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Journal articles on the topic 'Balanol'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Miyabe, Hideto, Mayumi Torieda, Toshiko Kiguchi, and Takeaki Naito. "Total Synthesis of (-)-Balanol." Synlett 1997, no. 5 (May 1997): 580–82. http://dx.doi.org/10.1055/s-1997-3236.

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2

Aggarwal, V., M. Unthank, and N. Hussain. "Formal Synthesis of (-)-Balanol." Synfacts 2007, no. 3 (March 2007): 0239. http://dx.doi.org/10.1055/s-2007-968199.

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3

Miyabe, Hideto, Mayumi Torieda, Kyoko Inoue, Kazumi Tajiri, Toshiko Kiguchi, and Takeaki Naito. "Total Synthesis of (−)-Balanol." Journal of Organic Chemistry 63, no. 13 (June 1998): 4397–407. http://dx.doi.org/10.1021/jo980208r.

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4

Nicolaou, K. C., Mark E. Bunnage, and Kazunori Koide. "Total Synthesis of Balanol." Journal of the American Chemical Society 116, no. 18 (September 1994): 8402–3. http://dx.doi.org/10.1021/ja00097a072.

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5

Lampe, John W., Philip F. Hughes, Christopher K. Biggers, Shelley H. Smith, and Hong Hu. "Total Synthesis of (-)-Balanol." Journal of Organic Chemistry 59, no. 18 (September 1994): 5147–48. http://dx.doi.org/10.1021/jo00097a014.

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6

Li, Rui-Qi, Xiang Liu, Min Zhang, Wei-Qun Xu, Yong-Quan Li, and Xin-Ai Chen. "Gram-Level Production of Balanol through Regulatory Pathway and Medium Optimization in Herb Fungus Tolypocladium ophioglossoides." Journal of Fungi 8, no. 5 (May 16, 2022): 510. http://dx.doi.org/10.3390/jof8050510.

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As a potential protein kinase C inhibitor, the fungus metabolite balanol has become more attractive in recent decades. In our previous work, we revealed its biosynthetic pathway through overexpression of the cluster-situated regulator gene blnR in Chinese herb fungus Tolypocladium ophioglossoides. However, information on the regulation of blnR is still largely unknown. In this study, we further investigated the regulation of balanol biosynthesis by BlnR through the analysis of affinity binding using EMSA and RNA-seq analysis. The results showed that BlnR positively regulates balanol biosynthesis through binding to all promoters of bln gene members, including its own promoter. Microscopic observation revealed blnR overexpression also affected spore development and hypha growth. Furthermore, RNA-seq analysis suggested that BlnR can regulate other genes outside of the balanol biosynthetic gene cluster, including those involved in conidiospore development. Finally, balanol production was further improved to 2187.39 mg/L using the optimized medium through statistical optimization based on response surface methodology.

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7

Saha, Tapan, Ratnava Maitra, and Shital K. Chattopadhyay. "A unified approach to the important protein kinase inhibitor balanol and a proposed analogue." Beilstein Journal of Organic Chemistry 9 (December 19, 2013): 2910–15. http://dx.doi.org/10.3762/bjoc.9.327.

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A common approach to the important protein kinase inhibitor (−)-balanol and an azepine-ring-modified balanol derivative has been developed using an efficient fragment coupling protocol which proceeded in good overall yield.

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8

Wong, Chung F., Philippe H. Hünenberger, Pearl Akamine, Narendra Narayana, Tom Diller, J. Andrew McCammon, Susan Taylor, and Nguyen-Huu Xuong. "Computational Analysis of PKA−Balanol Interactions." Journal of Medicinal Chemistry 44, no. 10 (May 2001): 1530–39. http://dx.doi.org/10.1021/jm000443d.

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9

LAMPE, J. W., P. F. HUGHES, C. K. BIGGERS, S. H. SMITH, and H. HU. "ChemInform Abstract: Total Synthesis of (-)-Balanol." ChemInform 26, no. 10 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199510301.

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10

MIYABE, H., M. TORIEDA, K. INOUE, K. TAJIRI, T. KIGUCHI, and T. NAITO. "ChemInform Abstract: Total Synthesis of (-)-Balanol." ChemInform 29, no. 45 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199845264.

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11

NICOLAOU, K. C., M. E. BUNNAGE, and K. KOIDE. "ChemInform Abstract: Total Synthesis of Balanol." ChemInform 26, no. 15 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199515307.

