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Journal articles on the topic 'Catharanthine'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Keglevich, András, Szabolcs Mayer, Réka Pápai, et al. "Attempted Synthesis of Vinca Alkaloids Condensed with Three-Membered Rings." Molecules 23, no. 10 (2018): 2574. http://dx.doi.org/10.3390/molecules23102574.

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Our successful work for the synthesis of cyclopropanated vinblastine and its derivatives by the Simmons–Smith reaction was followed to build up further three-membered rings into the 14,15-position of the vindoline part of the dimer alkaloid. Halogenated 14,15-cyclopropanovindoline was prepared by reactions with iodoform and bromoform, respectively, in the presence of diethylzinc. Reactions of dichlorocarbene with vindoline resulted in the 10-formyl derivative. Unexpectedly, in the case of the dimer alkaloids vinblastine and vincristine, the rearranged products containing an oxirane ring in the

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2

Zhu, Jianhua, Shuijie He, Pengfei Zhou, et al. "Eliciting Effect of Catharanthine on the Biosynthesis of Vallesiachotamine and Isovallesiachotamine in Catharanthus roseus Cambial Meristematic Cells." Natural Product Communications 13, no. 5 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300508.

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Vallesiachotamine and isovallesiachotamine are pharmacologically active monoterpene indole alkaloids produced by Catharanthus roseus. However, the biosynthetic pathway for these two alkaloids has not been characterized. The results of our experiments demonstrated that catharanthine induced the biosynthesis of vallesiachotamine and isovallesiachotamine in C. roseus cambial meristematic cells (CMCs) in a time- and dosage-dependent manner. The highest yields of vallesiachotamine and isovallesiachotamine (i.e., 1.49 mg l−1 and 1.08 mg l−1, respectively) were observed in CMCs treated with 10 mg cat

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3

Raucher, Stanley, and Brian L. Bray. "Total synthesis of (.+-.)-catharanthine." Journal of Organic Chemistry 50, no. 17 (1985): 3236–37. http://dx.doi.org/10.1021/jo00217a052.

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4

Moisan, Lionel, Pierre Thuéry, Marc Nicolas, Eric Doris, and Bernard Rousseau. "Formal Synthesis of (+)-Catharanthine." Angewandte Chemie International Edition 45, no. 32 (2006): 5334–36. http://dx.doi.org/10.1002/anie.200601307.

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5

Moisan, Lionel, Pierre Thuéry, Marc Nicolas, Eric Doris, and Bernard Rousseau. "Formal Synthesis of (+)-Catharanthine." Angewandte Chemie 118, no. 32 (2006): 5460–62. http://dx.doi.org/10.1002/ange.200601307.

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6

Pandiangan, Dingse. "Peningkatan Produksi Katarantin Melalui Teknik Elisitasi Pada Kultur Agregat Sel Catharanthus roseus." JURNAL ILMIAH SAINS 15, no. 1 (2011): 140. http://dx.doi.org/10.35799/jis.11.2.2011.178.

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ABSTRAK Penelitian ini bertujuan untuk optimasi dan peningkatan produksi antikanker katarantin khususnya elisitasi. Tujuan praktisnya adalah untuk mengetahui pertumbuhan kalus agregat sel C. roseus yang diberi elisitor, menemukan kurva tumbuh S. cerevisiae dan bahan elisitor, menemukan kandungan katarantin pada agregat sel dan medium perlakuan dan menemukan waktu panen perlakuan elisitasi yang menghasilkan kandungan katarantin yang paling tinggi. Dari hasil penelitian ini diharapkan dapat dihasilkan suatu informasi mengenai peningkatan katarantin yang dihasilkan (diproduksi) secara kultur (in

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7

Alehashem, Maryam Sadat, Chuan-Gee Lim, and Noel F. Thomas. "The radical cation mediated cleavage of catharanthine leading to the vinblastine type alkaloids: implications for total synthesis and drug design." RSC Advances 6, no. 22 (2016): 18002–25. http://dx.doi.org/10.1039/c5ra23074h.

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8

Pandya, Prateek, Surendra P. Gupta, Kumud Pandav, Ritu Barthwal, B. Jayaram, and Surat Kumar. "DNA Binding Studies of Vinca Alkaloids: Experimental and Computational Evidence." Natural Product Communications 7, no. 3 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700308.

