ACS Publications. Most Trusted. Most Cited. Most Read
Pyrrolidinoindoline Alkaloids from Psychotria colorata
My Activity
    Note

    Pyrrolidinoindoline Alkaloids from Psychotria colorata 1
    Click to copy article linkArticle link copied!

    View Author Information
    Dipartimento di Chimica Organica e Industriale, Università degli Studi, via Venezian 21, 20133 Milano, Italy, Centro per lo Studio delle Relazioni tra Struttura e Reattività Chimica del CNR, via Golgi 19, 20133 Milano, Italy, Structure Based Drug Design, Pharmacia & Upjohn, via Pasteur 10, 20014 Nerviano (MI), Italy, Departamento de Farmacologia, Universidade Federal do Rio Grande do Sul, CP 5072, Porto Alegre (RS), Brazil, and Curso de Pós-Graduação en Química, Universidade Federal do Parà, Belém (PA), Brazil
    Other Access Options

    Journal of Natural Products

    Cite this: J. Nat. Prod. 1998, 61, 3, 392–396
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np9701642
    Published February 25, 1998
    Copyright © 1998 American Chemical Society and American Society of Pharmacognosy

    Abstract

    Click to copy section linkSection link copied!

    Fractionation of an alkaloid extract of Psychotria colorata flowers led to the isolation of six alkaloids, identified by UV, 1D and 2D NMR, and MS as (−)-calycanthine, isocalycanthine, (+)-chimonanthine, hodgkinsine, quadrigemine C, and a new alkaloid (1), whose structure was deduced by X-ray analysis to be (8-8a),(8‘-8‘a)-tetradehydroisocalycanthine 3a(R), 3‘a(R).

    Copyright © 1998 American Chemical Society and American Society of Pharmacognosy

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

     To whom correspondence should be addressed. Tel.:  39 2 236 3469. FAX:  39 2 2364369. E-mail:  [email protected].

     Dipartimento di Chimica Organica e Industriale.

     Departamento de Farmacologia.

     Curso de Pós-Graduação en Química.

     Centro per lo Studio delle Relazioni tra Struttura e Reattività del CNR. ‡ Structure Based Drug Design, Pharmacia & Upjohn.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 85 publications.

