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Acetogenins

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https://read.qxmd.com/read/30755289/antiprotozoal-investigation-of-20-plant-metabolites-on-trypanosoma-cruzi-and-leishmania-amazonensis-amastigotes-atalantoflavone-alters-the-mitochondrial-membrane-potential
#1
Layzon Antonio Lemos da Silva, Milene Höehr de Moraes, Marcus Tullius Scotti, Luciana Scotti, Rafaela de Jesus Souza, Judith L Nantchouang Ouete, Maique Weber Biavatti, Mario Steindel, Louis Pergaud Sandjo
The study aims to evaluate the antiprotozoal activities of 20 plant metabolites on Trypanosoma cruzi and Leishmania amazonensis amastigotes. Compounds 1-20 were obtained and identified by using chromatographic and spectroscopic techniques. The antiparasitic assays were performed on the intracellular form of T. cruzi and L. amazonensis using human leukaemic THP-1 cells as the host. The mechanism of action of the most active compounds was explored in silico by molecular docking using T. cruzi trypanothione reductase (TR) as a target, whereas the in vitro studies were performed by enzymatic assay using T...
February 13, 2019: Parasitology
https://read.qxmd.com/read/30699968/rare-acetogenins-with-anti-inflammatory-effect-from-the-red-alga-laurencia-obtusa
#2
Walied Mohamed Alarif, Sultan Semran Al-Lihaibi, Nahed Obaid Bawakid, Ahmed Abdel-Lateff, Hamdan Salem Al-Malky
Three new rare C12 acetogenins (enyne derivatives 1 ⁻ 3 ) were isolated from the organic extract obtained from the red alga Laurencia obtusa , collected from the Red Sea. The chemical structures of the isolated compounds were established by spectroscopical data analyses. Potent anti-inflammatory effect of the isolated metabolites was evidenced by inhibition of the release of inflammatory mediators (e.g., TNF-α, IL-1β and IL-6) by employing Human Peripheral Blood Mononuclear Cells (PBMC).
January 29, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://read.qxmd.com/read/30607643/ontogenic-synchronization-of-bephratelloides-cubensis-annona-macroprophyllata-seeds-and-acetogenins-from-annonaceae
#3
Claudia Azucena Durán-Ruiz, Rocío Cruz-Ortega, Alejandro Zaldívar-Riverón, Hilda Araceli Zavaleta-Mancera, Iván De-la-Cruz-Chacón, Alma Rosa González-Esquinca
The seeds of Annona macroprophyllata Donn. Sm. contain idioblasts with toxic acetogenins, including laherradurin and rolliniastatin-2, in relatively high proportions. Both metabolites are cataloged as potent insecticides for several species, even so, the wasp Bephratelloides cubensis Ashmead fulfills almost its entire life cycle inside the seeds of this and other annonaceous species, to such a degree, that they constitute a strong selection pressure. In order to document the chemical relationship between the two species, it is reported for the first time in this paper the presence of idioblasts and acetogenins during the ontogenic development of the seeds of A...
January 3, 2019: Journal of Plant Research
https://read.qxmd.com/read/30600714/two-new-epimers-of-c-15-acetogenin-4-epi-isolaurallene-and-4-epi-itomanallene-a-as-diastereomeric-model
#4
Chin-Soon Phan, Takashi Kamada, Charles S Vairappan
Two new C15 -acetogenins, 4-epi-isolaurallene (1) and 4-epi-itomanallene A (2) were isolated from a population of marine red alga Laurencia nangii Masuda from Carrington Reef. The structures of these compounds were determined intensively by NMR and HRESIMS data. Their configurations were elucidated by detailed comparison of chemical shifts, germinal protons splitting and NOE correlations with known and synthesized analogues. In addition, antibacterial activities of these compounds were evaluated. These compounds would serve as diastereomeric models for future reference...
January 2, 2019: Natural Product Research
https://read.qxmd.com/read/30590155/chiron-approach-from-d-mannitol-to-access-a-diastereomer-of-the-reported-structure-of-an-acetogenin-an-amide-alkaloid-and-a-sex-pheromone
#5
Sandip Chatterjee, Avrajit Manna, Ipsita Chakraborty, Tanurima Bhaumik
A short, simple and convenient chiron approach to (3R,4S,5R)-(-)-3,5-dihydroxy-4-decanolide, a hitherto unknown diastereomer of the reported structure of a naturally occurring acetogenin, (+)-polyporolide has been accomplished starting from a commercially available, inexpensive chiral pool molecule D-(+)-mannitol in nine efficient steps. An advanced intermediate synthesized from D-(+)-mannitol in six steps toward this end was further employed successfully to access two different natural products bearing two contiguous stereogenic centers...