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Fluorescence studies on the indole alkaloids vinblastine sulfate, vincristine sulfate, vincamine and catharanthine have demonstrated the DNA binding ability of these molecules. The binding mode of these molecules in the minor groove of DNA is non-specific. A new parameter of the purine-pyrimidine base sequence specificty was observed in order to define the non-specific DNA binding of ligands. Catharanthine had shown ‘same’ pattern of ‘Pu-Py’ specificity while evaluating its DNA binding profile. The proton resonances of a DNA decamer duplex were assigned. The models of the drug:DNA complexes we

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9

Raucher, Stanley, Brian L. Bray, and Ross F. Lawrence. "Synthesis of (.+-.)-catharanthine, (+)-anhydrovinblastine, and (-)-anhydrovincovaline." Journal of the American Chemical Society 109, no. 2 (1987): 442–46. http://dx.doi.org/10.1021/ja00236a023.

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10

Sundberg, Richard J., Phyllis J. Hunt, Patrice Desos, and Kumar G. Gadamasetti. "Oxidative fragmentation of catharanthine by dichlorodicyanoquinone." Journal of Organic Chemistry 56, no. 5 (1991): 1689–92. http://dx.doi.org/10.1021/jo00005a007.

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11

Sundberg, Richard J., Patrice Desos, Kumar G. Gadamasetti, and Michal Sabat. "Photoactive C16-C21 fragmentation of catharanthine." Tetrahedron Letters 32, no. 26 (1991): 3035–38. http://dx.doi.org/10.1016/0040-4039(91)80680-5.

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12

Sundberg, Richard J., Jian Hong, Stanton Q. Smith, Michal Sabat, and Ibro Tabakovic. "Synthesis and oxidative fragmentation of catharanthine analogs. Comparison to the fragmentation — Coupling of catharanthine and vindoline." Tetrahedron 54, no. 23 (1998): 6259–92. http://dx.doi.org/10.1016/s0040-4020(98)00289-0.

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13

Deus-Neumann, B., J. Stöckigt, and M. Zenk. "Radioimmunoassay for the Quantitative Determination of Catharanthine." Planta Medica 53, no. 02 (1987): 184–88. http://dx.doi.org/10.1055/s-2006-962668.

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14

SUNDBERG, R. J., J. HONG, S. Q. SMITH, M. SABAT, and I. TABAKOVIC. "ChemInform Abstract: Synthesis and Oxidative Fragmentation of Catharanthine Analogues. Comparison to the Fragmentation-Coupling of Catharanthine and Vindoline." ChemInform 29, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199839243.

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15

Huang, Nan, Tao Jiang, Tiansheng Wang, et al. "The acyclic dienamine–indoloacrylate addition route to catharanthine." Tetrahedron 64, no. 42 (2008): 9850–56. http://dx.doi.org/10.1016/j.tet.2008.07.044.

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16

Drapeau, Denis, Harvey Blanch, and Charles Wilke. "Ajmalicine, Serpentine, and Catharanthine Accumulation inCatharanthus roseusBioreactor Cultures." Planta Medica 53, no. 04 (1987): 373–76. http://dx.doi.org/10.1055/s-2006-962741.

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17

Hirata, Kazumasa, Tomohiro Akagi, Supanee Duangteraprecha, et al. "Catharanthine oxidation in flavin mononucleotide-mediated catharanthine-vindoline coupling reaction for synthesis of dimeric indole alkaloids under near-ultraviolet light." Journal of Bioscience and Bioengineering 87, no. 6 (1999): 781–86. http://dx.doi.org/10.1016/s1389-1723(99)80153-4.

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18

Munigunti, Ranjith, Katja Becker, Reto Brun, and Angela I. Calderón. "Determination of Antiplasmodial Activity and Binding Affinity of Selected Natural Products towards PfTrxR and PfGR." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800827.

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In our study, the binding affinities of selected natural products towards PfTrxR, PfGR, human TrxR and human GR were determined using a mass spectrometry based ligand binding assay. The in vitro antimalarial activity and cytotoxicity of these ligands were also determined. Catharanthine, 11-(OH)-coronaridine, hernagine, vobasine and hispolone displayed antiplasmodial activity against PfK1 (IC50 = 0.996–3.63 μg/mL).

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19

Park, Hyung H., Suk K. Choi, Jae K. Kang, and Hyeon Y. Lee. "Enhancement of producing catharanthine by suspension growth ofCatharanthus roseus." Biotechnology Letters 12, no. 8 (1990): 603–8. http://dx.doi.org/10.1007/bf01030760.