    1. Arindam Khatua, Debgopal Jana, Monosij Nandy, Pranay Shyamal, Alakesh Bisai. Total Synthesis of (+)- and (−)-Calycanthine by Means of Thio-Urea-Catalyzed Sequential Michael Reactions of Bis-oxindoles. The Journal of Organic Chemistry 2024, 89 (7) , 4792-4801. https://doi.org/10.1021/acs.joc.4c00019
    2. Sulekha Sharma, Saina Shaheeda, Kundan Shaw, Alakesh Bisai, Amit Paul. Two-Electron- and One-Electron-Transfer Pathways for TEMPO-Catalyzed Greener Electrochemical Dimerization of 3-Substituted-2-Oxindoles. ACS Catalysis 2023, 13 (3) , 2118-2134. https://doi.org/10.1021/acscatal.2c06361
    3. Jordan J. Dotson, Ieva Liepuoniute, J. Logan Bachman, Vince M. Hipwell, Saeed I. Khan, K. N. Houk, Neil K. Garg, Miguel A. Garcia-Garibay. Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine. Journal of the American Chemical Society 2021, 143 (10) , 4043-4054. https://doi.org/10.1021/jacs.1c01100
    4. Jordan J. Dotson, J. Logan Bachman, Miguel A. Garcia-Garibay, Neil K. Garg. Discovery and Total Synthesis of a Bis(cyclotryptamine) Alkaloid Bearing the Elusive Piperidinoindoline Scaffold. Journal of the American Chemical Society 2020, 142 (27) , 11685-11690. https://doi.org/10.1021/jacs.0c04760
    5. Petra Lindovska and Mohammad Movassaghi . Concise Synthesis of (−)-Hodgkinsine, (−)-Calycosidine, (−)-Hodgkinsine B, (−)-Quadrigemine C, and (−)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines. Journal of the American Chemical Society 2017, 139 (48) , 17590-17596. https://doi.org/10.1021/jacs.7b09929
    6. Luiz C. Klein-Júnior, Sylvian Cretton, Pierre-Marie Allard, Grégory Genta-Jouve, Carolina S. Passos, Juliana Salton, Pablo Bertelli, Marion Pupier, Damien Jeannerat, Yvan Vander Heyden, André L. Gasper, Jean-Luc Wolfender, Philippe Christen, and Amélia T. Henriques . Targeted Isolation of Monoterpene Indole Alkaloids from Palicourea sessilis. Journal of Natural Products 2017, 80 (11) , 3032-3037. https://doi.org/10.1021/acs.jnatprod.7b00681
    7. Yu Peng, Long Luo, Chang-Song Yan, Jian-Jian Zhang, and Ya-Wen Wang . Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room Temperature and Its Synthetic Application. The Journal of Organic Chemistry 2013, 78 (21) , 10960-10967. https://doi.org/10.1021/jo401936v
    8. Xiao-Ning Li, Yu Zhang, Xiang-Hai Cai, Tao Feng, Ya-Ping Liu, Yan Li, Jie Ren, Hua-Jie Zhu, and Xiao-Dong Luo . Psychotripine: A New Trimeric Pyrroloindoline Derivative from Psychotria pilifera. Organic Letters 2011, 13 (21) , 5896-5899. https://doi.org/10.1021/ol202536b
    9. Mohammad Movassaghi, Omar K. Ahmad, and Stephen P. Lathrop . Directed Heterodimerization: Stereocontrolled Assembly via Solvent-Caged Unsymmetrical Diazene Fragmentation. Journal of the American Chemical Society 2011, 133 (33) , 13002-13005. https://doi.org/10.1021/ja2057852
    10. Jae Hong Seo,, Gerald D. Artman, III, and, Steven M. Weinreb. Synthetic Studies on Perophoramidine and the Communesins:  Construction of the Vicinal Quaternary Stereocenters. The Journal of Organic Chemistry 2006, 71 (23) , 8891-8900. https://doi.org/10.1021/jo061660a
    11. Ilias Muhammad,, D. Chuck Dunbar,, Shabana I. Khan,, Babu L. Tekwani,, Erdal Bedir,, Satoshi Takamatsu,, Daneel Ferreira, and, Larry A. Walker. Antiparasitic Alkaloids from Psychotria klugii. Journal of Natural Products 2003, 66 (7) , 962-967. https://doi.org/10.1021/np030086k
