor agents. Here, we report and discuss the mechanisms of action and structure-activity relationships of the most active Annona constituents...
April 17, 2017: Annals of the New York Academy of Sciences
https://www.readbyqxmd.com/read/28353149/toxicity-of-an-annonin-based-commercial-bioinsecticide-against-three-primary-pest-species-of-stored-products
#3
L P Ribeiro, O Z Zanardi, G L P Gonçalves, T F Ansante, P T Yamamoto, J D Vendramim
The effects of a bioinsecticide formulation based on extract of Annona squamosa L. (Annonaceae) containing 10,000 mg L(-1) of acetogenin annonin as the main active ingredient were investigated against three primary pest species of stored grains in Brazil [maize weevil Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae), Mexican bean weevil Zabrotes subfasciatus (Boheman) (Coleoptera: Chrysomelidae: Bruchinae), and cowpea weevil Callosobruchus maculatus (Fabricius) (Coleoptera: Chrysomelidae: Bruchinae)] by means of residual contact bioassays...
March 28, 2017: Neotropical Entomology
https://www.readbyqxmd.com/read/28254016/the-fruit-of-annona-squamosa-l-as-a-source-of-environmental-neurotoxins-from-quantification-of-squamocin-to-annotation-of-annonaceous-acetogenins-by-lc-ms-ms-analysis
#4
Natacha Bonneau, Lamia Baloul, Idensi Bajin Ba Ndob, François Sénéjoux, Pierre Champy
Annonaceous acetogenins (AAGs) are neurotoxins possibly responsible for atypical Parkinsonism/dementia clusters, via the consumption of edible Annonaceae fruits. Their presence was investigated in fruit pulps of Annona squamosa from different locations. Qualitative analysis of other AAGs was performed. We here report the identification of squamocin in batches from Asia, the Caribbean Basin and the Indian Ocean. This molecule was quantified by HPLC-UV, evidencing a content of 13.5-36.4mg/fruit. HPLC-ESI-Q-TOF allowed the detection of 25 different raw formulas matching with AAGs...
July 1, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28185724/simplifying-nature-towards-the-design-of-broad-spectrum-kinetoplastid-inhibitors-inspired-by-acetogenins
#5
Eoin R Gould, Elizabeth F B King, Stefanie K Menzies, Andrew L Fraser, Lindsay B Tulloch, Marija K Zacharova, Terry K Smith, Gordon J Florence
The need for new treatments for the neglected tropical diseases African sleeping sickness, Chagas disease and Leishmaniasis remains urgent with the diseases widespread in tropical regions, affecting the world's very poorest. We have previously reported bis-tetrahydropyran 1,4-triazole analogues designed as mimics of the annonaceous acetogenin natural product chamuvarinin, which maintained trypanocidal activity. Building upon these studies, we here report related triazole compounds with pendant heterocycles, mimicking the original butenolide of the natural product...
January 28, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28155166/a-histochemical-technique-for-the-detection-of-annonaceous-acetogenins
#6
Guillermo Laguna-Hernández, Alicia Enriqueta Brechú-Franco, Iván De la Cruz-Chacón, Alma Rosa González-Esquinca
Annonaceous acetogenins (ACGs) are molecules with carbon numbers C35-C37, usually with tetrahydrofuran and tetrahydropyran rings and one terminal γ-lactone (usually α,β-unsaturated), in a large aliphatic chain that is varyingly hydroxylated, acetoxylated or ketonized. ACGs have ecological functions as insecticides and are pharmacologically promising due to their cytotoxic and antitumoral properties. They are found in the seeds, leaves, roots, flowers and fruits of annonaceous plants and can be detected during isolation via thin-layer chromatography using Kedde's reagent, which reacts with the unsaturated lactone...
2017: Methods in Molecular Biology
https://www.readbyqxmd.com/read/28116099/a-novel-thiophene-3-carboxamide-analog-of-annonaceous-acetogenin-exhibits-antitumor-activity-via-inhibition-of-mitochondrial-complex-i
#7
Akinobu Akatsuka, Naoto Kojima, Mutsumi Okamura, Shingo Dan, Takao Yamori
Previously we synthesized JCI-20679, a novel thiophene-3-carboxamide analog of annonaceous acetogenins which have shown potent antitumor activity, with no serious side effects, in mouse xenograft models. In this study, we investigated the antitumor mechanism of JCI-20679. The growth inhibition profile (termed "fingerprint") of this agent across a panel of 39 human cancer cell lines (termed "JFCR39") was measured; this fingerprint was analyzed by the COMPARE algorithm utilizing the entire drug sensitivity database for the JFCR39 panel...
