Chloropupukeananin, the first chlorinated pupukeanane derivative, and its precursors from Pestalotiopsis fici

Ling Liu; Shuchun Liu; Lihua Jiang; Xulin Chen; Liangdong Guo; Yongsheng Che

doi:10.1021/ol800136t

Chloropupukeananin, the first chlorinated pupukeanane derivative, and its precursors from Pestalotiopsis fici

Org Lett. 2008 Apr 3;10(7):1397-400. doi: 10.1021/ol800136t. Epub 2008 Mar 4.

Authors

Ling Liu¹, Shuchun Liu, Lihua Jiang, Xulin Chen, Liangdong Guo, Yongsheng Che

Affiliation

¹ Key Laboratory of Systematic Mycology and Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100080, People's Republic of China.

PMID: 18314997
DOI: 10.1021/ol800136t

Abstract

Chloropupukeananin (1), the first pupukeanane chloride with highly functionalized tricyclo-[4.3.1.03,7]-decane skeleton and its possible biosynthetic precursors iso-A82775C (2) and pestheic acid (3), have been isolated from the plant endophyte Pestalotiopsis fici. The structure of 1 was determined by NMR spectroscopy and X-ray crystallography. Biogenetically, 1 could be derived from the Diels-Alder adduct of 2 and 3.

Publication types

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

MeSH terms

Anti-HIV Agents / chemical synthesis*
Anti-HIV Agents / chemistry
Anti-HIV Agents / pharmacology
Crystallography, X-Ray
HIV-1 / drug effects
Hydrocarbons, Chlorinated / chemical synthesis*
Hydrocarbons, Chlorinated / chemistry
Hydrocarbons, Chlorinated / pharmacology
Indinavir / pharmacology
Inhibitory Concentration 50
Microbial Sensitivity Tests
Molecular Conformation
Molecular Structure
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Sesquiterpenes / pharmacology
Staphylococcus aureus / drug effects
Xylariales / chemistry*

Substances

Anti-HIV Agents
Hydrocarbons, Chlorinated
Sesquiterpenes
chloropupukeananin
Indinavir