    12. Alec D. Lebsack,, J. T. Link,, Larry E. Overman, and, Brian A. Stearns. Enantioselective Total Synthesis of Quadrigemine C and Psycholeine. Journal of the American Chemical Society 2002, 124 (31) , 9008-9009. https://doi.org/10.1021/ja0267425
    13. Gary E. Martin and, Chad E. Hadden. Long-Range 1H−15N Heteronuclear Shift Correlation at Natural Abundance. Journal of Natural Products 2000, 63 (4) , 543-585. https://doi.org/10.1021/np9903191
    14. Larry E. Overman,, Daniel V. Paone, and, Brian A. Stearns. Direct Stereo- and Enantiocontrolled Synthesis of Vicinal Stereogenic Quaternary Carbon Centers. Total Syntheses of meso- and (−)-Chimonanthine and (+)-Calycanthine. Journal of the American Chemical Society 1999, 121 (33) , 7702-7703. https://doi.org/10.1021/ja991714g
    15. Arindam Khatua, Pranay Shyamal, Monosij Nandy, Debabrata Mondal, Kundan Shaw, Alakesh Bisai. Synthetic Approaches to Dimeric and Oligomeric Hexahydropyrrolo[2,3‐ b ]indole Alkaloids. Chemistry – An Asian Journal 2025, 34 https://doi.org/10.1002/asia.202401424
    16. Hélio Nitta Matsuura, Diogo Denardi Porto, Yve Verônica da Silva Magedans, Camila Fernanda Oliveira Junkes, Arthur Germano Fett-Neto. Bioactive Alkaloids from South American Rubiaceae with Emphasis on Psychotria and Related Genera. 2025, 1-33. https://doi.org/10.1007/978-3-642-36202-6_101-1
    17. Adrija Ghosh, Vishal Kumar Parida, Debasis Banerjee. Challenges and opportunities on sustainable electrochemical transformations: application towards the synthesis of pharmaceuticals and precursors of drug-like molecules. Green Chemistry 2024, 26 (10) , 5770-5789. https://doi.org/10.1039/D3GC04881K
    18. Tien Dong Tran, Anh Tuan Le, Dat Van Tran, Thang Quoc Le, Ty Viet Pham. Essential oil of the leaves of psychotria asiatica L.: chemical composition, antioxidant, anti-inflammatory, and cytotoxic properties. Natural Product Research 2024, 27 , 1-6. https://doi.org/10.1080/14786419.2024.2341286
    19. Anna Wójcicka. Synthesis and Biological Activity of 2,6-Naphthyridine Derivatives: A Mini Review. Current Organic Chemistry 2023, 27 (8) , 648-660. https://doi.org/10.2174/1385272827666230519165336
    20. Andreas Berger, Karin Valant-Vetschera, Johann Schinnerl, Lothar Brecker. A revised classification of the sister tribes Palicoureeae and Psychotrieae (Rubiaceae) indicates genus-specific alkaloid accumulation. Phytochemistry Reviews 2022, 21 (3) , 941-986. https://doi.org/10.1007/s11101-021-09769-x
    21. Arindam Khatua, Pranay Shyamal, Souvik Pal, Ayan Mondal, Alakesh Bisai. Concise total syntheses of bis(cyclotryptamine) alkaloids via thio-urea catalyzed one-pot sequential Michael addition. Chemical Communications 2022, 58 (24) , 3929-3932. https://doi.org/10.1039/D2CC01008A
    22. Sourav Kundu, Mintu Munda, Rhituparna Nandi, Alakesh Bisai. Pd(0)‐Catalyzed Deacylative Allylations (DaA) Strategy and Application in the Total Synthesis of Alkaloids. The Chemical Record 2021, 21 (12) , 3818-3838. https://doi.org/10.1002/tcr.202100267
    23. Craig A. Johnston, David B. Cordes, Tomas Lebl, Alexandra M. Z. Slawin, Nicholas J. Westwood. Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates. Molecules 2021, 26 (19) , 6039. https://doi.org/10.3390/molecules26196039
