Literature DB >> 26295461

Sesterterpenoids with Anticancer Activity.

Antonio Evidente1, Alexander Kornienko, Florence Lefranc, Alessio Cimmino, Ramesh Dasari, Marco Evidente, Véronique Mathieu, Robert Kiss.   

Abstract

Terpenes have received a great deal of attention in the scientific literature due to complex, synthetically challenging structures and diverse biological activities associated with this class of natural products. Based on the number of C5 isoprene units they are generated from, terpenes are classified as hemi- (C5), mono- (C10), sesqui- (C15), di- (C20), sester- (C25), tri (C30), and tetraterpenes (C40). Among these, sesterterpenes and their derivatives known as sesterterpenoids, are ubiquitous secondary metabolites in fungi, marine organisms, and plants. Their structural diversity encompasses carbotricyclic ophiobolanes, polycyclic anthracenones, polycyclic furan-2-ones, polycyclic hydroquinones, among many other carbon skeletons. Furthermore, many of them possess promising biological activities including cytotoxicity and the associated potential as anticancer agents. This review discusses the natural sources that produce sesterterpenoids, provides sesterterpenoid names and their chemical structures, biological properties with the focus on anticancer activities and literature references associated with these metabolites. A critical summary of the potential of various sesterterpenoids as anticancer agents concludes the review.

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Year:  2015        PMID: 26295461      PMCID: PMC4955362          DOI: 10.2174/0929867322666150821101047

Source DB:  PubMed          Journal:  Curr Med Chem        ISSN: 0929-8673            Impact factor:   4.530


  70 in total

1.  Herbicidal potential of ophiobolins produced by Drechslera gigantea.

Authors:  Antonio Evidente; Anna Andolfi; Alessio Cimmino; Maurizio Vurro; Mariano Fracchiolla; Raghavan Charudattan
Journal:  J Agric Food Chem       Date:  2006-03-08       Impact factor: 5.279

2.  The novel agent ophiobolin O induces apoptosis and cell cycle arrest of MCF-7 cells through activation of MAPK signaling pathways.

Authors:  Tingting Yang; Zhenyu Lu; Li Meng; Shanjian Wei; Kui Hong; Weiming Zhu; Caiguo Huang
Journal:  Bioorg Med Chem Lett       Date:  2011-10-31       Impact factor: 2.823

3.  Gastrin exerts pleiotropic effects on human melanoma cell biology.

Authors:  Véronique Mathieu; Tatjana Mijatovic; Marc van Damme; Robert Kiss
Journal:  Neoplasia       Date:  2005-10       Impact factor: 5.715

4.  Hypoxia-selective growth inhibition of cancer cells by furospinosulin-1, a furanosesterterpene isolated from an Indonesian marine sponge.

Authors:  Masayoshi Arai; Takashi Kawachi; Andi Setiawan; Motomasa Kobayashi
Journal:  ChemMedChem       Date:  2010-11-08       Impact factor: 3.466

5.  Effects of ophiobolin a on ion leakage and hexose uptake by maize roots.

Authors:  C L Tipton; P V Paulsen; R E Betts
Journal:  Plant Physiol       Date:  1977-05       Impact factor: 8.340

6.  Anti-angiogenic activity of sesterterpenes; natural product inhibitors of FGF-2-induced angiogenesis.

Authors:  S Hussain; M Slevin; S Matou; N Ahmed; M Iqbal Choudhary; R Ranjit; D West; J Gaffney
Journal:  Angiogenesis       Date:  2008-03-11       Impact factor: 9.596

7.  Incorporation of ophiobolin a into novel chemoembolization particles for cancer cell treatment.

Authors:  Rachel Morrison; Chris Gardiner; Antonio Evidente; Robert Kiss; Helen Townley
Journal:  Pharm Res       Date:  2014-05-03       Impact factor: 4.200

8.  Ophiobolin A induces paraptosis-like cell death in human glioblastoma cells by decreasing BKCa channel activity.

Authors:  M Bury; A Girault; V Mégalizzi; S Spiegl-Kreinecker; V Mathieu; W Berger; A Evidente; A Kornienko; P Gailly; C Vandier; R Kiss
Journal:  Cell Death Dis       Date:  2013-03-28       Impact factor: 8.469

9.  The sodium pump alpha1 sub-unit: a disease progression-related target for metastatic melanoma treatment.

Authors:  Véronique Mathieu; Christine Pirker; Elisabeth Martin de Lassalle; Mathieu Vernier; Tatjana Mijatovic; Nancy DeNeve; Jean-François Gaussin; Mischael Dehoux; Florence Lefranc; Walter Berger; Robert Kiss
Journal:  J Cell Mol Med       Date:  2009-02-20       Impact factor: 5.310

10.  Ophiobolin-O reverses adriamycin resistance via cell cycle arrest and apoptosis sensitization in adriamycin-resistant human breast carcinoma (MCF-7/ADR) cells.

