Pestaloporonins: Caryophyllene-Derived Sesquiterpenoids from a Fungicolous Isolate of Pestalotiopsis sp

In Hyun Hwang; Dale C Swenson; James B Gloer; Donald T Wicklow

doi:10.1021/acs.orglett.5b02080

Pestaloporonins: Caryophyllene-Derived Sesquiterpenoids from a Fungicolous Isolate of Pestalotiopsis sp

Org Lett. 2015 Sep 4;17(17):4284-7. doi: 10.1021/acs.orglett.5b02080. Epub 2015 Aug 19.

Authors

In Hyun Hwang¹, Dale C Swenson¹, James B Gloer¹, Donald T Wicklow²

Affiliations

¹ Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
² Bacterial Foodborne Pathogens & Mycology Research Unit, Agricultural Research Service, National Center for Agricultural Utilization Research, USDA , Peoria, Illinois 61604, United States.

PMID: 26287562
DOI: 10.1021/acs.orglett.5b02080

Abstract

Three new sesquiterpenoids (pestaloporonins A-C; 1-3) related to the caryophyllene-derived punctaporonins were isolated from cultures of a fungicolous isolate of Pestalotiopsis sp. The structures of 1-3 were determined by analysis of NMR and HRMS data, and the structure of 1, including its absolute configuration, was confirmed by X-ray crystallographic analysis. Compounds 1 and 2 contain new bicyclic and tricyclic ring systems, respectively.

Publication types

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

MeSH terms

Crystallography, X-Ray
Drug Screening Assays, Antitumor
HCT116 Cells
HeLa Cells
Humans
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Polycyclic Sesquiterpenes
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / pharmacology
Staphylococcus aureus / drug effects
Structure-Activity Relationship
Xylariales / chemistry*

Substances

Polycyclic Sesquiterpenes
Sesquiterpenes
caryophyllene