December 14, 2018: Carbohydrate Research
https://read.qxmd.com/read/30448539/non-targeted-metabolomic-analysis-on-multidrug-resistance-hepatocellular-carcinoma-cell-and-reversal-effect-of-annonaceous-acetogenins
#6
Chengyao Ma, Xu Yan, Geman Yin, Yaqi Wang, Shuang Hu, Wei Xia, Yong Chen, Xiao Liu, Jianwei Chen, Xiang Li
Multidrug-resistance (MDR) has been shown to play a critical role in the development of many diseases. In this study, we used metabolomic method to evaluate the MDR in hepatocellular carcinoma, and investigate regulatory of annonaceous acetogenins on MDR of hepatocellular carcinoma. Multivariate statistical analysis revealed that the MDR of SMMC 7721 together with changes in glutathione metabolism, arginine and proline metabolism, sphingolipid metabolism. Annonaceous acetogenins impact these metabolism pathways...
October 25, 2018: Journal of Pharmaceutical and Biomedical Analysis
https://read.qxmd.com/read/30354147/a-general-diastereoselective-strategy-for-both-cis-and-trans-2-6-disubstituted-tetrahydropyrans-formal-total-synthesis-of-muconin
#7
Beduru Srinivas, D Srinivas Reddy, N Arjunreddy Mallampudi, Debendra K Mohapatra
A protocol for general diastereoselective tandem dihydroxylation followed by SN 2 cyclization was developed for the convenient and efficient synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans from ζ-mesyloxy α,β-unsaturated esters. The application of this novel method was demonstrated through the concise formal synthesis of (+)-muconin, a nonclassical acetogenin, with sequential THP-THF ring formation.
November 2, 2018: Organic Letters
https://read.qxmd.com/read/30256642/correction-to-halogenated-c-15-acetogenin-analogues-of-obtusallene-iii-from-a-laurenciella-sp-collected-in-corsica
#8
Sylvain Sutour, Bruno Therrien, Stephan H von Reuss, Félix Tomi
No abstract text is available yet for this article.
October 26, 2018: Journal of Natural Products
https://read.qxmd.com/read/30151067/anticancer-properties-of-graviola-annona-muricata-a-comprehensive-mechanistic-review
#9
REVIEW
Islam Rady, Melissa B Bloch, Roxane-Cherille N Chamcheu, Sergette Banang Mbeumi, Md Rafi Anwar, Hadir Mohamed, Abiola S Babatunde, Jules-Roger Kuiate, Felicite K Noubissi, Khalid A El Sayed, G Kerr Whitfield, Jean Christopher Chamcheu
Graviola ( Annona muricata ) is a small deciduous tropical evergreen fruit tree, belonging to the Annonaceae family, and is widely grown and distributed in tropical and subtropical regions around the world. The aerial parts of graviola have several functions: the fruits have been widely used as food confectionaries, while several preparations, especially decoctions of the bark, fruits, leaves, pericarp, seeds, and roots, have been extensively used in traditional medicine to treat multiple ailments including cancers by local communities in tropical Africa and South America...
2018: Oxidative Medicine and Cellular Longevity
https://read.qxmd.com/read/30105068/-annona-muricata-leaf-extract-triggered-intrinsic-apoptotic-pathway-to-attenuate-cancerous-features-of-triple-negative-breast-cancer-mda-mb-231-cells
#10
Jee Young Kim, Thien T P Dao, Kwangho Song, Sait Byul Park, Hyeri Jang, Min Kyoung Park, Soo Ueng Gan, Yeong Shik Kim
Annona muricata L., known as graviola, is an evergreen plant of the tropical regions and is a rich source of natural products. Graviola has various biological activities, and it is best known for its anticancer activity. This study aimed to investigate the effects of crude graviola extract in vitro on breast cancer cells; in particular, we aimed to identify an agent against triple negative breast cancer (TNBC). We used the TNBC MDA-MB-231 cell line as the experimental model and the ER(+) non-TNBC MCF-7 breast cancer cell line as the control...
2018: Evidence-based Complementary and Alternative Medicine: ECAM
https://read.qxmd.com/read/30077947/targeted-and-non-targeted-analysis-of-annonaceous-alkaloids-and-acetogenins-from-asimina-and-annona-species-using-uhplc-qtof-ms
#11
Bharathi Avula, Ji-Yeong Bae, Taghreed Majrashi, Tung-Ying Wu, Yan-Hong Wang, Mei Wang, Zulfiqar Ali, Yang-Chang Wu, Ikhlas A Khan
In current work, targeted and non-targeted analysis of alkaloids and acetogenins from methanolic extracts of Asimina, Annona species and dietary supplements have been performed using UHPLC-QToF in positive ion mode. Thirty-five standard compounds (twelve alkaloids and twenty-three acetogenins) were used for the analysis. The fragment ions produced by collision induced dissociation (CID) revealed the characteristic cleavage and provided structural information. Aporphine alkaloids and acetogenins are the major groups found in Asimina and Annona species...
