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Acetogenins AND Cancer

Yong Chen, Yayun Chen, Yeye Shi, Chengyao Ma, Xunan Wang, Yue Li, Yunjie Miao, Jianwei Chen, Xiang Li
CONTEXT: Custard apple (Annona squamosa Linn.) is an edible tropical fruit, and its seeds have been used to treat "malignant sore" (cancer) and other usage as insecticide. A comparison of extraction processes, chemical composition analysis and antitumor activity of A. squamosa seed oil (ASO) were investigated. MATERIALS AND METHODS: The optimal extraction parameters of ASO were established by comparing percolation, soxhlet, ultrasonic and SFE-CO2 extraction methods...
August 23, 2016: Journal of Ethnopharmacology
Usein M Dzhemilev, Vladimir A D'yakonov, Regina A Tuktarova, Lilya U Dzhemileva, Svetlana R Ishmukhametova, Milyausha M Yunusbaeva, Armin de Meijere
An original synthesis of the acetogenin muricadienin, the bioprecursor of solamin, has been developed. The key step in the five-step 41% overall yield synthesis is the catalytic cross-cyclomagnesiation reaction of functionally substituted 1,2-dienes with EtMgBr in the presence of Cp2TiCl2 and magnesium metal. It has been demonstrated for the first time that muricadienin exhibits a moderate in vitro inhibitory activity against topoisomerases I and IIα, key cell cycle enzymes. Using flow cytometry, muricadienin was shown to have high cytotoxicity toward the HEK293 kidney cancer cells (IC50 0...
August 26, 2016: Journal of Natural Products
Jingyi Hong, Yanhong Li, Yijing Li, Yao Xiao, Haixue Kuang, Xiangtao Wang
Annonaceous acetogenins (ACGs) have shown superior antitumor activity against a variety of cancer cell lines, but their clinical application has been limited by their poor solubility. In this study, ACGs-nanosuspensions (NSps) were successfully prepared by a precipitation ultrasonic method using monomethoxypoly (ethylene glycol)2000-poly (ε-caprolactone)2000 (mPEG2000-PCL2000) as a stabilizer. The resultant ACGs-NSps had a mean particle size of 123.2 nm, a zeta potential of -20.17 mV, and a high drug payload of 73...
2016: International Journal of Nanomedicine
Fei Yuan, Ganggang Bai, Yunjie Miao, Yong Chen, Xiang Li, Jianwei Chen
CONTEXT: Multidrug resistance (MDR) is a major obstacle to efficient therapy of cancers. It is a prime concern for researchers to find compounds with anti-proliferative activity on MDR cell lines. In recent years, annonaceous acetogenins (ACGs) were reported to have anti-proliferative activity. However, the underlying mechanisms are still unknown. OBJECTIVE: This study determines the mechanisms of anti-proliferative activity induced by Annosquacin B (AB) against MCF-7/ADR cells...
July 22, 2016: Pharmaceutical Biology
Keerthana Prabhakaran, Gnanam Ramasamy, Uma Doraisamy, Jayakanthan Mannu, K Rajamani, Jayadeepa Rajamani Murugesan
BACKGROUND: Plants became the basis of traditional medicine system throughout the world for thousands of years and continue to provide mankind with new remedies. Annona muricata, the plant of Annonaceae family, is also known as sour sop or Graviola. In recent years, many compounds have been reported and have gained organic chemist's and biochemist's attention because of their novel structure and wide range of bioactivity. Local populations have used the bark, leaves, roots, fruit, seeds and flowers for thousands of years to treat everything from arthritis to liver problems...
May 31, 2016: Current Pharmaceutical Design
Jingyi Hong, Yanhong Li, Yao Xiao, Yijing Li, Yifei Guo, Haixue Kuang, Xiangtao Wang
Annonaceous acetogenins (ACGs) have exhibited antitumor activity against various cancers. However, these substances' poor solubility has limited clinical applications. In this study, hydroxypropyl-beta-cyclodextrin (HP-β-CD) and soybean lecithin (SPC) were self-assembled into an amphiphilic complex. ACGs nanosuspensions (ACGs-NSps) were prepared with a mean particle size of 144.4nm, a zeta potential of -22.9mV and a high drug payload of 46.17% using this complex as stabilizer. The ACGs-NSps demonstrated sustained release in vitro and good stability in plasma as well as simulated gastrointestinal fluid, and met the demand of both intravenous injection and oral administration...
September 1, 2016: Colloids and Surfaces. B, Biointerfaces
Priya Antony, Ranjit Vijayan
Apoptosis is a highly regulated process crucial for maintaining cellular homeostasis and development. The B-cell lymphoma 2 (Bcl-2) family of proteins play a crucial role in regulating apoptosis. Overexpressed Bcl-2 proteins are associated with the development and progression of several human cancers. Annona muricata is a tropical plant that belongs to the Annonaceae family and is well known for its anticancer properties. In this study, molecular docking and simulations were performed to investigate the inhibitory potential of phytochemicals present in A...
