Otteliones A and B: Potently cytotoxic 4-methylene-2-cyclohexenones from Ottelia alismoides

Seif Eldin N. Ayyad, Andrew S. Judd, W. Thomas Shier, Thomas R Hoye

Research output: Contribution to journalReview articlepeer-review

36 Scopus citations

Abstract

Two diastereomeric 4-methylene-2-cyclohexenones, otteliones A and B (1A and 1B), have been isolated from the freshwater plant Ottelia alismoides collected in the Nile Delta, Egypt. These natural products show remarkable in vitro cytotoxicity against various cancer cell lines. Ottelione B proved to have a constitution identical to that of the known (constitution only) ottelione A. The relative configurations of both 1A and 1B were studied by NOE and by the combination of molecular modeling and 1H NMR coupling constant analysis. A unique relative configurational assignment (1α,3β,3aβ,7aα) was deduced for 1B; 1A was assigned one of two alternative diastereomers (1α,3α,3aα,7aα or 1α,3α,3aβ,7aβ).

Original languageEnglish (US)
Pages (from-to)8102-8106
Number of pages5
JournalJournal of Organic Chemistry
Volume63
Issue number23
DOIs
StatePublished - Nov 13 1998

Fingerprint Dive into the research topics of 'Otteliones A and B: Potently cytotoxic 4-methylene-2-cyclohexenones from Ottelia alismoides'. Together they form a unique fingerprint.

Cite this