Abstract
Secondary metabolites of marine invertebrates continue to attract the attention of organic chemists, biochemists, and pharmacologists due to their novel structures and potent biological activities. One such example is cephalostatin 1 isolated from the Indian Ocean hemichordate Cephalodiscus gilchristi, which exhibited remarkable cytotoxic activity against a broad spectrum of malignant tumor cells. Similar marine alkaloids (e.g. ritterazine G) were found in the lipophilic extract of the tunicate Ritterella tokioka collected off the coast of Japan. These very potent compounds, cephalostatins and ritterazines, belong to the large family of trisdecacyclic pyrazines, consisting of two steroid units. The two steroid halves of cephalostatin 1 and other highly cytotoxic members of the family are different. The biological activity of the dimeric steroid-pyrazine marine alkaloids and their limited availability coupled with the new and intriguing structure make them an attractive challenge for the synthetic organic chemists. A few years ago a group of cholestane glycosides was isolated from the bulbs of Ornithogalum saundersiae, a species of the lily family without any medicinal folkloric background. Similar glycosides were recently isolated from Galtonia candicans. The major component of the mixture of saponins, OSW-1, exhibited sub-nanomolar antineoplastic activity. While OSW-1 is exceptionally cytotoxic against various tumor cells, it showed little toxicity to normal human pulmonary cells. The cytotoxicity profile of OSW-1 against different cancer cell lines was found to be surprisingly similar to that of the cephalostatins, which appears to imply a related mechanism of action. In this review article the synthetic efforts towards these compounds are described.
Keywords: Cephalostatins, cytotoxicity, glycosides
Current Organic Chemistry
Title: Approaches Towards the Synthesis of Cephalostatins, Ritterazines and Saponins from Ornithogalum saundersiae - New Natural Products With Cytostatic Activity
Volume: 7 Issue: 12
Author(s): A. Gryszkiewicz-Wojtkielewicz, I. Jastrzebska, J. W. Morzycki and D. B. Romanowska
Affiliation:
Keywords: Cephalostatins, cytotoxicity, glycosides
Abstract: Secondary metabolites of marine invertebrates continue to attract the attention of organic chemists, biochemists, and pharmacologists due to their novel structures and potent biological activities. One such example is cephalostatin 1 isolated from the Indian Ocean hemichordate Cephalodiscus gilchristi, which exhibited remarkable cytotoxic activity against a broad spectrum of malignant tumor cells. Similar marine alkaloids (e.g. ritterazine G) were found in the lipophilic extract of the tunicate Ritterella tokioka collected off the coast of Japan. These very potent compounds, cephalostatins and ritterazines, belong to the large family of trisdecacyclic pyrazines, consisting of two steroid units. The two steroid halves of cephalostatin 1 and other highly cytotoxic members of the family are different. The biological activity of the dimeric steroid-pyrazine marine alkaloids and their limited availability coupled with the new and intriguing structure make them an attractive challenge for the synthetic organic chemists. A few years ago a group of cholestane glycosides was isolated from the bulbs of Ornithogalum saundersiae, a species of the lily family without any medicinal folkloric background. Similar glycosides were recently isolated from Galtonia candicans. The major component of the mixture of saponins, OSW-1, exhibited sub-nanomolar antineoplastic activity. While OSW-1 is exceptionally cytotoxic against various tumor cells, it showed little toxicity to normal human pulmonary cells. The cytotoxicity profile of OSW-1 against different cancer cell lines was found to be surprisingly similar to that of the cephalostatins, which appears to imply a related mechanism of action. In this review article the synthetic efforts towards these compounds are described.
Export Options
About this article
Cite this article as:
Gryszkiewicz-Wojtkielewicz A., Jastrzebska I., Morzycki W. J. and Romanowska B. D., Approaches Towards the Synthesis of Cephalostatins, Ritterazines and Saponins from Ornithogalum saundersiae - New Natural Products With Cytostatic Activity, Current Organic Chemistry 2003; 7 (12) . https://dx.doi.org/10.2174/1385272033486512
DOI https://dx.doi.org/10.2174/1385272033486512 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
RING-, HECT-, and RBR-type E3 Ubiquitin Ligases: Involvement in Human Cancer
Current Cancer Drug Targets Titanocenes as Anticancer Agents: Recent Insights
Medicinal Chemistry Sphingolipid Modulation: A Strategy for Cancer Therapy
Anti-Cancer Agents in Medicinal Chemistry Metallothioneins and Cancer
Current Protein & Peptide Science Ontologies of Drug Discovery and Design for Neurology, Cardiology and Oncology
Current Pharmaceutical Design Nuclear Export Mediated Regulation of MicroRNAs: Potential Target for Drug Intervention
Current Drug Targets The Clinical Characteristics and Survival Profiles of Wilms Tumor in the United Arab Emirates: A Single-center Retrospective Analysis
New Emirates Medical Journal Histone Deacetylase Inhibitors: Molecular and Biological Activity as a Premise to Clinical Application
Current Drug Metabolism The Medical Potential of Antimicrobial Peptides from Insects
Current Topics in Medicinal Chemistry Pro-Oncogenic Cell Signaling Machinery as a Target for Oncolytic Viruses
Current Pharmaceutical Biotechnology Control of Copper Status for Cancer Therapy
Current Cancer Drug Targets The HOX Gene Network as a Potential Target for Cancer Therapy
Current Cancer Therapy Reviews Molecular Targeted Agents Combined with Chemo-Radiation in the Treatment of Locally Advanced Cervix Cancer
Reviews on Recent Clinical Trials Carbonic Anhydrase IX as a Target for Designing Novel Anticancer Drugs
Current Medicinal Chemistry SCAP/SREBPs are Central Players in Lipid Metabolism and Novel Metabolic Targets in Cancer Therapy
Current Topics in Medicinal Chemistry Integrative Analysis of Dysfunctional Modules Driven by Genomic Alterations at System Level Across 11 Cancer Types
Combinatorial Chemistry & High Throughput Screening Unveiling the Role of Nuclear Transport in Epithelial-to-Mesenchymal Transition
Current Cancer Drug Targets Targeting Angiogenic Pathways in Colorectal Cancer: Complexities, Challenges and Future Directions
Current Drug Targets 2D and 3D-QSAR analysis of pyrazole-thiazolinone derivatives as EGFR kinase inhibitors by CoMFA and CoMSIA
Current Computer-Aided Drug Design Reproducibility of Volumetric Assessment of the Inner Ear Using Three Dimensional Reconstruction of the High Resolution MR Sequence
Current Medical Imaging