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Journal articles on the topic 'Lamellarin'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Carroll, AR, BF Bowden, and JC Coll. "Studies of Australian Ascidians. I. Six New Lamellarin-Class Alkaloids From a Colonial Ascidian, Didemnum sp." Australian Journal of Chemistry 46, no. 4 (1993): 489. http://dx.doi.org/10.1071/ch9930489.

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Six new polyaromatic alkaloids, lamellarin I (3), J (6), K (7), L (9), M (11) and the triacetate (13) of lamellarin N, and four known alkaloids, lamellarin A (I), B (15), C (16) and the triacetate (14) of lamellarin D, have been isolated from the marine ascidian Didemnum sp. The structures were deduced by high-field n.m.r. spectroscopy including 13C-1H shift-correlated two-dimensional (2D) n.m.r. experiments and n.O.e . measurements. The triacetates (8) and (10) of two of the compounds, lamellarin K (7) and lamellarin L (9), were dehydrogenated in high yield by treatment with 2,3-dichloro-5,6-

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2

Lade, Dhanaji M., Amit B. Pawar, Prathama S. Mainkar, and Srivari Chandrasekhar. "Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H." Journal of Organic Chemistry 82, no. 9 (2017): 4998–5004. http://dx.doi.org/10.1021/acs.joc.7b00636.

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3

Imbri, Dennis, Johannes Tauber та Till Opatz. "A High-Yielding Modular Access to the Lamellarins: Synthesis of Lamellarin G Trimethyl Ether, Lamellarin η and Dihydrolamellarin η". Chemistry - A European Journal 19, № 45 (2013): 15080–83. http://dx.doi.org/10.1002/chem.201303563.

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4

Urban, S., and RJ Capon. "Lamellarin-S: a New Aromatic Metabolite From an Australian Tunicate, Didemnum sp." Australian Journal of Chemistry 49, no. 6 (1996): 711. http://dx.doi.org/10.1071/ch9960711.

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An Australian tunicate Didemnum sp. has yielded a new alkaloid lamellarin-S (1) along with the known compound lamellarin-K (12). Of this structure class, lamellarin-S (1) is the first example that demonstrates atropisomerism , and its structure was secured by spectroscopic analysis.

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5

Mei, Ruhuai, Shou-Kun Zhang, and Lutz Ackermann. "Concise Synthesis of Lamellarin Alkaloids by C–H/N–H Activation: Evaluation of Metal Catalysts in Oxidative Alkyne Annulation." Synlett 28, no. 14 (2017): 1715–18. http://dx.doi.org/10.1055/s-0036-1591209.

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The performance of various transition-metal catalysts was explored in the step-economical synthesis of naturally occurring lamellarin alkaloids by C–H/N–H activation. The oxidative alkyne annulation proceeded efficiently by using sustainable ruthenium(II) catalysis, which set the stage for a concise synthesis of lamellarin D, lamellarin H and derivatives thereof.

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6

Urban, S., MS Butler, and RJ Capon. "Lamellarins O and P: New Aromatic Metabolites From the Australian Marine Sponge Dendrilla cactos." Australian Journal of Chemistry 47, no. 10 (1994): 1919. http://dx.doi.org/10.1071/ch9941919.

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A specimen of Dendrilla cactos collected during trawling operations in Bass Strait, Australia, has yielded two new alkaloids, lamellarin-O (17) and lamellarin-P (18). Both these metabolites are examples of the lamellarin structure class, previously reported from tunicates and a mollusc; however, in these examples the pyrrole ring system is not fused to adjacent aromatic rings. The structures of (17) and (18) were secured by spectroscopic analysis and partial synthesis.

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7

Wang, Ailing, Zhuangzhi Zhao, Xuefang Zheng, and Hongyu Cao. "Recent Research Progress in Anticancer Alkaloid Lamellarin N and Lamellarin L." Chinese Journal of Organic Chemistry 33, no. 3 (2013): 483. http://dx.doi.org/10.6023/cjoc201209034.

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8

Satyanarayana, Iddum, Ding-Yah Yang, and Teau-Jiuan Liou. "Synthesis of lamellarin R, lukianol A, lamellarin O and their analogues." RSC Advances 10, no. 70 (2020): 43168–74. http://dx.doi.org/10.1039/d0ra09249e.

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9

Hasse, Katrin, Anthony C. Willis, and Martin G. Banwell. "Modular Total Syntheses of Lamellarin G Trimethyl Ether and Lamellarin S." European Journal of Organic Chemistry 2011, no. 1 (2010): 88–99. http://dx.doi.org/10.1002/ejoc.201001133.

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10

Izumida, Mai, Osamu Kotani, Hideki Hayashi, et al. "Unique Mode of Antiviral Action of a Marine Alkaloid against Ebola Virus and SARS-CoV-2." Viruses 14, no. 4 (2022): 816. http://dx.doi.org/10.3390/v14040816.

