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Journal articles on the topic 'Muricatacin'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Wang, Wencong, Rui Zhang, Jinxing Wang, Jun Tang, Mingan Wang, and Yu Kuang. "Antitumour Activity of Muricatacin Isomers and its Derivatives in Human Colorectal Carcinoma Cell HCT116." Anti-Cancer Agents in Medicinal Chemistry 20, no. 2 (2020): 254–63. http://dx.doi.org/10.2174/1871520619666191115111032.

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Background and Purpose: Colorectal cancer is one of the leading causes of cancer-related death in elderly people. The natural product muricatacin is an important member of the γ-lactone family, and it has exhibited antitumour activity in multiple cancer cell lines; however, the antitumour activities of muricatacin stereoisomers and their derivatives in colorectal cancer cells have not yet been systematically explored. Methods: The colorectal carcinoma cell line HCT116 was investigated in this study. Cell proliferation was assessed by MTT assay or crystal violet staining. Cell cycle arrest and

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2

Dong, Hong-Bo, Ming-Yan Yang, Bin Liu, and Ming-An Wang. "Concise stereoselective total synthesis of (+)-muricatacin and (+)-epi-muricatacin." Journal of Asian Natural Products Research 16, no. 8 (2014): 847–53. http://dx.doi.org/10.1080/10286020.2014.916695.

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3

Makabe, Hidefumi, Akira Tanaka, and Takayuki Oritani. "Synthesis of (–)-Muricatacin." Bioscience, Biotechnology, and Biochemistry 57, no. 6 (1993): 1028–29. http://dx.doi.org/10.1271/bbb.57.1028.

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4

Popsavin, Velimir, Sanja Grabez, Ivana Krstic, Mirjana Popsavin, and Dejan Djokovic. "A formal synthesis of (+)-muricatacin from D-xylose." Journal of the Serbian Chemical Society 68, no. 11 (2003): 795–804. http://dx.doi.org/10.2298/jsc0311795p.

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A multistep route towards the aldehydo-lactone 19, the final chiral precursor in a new stereospecific synthesis of (+)-muricatacin, has been developed starting from D-xylose. The key step of the synthesis involves an E-selective Wittig olefination of the lactol 6 with methoxycarbonylmethylidene triphenylphosphorane, followed by successive catalytic reduction and ?-lactonisation processes. Subsequent selective functional groups interconver- sions furnished the key six-carbon intermediate 19, which can be converted into the (+)-muricatacin via a three-step sequence already described in the chemi

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5

González, Maria, Zoila Gándara, Berta Covelo, Generosa Gómez, and Yagamare Fall. "Total synthesis of (−)-muricatacin." Tetrahedron Letters 52, no. 45 (2011): 5983–86. http://dx.doi.org/10.1016/j.tetlet.2011.08.160.

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6

Prasad, Kavirayani R., and Vasudevarao Gandi. "Facile enantiospecific synthesis of (−)-muricatacin." Tetrahedron: Asymmetry 19, no. 22 (2008): 2616–19. http://dx.doi.org/10.1016/j.tetasy.2008.11.004.

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7

Baussanne, Isabelle, Oliver Schwardt, Jacques Royer, Marianne Pichon, Bruno Figadère, and André Cavé. "Synthesis of aza-muricatacin: an analogue of the bioactive muricatacin an acetogenin of Annonaceae." Tetrahedron Letters 38, no. 13 (1997): 2259–62. http://dx.doi.org/10.1016/s0040-4039(97)00292-x.

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8

Chang, Sue-Wen, Chiu-Yong Hung, Hung-Hsin Liu та Biing-Jiun Uang. "Enantioselective synthesis of γ-lactones from thioglycolic acid: Syntheses of (−)-muricatacin and 5-epi-(−)-muricatacin". Tetrahedron: Asymmetry 9, № 3 (1998): 521–29. http://dx.doi.org/10.1016/s0957-4166(98)00007-x.

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9

Cooze, Christopher, Amarender Manchoju, and Sunil Pansare. "Synthesis of (–)-Muricatacin and (–)-(R,R)-L-Factor Involving an Organocatalytic Direct Vinylogous Aldol Reaction." Synlett 28, no. 20 (2017): 2928–32. http://dx.doi.org/10.1055/s-0036-1590858.

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Concise syntheses of the polyketide natural product (–)-muricatacin and (–)-(R,R)-L-factor (natural product enantiomer) were achieved in four steps by employing an organocatalytic asymmetric direct vinylogous aldol reaction of γ-crotonolactone and suitable aliphatic aldehydes as the key step.

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10

Somfai, Peter. "An enantiospecific total synthesis of (+)-muricatacin." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1995): 817. http://dx.doi.org/10.1039/p19950000817.