    24. Douglas Costa Gontijo, Maria Fernanda Alves do Nascimento, Hugo Vianna Silva Rody, Rodrigo Andrade Magalhães, Luciano Ferreira Margalho, Geraldo Célio Brandão, Alaíde Braga de Oliveira. In vitro antiplasmodial activity, targeted LC–MS metabolite profiling, and identification of major natural products in the bioactive extracts of Palicourea and Psychotria species from the Amazonia and Atlantic Forest biomes, Brazil. Metabolomics 2021, 17 (9) https://doi.org/10.1007/s11306-021-01833-z
    25. Gabriela Chabowska, Ewa Barg, Anna Wójcicka. Biological Activity of Naturally Derived Naphthyridines. Molecules 2021, 26 (14) , 4324. https://doi.org/10.3390/molecules26144324
    26. Amritpal Singh Saroya, Jaswinder Singh. Description of Psychoactive Medicinal Plants. 2020, 15-106. https://doi.org/10.1007/978-981-15-2313-7_3
    27. Erick Paul Gutiérrez-Grijalva, Leticia Xochitl López-Martínez, Laura Aracely Contreras-Angulo, Cristina Alicia Elizalde-Romero, José Basilio Heredia. Plant Alkaloids: Structures and Bioactive Properties. 2020, 85-117. https://doi.org/10.1007/978-981-15-2361-8_5
    28. Almir Ribeiro de Carvalho Junior, Rafaela Oliveira Ferreira, Michel de Souza Passos, Samyra Imad da Silva Boeno, Lorena de Lima Glória das Virgens, Thatiana Lopes Biá Ventura, Sanderson Dias Calixto, Elena Lassounskaia, Mario Geraldo de Carvalho, Raimundo Braz-Filho, Ivo Jose Curcino Vieira. Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra. Molecules 2019, 24 (6) , 1026. https://doi.org/10.3390/molecules24061026
    29. Alakesh Bisai, Vishnumaya Bisai. Protecting‐Group‐Free Synthesis of Natural Products and Analogs, Part III. 2018, 87-131. https://doi.org/10.1002/9781119295266.ch4
    30. Shu-Min Bai, Hong-Mei Ren, Guo-Jun Zheng, Guang Chen. Senobtusin, a novel alkaloid with amidine moiety from Senecio obtusatus Wall. ex DC. Natural Product Research 2017, 31 (20) , 2450-2453. https://doi.org/10.1080/14786419.2017.1309532
    31. Lin Wu, Qian-Ru Zhang, Ji-Rong Huang, Yang Li, Fu Su, Lin Dong. The application of Morita-Baylis-Hillman reaction: Synthetic studies on perophoramidine. Tetrahedron 2017, 73 (27-28) , 3966-3972. https://doi.org/10.1016/j.tet.2017.05.067
    32. Almir Carvalho Junior, Ivo Vieira, Mario Carvalho, Raimundo Braz-Filho, Mary S. Lima, Rafaela Ferreira, Edmilson José Maria, Daniela Oliveira. 13C-NMR Spectral Data of Alkaloids Isolated from Psychotria Species (Rubiaceae). Molecules 2017, 22 (1) , 103. https://doi.org/10.3390/molecules22010103
    33. Hongmei Yang, Hongmei Zhang, Caiqiong Yang, Yegao Chen. Chemical Constituents of Plants from the Genus Psychotria. Chemistry & Biodiversity 2016, 13 (7) , 807-820. https://doi.org/10.1002/cbdv.201500259
    34. Marcos A. dos S. Ribeiro, Carla M.B. Gomes, Anelise S.N. Formagio, Zefa V. Pereira, Ulisses Z. Melo, Ernani A. Basso, Willian F. da Costa, Débora C. Baldoqui, Maria H. Sarragiotto. Structural characterization of dimeric indole alkaloids from Psychotria brachybotrya by NMR spectroscopy and theoretical calculations. Tetrahedron Letters 2016, 57 (12) , 1331-1334. https://doi.org/10.1016/j.tetlet.2016.02.040
    35. Juan C. Santos, Rebecca D. Tarvin, Lauren A. O’Connell. A Review of Chemical Defense in Poison Frogs (Dendrobatidae): Ecology, Pharmacokinetics, and Autoresistance. 2016, 305-337. https://doi.org/10.1007/978-3-319-22026-0_21