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Lamellarin α 20-sulfate is a cell-impenetrable marine alkaloid that can suppress infection that is mediated by the envelope glycoprotein of human immunodeficiency virus type 1. We explored the antiviral action and mechanisms of this alkaloid against emerging enveloped RNA viruses that use endocytosis for infection. The alkaloid inhibited the infection of retroviral vectors that had been pseudotyped with the envelope glycoprotein of Ebola virus and SARS-CoV-2. The antiviral effects of lamellarin were independent of the retrovirus Gag-Pol proteins. Interestingly, although heparin and dextran sul

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11

Iwao, M., N. Fujikawa, T. Ohta, T. Yamaguchi, T. Fukada, and F. Ishibashi. "Synthesis of Lamellarin L." Synfacts 2006, no. 6 (2006): 0545. http://dx.doi.org/10.1055/s-2006-934488.

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12

Ruchirawat, Somsak, and Thumnoon Mutarapat. "An efficient synthesis of lamellarin alkaloids: synthesis of lamellarin G trimethyl ether." Tetrahedron Letters 42, no. 6 (2001): 1205–8. http://dx.doi.org/10.1016/s0040-4039(00)02222-x.

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13

Dialer, Clemes, Dennis Imbri, Steven Peter Hansen та Till Opatz. "Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization". Journal of Organic Chemistry 80, № 22 (2015): 11605–10. http://dx.doi.org/10.1021/acs.joc.5b02194.

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14

Kumar, Virendra, Abdus Salam, Dileep Kumar, and Tabrez Khan. "Concise and Scalable Total Syntheses of Lamellarin Z and other Natural Lamellarins." ChemistrySelect 5, no. 45 (2020): 14510–14. http://dx.doi.org/10.1002/slct.202004008.

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15

Imbri, Dennis, Johannes Tauber та Till Opatz. "ChemInform Abstract: A High-Yielding Modular Access to the Lamellarins: Synthesis of Lamellarin G Trimethyl Ether (Ia), Lamellarin η (II) and Dihydrolamellarin η (Ib)." ChemInform 45, № 13 (2014): no. http://dx.doi.org/10.1002/chin.201413228.

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16

Handy, Scott T., Yanan Zhang, and Howard Bregman. "A Modular Synthesis of the Lamellarins: Total Synthesis of Lamellarin G Trimethyl Ether." Journal of Organic Chemistry 69, no. 7 (2004): 2362–66. http://dx.doi.org/10.1021/jo0352833.

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17

Klintworth, Robin, Charles B. de Koning, and Joseph P. Michael. "Practical Decagram-Scale Synthesis of a Lamellarin Analogue and Deprotection of Lamellarin Isopropyl Ethers." European Journal of Organic Chemistry 2020, no. 25 (2020): 3860–71. http://dx.doi.org/10.1002/ejoc.202000499.

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18

Tauber, Johannes, Dennis Imbri, Vanessa C. Colligs, and Till Opatz. "Zugänge zu Isomeren und Verwandten der Lamellarin-Alkaloide / Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids." Zeitschrift für Naturforschung B 69, no. 5 (2014): 627–40. http://dx.doi.org/10.5560/znb.2014-4045.

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Synthetic approaches to novel isomers and unprecedented structural relatives of the lamellarin alkaloids are reported. During our studies on methods to construct the lamellarin skeleton, we found the condensation of chroman-4-one derivatives with 1-benzyl-3,4-dihydroisoquinolines or the Pdcatalyzed cyclocarbonylation of o-halogenated precursors followed by Baeyer-Villiger oxidation to be unsuitable. Nevertheless, these routes produced interesting structural relatives of the natural alkaloids.

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19

Ishibashi, Fumito, Yuka Miyazaki, and Masatomo Iwao. "Total Syntheses of Lamellarin D and H. The First Synthesis of Lamellarin-Class Marine Alkaloids." Tetrahedron 53, no. 17 (1997): 5951–62. http://dx.doi.org/10.1016/s0040-4020(97)00287-1.

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20

You, Ye-cheng, Guang Yang, Ai-ling Wang, and De-peng Li. "Synthesis of intermediate for lamellarin H." Current Applied Physics 5, no. 5 (2005): 535–37. http://dx.doi.org/10.1016/j.cap.2004.11.005.

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21

Pla, Daniel, Antonio Marchal, Christian A. Olsen, Fernando Albericio, and Mercedes Álvarez. "Modular Total Synthesis of Lamellarin D." Journal of Organic Chemistry 70, no. 20 (2005): 8231–34. http://dx.doi.org/10.1021/jo051083a.

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22

Banwell, Martin, and David Hockless. "Convergent total synthesis of lamellarin K†." Chemical Communications, no. 23 (1997): 2259–60. http://dx.doi.org/10.1039/a705874h.