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11

MAKABE, Hidefumi. "Synthesis of Annonaceous Acetogenins from Muricatacin." Bioscience, Biotechnology, and Biochemistry 71, no. 10 (2007): 2367–74. http://dx.doi.org/10.1271/bbb.70202.

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12

Saïah, Mohamed, Michel Bessodes, and Kostas Antonakis. "Regioselective opening of chiral hydroxy epoxides: A short route to muricatacin and its diastereomer epi-muricatacin." Tetrahedron Letters 34, no. 10 (1993): 1597–98. http://dx.doi.org/10.1016/0040-4039(93)85016-p.

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13

BAUSSANNE, I., O. SCHWARDT, J. ROYER, M. PICHON, B. FIGADERE, and A. CAVE. "ChemInform Abstract: Synthesis of Aza-Muricatacin: An Analogue of the Bioactive Muricatacin, an Acetogenin of Annonaceae." ChemInform 28, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199730209.

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14

Ghosal, Partha, Vikas Kumar, and Arun K. Shaw. "A chiron approach to the total synthesis of cytotoxic (+)-muricatacin and (+)-5-epi-muricatacin from d-ribose." Carbohydrate Research 345, no. 1 (2010): 41–44. http://dx.doi.org/10.1016/j.carres.2009.09.021.

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15

CHANG, S. W., C. Y. HUNG, H. H. LIU та B. J. UANG. "ChemInform Abstract: Enantioselective Synthesis of γ-Lactones from Thioglycolic Acid: Syntheses of (-)-Muricatacin and 5-epi-(-)-Muricatacin." ChemInform 29, № 28 (2010): no. http://dx.doi.org/10.1002/chin.199828294.

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16

Gómez Bouzó, Uxía, Irene Sánchez-Sanz, Maria González, Generosa Gómez, and Yagamare Fall. "First total synthesis of 7-thia-(-)-muricatacin." Results in Chemistry 4 (January 2022): 100431. http://dx.doi.org/10.1016/j.rechem.2022.100431.

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17

Marshall, James A., and Gregory S. Welmaker. "Stereoselective Synthesis of the Cytotoxic Acetogenins (+)- and (-)-Muricatacin." Synlett 1992, no. 06 (1992): 537–38. http://dx.doi.org/10.1055/s-1992-21408.

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18

Prasad, Kavirayani R., and Pazhamalai Anbarasan. "Enantiospecific synthesis of (−)-muricatacin from l-(+)-tartaric acid." Tetrahedron: Asymmetry 17, no. 17 (2006): 2465–67. http://dx.doi.org/10.1016/j.tetasy.2006.09.017.

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19

SOMFAI, P. "ChemInform Abstract: An Enantiospecific Total Synthesis of (+)-Muricatacin." ChemInform 26, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199534256.

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20

Fernandes, Rodney A., Amit Bhowmik, and Priyanka Choudhary. "Muricatacin, a Gateway Molecule to Higher Acetogenin Synthesis." Chemistry – An Asian Journal 15, no. 22 (2020): 3660–81. http://dx.doi.org/10.1002/asia.202000955.

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21

Yaragorla, Srinivasarao, and Ramaiah Muthyala. "Concise total synthesis of cytotoxic natural products (+) and (-)-muricatacin." Arkivoc 2010, no. 10 (2010): 178–84. http://dx.doi.org/10.3998/ark.5550190.0011.a15.

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22

Gómez, Generosa, Yagamare Fall, Maria González, Zoila Gándara, and Gonzalo Pazos. "Synthesis of (-)-Muricatacin from Tri-O-acetyl-d-glucal." Synthesis 45, no. 05 (2013): 625–32. http://dx.doi.org/10.1055/s-0032-1318113.

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23

Tsai, Shih-Hung, Pei-Chen Hsieh, Li-Lan Wei, Huey-Fen Chiu, Yang-Chang Wu, and Ming-Jung Wu. "Synthesis of a hydroxylated muricatacin analog related to squamocin." Tetrahedron Letters 40, no. 10 (1999): 1975–76. http://dx.doi.org/10.1016/s0040-4039(99)00127-6.

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24

Figadère, B., J.-C. Harmange, A. Laurens, and A. Cavé. "Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative." Tetrahedron Letters 32, no. 51 (1991): 7539–42. http://dx.doi.org/10.1016/0040-4039(91)80528-e.

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25

Teresa Barros, M., M. Adilia Januario Charmier, Christopher D. Maycock та Thierry Michaud. "Synthesis of γ-lactones by desymmetrization. A synthesis of (−)-muricatacin". Tetrahedron 65, № 1 (2009): 396–99. http://dx.doi.org/10.1016/j.tet.2008.10.020.