    36. A.R. de Carvalho, M.G. de Carvalho, R. Braz-Filho, I.J.C. Vieira. Psychotria Genus. 2016, 231-261. https://doi.org/10.1016/B978-0-444-63602-7.00007-2
    37. Barry M. Trost, Maksim Osipov. Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine. Chemistry – A European Journal 2015, 21 (46) , 16318-16343. https://doi.org/10.1002/chem.201501735
    38. Stephen M. Canham, Benjamin D. Hafensteiner, Alec D. Lebsack, Tricia L. May-Dracka, Sangkil Nam, Brian A. Stearns, Larry E. Overman. Stereocontrolled enantioselective total synthesis of the [2+2] quadrigemine alkaloids. Tetrahedron 2015, 71 (37) , 6424-6436. https://doi.org/10.1016/j.tet.2015.02.080
    39. Guang-Lei Ma, Guo-Xun Yang, Juan Xiong, Wen-Liang Cheng, Ke-Jun Cheng, Jin-Feng Hu. Salicifoxazines A and B, new cytotoxic tetrahydro-1,2-oxazine-containing tryptamine-derived alkaloids from the leaves of Chimonanthus salicifolius. Tetrahedron Letters 2015, 56 (27) , 4071-4075. https://doi.org/10.1016/j.tetlet.2015.05.008
    40. Daiane Martins, Cecilia Nunez. Secondary Metabolites from Rubiaceae Species. Molecules 2015, 20 (7) , 13422-13495. https://doi.org/10.3390/molecules200713422
    41. Anelise Formagio, Carla Volobuff, Matheus Santiago, Claudia Cardoso, Maria Vieira, Zefa Valdevina Pereira. Evaluation of Antioxidant Activity, Total Flavonoids, Tannins and Phenolic Compounds in Psychotria Leaf Extracts. Antioxidants 2014, 3 (4) , 745-757. https://doi.org/10.3390/antiox3040745
    42. Beatriz Pereira Moreno, Letycia Lopes Ricardo Fiorucci, Marta Regina Barrotto do Carmo, Maria Helena Sarragiotto, Debora Cristina Baldoqui. Terpenoids and a coumarin from aerial parts of Psychotria vellosiana Benth. (Rubiaceae). Biochemical Systematics and Ecology 2014, 56 , 80-82. https://doi.org/10.1016/j.bse.2014.04.013
    43. Qinpei Lu, Junsong Wang, Lingyi Kong. Chemical constituents from Psychotria yunnanensis and its chemotaxonomic study. Biochemical Systematics and Ecology 2014, 52 , 20-22. https://doi.org/10.1016/j.bse.2013.11.002
    44. Mitsuhiro Wada, Takahisa Murata, Hideaki Oikawa, Hiroki Oguri. Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: systematic access to chimonanthines, folicanthines and (+)-WIN 64821. Org. Biomol. Chem. 2014, 12 (2) , 298-306. https://doi.org/10.1039/C3OB41918E
    45. Anderson Marques de Oliveira, Rosangela P. Lyra Lemos, Lucia M. Conserva. β-Carboline alkaloids from Psychotria barbiflora DC. (Rubiaceae). Biochemical Systematics and Ecology 2013, 50 , 339-341. https://doi.org/10.1016/j.bse.2013.04.015
    46. Shinji Tadano, Yuri Mukaeda, Hayato Ishikawa. Bio‐Inspired Dimerization Reaction of Tryptophan Derivatives in Aqueous Acidic Media: Three‐Step Syntheses of (+)‐WIN 64821, (−)‐Ditryptophenaline, and (+)‐Naseseazine B. Angewandte Chemie 2013, 125 (31) , 8148-8152. https://doi.org/10.1002/ange.201303143
    47. Shinji Tadano, Yuri Mukaeda, Hayato Ishikawa. Bio‐Inspired Dimerization Reaction of Tryptophan Derivatives in Aqueous Acidic Media: Three‐Step Syntheses of (+)‐WIN 64821, (−)‐Ditryptophenaline, and (+)‐Naseseazine B. Angewandte Chemie International Edition 2013, 52 (31) , 7990-7994. https://doi.org/10.1002/anie.201303143
    48. Hélio Nitta Matsuura, Diogo Denardi Porto, Arthur Germano Fett-Neto. Bioactive Alkaloids from South American Psychotria and Related Rubiaceae. 2013, 119-147. https://doi.org/10.1007/978-3-642-22144-6_101
