Abstract
Epimeric 20S, 24-epoxy-dammarane-3β, 6α, 12β, 25-tetraol acetic ester was synthesized from 20(S)- protopanaxatriol in the presence of acetic anhydride and the product oxidated by m-CPBA. 20S, 24R-epoxy dammarane- 3β, 6α, 12β, 25-tetraol (ocotillol derivative) and its epimer were synthesized by saponification in the presence of sodium hydroxide in 1:1 molar ratio. The structures of the two compounds were characterized by X-ray diffraction method. The results showed the configuration of C-24 of two epimers as S-form (4, ocotillol derivative) and R-form (3, epimer), respectively.
Keywords: Ocotillol, derivative, epimer, synthesis, structure determination, ginsenoside, isoproterenol, ocotillol derivative, protopanaxadiol, saponin, protopanaxatriol, semi-solid, ORTEP representations
Letters in Organic Chemistry
Title: Synthesis, Structural Determination of a New Ocotillol Derivative and its Epimer
Volume: 8 Issue: 9
Author(s): Meng Qingguo, Bi Yi, Wang Liang, Jiang Naicaiv, Jiang Yongtao, Zhang Jiangfeng, Yi Songtao and Sun Haijun
Affiliation:
Keywords: Ocotillol, derivative, epimer, synthesis, structure determination, ginsenoside, isoproterenol, ocotillol derivative, protopanaxadiol, saponin, protopanaxatriol, semi-solid, ORTEP representations
Abstract: Epimeric 20S, 24-epoxy-dammarane-3β, 6α, 12β, 25-tetraol acetic ester was synthesized from 20(S)- protopanaxatriol in the presence of acetic anhydride and the product oxidated by m-CPBA. 20S, 24R-epoxy dammarane- 3β, 6α, 12β, 25-tetraol (ocotillol derivative) and its epimer were synthesized by saponification in the presence of sodium hydroxide in 1:1 molar ratio. The structures of the two compounds were characterized by X-ray diffraction method. The results showed the configuration of C-24 of two epimers as S-form (4, ocotillol derivative) and R-form (3, epimer), respectively.
Export Options
About this article
Cite this article as:
Qingguo Meng, Yi Bi, Liang Wang, Naicaiv Jiang, Yongtao Jiang, Jiangfeng Zhang, Songtao Yi and Haijun Sun, Synthesis, Structural Determination of a New Ocotillol Derivative and its Epimer, Letters in Organic Chemistry 2011; 8 (9) . https://dx.doi.org/10.2174/157017811799304377
DOI https://dx.doi.org/10.2174/157017811799304377 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
- 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
-
The Role of Mitochondrial Dysfunction in Heart Failure and Potential Therapeutic Targets
Current Pharmaceutical Design Cross-Talk Between NO and Arachidonic Acid in Inflammation
Current Medicinal Chemistry Ursolic Acid Attenuates HMGB1-induced LOX-1 Expression in Vascular Endothelial Cells in vitro and Inhibits Atherogenesis in Hypercholesterolemic Mice in vivo
Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry (Discontinued) A Survey on Synthesis Processes of Structured Materials for Biomedical Applications: Iron-based Magnetic Nanoparticles, Polymeric Materials and Polymerization Processes
Current Pharmaceutical Design Endothelial Effects of Drugs Designed to Treat Erectile Dysfunction
Current Pharmaceutical Design The Role of Anti-LeY Antibody in the Downregulation of MAPKs/COX-2 Pathway in Gastric Cancer
Current Drug Targets Natural Products Towards the Discovery of Potential Future Antithrombotic Drugs
Current Pharmaceutical Design Insights in microRNAs Biology
Current Topics in Medicinal Chemistry Coronary Artery Ectasia-A Review of Current Literature
Current Cardiology Reviews Potential Roles of HDAC Inhibitors in Mitigating Ischemia-induced Brain Damage and Facilitating Endogenous Regeneration and Recovery
Current Pharmaceutical Design Ruthenium as an Effective Nitric Oxide Scavenger
Current Topics in Medicinal Chemistry How Recent Patents Have Changed our Clinical Approach in Cardio-Thoracic Surgery
Recent Patents on Regenerative Medicine Effects of Kallistatin on Oxidative Stress and Inflammation on Renal Ischemia-Reperfusion Injury in Mice
Current Vascular Pharmacology The Effects of Newer Beta-Adrenoceptor Antagonists on Vascular Function in Cardiovascular Disease
Current Vascular Pharmacology Editorial [Hot topic: Stroke as a Target in Medicinal Chemistry and Drug Discovery (Guest Editor: Antonino Tuttolomondo)]
Current Topics in Medicinal Chemistry Cardiovascular and Metabolic Effects of Ghrelin
Current Diabetes Reviews Role of Renin Angiotensin System Inhibitors in Cardiovascular and Renal Protection: A Lesson from Clinical Trials
Current Pharmaceutical Design Resveratrol in Medicinal Chemistry: A Critical Review of its Pharmacokinetics, Drug-Delivery, and Membrane Interactions
Current Medicinal Chemistry Bleeding and Acute Coronary Syndromes: Defining, Predicting, and Managing Risk and Outcomes
Current Drug Targets MicroRNAs in Aortic Disease
Current Topics in Medicinal Chemistry