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Journal articles on the topic 'Englerin A'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Jaeger, Rolf, and Eckehard Cuny. "Terpenoids with Special Pharmacological Significance: A Review." Natural Product Communications 11, no. 9 (September 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100946.

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Terpenoids are a very prominent class of natural compounds produced in diverse genera of plants, fungi, algae and sponges. They gained significant pharmaceutical value since prehistoric times, due to their broad spectrum of medical applications. The fragrant leaves of Eucalyptus trees are a rich source of terpenoids. Therefore this review starts by summarizing the main terpenoid compounds present in Eucalyptus globulus, E. citriodora, E. radiata and E. resinifera and describing their biosynthetic pathways. Of the enormous number of pharmaceutically important terpenoids, this paper also reviews some well established and recently discovered examples and discusses their medical applications. In this context, the synthetic processes for (–)-menthol, (–)- cis-carveol, (+)-artemisinine, (+)-merrilactone A and (–)-sclareol are presented. The tricyclic sesquiterpene (–)-englerin A isolated from the stem bark of the Phyllanthus engleri plant ( Euphorbiaceae) is highly active against certain renal cancer cell lines. In addition, recent studies showed that englerin A is also a potent and selective activator of TRPC4 and TRPC5 calcium channels. These important findings were the motivation for several renowned research labs to achieve a total synthesis of (–)-englerin A. Two prominent examples – Christmann and Metz – are compared and discussed in detail.

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2

Xu, Jing, Eduardo J. E. Caro-Diaz, Ayse Batova, Steven D. E. Sullivan, and Emmanuel A. Theodorakis. "Formal Synthesis of (−)-Englerin A and Cytotoxicity Studies of Truncated Englerins." Chemistry - An Asian Journal 7, no. 5 (March 13, 2012): 1052–60. http://dx.doi.org/10.1002/asia.201101021.

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3

Ratnayake, Ranjala, David Covell, Tanya T. Ransom, Kirk R. Gustafson, and John A. Beutler. "Englerin A, a Selective Inhibitor of Renal Cancer Cell Growth, fromPhyllanthus engleri." Organic Letters 11, no. 1 (January 2009): 57–60. http://dx.doi.org/10.1021/ol802339w.

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4

Ma, D., Q. Zhou, and X. Chen. "Synthesis of (-)-Englerin A." Synfacts 2010, no. 09 (August 23, 2010): 0972. http://dx.doi.org/10.1055/s-0030-1257934.

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5

Christmann, M., M. Willot, L. Radtke, D. Könning, R. Fröhlich, V. Gessner, and C. Strohmann. "Synthesis of Englerin A." Synfacts 2010, no. 04 (March 22, 2010): 0500. http://dx.doi.org/10.1055/s-0029-1219631.

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6

Zhang, Jinghua, Shuyan Zheng, Wei Peng, and Zhengwu Shen. "Total synthesis of (−)-Englerin A." Tetrahedron Letters 55, no. 7 (February 2014): 1339–41. http://dx.doi.org/10.1016/j.tetlet.2014.01.012.

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7

Nicolaou, K. C., Qiang Kang, Sin Yee Ng, and David Y. K. Chen. "Total Synthesis of Englerin A." Journal of the American Chemical Society 132, no. 23 (June 16, 2010): 8219–22. http://dx.doi.org/10.1021/ja102927n.

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8

Rubaiy, Hussein N., Tobias Seitz, Sven Hahn, Axel Choidas, Peter Habenberger, Bert Klebl, Klaus Dinkel, et al. "Identification of an (−)-englerin A analogue, which antagonizes (−)-englerin A at TRPC1/4/5 channels." British Journal of Pharmacology 175, no. 5 (January 25, 2018): 830–39. http://dx.doi.org/10.1111/bph.14128.

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9

Li, Zhenwu, Mika Nakashige, and William J. Chain. "A Brief Synthesis of (−)-Englerin A." Journal of the American Chemical Society 133, no. 17 (May 4, 2011): 6553–56. http://dx.doi.org/10.1021/ja201921j.