    49. Robert H. Snell, Matthew J. Durbin, Robert L. Woodward, Michael C. Willis. Catalytic Enantioselective Desymmetrisation as a Tool for the Synthesis of Hodgkinsine and Hodgkinsine B. Chemistry – A European Journal 2012, 18 (52) , 16754-16764. https://doi.org/10.1002/chem.201203150
    50. George Brand, Amélia T. Henriques, Carolina dos S. Passos, Débora C. Baldoqui, Silvana M. de Oliveira Santin, Willian Ferreira da Costa, Maria Helena Sarragiotto. Pyrrolidinoindoline alkaloids from Margaritopsis cymuligera (Muell. Arg.) C.M. Taylor (Rubiaceae). Biochemical Systematics and Ecology 2012, 45 , 155-157. https://doi.org/10.1016/j.bse.2012.07.009
    51. Cui-Xian Zhang, Xi-Xin He, Shan-Yue Guan, Ying Zhong, Chao-Zhan Lin, Tian-Qin Xiong, Chen-Chen Zhu. New sphingolipid psychotramide A–D from the stem of Psychotria sp.. Natural Product Research 2012, 26 (20) , 1864-1868. https://doi.org/10.1080/14786419.2011.617747
    52. Pau Ruiz‐Sanchis, Svetlana A. Savina, Gerardo A. Acosta, Fernando Albericio, Mercedes Álvarez. Orthogonal Protecting Groups in the Synthesis of Tryptophanyl‐Hexahydropyrroloindoles. European Journal of Organic Chemistry 2012, 2012 (1) , 67-73. https://doi.org/10.1002/ejoc.201101057
    53. Robert H. Snell, Robert L. Woodward, Michael C. Willis. Catalytic Enantioselective Total Synthesis of Hodgkinsine B. Angewandte Chemie 2011, 123 (39) , 9282-9285. https://doi.org/10.1002/ange.201103864
    54. Robert H. Snell, Robert L. Woodward, Michael C. Willis. Catalytic Enantioselective Total Synthesis of Hodgkinsine B. Angewandte Chemie International Edition 2011, 50 (39) , 9116-9119. https://doi.org/10.1002/anie.201103864
    55. Sarah M. Bronner, G.‐Yoon J. Im, Neil K. Garg. Indoles and Indolizidines. 2011, 221-265. https://doi.org/10.1002/9783527634880.ch7
    56. Pau Ruiz‐Sanchis, Svetlana A. Savina, Fernando Albericio, Mercedes Álvarez. Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐ b ]indole. Chemistry – A European Journal 2011, 17 (5) , 1388-1408. https://doi.org/10.1002/chem.201001451
    57. Emiret O. Faria, Lucilia Kato, Cecília M.A. de Oliveira, Brenda G. Carvalho, Cleuza C. Silva, Lilian S. Sales, Ivânia T.A. Schuquel, Elisângela P. Silveira-Lacerda, Piero G. Delprete. Quaternary β-carboline alkaloids from Psychotria prunifolia (Kunth) Steyerm.. Phytochemistry Letters 2010, 3 (3) , 113-116. https://doi.org/10.1016/j.phytol.2010.02.008
    58. Antonia Ávila Torres Pimenta, Raimundo Braz-Filho, Piero Giuseppe Delprete, Elnatan Bezerra de Souza, Edilberto Rocha Silveira, Mary Anne Sousa Lima. Unusual monoterpene indole alkaloids from Psychotria stachyoides Benth. Biochemical Systematics and Ecology 2010, 38 (4) , 846-849. https://doi.org/10.1016/j.bse.2010.07.013
    59. Liangfeng Fu. Advances in the Total Syntheses of Complex Indole Natural Products. 2010, 433-480. https://doi.org/10.1007/7081_2010_49
    60. Diogo D. Porto, Amélia T. Henriques, Arthur G. Fett-Neto. Bioactive Alkaloids from South American Psychotria and Related Species. The Open Bioactive Compounds Journal 2009, 2 (1) , 29-36. https://doi.org/10.2174/1874847300902010029