2016: Drug Design, Development and Therapy
Gagan Deep, Rahul Kumar, Anil K Jain, Deepanshi Dhar, Gati K Panigrahi, Anowar Hussain, Chapla Agarwal, Tamam El-Elimat, Vincent P Sica, Nicholas H Oberlies, Rajesh Agarwal
Prostate cancer (PCa) is the leading malignancy among men. Importantly, this disease is mostly diagnosed at early stages offering a unique chemoprevention opportunity. Therefore, there is an urgent need to identify and target signaling molecules with higher expression/activity in prostate tumors and play critical role in PCa growth and progression. Here we report that NADPH oxidase (NOX) expression is directly associated with PCa progression in TRAMP mice, suggesting NOX as a potential chemoprevention target in controlling PCa...
March 16, 2016: Scientific Reports
Visveswaraiah Paranjyothi Magadi, Venkatadasappa Ravi, Anantharaju Arpitha, Litha, Kikkerilakshminarayana Kumaraswamy, Krishnappa Manjunath
INTRODUCTION: Malignancies constitute a wide variety of disorders having high mortality and morbidity rates. Current protocols for management include surgical intervention, chemotherapy, and radiation which possess numerous adverse effects. Many phytochemicals are available with anticancer properties similar to anticancer drugs. Major benefit of these compounds is apparent lack of toxicity to normal tissues. Graviola (botanical name: Annona Muricata) contain bioactive compound "annonaceous acetogenins" known for anticancer activity on cancer cell lines...
October 2015: Contemporary Clinical Dentistry
Chih-Chuang Liaw, Jing-Ru Liou, Tung-Ying Wu, Fang-Rong Chang, Yang-Chang Wu
In recent decades, annonaceous acetogenins have become highly studied plant secondary metabolites in terms of their isolation, structure elucidation, synthesis, biological evaluation, mechanism of action, and toxicity. The aim of the present contribution is to summarize chemical and biological reports published since 1997 on annonaceous acetogenins and synthetic acetogenin mimics. The compounds are considered biologically in terms of their cytotoxicity for cancer cell lines, neurotoxicity, pesticidal effects, and miscellaneous activities...
2016: Progress in the Chemistry of Organic Natural Products
Jun-Qiang Qian, Pei Sun, Zhan-Yu Pan, Zhi-Zhong Fang
Hepatocellular carcinoma (HCC) is the most common tumor in worldwide and chemotherapy resistant is a severe obstacle in HCC treatment. Annonaceous acetogenins was a nature compound from Uvaria accuminata and it has show the anti-tumor proliferation activity in many types cancer. In this study, we showed that annonaceous acetogenins is correlated with the drug resistance reversal in human hepatocellular carcinoma BEL-7402/5-FU and HepG2/ADM cell lines. We found that cell apoptosis was improved and cell cycle was arrested, further, multidrug-resistance proteins such as MDR1, MRP1, Topo-IIα, GST-π, cyclin D1, Survivin and bcl-2 are down-regulated, however, intracellular Rh-123 and caspase-3/8 was up-regulated by Annonaceous acetogenins treatment...
2015: International Journal of Clinical and Experimental Pathology
Y Miao, X Xu, F Yuan, Y Shi, Y Chen, J Chen, X Li
Four new annonaceous acetogenins (ACGs), squamocin-I (1), II (2) and III (3) and squamoxinone-D (4), together with seven known ACGs (5-11), were isolated from the seeds of Annona squamosa. The structures of all isolates were elucidated and characterised by spectral and chemical methods. Compounds 1-4 were evaluated for their cytotoxicities against Hep G2, SMMC 7721, BEL 7402, BGC 803 and H460 human cancer cell lines. Compound 1 exhibited better potent activity than the positive compound and compound 3 shows selectively cytotoxical activity against H460 with IC50 values of 0...
June 2016: Natural Product Research
Manu Mangal, Mohd Imran Khan, Subhash Mohan Agarwal
Acetogenins (ACG) are naturally occurring compounds that are chemically one of the least investigated families. In the review, we have provided a comprehensive listing of 133 of these compounds for which anti-tumor activity has been documented within the literature. We have compiled and studied their chemical structure, in-vitro as well as in-vivo anticancer biological activity. We observed that the relative potency of acetogenins can be categorized as adjacent bis-THF ACGs > nonadjacent bis-THF ACGs > mono-THF ACGs > linear-THF ACGs...
2015: Anti-cancer Agents in Medicinal Chemistry
Bing Han, Tong-Dan Wang, Shao-Ming Shen, Yun Yu, Chan Mao, Zhu-Jun Yao, Li-Shun Wang
BACKGROUND: Annonaceous acetogenins are a family of natural products with antitumor activities. Annonaceous acetogenin mimic AA005 reportedly inhibits mammalian mitochondrial NADH-ubiquinone reductase (Complex I) and induces gastric cancer cell death. However, the mechanisms underlying its cell-death-inducing activity are unclear. METHODS: We used SW620 colorectal adenocarcinoma cells to study AA005 cytotoxic activity. Cell deaths were determined by Trypan blue assay and flow cytometry, and related proteins were characterized by western blot...