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23

Heim, Alexander, Andreas Terpin, and Wolfgang Steglich. "Biomimetische Synthese von Lamellarin-G-trimethylether." Angewandte Chemie 109, no. 1-2 (1997): 158–59. http://dx.doi.org/10.1002/ange.19971090152.

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24

Liermann, Johannes C., та Till Opatz. "Synthesis of Lamellarin U and Lamellarin G Trimethyl Ether by Alkylation of a Deprotonated α-Aminonitrile". Journal of Organic Chemistry 73, № 12 (2008): 4526–31. http://dx.doi.org/10.1021/jo800467e.

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25

Manjappa, Kiran B., Jia-Ru Syu, and Ding-Yah Yang. "Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H." Organic Letters 18, no. 2 (2016): 332–35. http://dx.doi.org/10.1021/acs.orglett.5b03524.

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26

ISHIBASHI, F., Y. MIYAZAKI, and M. IWAO. "ChemInform Abstract: Total Syntheses of Lamellarin D and H. The First Synthesis of Lamellarin-Class Marine Alkaloids." ChemInform 28, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199737243.

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27

Heim, Alexander, Andreas Terpin, and Wolfgang Steglich. "Biomimetic Synthesis of Lamellarin G. Trimethyl Ether." Angewandte Chemie International Edition in English 36, no. 12 (1997): 155–56. http://dx.doi.org/10.1002/anie.199701551.

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28

B. Manjappa, Kiran, Jhih-Min Lin, and Ding-Yah Yang. "Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D." Journal of Organic Chemistry 82, no. 14 (2017): 7648–56. http://dx.doi.org/10.1021/acs.joc.7b01061.

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29

Steglich, Wolfgang, Christian Peschko, Christian Winklhofer, and Andreas Terpin. "Biomimetic Syntheses of Lamellarin and Lukianol-Type Alkaloids." Synthesis 2006, no. 18 (2006): 3048–57. http://dx.doi.org/10.1055/s-2006-950191.

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30

Bracegirdle, Joe, Luke P. Robertson, Paul A. Hume, et al. "Lamellarin Sulfates from the Pacific Tunicate Didemnum ternerratum." Journal of Natural Products 82, no. 7 (2019): 2000–2008. http://dx.doi.org/10.1021/acs.jnatprod.9b00493.

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31

Khiati, Salim, Yeonee Seol, Keli Agama, et al. "Poisoning of Mitochondrial Topoisomerase I by Lamellarin D." Molecular Pharmacology 86, no. 2 (2014): 193–99. http://dx.doi.org/10.1124/mol.114.092833.

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32

Yadav, Jhillu, Kamakolanu Gayathri, Basi Reddy, and Attaluri Prasad. "Modular Total Synthesis of Lamellarin G Trimethyl Ether." Synlett 2009, no. 01 (2008): 43–46. http://dx.doi.org/10.1055/s-0028-1087387.

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33

BANWELL, M., B. FLYNN, and D. HOCKLESS. "ChemInform Abstract: Convergent Total Synthesis of Lamellarin K." ChemInform 29, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199816215.

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34

Banwell, Martin G., Bernard L. Flynn, Ernest Hamel, and David C. R. Hockless. "Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners." Chemical Communications, no. 2 (1997): 207–8. http://dx.doi.org/10.1039/a606793j.

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35

Zhang, Kai, Xian Guan, Xiao Zhang, Lu Liu, Ruijuan Yin, and Tao Jiang. "Protective Effects of Marine Alkaloid Neolamellarin A Derivatives against Glutamate Induced PC12 Cell Apoptosis." Marine Drugs 20, no. 4 (2022): 262. http://dx.doi.org/10.3390/md20040262.

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Marine alkaloids obtained from sponges possess a variety of biological activities and potential medicinal value. The pyrrole-derived lamellarin-like alkaloids, especially their permethyl derivatives, show low cytotoxicity and potent MDR reversing activity. Neolamellarin A is a novel lamellarin-like alkaloid which was extracted from marine animal sponges. We reported the synthetic method of permethylated Neolamellarin A and its derivatives by a convergent strategy in 2015. In 2018, we reported the synthesis and the neuroprotective activity in PC12 cells of 3,4-bisaryl-N-alkylated permethylated

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36

Iwao, Masatomo, Tsutomu Fukuda, and Fumito Ishibashi. "Synthesis and Biological Activity of Lamellarin Alkaloids: An Overview." HETEROCYCLES 83, no. 3 (2011): 491. http://dx.doi.org/10.3987/rev-10-686.

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37

Pla, D., F. Albericio, and M. Alvarez. "Recent Advances in Lamellarin Alkaloids: Isolation, Synthesis and Activity." Anti-Cancer Agents in Medicinal Chemistry 8, no. 7 (2008): 746–60. http://dx.doi.org/10.2174/187152008785914789.