August 2016: Pharmacology Research & Perspectives
https://www.readbyqxmd.com/read/28092423/-1-h-qnmr-quantification-of-annonaceous-acetogenins-in-crude-extracts-of-annona-muricata-l-fruit-pulp
#8
Natacha Bonneau, Timothé Cynober, Jean-Christophe Jullian, Pierre Champy
INTRODUCTION: Annonaceous acetogenins (AAGs) constitute a group of environmental neurotoxins, possibly implicated in sporadic atypical Parkinsonism/dementia complexes. The recent evidencing of complex mixtures of AAGs in edible fruits and derived food products requires efficient and practical analytical tools for an estimation of human exposure. OBJECTIVE: To develop a simple method for the direct quantitation of the majority of AAGs (sub-types 1a and 1b) within crude extracts, using commonly available (1) H-NMR spectrometers, for food control...
January 16, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28079013/natural-product-inhibitors-of-topoisomerases-review-and-docking-study
#9
L Scotti, F J B Mendonça Júnior, F F Ribeiro, J F Tavares, M S Da Silva, J M Barbosa Filho, M T Scotti
Since ancient times, natural products have been used in treating various diseases effectively and safely. Nowadays, these natural compounds are submitted to sophisticated methodologies from isolation, computing, analytical, and even serving as pharmacophore suggestions for synthesis. The substances extracted from marine species, plants, and microorganisms present activities beneficial to our health, including protection against malignant tumors. The topoisomerase enzymes play an important role in DNA metabolism, and searching for enzyme inhibitors is an important target in the search for new anticancer drugs...
January 11, 2017: Current Protein & Peptide Science
https://www.readbyqxmd.com/read/28070565/activation-of-respiratory-complex-i-from-escherichia-coli-studied-by-fluorescent-probes
#10
Nikolai Belevich, Galina Belevich, Zhiyong Chen, Subhash C Sinha, Marina Verkhovskaya
Respiratory Complex I from E. coli may exist in two interconverting forms: resting (R) and active (A). The R/A transition of purified, solubilized Complex I occurring upon turnover was studied employing two different fluorescent probes, Annine 6+, and NDB-acetogenin. NADH-induced fluorescent changes of both dyes bound to solubilized Complex I from E. coli were characterized as a function of the protein:dye ratio, temperature, ubiquinone redox state and the enzyme activity. Analysis of this data combined with time-resolved optical measurements of Complex I activity and spectral changes indicated two ubiquinone-binding sites; a possibility of reduction of the tightly-bound quinone in the resting state and reduction of the loosely-bound quinone in the active state is discussed...
January 2017: Heliyon
https://www.readbyqxmd.com/read/28064519/three-new-antitumor-annonaceous-acetogenins-from-the-seeds-of-annona-squamosa
#11
Chengyao Ma, Qiwen Wang, Yeye Shi, Yue Li, Xunan Wang, Xiang Li, Yong Chen, Jianwei Chen
Two new annonaceous acetogenins squamocin P (2) and annosquatin III (3) and one new ACG precursor dieporeticenin B (1) along with five known precursors (4-8) were isolated from the seeds of Annona squamosa. Their structures were ascertained by chemical methods and various spectral evidences. These compounds showed inhibitory effects against three multidrug-resistant (MDR) cancer cell lines. Compound 2 and 3 displayed selective cytotoxicity against SMMC 7721/T (IC50 0.435 and 1.79 μM) and MCF-7/ADR (IC50 values 3...
January 9, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28043557/antimycobacterial-potency-and-cytotoxicity-study-of-three-medicinal-plants
#12
Patrick Valere Tsouh Fokou, Regina Appiah-Opong, Dorothy Yeboah-Manu, Abena Adomah Kissi-Twum, Lauve Rachel Tchokouaha Yamthe, Aristide Laurel Mokale Kognou, Phyllis Addo, Fabrice Fekam Boyom, Alexander Kwadwo Nyarko
OBJECTIVE/BACKGROUND: Mycobacterial infections including tuberculosis, leprosy, and buruli ulcer are among the most prevalent, debilitating, and deadly tropical diseases, especially in Sub-Saharan Africa. The development of drug resistance to the currently available drugs and the poor compliance emphasize the need for new chemotherapeutic agents. This study was designed to evaluate the in vitro activity of Cleistopholis patens, Annona reticulata, and Greenwayodendron suaveolens against Mycobacterium smegmatis...
December 2016: International Journal of Mycobacteriology
https://www.readbyqxmd.com/read/28000792/mechanistic-study-of-tetrahydrofuran-acetogenins-in-triggering-endoplasmic-reticulum-stress-response-apotoposis-in-human-nasopharyngeal-carcinoma
#13
Shin-Hun Juang, Chang-Ying Chiang, Fong-Pin Liang, Hsiu-Hui Chan, Jai-Sing Yang, Shih-Hao Wang, Yu-Chin Lin, Ping-Chung Kuo, Meng-Ru Shen, Tran Dinh Thang, Bui Thi Minh Nguyet, Sheng-Chu Kuo, Tian-Shung Wu
For past three decades, numerous studies have elucidated the antiproliferative effects of acetogenins in hopes of developing a new class of clinical anticancer agents. However, clear and definitive action mechanisms of acetogenins were less clarified. In the present study, three tetrahydrofuran (THF)-containing acetogenins were found to have potent and selective antiproliferative activity against human nasopharyngeal carcinoma (NPC) cell lines and their methotrexate-resistant counterparts. The THF-containing acetogenins induced G2/M phase arrest, mitochondrial damage and apoptosis, and increased cytosolic and mitochondrial Ca(2+) in NPCs...