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26

Srećo, Bojana, Goran Benedeković, Mirjana Popsavin, et al. "Heteroannelated (+)-muricatacin mimics: synthesis, antiproliferative properties and structure–activity relationships." Tetrahedron 67, no. 48 (2011): 9358–67. http://dx.doi.org/10.1016/j.tet.2011.09.132.

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27

Popsavin, Velimir, Bojana Srećo, Ivana Krstić, Mirjana Popsavin, Vesna Kojić, and Gordana Bogdanović. "Synthesis and antitumour activity of new muricatacin and goniofufurone analogues." European Journal of Medicinal Chemistry 41, no. 10 (2006): 1217–22. http://dx.doi.org/10.1016/j.ejmech.2006.06.008.

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28

Popsavin, Velimir, Ivana Krstić, Mirjana Popsavin, et al. "Enantiodivergent synthesis of muricatacin related lactones from d-xylose based on the latent symmetry concept: preparation of two novel cytotoxic (+)- and (−)-muricatacin 7-oxa analogs." Tetrahedron 62, no. 48 (2006): 11044–53. http://dx.doi.org/10.1016/j.tet.2006.09.054.

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29

Yoon, Sung-Hwa, Ho-Sang Moon, Sung-Kwan Hwang, SeungRyong Choi, and Suk-Ku Kang. "Syntheses and Cytotoxicities of Four Stereoisomers of Muricatacin from d -Glucose." Bioorganic & Medicinal Chemistry 6, no. 7 (1998): 1043–49. http://dx.doi.org/10.1016/s0968-0896(98)00062-5.

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30

Popsavin, Velimir, Bojana Srećo, Goran Benedeković, et al. "Design, synthesis and antiproliferative activity of two new heteroannelated (−)-muricatacin mimics." Bioorganic & Medicinal Chemistry Letters 18, no. 19 (2008): 5182–85. http://dx.doi.org/10.1016/j.bmcl.2008.08.097.

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31

Scholz, Gerhard, та Werner Tochtermann. "Optisch aktive γ-lactone aus cyclooctin und furan - synthese von (−)-muricatacin". Tetrahedron Letters 32, № 40 (1991): 5535–38. http://dx.doi.org/10.1016/0040-4039(91)80077-j.

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32

Quinn, Kevin J., André K. Isaacs, and Rebecca A. Arvary. "Concise Total Synthesis of (−)-Muricatacin by Tandem Ring-Closing/Cross Metathesis." Organic Letters 6, no. 23 (2004): 4143–45. http://dx.doi.org/10.1021/ol040047f.

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33

Tsai, Shih-Hung, Pei-Chen Hsieh, Li-Lan Wei, Huey-Fen Chiu, Yang-Chang Wu, and Ming-Jung Wu. "ChemInform Abstract: Synthesis of a Hydroxylated Muricatacin Analogue Related to Squamocin." ChemInform 30, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199923295.

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34

Srinivas, Chiguru, Chebolu Naga Sesha Sai Pavan Kumar, Bhimapaka China Raju, and Vaidya Jayathirtha Rao. "An Efficient Stereoselective Approach for the Synthesis of (+)-(4S,5S)-Muricatacin." Helvetica Chimica Acta 94, no. 4 (2011): 669–74. http://dx.doi.org/10.1002/hlca.201000291.

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35

Guiry, Patrick, та Robert Doran. "Asymmetric Synthesis of Both Enantiomers of a δ-Lactone Analogue of Muricatacin". Synthesis 46, № 06 (2014): 761–70. http://dx.doi.org/10.1055/s-0033-1340850.

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36

Raghavan, Sadagopan, and S. C. Joseph. "The sulfinyl moiety as an intramolecular nucleophile. Part 3: Synthesis of (−)-muricatacin." Tetrahedron: Asymmetry 14, no. 1 (2003): 101–5. http://dx.doi.org/10.1016/s0957-4166(02)00782-6.

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37

Huizar Lopez, Maria del Rosario, Josefina Casas Solis, Itzel Citlalli Alcazar Rios, Lucia Barrientos Ramirez, and Anne Santerre. "Selective cytotoxic effect of Annona muricataL. in HCC1954 (HER2+) breast cancer cells." Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas 22, no. 5 (2023): 688–99. http://dx.doi.org/10.37360/blacpma.23.22.5.50.