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38

Wang, Ailing, Xueliang Zheng, Zhuangzhi Zhao, Changping Li, Bo Tao та Xuefanng Zheng. "Synthesis of Novel 5,6-2H-Lamellarin η and Analogues". Chinese Journal of Organic Chemistry 34, № 2 (2014): 429. http://dx.doi.org/10.6023/cjoc201307023.

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39

Ishibashi, Fumito, Shinji Tanabe, Tatsuya Oda, and Masatomo Iwao. "Synthesis and Structure−Activity Relationship Study of Lamellarin Derivatives." Journal of Natural Products 65, no. 4 (2002): 500–504. http://dx.doi.org/10.1021/np0104525.

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40

Davis, Rohan A., Anthony R. Carroll, Gregory K. Pierens, and Ronald J. Quinn. "New Lamellarin Alkaloids from the Australian Ascidian,Didemnum chartaceum." Journal of Natural Products 62, no. 3 (1999): 419–24. http://dx.doi.org/10.1021/np9803530.

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41

Praud‐Tabariès, Annie, Olivier Bottzeck, and Yves Blache. "Synthesis of Lamellarin Q Analogues as Potential Antibiofilm Compounds." Journal of Heterocyclic Chemistry 56, no. 4 (2019): 1458–63. http://dx.doi.org/10.1002/jhet.3512.

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42

Zheng, Kai-Lu, Min-Qi You, Wen-Ming Shu, Yan-Dong Wu, and An-Xin Wu. "Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and Lamellarin G Trimethyl Ether." Organic Letters 19, no. 9 (2017): 2262–65. http://dx.doi.org/10.1021/acs.orglett.7b00769.

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43

BANWELL, M. G., B. L. FLYNN, E. HAMEL, and D. C. R. HOCKLESS. "ChemInform Abstract: Convergent Syntheses of the Pyrrolic Marine Natural Products Lamellarin-O, Lamellarin-Q, Lukianol-A, and Some More Highly Oxygenated Congeners." ChemInform 28, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199723247.

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44

Banwell, Martin G., David C. R. Hockless, Bernard L. Flynn, Robert W. Longmore, and David Rae. "Assessment of Double-Barrelled Heck Cyclizations as a Means for Construction of the 14-Phenyl-8,9-dihydro- 6H-[1]benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin- 6-one Core Associated with Certain Members of the Lamellarin Class of Marine Natural Product." Australian Journal of Chemistry 52, no. 8 (1999): 755. http://dx.doi.org/10.1071/ch99021.

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The 1,2,4-trisubstituted pyrrole (4), which is readily prepared from pyrrole itself, undergoes double- barrelled Heck cyclizations to give, inter alia, compounds (3) and (17) for which crystal structures have been determined. Product (3) constitutes the core associated with several key members, e.g. (1) and (2), of the lamellarin class of marine alkaloid.

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45

Shirley, Harry J., Maria Koyioni, Filip Muncan та Timothy J. Donohoe. "Synthesis of lamellarin alkaloids using orthoester-masked α-keto acids". Chemical Science 10, № 15 (2019): 4334–38. http://dx.doi.org/10.1039/c8sc05678a.

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46

Ridley, C. "Total synthesis and evaluation of lamellarin α 20-Sulfate analogues". Bioorganic & Medicinal Chemistry 10, № 10 (2002): 3285–90. http://dx.doi.org/10.1016/s0968-0896(02)00237-7.

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47

Malla Reddy, S., M. Srinivasulu, N. Satyanarayana, Anand K. Kondapi, and Y. Venkateswarlu. "New potent cytotoxic lamellarin alkaloids from Indian ascidian Didemnum obscurum." Tetrahedron 61, no. 39 (2005): 9242–47. http://dx.doi.org/10.1016/j.tet.2005.07.067.

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48

Bracegirdle, Joe, Luke P. Robertson, Paul A. Hume, et al. "Correction to Lamellarin Sulfates from the Pacific Tunicate Didemnum ternerratum." Journal of Natural Products 83, no. 10 (2020): 3213. http://dx.doi.org/10.1021/acs.jnatprod.0c00997.

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49

Krishnaiah, P., V. L. N. Reddy, G. Venkataramana, et al. "New Lamellarin Alkaloids from the Indian AscidianDidemnumobscurumand Their Antioxidant Properties⊥." Journal of Natural Products 67, no. 7 (2004): 1168–71. http://dx.doi.org/10.1021/np030503t.

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50

Ohta, Takeshi, Tsutomu Fukuda, Fumito Ishibashi, and Masatomo Iwao. "Design and Synthesis of Lamellarin D Analogues Targeting Topoisomerase I." Journal of Organic Chemistry 74, no. 21 (2009): 8143–53. http://dx.doi.org/10.1021/jo901589e.

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