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Acetogenins

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https://www.readbyqxmd.com/read/29204721/molecular-docking-studies-of-bioactive-compounds-from-annona-muricata-linn-as-potential-inhibitors-for-bcl-2-bcl-w-and-mcl-1-antiapoptotic-proteins
#1
Mohamad Norisham Mohamad Rosdi, Shahkila Mohd Arif, Mohamad Hafizi Abu Bakar, Siti Aisyah Razali, Razauden Mohamed Zulkifli, Harisun Ya'akob
Annona muricata Linn or usually identified as soursop is a potential anticancer plant that has been widely reported to contain valuable chemopreventive agents known as annonaceous acetogenins. The antiproliferative and anticancer activities of this tropical and subtropical plant have been demonstrated in cell culture and animal studies. A. muricata L. exerts inhibition against numerous types of cancer cells, involving multiple mechanism of actions such as apoptosis, a programmed cell death that are mainly regulated by Bcl-2 family of proteins...
December 4, 2017: Apoptosis: An International Journal on Programmed Cell Death
https://www.readbyqxmd.com/read/29158127/characterization-of-interactions-of-eggpc-lipid-structures-with-different-biomolecules
#2
F Corrales Chahar, S B Díaz, A Ben Altabef, C Gervasi, P E Alvarez
In this paper we study the interactions of two biomolecules (ascorbic acid and Annonacin) with a bilayer lipid membrane. Egg yolk phosphatidylcholine (eggPC) liposomes (in crystalline liquid state) were prepared in solutions of ascorbic acid (AA) at different concentration levels. On the other hand, liposomes were doped with Annonacin (Ann), a mono-tetrahydrofuran acetogenin (ACG), which is an effective citotoxic substance. While AA pharmacologic effect and action mechanisms are widely known, those of Ann's are only very recently being studied...
November 17, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/29126019/a-set-of-biogenetically-interesting-polyhalogenated-acetogenins-from-ptilonia-magellanica
#3
Amalia B Gallardo, Mercedes Cueto, Ana R Díaz-Marrero, José M de la Rosa, Victor Fajardo, Aurelio San-Martín, José Darias
Ptilonines A-F, pyranosylmagellanicus D-E and magellenediol are previously undescribed acetogenins isolated from the red alga Ptilonia magellanica. Their structures were determined from spectroscopic evidence. The absolute configuration of the known pyranosylmagellanicus A, was established by derivatization with (R)- and (S)-α-methoxy -α-phenylacetic acids (MPA). Ptilonines exhibit an unusual halogenation pattern, that may confer evolutionary advantages to Ptilonia magellanica, for which a biogenetic origin is proposed...
November 7, 2017: Phytochemistry
https://www.readbyqxmd.com/read/29112433/construction-of-6-10-syn-and-anti-2-5-dioxabicyclo-2-2-1-heptane-skeletons-via-oxonium-ion-formation-fragmentation-prediction-of-structure-of-e-ocellenyne-by-nmr-calculation
#4
Daeyeon Jeong, Te-Ik Sohn, Jong Yup Kim, Gyudong Kim, Deukjoon Kim, Robert S Paton
A highly efficient and stereoselective route to potential synthetic intermediates for ocellenyne and related C15 acetogenin natural products with 6,10-syn- and 6,10-anti-2,5-dioxabicyclo[2.2.1]heptane core structures has been developed by means of an iterative biogenesis-inspired oxonium ion formation/fragmentation sequence. In accordance with chemical transformations, the most likely stereostructure for (E)-ocellenyne on the basis of GIAO (13)C NMR calculations possesses a 6,10-anti-2,5-dioxabicyclo[2.2.1]heptane core, as predicted from a plausible biosynthetic pathway, instead of the spectroscopically proposed 6,10-syn-2,5-dioxabicyclo[2...
November 17, 2017: Organic Letters
https://www.readbyqxmd.com/read/29104539/annonaceae-breaking-the-wall-of-inflammation
#5
REVIEW
Ali Attiq, Juriyati Jalil, Khairana Husain
Inventories of tropical forests have listed Annonaceae as one of the most diverse plant families. For centuries, it is employed in traditional medicines to cure various pathological conditions including snakebite, analgesic, astringent, diarrhea, dysentery, arthritis pain, rheumatism, neuralgia, and weight loss etc. Phytochemical analysis of Annonaceae family have reported the occurrence of alkaloids, flavonoids, triterpenes, diterpenes and diterpene flavone glycosides, sterols, lignans, and annonaceous acetogenin characteristically affiliated with Annonaceae sp...