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12

MIYABE, H., M. TORIEDA, T. KIGUCHI, and T. NAITO. "ChemInform Abstract: Total Synthesis of (-)-Balanol." ChemInform 28, no. 43 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199743261.

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13

Oh, Hong-Se, and Han-Young Kang. "Synthesis of the Hexahydroazepine Core of (-)-Balanol." Bulletin of the Korean Chemical Society 33, no. 11 (November 20, 2012): 3895–98. http://dx.doi.org/10.5012/bkcs.2012.33.11.3895.

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14

BORMAN, STU. "Balanol total synthesis achieved by two groups." Chemical & Engineering News 72, no. 37 (September 12, 1994): 6–7. http://dx.doi.org/10.1021/cen-v072n037.p006.

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15

Nielsen, John, and Lars O. Lyngsø. "Combinatorial solid-phase synthesis of balanol analogues." Tetrahedron Letters 37, no. 46 (November 1996): 8439–42. http://dx.doi.org/10.1016/0040-4039(96)01913-2.

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16

Nicolaou, K. C., Kazunori Koide, and Mark E. Bunnage. "Total Synthesis of Balanol and Designed Analogues." Chemistry - A European Journal 1, no. 7 (October 1995): 454–66. http://dx.doi.org/10.1002/chem.19950010711.

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17

LAMPE, J. W., P. F. HUGHES, C. K. BIGGERS, S. H. SMITH, and H. HU. "ChemInform Abstract: Total Synthesis of (-)- and (+)-Balanol." ChemInform 27, no. 47 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199647277.

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18

Patil, Mahesh L., Vishnu H. Deshpande, S. Ramlingam, and Hanumant B. Borate. "Synthetic studies towards the benzophenone precursor for balanol." Tetrahedron 60, no. 8 (February 2004): 1869–73. http://dx.doi.org/10.1016/j.tet.2003.12.029.

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19

BARBIER, P., and J. STADLWIESER. "ChemInform Abstract: Total Synthesis of Enantiomerically Pure (-)-Balanol." ChemInform 28, no. 11 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199711313.

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20

Yaragorla, Srinivasarao, and Ramaiah Muthyala. "Formal total synthesis of (−)-balanol: a potent PKC inhibitor." Tetrahedron Letters 51, no. 3 (January 2010): 467–70. http://dx.doi.org/10.1016/j.tetlet.2009.10.120.

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21

He, Xian, Min Zhang, Yuan-Yang Guo, Xu-Ming Mao, Xin-Ai Chen, and Yong-Quan Li. "Revelation of the Balanol Biosynthetic Pathway in Tolypocladium ophioglossoides." Organic Letters 20, no. 20 (October 2, 2018): 6323–26. http://dx.doi.org/10.1021/acs.orglett.8b01543.

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22

Raghavan, Sadagopan, and Ch Naveen Kumar. "A stereoselective synthesis of the hexahydroazepine core of (−)-balanol." Tetrahedron Letters 47, no. 10 (March 2006): 1585–88. http://dx.doi.org/10.1016/j.tetlet.2005.12.123.

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23

NICOLAOU, K. C., K. KOIDE, and M. E. BUNNAGE. "ChemInform Abstract: Total Synthesis of Balanol and Designed Analogues." ChemInform 27, no. 4 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199604280.

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24

Masse, Craig E., Adam J. Morgan, and James S. Panek. "An Asymmetric Aminohydroxylation Approach to the Azepine Core of (−)-Balanol." Organic Letters 2, no. 17 (August 2000): 2571–73. http://dx.doi.org/10.1021/ol0061034.

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25

Hudlický, Tomáš. "Recent chemoenzymatic total syntheses of natural and unnatural products: Codeine, balanol, pancratistatin, and oseltamivir." Pure and Applied Chemistry 82, no. 9 (June 4, 2010): 1785–96. http://dx.doi.org/10.1351/pac-con-09-10-07.

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Presented here is a short summary of the recent accomplishments in total synthesis in our laboratories. In particular, recent generations of the syntheses of pancratistatin derivatives, codeine, balanol, and oseltamivir (Tamiflu) are described in relation to their common chemoenzymatic origin in toluene-dioxygenase-mediated dioxygenation of aromatic substrates. Perspectives and projections are discussed in the conclusion.

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26

BOROS, CHRISTIE, SEAN M. HAMILTON, BARRY KATZ, and PALANIAPPAN KULANTHAIVEL. "Comparison of balanol from Verticillium balanoides and ophiocordin from Cordyceps ophioglossoides." Journal of Antibiotics 47, no. 9 (1994): 1010–16. http://dx.doi.org/10.7164/antibiotics.47.1010.