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20

Kono, Masato, Shingo Harada, Tomoyuki Nozaki, et al. "Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine." Organic Letters 21, no. 10 (2019): 3750–54. http://dx.doi.org/10.1021/acs.orglett.9b01198.

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21

Dwivedi, Gaurav Raj, Rekha Tyagi, Sanchita, et al. "Antibiotics potentiating potential of catharanthine against superbug Pseudomonas aeruginosa." Journal of Biomolecular Structure and Dynamics 36, no. 16 (2018): 4270–84. http://dx.doi.org/10.1080/07391102.2017.1413424.

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22

Liang, Chuxin, Chang Chen, Pengfei Zhou, et al. "Effect of Aspergillus flavus Fungal Elicitor on the Production of Terpenoid Indole Alkaloids in Catharanthus roseus Cambial Meristematic Cells." Molecules 23, no. 12 (2018): 3276. http://dx.doi.org/10.3390/molecules23123276.

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This study reported the inducing effect of Aspergillus flavus fungal elicitor on biosynthesis of terpenoid indole alkaloids (TIAs) in Catharanthus roseus cambial meristematic cells (CMCs) and its inducing mechanism. According to the results determined by HPLC and HPLC-MS/MS, the optimal condition of the A. flavus elicitor was as follows: after suspension culture of C. roseus CMCs for 6 day, 25 mg/L A. flavus mycelium elicitor were added, and the CMC suspensions were further cultured for another 48 h. In this condition, the contents of vindoline, catharanthine, and ajmaline were 1.45-, 3.29-, a

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23

Reding, Matthew T., and Tohru Fukuyama. "Stereocontrolled Total Synthesis of (±)-Catharanthine via Radical-Mediated Indole Formation." Organic Letters 1, no. 7 (1999): 973–76. http://dx.doi.org/10.1021/ol990749i.

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24

V�zquez-Flota, F., O. Moreno-Valenzuela, M. L. Miranda-Ham, J. Coello-Coello, and V. M. Loyola-Vargas. "Catharanthine and ajmalicine synthesis in Catharanthus roseus hairy root cultures." Plant Cell, Tissue and Organ Culture 38, no. 2-3 (1994): 273–79. http://dx.doi.org/10.1007/bf00033887.

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25

Auriola, S., T. Naaranlahti, and S. P. Lapinjoki. "Synthesis of [methyl-2H]-labelled ajmalicine, yohimbine, tabersonine and catharanthine." Journal of Labelled Compounds and Radiopharmaceuticals 29, no. 1 (1991): 117–21. http://dx.doi.org/10.1002/jlcr.2580290116.

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26

Arias, Hugo R., Dominik Feuerbach, Katarzyna M. Targowska-Duda, and Krzysztof Jozwiak. "Catharanthine alkaloids are noncompetitive antagonists of muscle-type nicotinic acetylcholine receptors." Neurochemistry International 57, no. 2 (2010): 153–61. http://dx.doi.org/10.1016/j.neuint.2010.05.007.

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27

Prakash, V., and Serge N. Timasheff. "Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline." Biochemistry 30, no. 3 (1991): 873–80. http://dx.doi.org/10.1021/bi00217a042.

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28

Tam, Mai Ngoc, B. Nikolova-Damyanova, and B. Pyuskyulev. "Quantitative Thin Layer Chromatography of Indole Alkaloids. II. Catharanthine and Vindoline." Journal of Liquid Chromatography 18, no. 5 (1995): 849–58. http://dx.doi.org/10.1080/10826079508010396.

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29

Tabakovic, Ibro, Esmir Gunic, and Ivan Juranic. "Anodic Fragmentation of Catharanthine and Coupling with Vindoline. Formation of Anhydrovinblastine." Journal of Organic Chemistry 62, no. 4 (1997): 947–53. http://dx.doi.org/10.1021/jo9621128.

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30

Moaddel, Ruin. "Catharanthine Alkaloids are Noncompetitive Inhibitors of Muscle-Type Nicotinic Acetylcholine Receptors." Biophysical Journal 100, no. 3 (2011): 548a. http://dx.doi.org/10.1016/j.bpj.2010.12.3194.

