Caesanines A-D, new cassane diterpenes with unprecedented N bridge from Caesalpinia sappan

Jingyu Zhang; Wael M Abdel-Mageed; Miaomiao Liu; Pei Huang; Wenni He; Li Li; Fuhang Song; Huanqin Dai; Xueting Liu; Jingyu Liang; Lixin Zhang

doi:10.1021/ol402058z

Caesanines A-D, new cassane diterpenes with unprecedented N bridge from Caesalpinia sappan

Org Lett. 2013 Sep 20;15(18):4726-9. doi: 10.1021/ol402058z. Epub 2013 Sep 4.

Authors

Jingyu Zhang¹, Wael M Abdel-Mageed, Miaomiao Liu, Pei Huang, Wenni He, Li Li, Fuhang Song, Huanqin Dai, Xueting Liu, Jingyu Liang, Lixin Zhang

Affiliation

¹ Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology Chinese Academy of Sciences , Beijing, 100080, China, Department of Natural Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, China, Department of Pharmacognosy, College of Pharmacy, King Saud University , Riyadh 11451, Kingdom of Saudi Arabia, Department of Pharmacognosy, Faculty of Pharmacy, Assiut University , Assiut 71526, Egypt, Department of Medicinal Chemistry, Institute of Materia Medica , Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, 100050, China, and University of Chinese Academy of Sciences , Beijing, 100049, China.

PMID: 24004304
DOI: 10.1021/ol402058z

Abstract

Serial antibacterial furanoditerpenes caesanines A-D (1-4), possessing a cassane-type diterpenoid skeleton with an unusual N bridge between C-19/C-20, were identified from a Chinese herb Caesalpinia sappan Linn. In addition, caesanine D (4) showed the first class of dicassane diterpenoid ethers. Their structures were determined by different spectroscopic methods and ECD calculation. Caesanines A and B exhibited strong activities against MRSA suggesting a promising entry point for the development of anti-infective drugs.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification*
Anti-Bacterial Agents / pharmacology
Caesalpinia / chemistry*
Diterpenes / chemistry*
Diterpenes / isolation & purification*
Diterpenes / pharmacology
Humans
Methicillin-Resistant Staphylococcus aureus / drug effects
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular

Substances

Anti-Bacterial Agents
Diterpenes
caesanine D