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10

Takahashi, Keisuke, Keita Komine, Yuichi Yokoi, Jun Ishihara, and Susumi Hatakeyama. "Stereocontrolled Total Synthesis of (−)-Englerin A." Journal of Organic Chemistry 77, no. 17 (August 17, 2012): 7364–70. http://dx.doi.org/10.1021/jo301145r.

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11

de Sousa Valente, João, Khadija M. Alawi, Sabah Bharde, Ali A. Zarban, Xenia Kodji, Dibesh Thapa, Fulye Argunhan, Brentton Barrett, Istvan Nagy, and Susan D. Brain. "(-)-Englerin-A Has Analgesic and Anti-Inflammatory Effects Independent of TRPC4 and 5." International Journal of Molecular Sciences 22, no. 12 (June 15, 2021): 6380. http://dx.doi.org/10.3390/ijms22126380.

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Recently, we found that the deletion of TRPC5 leads to increased inflammation and pain-related behaviour in two animal models of arthritis. (-)-Englerin A (EA), an extract from the East African plant Phyllanthus engleri has been identified as a TRPC4/5 agonist. Here, we studied whether or not EA has any anti-inflammatory and analgesic properties via TRPC4/5 in the carrageenan model of inflammation. We found that EA treatment in CD1 mice inhibited thermal hyperalgesia and mechanical allodynia in a dose-dependent manner. Furthermore, EA significantly reduced the volume of carrageenan-induced paw oedema and the mass of the treated paws. Additionally, in dorsal root ganglion (DRG) neurons cultured from WT 129S1/SvIm mice, EA induced a dose-dependent cobalt uptake that was surprisingly preserved in cultured DRG neurons from 129S1/SvIm TRPC5 KO mice. Likewise, EA-induced anti-inflammatory and analgesic effects were preserved in the carrageenan model in animals lacking TRPC5 expression or in mice treated with TRPC4/5 antagonist ML204.This study demonstrates that while EA activates a sub-population of DRG neurons, it induces a novel TRPC4/5-independent analgesic and anti-inflammatory effect in vivo. Future studies are needed to elucidate the molecular and cellular mechanisms underlying EA’s anti-inflammatory and analgesic effects.

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12

Zhang, Jinghua, Shuyan Zheng, Wei Peng, and Zhengwu Shen. "ChemInform Abstract: Total Synthesis of (-)-Englerin A." ChemInform 45, no. 31 (July 17, 2014): no. http://dx.doi.org/10.1002/chin.201431198.

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13

Zahel, Martin, Anton Keßberg, and Peter Metz. "Eine kurze enantioselektive Totalsynthese von (−)-Englerin A." Angewandte Chemie 125, no. 20 (April 15, 2013): 5500–5502. http://dx.doi.org/10.1002/ange.201301247.

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14

Kumar Palli, Kishore, Raghunath Reddy Anugu, and Srivari Chandrasekhar. "Total Synthesis of (−)‐4‐ epi ‐Englerin A." European Journal of Organic Chemistry 2021, no. 22 (June 10, 2021): 3190–96. http://dx.doi.org/10.1002/ejoc.202100354.

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15

Chain, William. "Synthetic Strategies toward the Guaiane Sesquiterpene Englerin A." Synlett 2011, no. 18 (October 6, 2011): 2605–8. http://dx.doi.org/10.1055/s-0030-1289521.

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16

Zahel, Martin, Anton Keßberg, and Peter Metz. "A Short Enantioselective Total Synthesis of (−)-Englerin A." Angewandte Chemie International Edition 52, no. 20 (April 15, 2013): 5390–92. http://dx.doi.org/10.1002/anie.201301247.

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17

López-Suárez, Laura, Lorena Riesgo, Fernando Bravo, Tanya T. Ransom, John A. Beutler, and Antonio M. Echavarren. "Synthesis and Biological Evaluation of New (−)-Englerin Analogues." ChemMedChem 11, no. 9 (March 23, 2016): 1003–7. http://dx.doi.org/10.1002/cmdc.201600040.

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18

Zahel, Martin, and Peter Metz. "A concise enantioselective synthesis of the guaiane sesquiterpene (−)-oxyphyllol." Beilstein Journal of Organic Chemistry 9 (October 8, 2013): 2028–32. http://dx.doi.org/10.3762/bjoc.9.239.

