Abstract
Ginseng has been used extensively for medicinal purposes, with suggested utility for indications as diverse as diabetes, cardiovascular disease and cancer. Herein we report the discovery and characterization of 20(S)-25-OCH3-PPD, a ginsenoside that inhibits growth and survival of cancer cells. The novel dammarane triterpene sapogenin (C31H56O4; molecular weight 492) was isolated from the total hydrolyzed saponins extracted from the leaves of Panax notoginseng using conventional and reverse-phase silica gel chromatography. Based on physicochemical characteristics and NMR data, the compound was identified as 20(S)-25-OCH3-PPD. The biological activities of 20(S)-25-OCH3-PPD and its known analogs, 20(S)-PPD and Rg3, were evaluated in 12 human cancer cell lines. In all cell lines, the order of cytotoxicity of the test compounds was 20(S)-25-OCH3-PPD 20(S)-PPD Rg3. 20(S)-25-OCH3-PPD also induced apoptosis and cell cycle arrest in the G1 phase, and inhibited proliferation in breast cancer cell lines, demonstrating its potent biological effects. In regard to cytotoxicity, the IC50 values of 20(S)-25-OCH3-PPD for most cell lines were in the lower μM range, a 5-15- fold greater cytotoxicity relative to 20(S)-PPD and a 10-100-fold increase over Rg3. These findings suggest a structureactivity relationship among dammarane-type sapogenins. The data presented here may provide a basis for the future development of 20(S)-25-OCH3-PPD as a novel anti-cancer agent.
Keywords: Panax notoginseng, 20(S)-25-OCH3-PPD, ginsenoside, stereochemical structure, natural product
Medicinal Chemistry
Title: Isolation, Structural Determination, and Evaluation of the Biological Activity of 20(S)-25-methoxyl-dammarane-3β, 12β, 20-triol [20(S)-25-OCH3-PPD], a Novel Natural Product from Panax notoginseng
Volume: 3 Issue: 1
Author(s): Y. Zhao, W. Wang, L. Han, E R. Rayburn, D. L. Hil, H. Wang and R. Zhang
Affiliation:
Keywords: Panax notoginseng, 20(S)-25-OCH3-PPD, ginsenoside, stereochemical structure, natural product
Abstract: Ginseng has been used extensively for medicinal purposes, with suggested utility for indications as diverse as diabetes, cardiovascular disease and cancer. Herein we report the discovery and characterization of 20(S)-25-OCH3-PPD, a ginsenoside that inhibits growth and survival of cancer cells. The novel dammarane triterpene sapogenin (C31H56O4; molecular weight 492) was isolated from the total hydrolyzed saponins extracted from the leaves of Panax notoginseng using conventional and reverse-phase silica gel chromatography. Based on physicochemical characteristics and NMR data, the compound was identified as 20(S)-25-OCH3-PPD. The biological activities of 20(S)-25-OCH3-PPD and its known analogs, 20(S)-PPD and Rg3, were evaluated in 12 human cancer cell lines. In all cell lines, the order of cytotoxicity of the test compounds was 20(S)-25-OCH3-PPD 20(S)-PPD Rg3. 20(S)-25-OCH3-PPD also induced apoptosis and cell cycle arrest in the G1 phase, and inhibited proliferation in breast cancer cell lines, demonstrating its potent biological effects. In regard to cytotoxicity, the IC50 values of 20(S)-25-OCH3-PPD for most cell lines were in the lower μM range, a 5-15- fold greater cytotoxicity relative to 20(S)-PPD and a 10-100-fold increase over Rg3. These findings suggest a structureactivity relationship among dammarane-type sapogenins. The data presented here may provide a basis for the future development of 20(S)-25-OCH3-PPD as a novel anti-cancer agent.