September 10, 2018: Journal of Pharmaceutical and Biomedical Analysis
https://read.qxmd.com/read/30028612/antiangiogenic-activity-and-chemical-derivatization-of-the-neurotoxic-acetogenin-annonacin-isolated-from-asimina-triloba
#12
Paige J Monsen, Frederick A Luzzio
Annonacin (1) was isolated from the North American pawpaw ( Asimina triloba), as reported earlier from these laboratories. Natural 1 was submitted to the rat aortic ring bioassay for evaluation of antiangiogenic activity and was found to inhibit microvessel growth (IC50 value of 3 μM). 4,10,15,20-Tetraazido derivatives of 1 were prepared by permesylation followed by azide displacement or by iodination followed by azide displacement. The tetraazide derived from mesylation/azidation was antiangiogenic, while that derived from iodination/azidation exhibited no appreciable activity...
August 24, 2018: Journal of Natural Products
https://read.qxmd.com/read/29988040/annonacin-promotes-selective-cancer-cell-death-via-nka-dependent-and-serca-dependent-pathways
#13
Andreas Yiallouris, Ioannis Patrikios, Elizabeth O Johnson, Evangelia Sereti, Konstantinos Dimas, Cristian De Ford, Natalia U Fedosova, Wolfgang F Graier, Kleitos Sokratous, Kyriakos Kyriakou, Anastasis Stephanou
In the healthcare sector, phytocompounds are known to be beneficial by contributing or alleviating a variety of diseases. Studies have demonstrated the progressive effects of phytocompounds on immune-related diseases and to exhibit anticancer effects. Graviola tree is an evergreen tree with its extracts (leafs and seeds) been reported having anticancer properties, but the precise target of action is not clear. Using an in silico approach, we predicted that annonacin, an Acetogenin, the active agent found in Graviola leaf extract (GLE) to potentially act as a novel inhibitor of both sodium/potassium (NKA) and sarcoplasmic reticulum (SERCA) ATPase pumps...
July 9, 2018: Cell Death & Disease
https://read.qxmd.com/read/29973884/exploring-the-leaves-of-annona-muricata-l-as-a-source-of-potential-anti-inflammatory-and-anticancer-agents
#14
REVIEW
Siti Mariam Abdul Wahab, Ibrahim Jantan, Md Areeful Haque, Laiba Arshad
The use of anti-inflammatory natural products to treat inflammatory disorders for cancer prevention and therapy is an appealing area of interest in the last decades. Annona muricata L. is one of the many plant extracts that have been explored owing to their anti-inflammatory and anticancer effects. Different parts of A. muricata especially the leaves have been used for various ethnomedicinal purposes by traditional healers to treat several diseases including cancer, inflammation, diabetes, liver diseases, and abscesses...
2018: Frontiers in Pharmacology
https://read.qxmd.com/read/29933016/potential-therapeutic-applications-of-the-genus-annona-local-and-traditional-uses-and-pharmacology
#15
REVIEW
A M Quílez, M A Fernández-Arche, M D García-Giménez, R De la Puerta
ETHNO-PHARMACOLOGICAL RELEVANCE: Annona species (Annonaceae) have long been used as traditional herbal medicines by native peoples in tropical areas. In different countries they are used against a large variety of illnesses, such as parasitic and infectious diseases, cancer, diabetes, peptic ulcers, and mental disorders. AIM OF THE STUDY: This review aims to achieve a comprehensive understanding of the research conducted so far on the local and traditional uses, pharmacological activities, mechanism of actions of active compounds, toxicity, and possible interactions with other drugs of the Annona species...
October 28, 2018: Journal of Ethnopharmacology
https://read.qxmd.com/read/29921883/annonaceous-acetogenin-mimic-aa005-suppresses-human-colon-cancer-cell-growth-in-vivo-through-downregulation-of-mcl-1
#16
Bing Han, Yu-Xia Cao, Zhan-Ming Li, Zhao-Xia Wu, Yu-Qin Mao, Hui-Ling Chen, Zhu-Jun Yao, Li-Shun Wang
Annonaceous acetogenins are a well-established family of natural products with significant bioactivities, especially high cytotoxic and antitumor activities. AA005 is an annonaceous acetogenin mimic that has shown significant cytotoxicity against a variety of cancer cell lines, but its in vivo antitumor effects have not been demonstrated so far, and its anticancer mechanisms remain ambiguous. In this study, we investigated the effects of AA005 on human colon cancer cell lines in vivo. Human colon carcinoma cell line SW620 xenograft nude mice were treated with AA005 (5 mg/kg/day, i...