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(−)-Oxyphyllol was prepared in only 4 steps from an epoxy enone that already served as an intermediate for the total synthesis of the anticancer guaiane (−)-englerin A. A regio- and diastereoselective Co(II)-catalyzed hydration of the olefin and a transannular epoxide opening were used as the key reactions.

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19

Zhou, Qianghui, Xiaofei Chen, and Dawei Ma. "Asymmetric, Protecting-Group-Free Total Synthesis of (−)-Englerin A." Angewandte Chemie 122, no. 20 (April 6, 2010): 3591–94. http://dx.doi.org/10.1002/ange.201000888.

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20

Zhou, Qianghui, Xiaofei Chen, and Dawei Ma. "Asymmetric, Protecting-Group-Free Total Synthesis of (−)-Englerin A." Angewandte Chemie International Edition 49, no. 20 (April 6, 2010): 3513–16. http://dx.doi.org/10.1002/anie.201000888.

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21

Willot, Matthieu, Lea Radtke, Daniel Könning, Roland Fröhlich, Viktoria H Gessner, Carsten Strohmann, and Mathias Christmann. "Totalsynthese und absolute Konfiguration des Guaian-Sesquiterpens Englerin A." Angewandte Chemie 121, no. 48 (October 30, 2009): 9269–72. http://dx.doi.org/10.1002/ange.200905032.

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22

Reagan, Colleen, Graham Trevitt, and Kirill Tchabanenko. "Total Synthesis of (±)-Englerin A and Its Tuncated Analogues." European Journal of Organic Chemistry 2019, no. 5 (January 25, 2019): 1027–37. http://dx.doi.org/10.1002/ejoc.201801544.

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23

Fash, David M., Cody J. Peer, Zhenwu Li, Ian J. Talisman, Sima Hayavi, Florian J. Sulzmaier, Joe W. Ramos, et al. "Synthesis of a stable and orally bioavailable englerin analogue." Bioorganic & Medicinal Chemistry Letters 26, no. 11 (June 2016): 2641–44. http://dx.doi.org/10.1016/j.bmcl.2016.04.016.

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24

Chan, Kok Ping, and David Y. K. Chen. "Chemical Synthesis and Biological Evaluation of the Englerin Analogues." ChemMedChem 6, no. 3 (January 18, 2011): 420–23. http://dx.doi.org/10.1002/cmdc.201000544.

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25

Ushakov, Dmitry B., Vaidotas Navickas, Markus Ströbele, Cäcilia Maichle-Mössmer, Florenz Sasse, and Martin E. Maier. "Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A." Organic Letters 13, no. 8 (April 15, 2011): 2090–93. http://dx.doi.org/10.1021/ol200499t.

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26

Chain, William J. "ChemInform Abstract: Synthetic Strategies Toward the Guaiane Sesquiterpene Englerin A." ChemInform 43, no. 7 (January 23, 2012): no. http://dx.doi.org/10.1002/chin.201207254.

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27

Sulzmaier, Florian J., Zhenwu Li, Mika L. Nakashige, David M. Fash, William J. Chain, and Joe W. Ramos. "Englerin A Selectively Induces Necrosis in Human Renal Cancer Cells." PLoS ONE 7, no. 10 (October 22, 2012): e48032. http://dx.doi.org/10.1371/journal.pone.0048032.

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28

Rodrigues, Tiago, Florian Sieglitz, Víctor J. Somovilla, Pedro M. S. D. Cal, Antony Galione, Francisco Corzana, and Gonçalo J. L. Bernardes. "Unveiling (−)-Englerin A as a Modulator of L-Type Calcium Channels." Angewandte Chemie 128, no. 37 (July 8, 2016): 11243–47. http://dx.doi.org/10.1002/ange.201604336.

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29

Willot, Matthieu, Lea Radtke, Daniel Könning, Roland Fröhlich, Viktoria H Gessner, Carsten Strohmann, and Mathias Christmann. "Total Synthesis and Absolute Configuration of the Guaiane Sesquiterpene Englerin A." Angewandte Chemie International Edition 48, no. 48 (October 30, 2009): 9105–8. http://dx.doi.org/10.1002/anie.200905032.