Authors:  Wenxia Sun; Cuiting Lv; Tonghan Zhu; Xue Yang; Shanjian Wei; Jieyin Sun; Kui Hong; Weiming Zhu; Caiguo Huang
Journal:  Mar Drugs       Date:  2013-11-14       Impact factor: 5.118

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  18 in total

Review 1.  Marine Mollusk-Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance.

Authors:  Maria Letizia Ciavatta; Florence Lefranc; Marianna Carbone; Ernesto Mollo; Margherita Gavagnin; Tania Betancourt; Ramesh Dasari; Alexander Kornienko; Robert Kiss
Journal:  Med Res Rev       Date:  2016-12-07       Impact factor: 12.944

Review 2.  Bioactive Compounds from Marine Heterobranchs.

Authors:  Conxita Avila; Carlos Angulo-Preckler
Journal:  Mar Drugs       Date:  2020-12-21       Impact factor: 5.118

3.  Antiproliferative Scalarane-Based Metabolites from the Red Sea Sponge Hyrtios erectus.

Authors:  Sameh S Elhady; Ahmed M Al-Abd; Ali M El-Halawany; Abdulrahman M Alahdal; Hashim A Hassanean; Safwat A Ahmed
Journal:  Mar Drugs       Date:  2016-07-08       Impact factor: 5.118

Review 4.  The Biological Activities of Sesterterpenoid-Type Ophiobolins.

Authors:  Wei Tian; Zixin Deng; Kui Hong
Journal:  Mar Drugs       Date:  2017-07-18       Impact factor: 5.118

5.  Ophiobolin A, a sesterpenoid fungal phytotoxin, displays different mechanisms of cell death in mammalian cells depending upon the cancer cell origin.

Authors:  Rachel Morrison; Tiffany Lodge; Antonio Evidente; Robert Kiss; Helen Townley
Journal:  Int J Oncol       Date:  2017-01-19       Impact factor: 5.650

6.  Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining reveals convergent evolution.

Authors:  Ancheng C Huang; Satria A Kautsar; Young J Hong; Marnix H Medema; Andrew D Bond; Dean J Tantillo; Anne Osbourn
Journal:  Proc Natl Acad Sci U S A       Date:  2017-07-03       Impact factor: 12.779

Review 7.  Killing cancer with platycodin D through multiple mechanisms.

Authors:  Muhammad Khan; Amara Maryam; He Zhang; Tahir Mehmood; Tonghui Ma
Journal:  J Cell Mol Med       Date:  2015-12-09       Impact factor: 5.310

8.  Phorbaketal A, Isolated from the Marine Sponge Phorbas sp., Exerts Its Anti-Inflammatory Effects via NF-κB Inhibition and Heme Oxygenase-1 Activation in Lipopolysaccharide-Stimulated Macrophages.

Authors:  Yun-Ji Seo; Kyung-Tae Lee; Jung-Rae Rho; Jung-Hye Choi
Journal:  Mar Drugs       Date:  2015-11-19       Impact factor: 5.118

9.  Diverged Plant Terpene Synthases Reroute the Carbocation Cyclization Path towards the Formation of Unprecedented 6/11/5 and 6/6/7/5 Sesterterpene Scaffolds.

Authors:  Ancheng C Huang; Young J Hong; Andrew D Bond; Dean J Tantillo; Anne Osbourn
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-28       Impact factor: 16.823

10.  Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification.

Authors:  Yuan-Fei Zhou; Hai-Xia Shi; Kun Hu; Jian-Wei Tang; Xing-Ren Li; Xue Du; Han-Dong Sun; Li-Song Wang; Jian-Xin Pu
Journal:  Molecules       Date:  2017-10-09       Impact factor: 4.411

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