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31

Hirata, Kazumasa, Masato Horiuchi, Teru Ando, Kazuhisa Miyamoto, and Yoshiharu Miura. "Vindoline and catharanthine production in multiple shoot cultures of Catharanthus roseus." Journal of Fermentation and Bioengineering 70, no. 3 (1990): 193–95. http://dx.doi.org/10.1016/0922-338x(90)90186-z.

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32

Mersey, Brent G., and Adrian J. Cutler. "Differential distribution of specific indole alkaloids in leaves of Catharanthus roseus." Canadian Journal of Botany 64, no. 5 (1986): 1039–45. http://dx.doi.org/10.1139/b86-141.

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In leaves of the periwinkle plant (Catharanthus roseus (L.) G. Don) idioblasts are randomly distributed in the mesophyll. They are distinguishable from ordinary palisade and spongy parenchyma cells as large, refractile, and autofluorescent cells. Density gradient centrifugation of protoplasts derived from leaves resulted in fractions enriched in idioblast protoplasts. Analysis of indole alkaloid composition by high pressure liquid chromatography has shown that idioblasts are enriched in vindoline and catharanthine relative to other mesophyll cells. The significance of these observations for at

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33

Qu, Yang, Michael L. A. E. Easson, Jordan Froese, Razvan Simionescu, Tomas Hudlicky, and Vincenzo De Luca. "Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast." Proceedings of the National Academy of Sciences 112, no. 19 (2015): 6224–29. http://dx.doi.org/10.1073/pnas.1501821112.

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Antitumor substances related to vinblastine and vincristine are exclusively found in the Catharanthus roseus (Madagascar periwinkle), a member of the Apocynaceae plant family, and continue to be extensively used in cancer chemotherapy. Although in high demand, these valuable compounds only accumulate in trace amounts in C. roseus leaves. Vinblastine and vincristine are condensed from the monoterpenoid indole alkaloid (MIA) precursors catharanthine and vindoline. Although catharanthine biosynthesis remains poorly characterized, the biosynthesis of vindoline from the MIA precursor tabersonine is

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34

Pietrosiuk, Agnieszka, and Mirosława Furmanowa. "Preliminary results of indole alkaloids production in different roots of Catharanthus roseus cultured in vitro." Acta Societatis Botanicorum Poloniae 70, no. 4 (2014): 261–65. http://dx.doi.org/10.5586/asbp.2001.033.

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Six groups of untransformed and hairy root cultures of <em>Catharunthus roseus</em> (L.) G. Don were established. <em>Agrobacterium rhizogenes</em> strains: ATCC 15834, LBA 9403, and TR 105 were used for infection of the 3-week old rooted plantlets of <em>C. roseus</em>. The highest contents of examined indole alkaloids were found in: roots of intact plants - yohimbine and serpentine; in hairy roots - catharanthine. Vinblastine and ajmalicine were detected in untransformed roots of plants regenerated in vitro, and transferred to the soil for 5 months.

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35

Tabakovic, Ibro, Esmir Gunic, and Miroslav J. Gasic. "Anodic C16–C21 fragmentation of catharanthine in methanol. Synthesis of 16-methoxycleavamine." J. Chem. Soc., Perkin Trans. 2, no. 12 (1996): 2741–45. http://dx.doi.org/10.1039/p29960002741.

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36

Reding, Matthew T., and Tohru Fukuyama. "ChemInform Abstract: Stereocontrolled Total Synthesis of (.+-.)-Catharanthine via Radical-Mediated Indole Formation." ChemInform 30, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199952215.

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37

Caputi, Lorenzo, Jakob Franke, Scott C. Farrow, et al. "Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle." Science 360, no. 6394 (2018): 1235–39. http://dx.doi.org/10.1126/science.aat4100.

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Vinblastine, a potent anticancer drug, is produced byCatharanthus roseus(Madagascar periwinkle) in small quantities, and heterologous reconstitution of vinblastine biosynthesis could provide an additional source of this drug. However, the chemistry underlying vinblastine synthesis makes identification of the biosynthetic genes challenging. Here we identify the two missing enzymes necessary for vinblastine biosynthesis in this plant: an oxidase and a reductase that isomerize stemmadenine acetate into dihydroprecondylocarpine acetate, which is then deacetoxylated and cyclized to either catharant

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38

Szántay, Csaba, Hedvig Bölcskei, and Eszter Gács-Baitz. "Synthesis of vinca alkaloids and related compounds XLVIII synthesis of (+)-catharanthine and (±)-allocatharanthine." Tetrahedron 46, no. 5 (1990): 1711–32. http://dx.doi.org/10.1016/s0040-4020(01)81977-3.