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30

Rodrigues, Tiago, Florian Sieglitz, Víctor J. Somovilla, Pedro M. S. D. Cal, Antony Galione, Francisco Corzana, and Gonçalo J. L. Bernardes. "Unveiling (−)-Englerin A as a Modulator of L-Type Calcium Channels." Angewandte Chemie International Edition 55, no. 37 (July 8, 2016): 11077–81. http://dx.doi.org/10.1002/anie.201604336.

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31

Caropreso, Vittorio, Emad Darvishi, Thomas J. Turbyville, Ranjala Ratnayake, Patrick J. Grohar, James B. McMahon, and Girma M. Woldemichael. "Englerin A Inhibits EWS-FLI1 DNA Binding in Ewing Sarcoma Cells." Journal of Biological Chemistry 291, no. 19 (March 9, 2016): 10058–66. http://dx.doi.org/10.1074/jbc.m115.701375.

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32

Elliott, Daniel C., John A. Beutler, and Kathlyn A. Parker. "Importance of a 4-Alkyl Substituent for Activity in the Englerin Series." ACS Medicinal Chemistry Letters 8, no. 7 (June 12, 2017): 746–50. http://dx.doi.org/10.1021/acsmedchemlett.7b00161.

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33

Hagihara, Shuichi, Kengo Hanaya, Takeshi Sugai, and Mitsuru Shoji. "Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition." Journal of Antibiotics 71, no. 2 (August 2, 2017): 257–62. http://dx.doi.org/10.1038/ja.2017.91.

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34

Szostak, Michal, and David J. Procter. "Kurze Synthesen von Strychnin und Englerin A durch Samariumiodid-vermittelte reduktive Cyclisierungen." Angewandte Chemie 123, no. 34 (July 20, 2011): 7881–83. http://dx.doi.org/10.1002/ange.201103128.

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35

Zhou, Qianghui, Xiaofei Chen, and Dawei Ma. "ChemInform Abstract: Asymmetric, Protecting-Group-Free Total Synthesis of (-)-Englerin A (I)." ChemInform 41, no. 37 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.201037179.

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36

Lu, Yunyu, Hequan Yao, and Bingfeng Sun. "Progresses in Total Synthesis of Englerin A and Biological Evaluations of Its Analogues." Chinese Journal of Organic Chemistry 32, no. 1 (2012): 1. http://dx.doi.org/10.6023/cjoc1110141.

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37

Williams, Richard T., Alice L. Yu, Mitchell B. Diccianni, Emmanuel A. Theodorakis, and Ayse Batova. "Renal cancer-selective Englerin A induces multiple mechanisms of cell death and autophagy." Journal of Experimental & Clinical Cancer Research 32, no. 1 (2013): 57. http://dx.doi.org/10.1186/1756-9966-32-57.

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38

Jeong, SeungJoo, Juyeon Ko, Minji Kim, Ki Chul Park, Eunice Yon June Park, Jinsung Kim, Youngjoo Baik, et al. "Englerin A-sensing charged residues for transient receptor potential canonical 5 channel activation." Korean Journal of Physiology & Pharmacology 23, no. 3 (2019): 191. http://dx.doi.org/10.4196/kjpp.2019.23.3.191.

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39

Cheung, Sin Ying, Matthias Henrot, Mohammad Al-Saad, Matthias Baumann, Heiko Muller, Anke Unger, Hussein N. Rubaiy, et al. "TRPC4/TRPC5 channels mediate adverse reaction to the cancer cell cytotoxic agent (-)-Englerin A." Oncotarget 9, no. 51 (July 3, 2018): 29634–43. http://dx.doi.org/10.18632/oncotarget.25659.

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40

Xu, Jing, Eduardo J. E. Caro-Diaz, and Emmanuel A. Theodorakis. "Enantioselective Formal Synthesis of (−)-Englerin A via a Rh-Catalyzed [4 + 3] Cycloaddition Reaction." Organic Letters 12, no. 16 (August 20, 2010): 3708–11. http://dx.doi.org/10.1021/ol1015652.