    61. Hiroshi Takeda, Takayuki Ishida, Yoshiji Takemoto. Synthesis of Indolo[2,3- b ]quinolines by Palladium-catalyzed Annulation of Unsaturated Isothioureas. Chemistry Letters 2009, 38 (8) , 772-773. https://doi.org/10.1246/cl.2009.772
    62. Michael A. Evans, Joshua R. Sacher, Steven M. Weinreb. Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine. Tetrahedron 2009, 65 (33) , 6712-6719. https://doi.org/10.1016/j.tet.2008.10.060
    63. Ji‐Wen Zhang, Jin‐Ming Gao, Tian Xu, Xing‐Chang Zhang, Ya‐Tuan Ma, Suwatchai Jarussophon, Yasuo Konishi. Antifungal Activity of Alkaloids from the Seeds of Chimonanthus praecox. Chemistry & Biodiversity 2009, 6 (6) , 838-845. https://doi.org/10.1002/cbdv.200800089
    64. Gary E. Martin, Marina Solntseva, Antony J. Williams. Applications of 15 N NMR Spectroscopy in Alkaloid Chemistry. 2007, 409-471. https://doi.org/10.1002/9783527621071.ch14
    65. Alan Steven, Larry E. Overman. Totalsynthese komplexer Cyclotryptaminalkaloide: stereokontrollierter Aufbau quartärer Kohlenstoffstereozentren. Angewandte Chemie 2007, 119 (29) , 5584-5605. https://doi.org/10.1002/ange.200700612
    66. Alan Steven, Larry E. Overman. Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters. Angewandte Chemie International Edition 2007, 46 (29) , 5488-5508. https://doi.org/10.1002/anie.200700612
    67. Egidio Giorgio, Katsunori Tanaka, Luisella Verotta, Koji Nakanishi, Nina Berova, Carlo Rosini. Determination of the absolute configurations of flexible molecules: Synthesis and theoretical simulation of electronic circular dichroism/optical rotation of some pyrrolo[2,3‐ b ]indoline alkaloids—A case study. Chirality 2007, 19 (6) , 434-445. https://doi.org/10.1002/chir.20395
    68. Peter I. Dalko, Candice Menozzi, Janine Cossy. Studies on Enol Carbonate Chemistry: Stereoselective Construction of Vicinal Quaternary Benzylic Centers in the Bis-oxindole Series. HETEROCYCLES 2007, 72 (1) , 199. https://doi.org/10.3987/COM-07-S(K)59
    69. Jeremy A. May, Brian Stoltz. The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids, the communesins, and nomofungin. Tetrahedron 2006, 62 (22) , 5262-5271. https://doi.org/10.1016/j.tet.2006.01.105
    70. Toh-Seok Kam, Yeun-Mun Choo. Chapter 4 Bisindole Alkaloids. 2006, 181-337. https://doi.org/10.1016/S1099-4831(06)63004-6
    71. Candice Menozzi, Peter I. Dalko, Janine Cossy. Concise synthesis of the (±)-N b -desmethyl-meso-chimonanthine. Chem. Commun. 2006, 93 (44) , 4638-4640. https://doi.org/10.1039/B610497E
    72. Sílvia Lopes, Gilsane L. von Poser, Vitor A. Kerber, Fabiane M. Farias, Eduardo L. Konrath, Paulo Moreno, Marcos E. Sobral, José A.S. Zuanazzi, Amélia T. Henriques. Taxonomic significance of alkaloids and iridoid glucosides in the tribe Psychotrieae (Rubiaceae). Biochemical Systematics and Ecology 2004, 32 (12) , 1187-1195. https://doi.org/10.1016/j.bse.2004.04.015
    73. Joel F. Austin, Sung-Gon Kim, Christopher J. Sinz, Wen-Jing Xiao, David W. C. MacMillan. Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B. Proceedings of the National Academy of Sciences 2004, 101 (15) , 5482-5487. https://doi.org/10.1073/pnas.0308177101
    74. Hiromitsu Takayama, Yohei Matsuda, Kyohei Masubuchi, Atsushi Ishida, Mariko Kitajima, Norio Aimi. Isolation, structure elucidation, and total synthesis of two new Chimonanthus alkaloids, chimonamidine and chimonanthidine. Tetrahedron 2004, 60 (4) , 893-900. https://doi.org/10.1016/j.tet.2003.11.034