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39

Xu, Maojun, Jufang Dong, and Muyuan Zhu. "Effect of nitric oxide on catharanthine production and growth ofCatharanthus roseus suspension cells." Biotechnology and Bioengineering 89, no. 3 (2005): 367–71. http://dx.doi.org/10.1002/bit.20334.

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40

Chung, Ill-Min, Eun-Hye Kim, Mai Li, et al. "Screening 64 cultivars Catharanthus roseus for the production of vindoline, catharanthine, and serpentine." Biotechnology Progress 27, no. 4 (2011): 937–43. http://dx.doi.org/10.1002/btpr.557.

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41

Gács-Baitz, Eszter, Hedvig Bölcskei, and Csaba Szántay. "NMR study of 6-azabicyclo[3.2.1 ]octene derivatives, by-products of catharanthine synthesis." J. Chem. Soc., Perkin Trans. 2, no. 2 (1994): 213–18. http://dx.doi.org/10.1039/p29940000213.

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42

Giovanelli, Emerson, Lionel Moisan, Sébastien Comesse, et al. "Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline." Organic & Biomolecular Chemistry 11, no. 35 (2013): 5885. http://dx.doi.org/10.1039/c3ob41170b.

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43

Zhou, Mei-Liang, Hong-Li Hou, Xue-Mei Zhu, Ji-Rong Shao, Yan-Min Wu, and Yi-Xiong Tang. "Soybean transcription factor GmMYBZ2 represses catharanthine biosynthesis in hairy roots of Catharanthus roseus." Applied Microbiology and Biotechnology 91, no. 4 (2011): 1095–105. http://dx.doi.org/10.1007/s00253-011-3288-1.

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44

Wang, Yanyan, Bingrun Yang, Mengxia Zhang, Shanshan Jia, and Fang Yu. "Application of transport engineering to promote catharanthine production in Catharanthus roseus hairy roots." Plant Cell, Tissue and Organ Culture (PCTOC) 139, no. 3 (2019): 523–30. http://dx.doi.org/10.1007/s11240-019-01696-2.

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45

Ferroud, Clotilde, and Patrice Rool. "A Singlet Oxygen Mediated New Access to Hydroxyindolenine-Catharanthine Derivatives by Two Sequential Oxidations." HETEROCYCLES 55, no. 3 (2001): 545. http://dx.doi.org/10.3987/com-00-9138.

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46

Sertel, Serkan, Yujie Fu, Yuangang Zu, et al. "Molecular docking and pharmacogenomics of Vinca alkaloids and their monomeric precursors, vindoline and catharanthine." Biochemical Pharmacology 81, no. 6 (2011): 723–35. http://dx.doi.org/10.1016/j.bcp.2010.12.026.

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47

Keglevich, Péter, Péter Ábrányi-Balogh, Áron Szigetvári, Csaba Szántay, Csaba Szántay, and László Hazai. "Studies on the mechanism of quaternization of the catharanthine part of vinblastine and vincristine." Tetrahedron Letters 57, no. 15 (2016): 1672–77. http://dx.doi.org/10.1016/j.tetlet.2016.03.004.

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48

Ishikawa, Hayato, David A. Colby, and Dale L. Boger. "Direct Coupling of Catharanthine and Vindoline to Provide Vinblastine: Total Synthesis of (+)- andent-(−)-Vinblastine." Journal of the American Chemical Society 130, no. 2 (2008): 420–21. http://dx.doi.org/10.1021/ja078192m.

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49

Bolcskei, Hedvig, Eszter Gacs-Baitz, and C. Szántay. "Azabicyclo[3.2.1]octene derivatives obtained by rearrangement reactions in course of the catharanthine synthesis." Pure and Applied Chemistry 66, no. 10-11 (1994): 2179–82. http://dx.doi.org/10.1351/pac199466102179.

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50

Goodbody, Anne, Tsuyoshi Endo, John Vukovic, James Kutney, Lewis Choi, and Masanaru Misawa. "Enzymic Coupling of Catharanthine and Vindoline to form 3′,4′-Anhydrovinblastine by Horseradish Peroxidase." Planta Medica 54, no. 02 (1988): 136–40. http://dx.doi.org/10.1055/s-2006-962371.

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