June 19, 2018: Acta Pharmacologica Sinica
https://read.qxmd.com/read/29914183/graviola-annona-muricata-exerts-anti-proliferative-anti-clonogenic-and-pro-apoptotic-effects-in-human-non-melanoma-skin-cancer-uw-bcc1-and-a431-cells-in-vitro-involvement-of-hedgehog-signaling
#17
Jean Christopher Chamcheu, Islam Rady, Roxane-Cherille N Chamcheu, Abu Bakar Siddique, Melissa B Bloch, Sergette Banang Mbeumi, Abiola S Babatunde, Mohammad B Uddin, Felicite K Noubissi, Peter W Jurutka, Yong-Yu Liu, Vladimir S Spiegelman, G Kerr Whitfield, Khalid A El Sayed
Non-melanoma skin cancers (NMSCs) are the leading cause of skin cancer-related morbidity and mortality. Effective strategies are needed to control NMSC occurrence and progression. Non-toxic, plant-derived extracts have been shown to exert multiple anti-cancer effects. Graviola ( Annona muricata ), a tropical fruit-bearing plant, has been used in traditional medicine against multiple human diseases including cancer. The current study investigated the effects of graviola leaf and stem extract (GLSE) and its solvent-extracted fractions on two human NMSC cell lines, UW-BCC1 and A431...
June 16, 2018: International Journal of Molecular Sciences
https://read.qxmd.com/read/29873386/scope-of-the-2-5h-furanone-helicity-rule-a-combined-ecd-vcd-and-dft-investigation
#18
Fernando M Dos Santos Jr, Keylla U Bicalho, Ítalo H Calisto, Gabriel S Scatena, João B Fernandes, Quezia B Cass, João M Batista Jr
One of the most widely used methods to assess the stereochemistry of chiral 2(5H)-furanones is an empirical electronic circular dichroism (ECD) helicity rule. In the present work, an extensive experimental and theoretical investigation of the scope of the above-mentioned empirical rule for acetogenins with a hydroxyl group substituted at C-4 revealed a possible exception to this rule. The underlying causes for this observation are discussed with respect to side chain substitutions, conformational requirements, chromophore handedness as well as a qualitative orbital analysis...
June 20, 2018: Organic & Biomolecular Chemistry
https://read.qxmd.com/read/29750943/metabolomics-analysis-of-the-potential-anticancer-mechanism-of-annonaceous-acetogenins-on-a-multidrug-resistant-mammary-adenocarcinoma-cell
#19
Chengyao Ma, Yue Li, Hanqing Wu, Junyang Ji, Qianqian Sun, Yilin Song, Shen Wang, Xiang Li, Yong Chen, Jianwei Chen
Although annonaceous acetogenins (ACGs) have been reported to have antitumor activity for over three decades, and many of the underlying mechanism of ACGs on cancer have been clarified, there are still outstanding issues. In particular, the changes of small metabolite in cancer cells, caused by ACGs intake, have been reported rarely. Recent research has showed that cellular metabolic profiling coupled with ultra-flow liquid chromatography coupled to quadrupole-time-of-flight mass spectrometry (UFLC-Q-TOF-MS) and multivariable statistical analysis enables a good understanding of ACGs' effects on multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells...
July 15, 2018: Analytical Biochemistry
https://read.qxmd.com/read/29660776/correlation-between-acetogenin-content-and-antiproliferative-activity-of-pawpaw-asimina-triloba-l-dunal-fruit-pulp-grown-in-korea
#20
Jin-Sik Nam, Seo-Yeon Park, Hyo-Jeong Lee, Seon-Ok Lee, Hye-Lim Jang, Young Ha Rhee
Pawpaw (Asimina triloba [L.] Dunal) is widely cultivated in Korea for its fruit, which contains bioactive compounds, such as acetogenins. In this study, we investigated the acetogenin content and antiproliferative activity of pawpaw fruit pulp against various cancer cell lines and evaluated the relationship between these two variables at different maturation stages. Unripe fruit had higher antiproliferative activity than ripe fruit, and the activity level depended on acetogenin content. In addition, the presence of specific acetogenins was related to inhibition of certain cancer cell types...
May 2018: Journal of Food Science
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