Export Options
About this article
Cite this article as:
Zhao Y., Wang W., Han L., Rayburn R. E, Hil L. D., Wang H. and Zhang R., Isolation, Structural Determination, and Evaluation of the Biological Activity of 20(S)-25-methoxyl-dammarane-3β, 12β, 20-triol [20(S)-25-OCH3-PPD], a Novel Natural Product from Panax notoginseng, Medicinal Chemistry 2007; 3 (1) . https://dx.doi.org/10.2174/157340607779317508
DOI https://dx.doi.org/10.2174/157340607779317508 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
Call for Papers in Thematic Issues
Carbohydrates in Computational and Medicinal Chemistry
Carbohydrates are the most essential organic molecules and are involved in the maintenance of various physiological and metabolic processes in living organisms. Carbohydrate-based compounds have come to the attention of researchers because of their significant contributions to biological functions, such as cell development and cell proliferation, connections between several cells, ...read more
Recent Advances in the Medicinal Chemistry of Cancer
Scope of the Thematic Issue: Correlation between structure and function is one of the important aspects of the success of anti-cancer compounds associated with their structure-activity interactions, physiology, biochemical, molecular, and genetic processes. Overcoming these obstacles is key to obtaining further insights into developments in rational drug design, bioorganic chemistry, ...read more
- 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
Related Articles
-
Synthesis and In Vitro Antitumor Activity of Novel Fluorine Containing Pyrazoles and Pyrazolines
Letters in Drug Design & Discovery Antitumor Effects of Celastrol and Semi-Synthetic Derivatives
Mini-Reviews in Organic Chemistry Novel Drug Delivery Systems for Sustained and Targeted Delivery of Anti-Cancer Drugs: Current Status and Future Prospects
Current Drug Delivery Expression and Function of Bcl-2 Proteins in Melanoma
Current Genomics Mangrove Plants as a Source of Bioactive Compounds: A Review
The Natural Products Journal Small Molecular Inhibitors of p-STAT3: Novel Agents for Treatment of Primary and Metastatic CNS Cancers
Recent Patents on CNS Drug Discovery (Discontinued) Molecular Targets in Gastrointestinal Stromal Tumors (GIST) Therapy
Current Cancer Drug Targets Re-Sensitizing Tumor Cells to Cancer Drugs with Epigenetic Regulators
Current Cancer Drug Targets Application of Mesenchymal Stem Cells in Melanoma: A Potential Therapeutic Strategy for Delivery of Targeted Agents
Current Medicinal Chemistry Multi-Target Profile of Oleocanthal, An Extra-Virgin Olive Oil Component
Current Bioactive Compounds Therapeutic Outlook of Pyrazole Analogs: A Mini Review
Mini-Reviews in Medicinal Chemistry In Vitro Inhibitory Effect of Recombinant Human Calprotectin on Nalm6 Leukemia Cell Line
Anti-Cancer Agents in Medicinal Chemistry Defective Insulin Signalling, Mediated by Inflammation, Connects Obesity to Alzheimer Disease; Relevant Pharmacological Therapies and Preventive Dietary Interventions
Current Alzheimer Research Anti-Cancer Effect of Melatonin via Downregulation of Delta-like Ligand 4 in Estrogen-Responsive Breast Cancer Cells
Recent Patents on Anti-Cancer Drug Discovery Noble metal-dithiocarbamates precious allies in the fight against cancer
Mini-Reviews in Medicinal Chemistry Vitamin D and Breast Cancer Incidence and Outcome
Anti-Cancer Agents in Medicinal Chemistry Development of Novel Rhodanine Analogs as Anticancer Agents: Design, Synthesis, Evaluation and CoMSIA Study
Medicinal Chemistry Contemporary Treatment of Amyloid Heart Disease
Current Pharmaceutical Design Physicochemical Characterization of Curcumin Loaded Chitosan Nanoparticles: Implications in Cervical Cancer
Anti-Cancer Agents in Medicinal Chemistry Machine Learning for Mass Spectrometry Data Analysis in Proteomics
Current Proteomics