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27

Wong, Chung F., Jeremy Kua, Yingkai Zhang, T. P. Straatsma, and J. Andrew McCammon. "Molecular docking of balanol to dynamics snapshots of protein kinase A." Proteins: Structure, Function, and Bioinformatics 61, no. 4 (October 21, 2005): 850–58. http://dx.doi.org/10.1002/prot.20688.

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28

Yadav, J. S., and Ch Srinivas. "An efficient approach for the synthesis of the hexahydroazepine segment of balanol." Tetrahedron Letters 43, no. 21 (May 2002): 3837–39. http://dx.doi.org/10.1016/s0040-4039(02)00681-0.

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29

Heerding, Julia M., John W. Lampe, James W. Darges, and Mark L. Stamper. "Protein kinase C inhibitory activities of balanol analogs bearing carboxylic acid replacements." Bioorganic & Medicinal Chemistry Letters 5, no. 16 (August 1995): 1839–42. http://dx.doi.org/10.1016/0960-894x(95)00303-b.

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30

Erik Jagdmann, G., Jean M. Defauw, Yen-Shi Lai, Heidi M. Crane, Steven E. Hall, John A. Buben, Hong Hu, and Paul A. Gosnell. "Novel PKC inhibitory analogs of balanol with replacement of the ester functionality." Bioorganic & Medicinal Chemistry Letters 5, no. 17 (September 1995): 2015–20. http://dx.doi.org/10.1016/0960-894x(95)00344-s.

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31

Lai, Yen-Shi, and Mark Stamper. "Heteroatom effect in the PKC inhibitory activities of perhydroazepine analogs of balanol." Bioorganic & Medicinal Chemistry Letters 5, no. 18 (September 1995): 2147–50. http://dx.doi.org/10.1016/0960-894x(95)00364-y.

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32

Lai, Yen-Shi, JoséS Mendoza, Fred Hubbard, and Kiyomi Kalter. "Synthesis and PKC inhibitory activities of balanol analogs with a cyclopentane substructure." Bioorganic & Medicinal Chemistry Letters 5, no. 18 (September 1995): 2155–60. http://dx.doi.org/10.1016/0960-894x(95)00367-3.

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33

Hong Hu, Sean P. Hollinshead, Steven E. Hall, Kiyomi Kalter, and Lawrence M. Ballas. "Synthesis and protein kinase C inhibitory activities of indane analogs of balanol." Bioorganic & Medicinal Chemistry Letters 6, no. 8 (April 1996): 973–78. http://dx.doi.org/10.1016/0960-894x(96)00151-5.

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34

Denieul, Marie-Pierre, Bolette Laursen, Rita Hazell, and Troels Skrydstrup. "Synthesis of the Benzophenone Fragment of Balanol via an Intramolecular Cyclization Event." Journal of Organic Chemistry 65, no. 19 (September 2000): 6052–60. http://dx.doi.org/10.1021/jo000750r.

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35

Masse, Craig E., Adam J. Morgan, and James S. Panek. "ChemInform Abstract: An Asymmetric Aminohydroxylation Approach to the Azepine Core of (-)-Balanol." ChemInform 31, no. 47 (November 21, 2000): no. http://dx.doi.org/10.1002/chin.200047228.

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36

Phansavath, Phannarath, Sébastien Duprat de Paule, Virginie Ratovelomanana-Vidal, and Jean-Pierre Genêt. "An Efficient Formal Synthesis of (−)-Balanol by Using Ruthenium-Catalyzed Asymmetric Hydrogenation." European Journal of Organic Chemistry 2000, no. 23 (December 2000): 3903–7. http://dx.doi.org/10.1002/1099-0690(200012)2000:23<3903::aid-ejoc3903>3.0.co;2-q.

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37

Pande, Vineet, Maria Ramos, and Federico Gago. "The Protein Kinase Inhibitor Balanol: Structure – Activity Relationships and Structure-Based Computational Studies." Anti-Cancer Agents in Medicinal Chemistry 8, no. 6 (August 1, 2008): 638–45. http://dx.doi.org/10.2174/187152008785133056.

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38

Adams, C. P., S. M. Fairway, C. J. Hardy, D. E. Hibbs, M. B. Hursthouse, A. D. Morley, B. W. Sharp, N. Vicker, and I. Warner. "Total synthesis of balanol: a potent protein kinase C inhibitor of fungal origin." Journal of the Chemical Society, Perkin Transactions 1, no. 18 (1995): 2355. http://dx.doi.org/10.1039/p19950002355.

