(+)- and (-)-Preuisolactone A: A Pair of Caged Norsesquiterpenoidal Enantiomers with a Tricyclo[4.4.01,6.02,8]decane Carbon Skeleton from the Endophytic Fungus Preussia isomera

Lu-Lin Xu; Hai-Li Chen; Ping Hai; Yuan Gao; Chuan-Dong Xie; Xiao-Long Yang; Ikuro Abe

doi:10.1021/acs.orglett.8b04123

(+)- and (-)-Preuisolactone A: A Pair of Caged Norsesquiterpenoidal Enantiomers with a Tricyclo[4.4.0^1,6.0^2,8]decane Carbon Skeleton from the Endophytic Fungus Preussia isomera

Org Lett. 2019 Feb 15;21(4):1078-1081. doi: 10.1021/acs.orglett.8b04123. Epub 2019 Feb 7.

Authors

Lu-Lin Xu^{1

2}, Hai-Li Chen^{1

2}, Ping Hai³, Yuan Gao³, Chuan-Dong Xie², Xiao-Long Yang^{1

2}, Ikuro Abe⁴

Affiliations

¹ School of Pharmaceutical Sciences , South-Central University for Nationalities , Wuhan 430074 , People's Republic of China.
² Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences , Chongqing University , Chongqing 401331 , People's Republic of China.
³ Department of Chemical Engineering , Yibin University , Yibin 644000 , People's Republic of China.
⁴ Graduate School of Pharmaceutical Sciences , The University of Tokyo , Bunkyo-ku, Tokyo 113-0033 , Japan.

PMID: 30730149
DOI: 10.1021/acs.orglett.8b04123

Abstract

A pair of enantiomeric norsesquiterpenoids, (+)- and (-)-preuisolactone A (1) [(+)-1 and (-)-1)] featuring an unprecedented tricyclo[4.4.0^1,6.0^2,8]decane carbon scaffold were isolated from Preussia isomera. Their structures were determined by spectroscopic and computed methods and X-ray crystallography. Compounds (+)-1 and (-)-1 are two rare naturally occurring sesquiterpenoidal enantiomers. A plausible biosynthetic pathway for 1 is proposed. Additionally, (±)-1 exhibited remarkable antibacterial activity against Micrococcus luteus with an MIC value of 10.2 μM.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Ascomycota / chemistry*
Heterocyclic Compounds / chemistry
Heterocyclic Compounds / isolation & purification
Heterocyclic Compounds / pharmacology*
Microbial Sensitivity Tests
Micrococcus luteus / drug effects*
Molecular Conformation
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Stereoisomerism

Substances

Anti-Bacterial Agents
Heterocyclic Compounds
Sesquiterpenes