2017: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/29083058/total-synthesis-of-two-possible-diastereomers-of-natural-6-chlorotetrahydrofuran-acetogenin-and-its-stereostructural-elucidation
#6
Hiroyoshi Takamura, Tomoya Katsube, Kazuki Okamoto, Isao Kadota
The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, (Z)-selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1H and 13C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (-)-6-chlorotetrahydrofuran acetogenin 1.
October 30, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29080611/annona-muricata-is-the-natural-therapy-to-most-disease-conditions-including-cancer-growing-in-our-backyard-a-systematic-review-of-its-research-history-and-future-prospects
#7
REVIEW
Yahaya Gavamukulya, Fred Wamunyokoli, Hany A El-Shemy
Annona muricata (A. muricata) is a tropical plant species belonging to family Annonaceae and known for its many medicinal uses. This review focuses on the research history of its traditional uses, phytochemicals, pharmacological activities, toxicological aspects of the extracts and isolated compounds, as well as the in vitro propagation studies with the objective of stimulating further studies on this plant for human consumption and treatment. A. muricata extracts have been identified in tropical regions to traditionally treat diverse conditions ranging from fever to diabetes and cancer...
September 2017: Asian Pacific Journal of Tropical Medicine
https://www.readbyqxmd.com/read/28969589/avocado-fruit-maturation-and-ripening-dynamics-of-aliphatic-acetogenins-and-lipidomic-profiles-from-mesocarp-idioblasts-and-seed
#8
Carlos Eduardo Rodríguez-López, Carmen Hernández-Brenes, Víctor Treviño, Rocío I Díaz de la Garza
BACKGROUND: Avocado fruit contains aliphatic acetogenins (oft-acetylated, odd-chain fatty alcohols) with promising bioactivities for both medical and food industries. However, we have scarce knowledge about their metabolism. The present work aimed to study changes in acetogenin profiles from mesocarp, lipid-containing idioblasts, and seeds from 'Hass' cultivar during fruit development, germination, and three harvesting years. An untargeted LC-MS based lipidomic analysis was also conducted to profile the lipidome of avocado fruit in each tissue...
September 29, 2017: BMC Plant Biology
https://www.readbyqxmd.com/read/28937967/acetogenins-and-alkaloids-during-the-initial-development-of-annona-muricata-l-annonaceae
#9
Christian Anabí Riley-Saldaña, María Del Rocío Cruz-Ortega, Mariano Martínez Vázquez, Iván De-la-Cruz-Chacón, Marisol Castro-Moreno, Alma Rosa González-Esquinca
In plants, the presence and distribution of specialized metabolites during the early stages of development are not documented enough, even though their biosynthesis is one of the most important strategies for survival. In this study, five alkaloids and four acetogenins were detected in Annona muricata L. during early development seedling, including three phases of root emergence and three of seedling formation. Hexane and alkaloid extracts were obtained from each organ, which were analyzed in a gas-mass chromatograph and in a high-performance liquid chromatograph coupled with a photodiode array UV detector (HPLC-DAD)...
October 26, 2017: Zeitschrift Für Naturforschung. C, A Journal of Biosciences
https://www.readbyqxmd.com/read/28873407/photo-affinity-labelling-and-biochemical-analyses-identify-the-target-of-trypanocidal-simplified-natural-product-analogues
#10
Lindsay B Tulloch, Stefanie K Menzies, Andrew L Fraser, Eoin R Gould, Elizabeth F King, Marija K Zacharova, Gordon J Florence, Terry K Smith
Current drugs to treat African sleeping sickness are inadequate and new therapies are urgently required. As part of a medicinal chemistry programme based upon the simplification of acetogenin-type ether scaffolds, we previously reported the promising trypanocidal activity of compound 1, a bis-tetrahydropyran 1,4-triazole (B-THP-T) inhibitor. This study aims to identify the protein target(s) of this class of compound in Trypanosoma brucei to understand its mode of action and aid further structural optimisation...