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41

Akbulut, Yasemin, Hannah J. Gaunt, Katsuhiko Muraki, Melanie J. Ludlow, Mohamed S. Amer, Alexander Bruns, Naveen S. Vasudev, et al. "(−)-Englerin A is a Potent and Selective Activator of TRPC4 and TRPC5 Calcium Channels." Angewandte Chemie 127, no. 12 (February 23, 2015): 3858–62. http://dx.doi.org/10.1002/ange.201411511.

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42

Hanari, Taiki, Naoyuki Shimada, Yasunobu Kurosaki, Neetipalli Thrimurtulu, Hisanori Nambu, Masahiro Anada, and Shunichi Hashimoto. "Asymmetric Total Synthesis of (−)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition." Chemistry - A European Journal 21, no. 33 (July 15, 2015): 11671–76. http://dx.doi.org/10.1002/chem.201502009.

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43

Akbulut, Yasemin, Hannah J. Gaunt, Katsuhiko Muraki, Melanie J. Ludlow, Mohamed S. Amer, Alexander Bruns, Naveen S. Vasudev, et al. "(−)-Englerin A is a Potent and Selective Activator of TRPC4 and TRPC5 Calcium Channels." Angewandte Chemie International Edition 54, no. 12 (February 23, 2015): 3787–91. http://dx.doi.org/10.1002/anie.201411511.

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44

Carson, Cheryl, Pichai Raman, Jennifer Tullai, Lei Xu, Martin Henault, Emily Thomas, Sarita Yeola, et al. "Englerin A Agonizes the TRPC4/C5 Cation Channels to Inhibit Tumor Cell Line Proliferation." PLOS ONE 10, no. 6 (June 22, 2015): e0127498. http://dx.doi.org/10.1371/journal.pone.0127498.

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45

Lee, Jungyong, and Kathlyn A. Parker. "A Formal Synthesis of (−)-Englerin A by Relay Ring Closing Metathesis and Transannular Etherification." Organic Letters 14, no. 11 (May 7, 2012): 2682–85. http://dx.doi.org/10.1021/ol3007524.

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46

Sun, Bing-Feng, Chao-Lei Wang, Rui Ding, Jin-Yi Xu, and Guo-Qiang Lin. "Concise approach to the core of englerin A via an organocatalytic [4+3] cycloaddition reaction." Tetrahedron Letters 52, no. 17 (April 2011): 2155–58. http://dx.doi.org/10.1016/j.tetlet.2010.11.087.

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47

Ludlow, Melanie J., Hannah J. Gaunt, Hussein N. Rubaiy, Katie E. Musialowski, Nicola M. Blythe, Naveen S. Vasudev, Katsuhiko Muraki, and David J. Beech. "(−)-Englerin A-evoked Cytotoxicity Is Mediated by Na+Influx and Counteracted by Na+/K+-ATPase." Journal of Biological Chemistry 292, no. 2 (November 14, 2016): 723–31. http://dx.doi.org/10.1074/jbc.m116.755678.

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48

Grant, Corena V., Chase M. Carver, Shayne D. Hastings, Karthik Ramachandran, Madesh Muniswamy, April L. Risinger, John A. Beutler, and Susan L. Mooberry. "Triple-negative breast cancer cell line sensitivity to englerin A identifies a new, targetable subtype." Breast Cancer Research and Treatment 177, no. 2 (June 22, 2019): 345–55. http://dx.doi.org/10.1007/s10549-019-05324-7.

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49

Mou, Shu-Bin, Wen Xiao, Hua-Qi Wang, Su-Jing Wang, and Zheng Xiang. "Syntheses of Epoxyguaiane Sesquiterpenes (−)-Englerin A, (−)-Oxyphyllol, (+)-Orientalol E, and (+)-Orientalol F: A Synthetic Biology Approach." Organic Letters 22, no. 5 (February 13, 2020): 1976–79. http://dx.doi.org/10.1021/acs.orglett.0c00325.

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50

Wu, Zhenhua, Jean-Simon Suppo, Sarka Tumova, Jonathan Strope, Fernando Bravo, Melody Moy, Ethan S. Weinstein, et al. "Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition." ACS Medicinal Chemistry Letters 11, no. 9 (August 3, 2020): 1711–16. http://dx.doi.org/10.1021/acsmedchemlett.0c00186.

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