Revised structure of bistramide A (bistratene A): application of a new program for the automated analysis of 2D INADEQUATE spectra

Synthesis of a 35-Member Stereoisomer Library of Bistramide A: Evaluation of Effects on actin State, Cell Cycle and Tumor Cell Growth

“…8 The structure of bistramide A was originally proposed to be a 19-membered macrolactam 9 but later revised to a linear carbon framework (Scheme 1). 10 The skeletal architecture of bistramide A consists of a substituted tetrahydropyran and a spiroketal subunit joined at the center by a γ-amino acid linker. Subsequent spectroscopic and computational studies allowed for accurate prediction of relative and absolute configurations of bistramides.…”

“…In addition to the structural 9,10,11 and synthetic challenges posed by this family of natural products, numerous reports describing their diverse bioactivity have recently emerged. 16 Bistramides were shown to exhibit various biological activities, encompassing neurotoxic, 7b antiproliferative 16d and cytotoxic properties.…”

Use of continuous optimization methods to find carbon links in 2D INADEQUATE spectra

“…While the examples shown in this paper use unprocessed data, running the Fourier transforms in MATLAB, this method will work equally well with processed data as the processing will not change any of these assumptions made. Many existing techniques developed for INADEQUATE spectra rely on complex line-shape fitting and large numbers of assumptions on the form of the experimental results [24][25][26][27][28][29][30][31]. Our technique is based on the magnitude of the signal, making this technique insensitive to phase errors in the experiments and uses comparably few assumptions about the form of the experiment in order to simplify our model.…”

Bistramide A‐induced irreversible arrest of cell proliferation in a non‐small‐cell bronchopulmonary carcinoma is similar to induction of terminal maturation

“…We previously studied bistramide A [14], a toxin from the marine invertebrate Lissoclinum bistratum Sluitter [4,7], determining that its antiproliferative effect against a lung carcinoma cell line resulted from blockage of GI phase cells associated with polyploidy due to an incapacity for cytodieresis [14]. The purpose of the present work was to determine whether this arrest of cell proliferation was reversible once the drug was removed from culture medium.…”