September 2017: PLoS Neglected Tropical Diseases
https://www.readbyqxmd.com/read/28840693/-structure-activity-relationship-of-annonaceous-acetogenins-against-multidrug-resistant-human-hepatic-carcinoma-cell-line-smmc-7721-adr
#11
Xu-Nan Wang, Xiang Li, Yong Chen, Yue Li
The present research was launched to investigate the effects of 12 annonaceous acetogenins (ACGs) on human hepatic carcinoma cell line SMMC-7721/ADR, and to find out their structure-activity relationship. SMMC-7721/ADR cells were treated with 12 ACGs including annosquamin A(1),annosquamin B(2),annotemoyin-1(3),uvariamicin Ⅱ(4),annosquacin D(5),annosquacin B(6),isodesacetyluvaricin(7),uvarigrandin A(8),squamostatin D(9),squamostatin E(10),squamostatin A(11),and 12,15-cis-squamostatin A(12) for 24 h, and the different expression of the target gene NDUFV2 were detected by quantitative real-time PCR...
July 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/28765708/folate-modified-annonaceous-acetogenins-nanosuspensions-and-their-improved-antitumor-efficacy
#12
Jingyi Hong, Zhonghao Sun, Yijing Li, Yifei Guo, Yonghong Liao, Meifeng Liu, Xiangtao Wang
Annonaceous acetogenins (ACGs) are a large family of fatty acid derived natural products that are exclusively isolated from the Annonaceae species. Many members of this diverse family have a broad spectrum of biological activities, the most impressive of which is anticancer activity. However, their poor solubility and severe toxicity restrict their clinical application, and their complicated composition hinders their formulation and drug delivery. In this study, β-cyclodextrin was modified with folic acid (FA) and then combined with soybean lecithin to prepare FA-modified ACGs nanosuspensions (FA-ACGs-NSps)...
2017: International Journal of Nanomedicine
https://www.readbyqxmd.com/read/28714315/two-new-linear-acetogenins-from-the-fruits-of-goniothalamus-gracilipes
#13
Quy Hung Trieu, Huong Doan Thi Mai, Marc Litaudon, Dao Phi Thi, Tuan Anh Tran, Van Hung Nguyen, Van Minh Chau, Van Cuong Pham
Two new linear acetogenins, gracilipin A (1) and methylsaccopetrin A (2) along with seven known compounds, saccopetrin A (3), 7,3',4'-trimethylquercetin (4), rhamnazin (5), casticin (6), isokanugin (7), melisimplexin (8) and 5-hydroxy-3,7-dimethoxy-3',4'-methylenedioxyflavone (9) were isolated from the fruits of Goniothalamus gracilipes Bân. Their structures were established by spectral analysis, such as mass spectrometry, 1D-NMR, 2D-NMR and circular dichroism (CD). Compounds 1 and 3 showed cytotoxic activity against KB cell line with IC50 values of 14...
July 16, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28659034/a-review-on-annona-squamosa-l-phytochemicals-and-biological-activities
#14
REVIEW
Chengyao Ma, Yayun Chen, Jianwei Chen, Xiang Li, Yong Chen
Annona squamosa L. (Annonaceae) is a fruit tree with a long history of traditional uses. A. squamosa is an evergreen plant mainly located in tropical and subtropical regions. Srikayas, the fruits of A. squamosa, are extensively used to prepare candies, ice creams and beverages. A wide range of ethno-medicinal uses has been related to different portions of A. squamosa, such as tonic, apophlegmatisant, cool medicine, abortient and heart sedative. Numerous research projects on A. squamosa have found that it has anticancer, anti-oxidant, antidiabetic, antihypertensive, hepatoprotective, antiparasitic, antimalarial, insecticidal, microbicidel and molluscicidal activities...
2017: American Journal of Chinese Medicine
https://www.readbyqxmd.com/read/28626912/structural-characterisation-of-acetogenins-from-annona-muricata-by-supercritical-fluid-chromatography-coupled-to-high-resolution-tandem-mass-spectrometry
#15
Laurent Laboureur, Natacha Bonneau, Pierre Champy, Alain Brunelle, David Touboul
INTRODUCTION: Acetogenins are plant polyketides known to be cytotoxic and proposed as antitumor candidates. They are also suspected to be alimentary neurotoxins. Their occurrence as complex mixtures renders their dereplication and structural identification difficult using liquid chromatography coupled to tandem mass spectrometry and efforts are required to improve the methodology. OBJECTIVE: To develop a supercritical fluid chromatography (SFC) high-resolution tandem mass spectrometry method, involving lithium post-column cationisation, for the structural characterisation of Annonaceous acetogenins in crude extracts...
