Paracaseolide A, first α-alkylbutenolide dimer with an unusual tetraquinane oxa-cage bislactone skeleton from Chinese mangrove Sonneratia paracaseolaris

Xue-Lian Chen; Hai-Li Liu; Jia Li; Guo-Rong Xin; Yue-Wei Guo

doi:10.1021/ol201809q

Paracaseolide A, first α-alkylbutenolide dimer with an unusual tetraquinane oxa-cage bislactone skeleton from Chinese mangrove Sonneratia paracaseolaris

Org Lett. 2011 Oct 7;13(19):5032-5. doi: 10.1021/ol201809q. Epub 2011 Aug 29.

Authors

Xue-Lian Chen¹, Hai-Li Liu, Jia Li, Guo-Rong Xin, Yue-Wei Guo

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zu Chong Zhi Road, 555, Shanghai 201203, China.

PMID: 21875121
DOI: 10.1021/ol201809q

Abstract

A novel α-alkylbutenolide dimer, paracaseolide A (2), characterized by an unusual tetraquinane oxa-cage bislactone skeleton bearing two linear alkyl chains, was isolated from the mangrove plant Sonneratia paracaseolaris. The structure of 2 was elucidated by extensive spectroscopic analysis. A plausible retrosynthetic pathway for paracaseolide A (2) was proposed. Compound 2 exhibited significant inhibitory activity against dual specificity phosphatase CDC25B, a key enzyme for cell cycle progression, with an IC(50) value of 6.44 μM.

Publication types

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

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemistry
4-Butyrolactone / isolation & purification
Dimerization
Lythraceae / chemistry*
Models, Molecular
Molecular Structure

Substances

paracaseolide A
butenolide
4-Butyrolactone