Literature DB >> 22413911

Antineoplastic agents. 587. Isolation and structure of 3-epipancratistatin from Narcissus cv. Ice Follies.

George R Pettit1, Rui Tan, Guan-Hu Bao, Noeleen Melody, Dennis L Doubek, Song Gao, Jean-Charles Chapuis, Lee Williams.   

Abstract

Bioassay-guided (cancer cell line) separation of an extract prepared from n class="Species">Narcissus cv. Ice Follies (from The Netherlands) led to the isolation of a new Amaryllidaceae isocarbostiryl, 3-epipancratistatin (1b), as well as narciclasine (2). This Narcissus cultivar was found to be a good source of narciclasine. The structure of 1b was established by high-resolution mass and high-field 2D NMR spectroscopic analyses. Against a panel of murine and human cancer cell lines, 3-epipancratistatin (1b) led to cell growth inhibition (GI(50) 2.2-0.69 μg/mL) some 100× less than that found for pancratistatin (1a) and narciclasine (2), thereby revealing an important configurational requirement in 1a for strong cancer cell growth inhibition.
© 2012 American Chemical Society and American Society of Pharmacognosy

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Year:  2012        PMID: 22413911      PMCID: PMC3372531          DOI: 10.1021/np200862y

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  17 in total

1.  Alkaloid content of different bulb parts of Narcissus cv. Ice Follies.

Authors:  R M Moraes-Cerdeira; J K Bastos; C L Burandt; N P Nanayakkara; J Mikell; J D McChesney
Journal:  Planta Med       Date:  1997-02       Impact factor: 3.352

Review 2.  Chemistry, biology, and medicinal potential of narciclasine and its congeners.

Authors:  Alexander Kornienko; Antonio Evidente
Journal:  Chem Rev       Date:  2008-05-20       Impact factor: 60.622

3.  Antineoplastic agents 453. Synthesis of pancratistatin prodrugs.

Authors:  G R Pettit; B Orr; S Ducki
Journal:  Anticancer Drug Des       Date:  2000-12

4.  Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay(1a).

Authors:  G R Pettit; N Melody; D L Herald
Journal:  J Org Chem       Date:  2001-04-20       Impact factor: 4.354

5.  Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines.

Authors:  A Monks; D Scudiero; P Skehan; R Shoemaker; K Paull; D Vistica; C Hose; J Langley; P Cronise; A Vaigro-Wolff
Journal:  J Natl Cancer Inst       Date:  1991-06-05       Impact factor: 13.506

6.  Isolation of human cancer cell growth inhibitory, antimicrobial lateritin from a mixed fungal culture.

Authors:  Robin K Pettit; George R Pettit; Jung-Ping Xu; Christine A Weber; Linda A Richert
Journal:  Planta Med       Date:  2009-11-25       Impact factor: 3.352

7.  Synergy of Pancratistatin and Tamoxifen on breast cancer cells in inducing apoptosis by targeting mitochondria.

Authors:  Peter Siedlakowski; Amanda McLachlan-Burgess; Carly Griffin; Sridhar S Tirumalai; James McNulty; Siyaram Pandey
Journal:  Cancer Biol Ther       Date:  2007-12-02       Impact factor: 4.742

Review 8.  Discovery of natural product anticancer agents from biodiverse organisms.

Authors:  A Douglas Kinghorn; Young-Won Chin; Steven M Swanson
Journal:  Curr Opin Drug Discov Devel       Date:  2009-03

9.  Antineoplastic agents. 511. Direct phosphorylation of phenpanstatin and pancratistatin.

Authors:  George R Pettit; Noeleen Melody; Delbert L Herald
Journal:  J Nat Prod       Date:  2004-03       Impact factor: 4.050

10.  Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents.

Authors:  Laurent Ingrassia; Florence Lefranc; Janique Dewelle; Laurent Pottier; Véronique Mathieu; Sabine Spiegl-Kreinecker; Sébastien Sauvage; Mohamed El Yazidi; Mischaël Dehoux; Walter Berger; Eric Van Quaquebeke; Robert Kiss
Journal:  J Med Chem       Date:  2009-02-26       Impact factor: 7.446

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  3 in total

1.  Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.

Authors:  Sergey Vshyvenko; Jon Scattolon; Tomas Hudlicky; Anntherese E Romero; Alexander Kornienko; Dennis Ma; Ian Tuffley; Siyaram Pandey
Journal:  Can J Chem       Date:  2012-09-19       Impact factor: 1.118

2.  Asymmetric Entry into 10b-aza-Analogues of Amaryllidaceae Alkaloids Reveals a Pronounced Electronic Effect on Antiviral Activity.

Authors:  Carla E Brown; Tiffany Kong; James F Britten; Nick H Werstiuk; James McNulty; Leonardo D'Aiuto; Matthew Demers; Vishwajit L Nimgaonkar
Journal:  ACS Omega       Date:  2018-09-20

3.  Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity.

Authors:  Kateřina Breiterová; Darja Koutová; Jana Maříková; Radim Havelek; Jiří Kuneš; Martina Majorošová; Lubomír Opletal; Anna Hošťálková; Jaroslav Jenčo; Martina Řezáčová; Lucie Cahlíková
Journal:  Plants (Basel)       Date:  2020-01-22
  3 in total

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