June 19, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28554707/squamocin-an-annonaceous-acetogenin-enhances-naphthalene-degradation-mediated-by-bacillus-atrophaeus-cn4
#16
Eduardo A Parellada, Mercedes Igarza, Paula Isacc, Alicia Bardón, Marcela Ferrero, Keshav Lalit Ameta, Adriana Neske
Squamocin belongs to a group of compounds called annonaceous acetogenins. They are secondary products of Annonaceae metabolism and can be isolated from Annona cherimolia seeds. This paper deals with the stimulation of biofilm formation of Bacillus atrophaeus CN4 by employing low squamocin concentrations to increase naphthalene degradation. Bacillus atrophaeus CN4, isolated from contaminated soil, has the ability to degrade naphthalene as the only source of carbon and energy. In the absence of additional carbon sources, the strain removed 69% of the initial concentration of naphthalene (approx...
May 26, 2017: Revista Argentina de Microbiología
https://www.readbyqxmd.com/read/28505125/isolaurenidificin-and-bromlaurenidificin-two-new-c15-acetogenins-from-the-red-alga-laurencia-obtusa
#17
Nahed O Bawakid, Walied M Alarif, Najla A Alburae, Hajer S Alorfi, Khalid O Al-Footy, Sultan S Al-Lihaibi, Mohamed A Ghandourah
Chromatographic fractionation of the CH₂Cl₂/MeOH extract of the Red Sea red alga Laurencia obtusa gave two new hexahydrofuro[3,2-b]furan-based C15-acetogenins, namely, isolaurenidificin (1) and bromlaurenidificin (2). The chemical structures were elucidated based on extensive analyses of their spectral data. Compounds 1 and 2 showed no toxicity (LC50 > 12 mM) using Artemia salina as test organism. Both compounds showed weak cytotoxicity against A549, HepG-2, HCT116, MCF-7, and PC-3 cells, however, they exhibited a relatively potent cytotoxic activity against peripheral blood neutrophils...
May 15, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28492496/chemical-composition-of-laurencia-obtusa-extract-and-isolation-of-a-new-c15-acetogenin
#18
Hélène Esselin, Sylvain Sutour, Joana Liberal, Maria Teresa Cruz, Ligia Salgueiro, Benjamin Siegler, Ingrid Freuze, Vincent Castola, Mathieu Paoli, Ange Bighelli, Félix Tomi
A new C15-acetogenin, sagonenyne (20), exhibiting an unusual single tetrahydropyran ring was isolated from an ethyl acetate extract of Laurencia obtusa collected on the Corsican coastline. Its structure was established by detailed NMR spectroscopic analysis, mass spectrometry, and comparison with literature data. Twenty-three known compounds were identified in the same extract by means of column chromatography steps, using a (13)C-NMR computer aided method developed in our laboratory. In addition to sesquiterpenes, which represent the main chemical class of this extract, diterpenes, sterols, and C15-acetogenins were identified...
May 11, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28487731/the-value-of-caspase-3-after-the-application-of-annona-muricata-leaf-extract-in-colo-205-colorectal-cancer-cell-line
#19
Murdani Abdullah, Ari Fahrial Syam, Sofy Meilany, Bayu Laksono, Oryza Gryagus Prabu, Heri Setiyo Bekti, Lili Indrawati, Dadang Makmun
Annona muricata, commonly known as soursop, contains annonacin, acetogenin, and polyphenol which are known to have chemopreventive effects on cancer. In this study, we tend to evaluate the apoptosis-inducing effect of soursop (Annona muricata) leaf extract on the colorectal cancer cell line COLO-205 through the activities of caspase-3 which is a marker of cell apoptosis. Cell cultures were incubated with soursop leaf with a concentration of 10 μg/ml and then compared with those of the incubated positive control leucovorin 10 μg/ml and placebo as a negative control...
2017: Gastroenterology Research and Practice
https://www.readbyqxmd.com/read/28416750/annonaceous-acetogenins-mediated-up-regulation-of-notch2-exerts-growth-inhibition-in-human-gastric-cancer-cells-in-vitro
#20
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
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