2015: BMC Cancer
Chunhua Yang, Sushma Reddy Gundala, Rao Mukkavilli, Subrahmanyam Vangala, Michelle D Reid, Ritu Aneja
Phytochemical complexity of plant extracts may offer health-promoting benefits including chemotherapeutic and chemopreventive effects. Isolation of 'most-active fraction' or single constituents from whole extracts may not only compromise the therapeutic efficacy but also render toxicity, thus emphasizing the importance of preserving the natural composition of whole extracts. The leaves of Annona muricata, commonly known as Graviola, are known to be rich in flavonoids, isoquinoline alkaloids and annonaceous acetogenins...
June 2015: Carcinogenesis
Soheil Zorofchian Moghadamtousi, Elham Rouhollahi, Hamed Karimian, Mehran Fadaeinasab, Mohammad Firoozinia, Mahmood Ameen Abdulla, Habsah Abdul Kadir
Annona muricata has been used in folk medicine for the treatment of cancer and tumors. This study evaluated the chemopreventive properties of an ethyl acetate extract of A. muricata leaves (EEAML) on azoxymethane-induced colonic aberrant crypt foci (ACF) in rats. Moreover, the cytotoxic compound of EEAML (Annomuricin E) was isolated, and its apoptosis-inducing effect was investigated against HT-29 colon cancer cell line using a bioassay-guided approach. This experiment was performed on five groups of rats: negative control, cancer control, EEAML (250 mg/kg), EEAML (500 mg/kg) and positive control (5-fluorouracil)...
2015: PloS One
Naoto Kojima, Yuki Suga, Takuya Matsumoto, Tetsuaki Tanaka, Akinobu Akatsuka, Takao Yamori, Shingo Dan, Hiroki Iwasaki, Masayuki Yamashita
The convergent synthesis of the dansyl-labeled probe of the thiophene-3-carboxamide analogue of annonaceous acetogenins, which shows potent antitumor activity, was accomplished by two asymmetric alkynylations of the 2,5-diformyl THF equivalent with an alkyne having a thiophene moiety and another alkyne tagged with a dansyl group. The growth inhibitory profiles toward 39 human cancer cell lines revealed that the probe retained the biological function of its mother compound, and would be useful for studying cellular activity...
March 15, 2015: Bioorganic & Medicinal Chemistry
Chiarpha Thiplueang, Sittiporn Punyanitya, Ratana Banjerdpongchai, Benjawan Wudtiwai, Phansuang Udomputtimekakul, Mongkol Buayairaksa, Narong Nuntasaen, Wilart Pompimon
A new acetogenin has been isolated from the ethyl acetate extract of leaves and twigs of G. sawtehii (Annonaceae). The structure of compound 1 was identified as sawtehtetronenin on the basis of spectral evidence (UV, IR, MS and 1H, and 13C NMR) and by comparison with related compounds. Sawtehtetronenin was found to be cytotoxic to human hepatocellular carcinoma HepG2 and breast cancer MDA-MB231 cells with IC50 values of 79.3 ± 11.9 μM and 108.1 ± 1.5 μM, respectively. Compound 1 was less toxic to both cell lines when compared with camptothecin, a chemotherapeutic drug...
December 2014: Natural Product Communications
Fei Yuan, Ganggang Bai, Yong Chen, Yunjie Miao, Jianwei Chen, Xiang Li
Fifteen annonaceous acetogenins (ACGs) with different stereochemical structures and configuration, representing three main classes of bis-adjacent-tetrahydrofuran (THF), bis-nonadjacent-THF, and mono-THF ACGs, were selected to tested for their inhibition activity on A549/Taxol cell line, which is multidrug resistant (MDR). The present study showed that some tested compounds showed significant activity toward A549/Taxol cells, and were more potent than the positive control Verapamil. For example, squamostatin-D (14) (IC50 value=16...
February 15, 2015: Bioorganic & Medicinal Chemistry Letters
Naoto Kojima, Tetsuya Fushimi, Takahiro Tatsukawa, Tetsuaki Tanaka, Mutsumi Okamura, Akinobu Akatsuka, Takao Yamori, Shingo Dan, Hiroki Iwasaki, Masayuki Yamashita
Five novel acetogenin analogues with a furan, thiophene, or thiazole ring were synthesized, and their inhibitory activities toward human cancer cell lines were evaluated. The analogues showed more potent activities than natural acetogenin. One of them, the thiophene-3-carboxamide analogue, strongly inhibited the growth of human lung cancer cell line NCI-H23 in the xenograft mouse assay without critical toxicity.
October 30, 2014: European Journal of Medicinal Chemistry
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