A new adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Uvaria chamae

Djibril Fall; Lorena Pimentel; Pierre Champy; Christophe Gleye; Alain Laurens; Reynald Hocquemiller

doi:10.1055/s-2006-941542

A new adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Uvaria chamae

Planta Med. 2006 Aug;72(10):938-40. doi: 10.1055/s-2006-941542. Epub 2006 Jul 25.

Authors

Djibril Fall¹, Lorena Pimentel, Pierre Champy, Christophe Gleye, Alain Laurens, Reynald Hocquemiller

Affiliation

¹ Laboratoire de Pharmacognosie, UMR CNRS 8076 (BioCIS), Faculté de Pharmacie, Université Paris Sud 11, Châtenay-Malabry, France.

PMID: 16868865
DOI: 10.1055/s-2006-941542

Abstract

A novel acetogenin, joolanin ( 1), along with eight known acetogenins, squamocin ( 2), desacetyluvaricin ( 3), chamuvarinin ( 4), tripoxyrollin ( 5), diepoxyrollin ( 6), dieporeticanin-1 ( 7), dieporeticanin-2 ( 8) and dieporeticenin ( 9) were isolated from the seeds of Uvaria chamae (Annonaceae). Compound 1, the first adjacent bis-tetrahydrofuranic ring acetogenin bearing a ketone group at C-5, shows significant cytotoxicity towards the KB 3 - 1 cell line (IC (50) = 0.4 nM).

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemistry
4-Butyrolactone / isolation & purification
4-Butyrolactone / toxicity
Acetogenins
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / toxicity
Cell Line, Tumor
Fatty Alcohols / chemistry
Fatty Alcohols / isolation & purification
Fatty Alcohols / toxicity*
Humans
Lactones / chemistry
Lactones / isolation & purification
Lactones / toxicity*
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
Seeds / chemistry
Uvaria / chemistry*

Substances

Acetogenins
Antineoplastic Agents, Phytogenic
Fatty Alcohols
Lactones
joolanin
4-Butyrolactone