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Annona muricataLinn. (Annonaceae) is a tropical plant with multiple beneficial health effects including anticancer properties. In breast cancer patients, overexpression of the HER2 oncoprotein corresponds to a poor prognosis, thus the main purpose of this study was to evaluate the cytotoxicity of ethanolic extracts from dried and fresh leaf of A. muricataon HER2+ breast cancer cells. MTT assays were performed and IC50determined in HCC1954 (HER2+) cells, as well as in MCF7 (HER-) and peripheral blood mononuclear cells (PBMC) used as controls. Total polyphenol content evaluation and phytochemica

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38

Yoshimitsu, Takehiko, Toshiyuki Makino та Hiroto Nagaoka. "Synthesis of (−)-Muricatacin via α- and α‘-C−H Bond Functionalization of Tetrahydrofuran". Journal of Organic Chemistry 68, № 19 (2003): 7548–50. http://dx.doi.org/10.1021/jo0301696.

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39

Cossy, Janine, Laurent Ferrié, Sébastien Reymond, and Patrice Capdevielle. "Concise Total Synthesis of (-)-Muricatacin and (-)-iso-Cladospolide B Using Chemoselective Cross-Metathesis." Synlett 2007, no. 18 (2007): 2891–93. http://dx.doi.org/10.1055/s-2007-990958.

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40

Ahmed, Md Moinuddin, Hu Cui, and George A. O'Doherty. "De Novo Asymmetric Syntheses of Muricatacin and Its Analogues via Dihydroxylation of Dienoates." Journal of Organic Chemistry 71, no. 17 (2006): 6686–89. http://dx.doi.org/10.1021/jo061057s.

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41

YOON, S. H., H. S. MOON, and S. K. KANG. "ChemInform Abstract: Synthesis and Cytotoxicity of (-)-(4R,5R)-5-C-(11-Methoxy)muricatacin." ChemInform 30, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199903232.

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42

Cavé, A., C. Chaboche, B. Figadère, et al. "Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues." European Journal of Medicinal Chemistry 32, no. 7-8 (1997): 617–23. http://dx.doi.org/10.1016/s0223-5234(97)83287-4.

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43

Rieser, Matthew J., John F. Kozlowski, Karl V. Wood, and Jerry L. McLaughlin. "Muricatacin: A simple biologically active acetogenin derivative from the seeds of annona muricata (annonaceae)." Tetrahedron Letters 32, no. 9 (1991): 1137–40. http://dx.doi.org/10.1016/s0040-4039(00)92027-6.

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44

Kang, Suk-Ku, Hyun-Sung Cho, Hyeong-Su Sim, and Beon-Kyu Kim. "Synthesis of (4R,5S)-(−)- and (4S,5S)-(+)-L-Factors and Muricatacin from D-Glucose." Journal of Carbohydrate Chemistry 11, no. 6 (1992): 807–12. http://dx.doi.org/10.1080/07328309208020094.

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45

Gómez, Generosa, Yagamare Fall, Maria González, Zoila Gándara, and Andrea Martínez. "Synthesis of (+)-Muricatacin and a Formal Synthesis of CMI-977 from l-Malic Acid." Synthesis 45, no. 12 (2013): 1693–700. http://dx.doi.org/10.1055/s-0033-1338934.

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46

Sanière, Michèle, Isabelle Charvet, Yves Le Merrer, and Jean-Claude Depezay. "Enantiopure hydroxylactones from L-ascorbic and D-isoascorbic acids. Part I. Synthesis of (−)-muricatacin." Tetrahedron 51, no. 6 (1995): 1653–62. http://dx.doi.org/10.1016/0040-4020(94)01032-u.

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47

Doran, Robert, та Patrick J. Guiry. "ChemInform Abstract: Asymmetric Synthesis of Both Enantiomers of a δ-Lactone Analogue of Muricatacin." ChemInform 45, № 35 (2014): no. http://dx.doi.org/10.1002/chin.201435217.

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48

Szlosek, Magali, Xavier Franck, Bruno Figadère, and André Cavé. "Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes: Application to Muricatacin Synthesis." Journal of Organic Chemistry 63, no. 15 (1998): 5169–72. http://dx.doi.org/10.1021/jo9804137.

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49

Wang, Zhi-Min, Xiu-Lian Zhang, K. Barry Sharpless, Subhash C. Sinha, Anjana Sinha-Bagchi та Ehud Keinan. "A general approach to γ-lactones via osmium-catalyzed asymmetric dihydroxylation. Synthesis of (−)- and (+)-muricatacin." Tetrahedron Letters 33, № 43 (1992): 6407–10. http://dx.doi.org/10.1016/s0040-4039(00)79001-0.

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50

Raji Reddy, Chada, Devatha Suman, and Nagavaram Narsimha Rao. "Alkyne-Mediated Approach to the Synthesis of (4R,5R)-5-Hydroxy-4-decanolide and (−)-Muricatacin." Helvetica Chimica Acta 98, no. 7 (2015): 967–72. http://dx.doi.org/10.1002/hlca.201400356.

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