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39

Wong, Chung F., J. Andrew McCammon, and Gergely Gidofalvi. "Entropy Loss of Hydroxyl Groups of Balanol upon Binding to Protein Kinase A." Journal of Chemical Education 79, no. 9 (September 2002): 1122. http://dx.doi.org/10.1021/ed079p1122.

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40

Roy, Sankar P., and Shital K. Chattopadhyay. "Concise syntheses of stereoisomeric hexahydroazepine derivatives related to the protein kinase inhibitor balanol." Tetrahedron Letters 49, no. 38 (September 2008): 5498–501. http://dx.doi.org/10.1016/j.tetlet.2008.07.031.

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41

Lampe, John W., Christopher K. Biggers, Jean M. Defauw, Robert J. Foglesong, Steven E. Hall, Julia M. Heerding, Sean P. Hollinshead, et al. "Synthesis and Protein Kinase Inhibitory Activity of Balanol Analogues with Modified Benzophenone Subunits." Journal of Medicinal Chemistry 45, no. 12 (June 2002): 2624–43. http://dx.doi.org/10.1021/jm020018f.

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42

Crane, Heidi M., David S. Menaldino, G. Erik Jagdmann, James W. Darges, and John A. Buben. "Increasing the cellular PKC inhibitory activity of balanol: A study of ester analogs." Bioorganic & Medicinal Chemistry Letters 5, no. 18 (September 1995): 2133–38. http://dx.doi.org/10.1016/0960-894x(95)00361-v.

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43

Lai, Yen-Shi, David S. Menaldino, Jeffrey B. Nichols, G. Erik Jagdmann, Frankie Mylott, Jan Gillespie, and Steven E. Hall. "Ring size effect in the PKC inhibitory activities of perhydroazepine analogs of balanol." Bioorganic & Medicinal Chemistry Letters 5, no. 18 (September 1995): 2151–54. http://dx.doi.org/10.1016/0960-894x(95)00365-z.

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44

Wu, Michael H., and Eric N. Jacobsen. "An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction." Tetrahedron Letters 38, no. 10 (March 1997): 1693–96. http://dx.doi.org/10.1016/s0040-4039(97)00192-5.

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45

Cook, Gregory R., P. Sathya Shanker, and Scott L. Peterson. "Asymmetric Synthesis of the Balanol Heterocycle via a Palladium-Mediated Epimerization and Olefin Metathesis." Organic Letters 1, no. 4 (August 1999): 615–18. http://dx.doi.org/10.1021/ol990705+.

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46

Storm, J. Peter, and Carl-Magnus Andersson. "An Organoiron Approach to the Benzophenone Appendage of the Protein Kinase C Inhibitor Balanol." Organic Letters 1, no. 9 (November 1999): 1451–53. http://dx.doi.org/10.1021/ol9910060.

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47

Fürstner, Alois, and Oliver R. Thiel. "Formal Total Synthesis of (−)-Balanol: Concise Approach to the Hexahydroazepine Segment Based on RCM." Journal of Organic Chemistry 65, no. 6 (March 2000): 1738–42. http://dx.doi.org/10.1021/jo991611g.

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48

Gilmet, Jacqueline, Bradford Sullivan, and Tomas Hudlicky. "Formal total synthesis of (–)- and (+)-balanol: two complementary enantiodivergent routes from vinyloxiranes and vinylaziridines." Tetrahedron 65, no. 1 (January 2009): 212–20. http://dx.doi.org/10.1016/j.tet.2008.10.070.

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49

Sullivan, Bradford, and Tomas Hudlicky. "Chemoenzymatic formal synthesis of (−)-balanol. Provision of optical data for an often-reported intermediate." Tetrahedron Letters 49, no. 35 (August 2008): 5211–13. http://dx.doi.org/10.1016/j.tetlet.2008.06.026.

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50

Setyawan, Juliana, Kazunori Koide, Thomas C. Diller, Mark E. Bunnage, Susan S. Taylor, K. C. Nicolaou, and Laurence L. Brunton. "Inhibition of Protein Kinases by Balanol: Specificity within the Serine/Threonine Protein Kinase Subfamily." Molecular Pharmacology 56, no. 2 (August 1, 1999): 370–76. http://dx.doi.org/10.1124/mol.56.2.370.

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