December 21, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27976249/quantification-of-the-neurotoxins-annonaceous-acetogenins-in-the-edible-fruits-of-several-annona-species-using-1h-nmr
#14
N Bonneau, T Cynober, P Coulerie, V Kagy, P Champy
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27975649/chitosan-tripolyphosphate-microparticles-for-controlled-release-of-acetogenins-extracted-from-annona-muricata-leaves
#15
K Mulia, F Fauzia, E Krisanti, A Faried
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27975485/annonaceous-acetogenins-from-the-fruit-pulps-of-annona-reticulata-and-a-squamosa-dereplicative-studies
#16
N Bonneau, P Champy
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27876785/characterization-of-the-annonaceous-acetogenin-annonacinone-a-natural-product-inhibitor-of-plasminogen-activator-inhibitor-1
#17
Stéphane Pautus, Mouad Alami, Fréderic Adam, Guillaume Bernadat, Daniel A Lawrence, Allan De Carvalho, Gilles Ferry, Alain Rupin, Abdallah Hamze, Pierre Champy, Natacha Bonneau, Philippe Gloanec, Jean-Louis Peglion, Jean-Daniel Brion, Elsa P Bianchini, Delphine Borgel
Plasminogen activator inhibitor-1 (PAI-1) is the main inhibitor of the tissue type and urokinase type plasminogen activators. High levels of PAI-1 are correlated with an increased risk of thrombotic events and several other pathologies. Despite several compounds with in vitro activity being developed, none of them are currently in clinical use. In this study, we evaluated a novel PAI-1 inhibitor, annonacinone, a natural product from the Annonaceous acetogenins group. Annonacinone was identified in a chromogenic screening assay and was more potent than tiplaxtinin...
November 23, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27871119/inhibitory-activity-of-avocado-seed-fatty-acid-derivatives-acetogenins-against-listeria-monocytogenes
#18
Carmen Salinas-Salazar, Carmen Hernández-Brenes, Dariana Graciela Rodríguez-Sánchez, Elena Cristina Castillo, Jesús Manuel Navarro-Silva, Adriana Pacheco
High standards regarding Listeria monocytogenes control and consumer demands for food products without synthetic additives represent a challenge to food industry. We determined the antilisterial properties of an enriched acetogenin extract (EAE) from avocado seed, compared it to two commercial antimicrobials (one enriched in avocado acetogenins), and tested purified molecules. Acetogenin composition in pulp and seed of Hass avocado was quantified. EAE were obtained by two sequential centrifuge partition chromatography separations and molecules purified by preparative chromatography and quantified by HPLC-MS-TOF and HPLC-PDA...
January 2017: Journal of Food Science
https://www.readbyqxmd.com/read/27813410/total-synthesis-of-the-proposed-structure-for-aromin-and-its-structural-revision
#19
Shunya Takahashi, Daisuke Satoh, Misato Hayashi, Kohta Takahashi, Kazunori Yamaguchi, Takemichi Nakamura, Hiroyuki Koshino
This paper describes the first total synthesis of the proposed structure for aromin, an annonaceous acetogenin possessing an unusual bis-THF ring system, and its 4S,7R-isomer. The key steps involve an oxidative cyclization of a couple of terminal-diene alcohols and an intermolecular metathesis of an alkenyl tetrahydrofuran with an enone carrying a tetrahydrofuranyl lactone. The spectral data of both samples did not match those of aromin. Re-examination of the NMR data using the CAST/CNMR Structure Elucidator and chemical derivations suggested that the real structure of aromin should be revised to be a tetrahydropyran acetogenin, montanacin D...
November 18, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27704814/epimeric-face-selective-oxidations-and-diastereodivergent-transannular-oxonium-ion-formation-fragmentations-computational-modeling-and-total-syntheses-of-12-epoxyobtusallene-iv-12-epoxyobtusallene-ii-obtusallene-x-marilzabicycloallene-c-and-marilzabicycloallene
#20
James Clarke, Karl J Bonney, Muhammad Yaqoob, Savade Solanki, Henry S Rzepa, Andrew J P White, David S Millan, D Christopher Braddock
The total syntheses of 12-epoxyobtusallene IV, 12-epoxyobtusallene II, obtusallene X, marilzabicycloallene C, and marilzabicycloallene D as halogenated C15-acetogenin 12-membered bicyclic and tricyclic ether bromoallene-containing marine metabolites from Laurencia species are described. Two enantiomerically pure C4-epimeric dioxabicyclo[8.2.1]tridecenes were synthesized by E-selective ring-closing metathesis where their absolute stereochemistry was previously set via catalytic asymmetric homoallylic epoxidation and elaborated via regioselective epoxide-ring opening and diastereoselective bromoetherification...
October 21, 2016: Journal of Organic Chemistry
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