    75. Débora Gomes Agripino, Marcos Enoque Leite Lima, Marcelo Rogério da Silva, Cristiane Infante Meda, Vanderlan da Silva Bolzani, Inês Cordeiro, Maria Claudia Marx Young, Paulo Roberto H. Moreno. Screening of Brazilian plants for antimicrobial and dnadamaging activities: I. Atlantic rain forest . Ecological station juréia-itatins. Biota Neotropica 2004, 4 (2) , 1-15. https://doi.org/10.1590/S1676-06032004000200009
    76. Jeremy J. Kodanko, Larry E. Overman. Enantioselective Total Syntheses of the Cyclotryptamine Alkaloids Hodgkinsine and Hodgkinsine B. Angewandte Chemie 2003, 115 (22) , 2632-2635. https://doi.org/10.1002/ange.200351261
    77. Jeremy J. Kodanko, Larry E. Overman. Enantioselective Total Syntheses of the Cyclotryptamine Alkaloids Hodgkinsine and Hodgkinsine B. Angewandte Chemie International Edition 2003, 42 (22) , 2528-2531. https://doi.org/10.1002/anie.200351261
    78. Hayato Ishikawa, Hiromitsu Takayama, Norio Aimi. Dimerization of indole derivatives with hypervalent iodines(III): a new entry for the concise total synthesis of rac- and meso-chimonanthines. Tetrahedron Letters 2002, 43 (32) , 5637-5639. https://doi.org/10.1016/S0040-4039(02)01137-1
    79. L Verotta, F Orsini, M Sbacchi, M.A Scheildler, T.A Amador, E Elisabetsky. Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-Type alkaloids. Bioorganic & Medicinal Chemistry 2002, 10 (7) , 2133-2142. https://doi.org/10.1016/S0968-0896(02)00078-0
    80. Elaine Elisabetsky. Traditional medicines and the new paradigm of psychotropic drug action. 2002, 133-144. https://doi.org/10.1016/S1572-557X(02)80020-4
    81. T.A. Amador, L. Verotta, D.S. Nunes, E. Elisabetsky. Involvement of nmda receptors in the analgesicproperties of psychotridine. Phytomedicine 2001, 8 (3) , 202-206. https://doi.org/10.1078/0944-7113-00025
    82. Larry E. Overman, Jay F. Larrow, Brian A. Stearns, Jennifer M. Vance. Enantioselective Construction of Vicinal Stereogenic Quaternary Centers by Dialkylation: Practical Total Syntheses of (+)- andmeso-Chimonanthine. Angewandte Chemie 2000, 112 (1) , 219-221. https://doi.org/10.1002/(SICI)1521-3757(20000103)112:1<219::AID-ANGE219>3.0.CO;2-V
    83. Hiroyuki Koshino, Yoshiki Kono, Katsuyoshi Yoneyama, Jun Uzawa. 15N Nmr Study of Toxoflavin and Fervenulin. HETEROCYCLES 2000, 52 (2) , 811. https://doi.org/10.3987/COM-99-S90
    84. L Verotta, F Peterlongo, Elaine Elisabetsky, Tania A Amador, D.S Nunes. High-performance liquid chromatography–diode array detection–tandem mass spectrometry analyses of the alkaloid extracts of Amazon Psychotria species. Journal of Chromatography A 1999, 841 (2) , 165-176. https://doi.org/10.1016/S0021-9673(99)00298-8
    85. Radek Marek, Otakar Humpa, Jiří Dostál, Jiří Slavík, Vladimír Sklenář. 15N NMR study of isoquinoline alkaloids. Magnetic Resonance in Chemistry 1999, 37 (3) , 195-202. https://doi.org/10.1002/(SICI)1097-458X(199903)37:3<195::AID-MRC435>3.0.CO;2-D

    Journal of Natural Products

    Cite this: J. Nat. Prod. 1998, 61, 3, 392–396
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np9701642
    Published February 25, 1998
    Copyright © 1998 American Chemical Society and American Society of Pharmacognosy

    Article Views

    1187

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.