Literature DB >> 24159245

A cytotoxic dimeric furanoheliangolide from Piptocoma rufescens.

Yulin Ren1, Francisco Jiménez, Ricardo García, Milciades Mejía, Heebyung Chai, Norman R Farnsworth, Djaja D Soejarto, A Douglas Kinghorn.   

Abstract

A new sesquiterpene lactone, rufescenolide C (1), the first furanoheliangolide dimer, was isolated from the leaves of Piptocoma rufescens, collected in the Dominican Republic. Its structure was determined by analysis of its spectroscopic data, with the absolute configuration being established by analysis of the CD spectrum. A plausible biogenesis of this dimer is proposed. This compound showed potent cytotoxicity with an IC50 value of 150 nM, when tested against HT-29 human colon cancer cells.

Entities:  

Keywords:  Cytotoxicity; Furanoheliangolide dimer; Piptocoma rufescens

Year:  2013        PMID： 24159245      PMCID： PMC3804354          DOI： 10.1016/j.tetlet.2013.07.128

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  25 in total

1.  NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities.

Authors:  Hugo E. Gottlieb; Vadim Kotlyar; Abraham Nudelman
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

2.  The crystal structure of biatractylolide, an 8,8' (C-C) linked dimeric 12,8-eudesmanolide from the resin of Trattinickia rhoifolia WILLD.

Authors:  Carmelo Rosquete; Esther Del Olmo; Francisca Sanz; Arturo San Feliciano
Journal:  Chem Pharm Bull (Tokyo)       Date:  2002-07       Impact factor: 1.645

3.  Cytotoxic and NF-κB inhibitory sesquiterpene lactones from Piptocoma rufescens.

Authors:  Yulin Ren; Ulyana Muñoz Acuña; Francisco Jiménez; Ricardo García; Melciades Mejía; Heebyung Chai; Judith C Gallucci; Norman R Farnsworth; Djaja D Soejarto; Esperanza J Carcache de Blanco; A Douglas Kinghorn
Journal:  Tetrahedron       Date:  2012-01-26       Impact factor: 2.457

4.  Guaiane sesquiterpene lactones from Salvia nubicola (Lamiaceae).

Authors:  Muhammad S Ali; Syed A Ibrahim; Shakeel Ahmed; Emil Lobkovsky
Journal:  Chem Biodivers       Date:  2007-01       Impact factor: 2.408

5.  A bis-sesquiterpene and sesquiterpenolides from Inula macrophylla.

Authors:  B Fu; B N Su; Y Takaishi; G Honda; M Ito; Y Takeda; O K Kodzhimatov; O Ashurmetov
Journal:  Phytochemistry       Date:  2001-12       Impact factor: 4.072

6.  Malaria-infected mice are cured by a single oral dose of new dimeric trioxane sulfones which are also selectively and powerfully cytotoxic to cancer cells.

Authors:  Andrew S Rosenthal; Xiaochun Chen; Jun O Liu; Diana C West; Paul J Hergenrother; Theresa A Shapiro; Gary H Posner
Journal:  J Med Chem       Date:  2009-02-26       Impact factor: 7.446

7.  New sesquiterpenoids from the New Zealand liverwort Chiloscyphus subporosus.

Authors:  Fumihiro Nagashima; Moyoko Murakami; Shigeru Takaoka; Yoshinori Asakawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  2004-08       Impact factor: 1.645

8.  Japonicones A-D, bioactive dimeric sesquiterpenes from Inula japonica Thunb.

Authors:  Jiang Jiang Qin; Hui Zi Jin; Jian Jun Fu; Xiao Jia Hu; Yan Wang; Shi Kai Yan; Wei Dong Zhang
Journal:  Bioorg Med Chem Lett       Date:  2008-12-14       Impact factor: 2.823

9.  Japonicones E-L, dimeric sesquiterpene lactones from Inula japonica Thunb.

Authors:  Jiang Jiang Qin; Hui Zi Jin; Jia Xian Zhu; Jian Jun Fu; Xiao Jia Hu; Xiao Hua Liu; Yan Zhu; Shi Kai Yan; Wei Dong Zhang
Journal:  Planta Med       Date:  2009-09-09       Impact factor: 3.352

10.  An artemisinin-derived dimer has highly potent anti-cytomegalovirus (CMV) and anti-cancer activities.

Authors:  Ran He; Bryan T Mott; Andrew S Rosenthal; Douglas T Genna; Gary H Posner; Ravit Arav-Boger
Journal:  PLoS One       Date:  2011-08-31       Impact factor: 3.240
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  5 in total

Review 1.  Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones.

Authors:  Yulin Ren; Jianhua Yu; A Douglas Kinghorn
Journal:  Curr Med Chem       Date:  2016       Impact factor: 4.530

2.  Potential Anticancer Agents Characterized from Selected Tropical Plants.

Authors:  Yulin Ren; Esperanza J Carcache de Blanco; James R Fuchs; Djaja D Soejarto; Joanna E Burdette; Steven M Swanson; A Douglas Kinghorn
Journal:  J Nat Prod       Date:  2019-03-04       Impact factor: 4.050

3.  Antiproliferative and antimalarial sesquiterpene lactones from Piptocoma antillana from Puerto Rico.

Authors:  Yixi Liu; L Harinantenaina Rakotondraibea; Peggy J Brodie; Jessica D Wiley; Maria B Cassera; Michael Goetzc; David G I Kingstona
Journal:  Nat Prod Commun       Date:  2014-10       Impact factor: 0.986

4.  Crystal Structures and Human Leukemia Cell Apoptosis Inducible Activities of Parthenolide Analogues Isolated from Piptocoma rufescens.

Authors:  Yulin Ren; Judith C Gallucci; Xinxin Li; Lichao Chen; Jianhua Yu; A Douglas Kinghorn
Journal:  J Nat Prod       Date:  2018-01-19       Impact factor: 4.050

5.  Induction of G2/M arrest and apoptosis through mitochondria pathway by a dimer sesquiterpene lactone from Smallanthus sonchifolius in HeLa cells.

Authors:  Yurika Kitai; Xia Zhang; Yushi Hayashida; Yoshiyuki Kakehi; Hirotoshi Tamura
Journal:  J Food Drug Anal       Date:  2016-12-01       Impact factor: 6.157
  5 in total

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