Impact of environmental conditions on the marine natural product bryostatin 1.
Marine Natural Products (MNPs), such as bryostatin 1, are exposed to a range of physical and chemical conditions through the life cycle of the host organism. These include exposure to sunlight, oxidizing and reducing agents, cation binding, and adsorption to reactive metal oxide surfaces. Using Fourier Transform-Ion Cyclotron Resonance (FT-ICR), Matrix Assisted Laser Desorption Ionization Mass Spectrometry (MALDI-MS), UV/Vis absorbance spectroscopy, and molecular modeling, we studied the impact of UV light, TiO2, I2, and reaction with FeCl3 on the structure of bryostatin 1. Our results demonstrate that natural conditions transform bryostatin to a number of structures, including one with a molar mass of 806 Da, which we have previously identified in the sediment collected from the Gulf of Mexico. To date, at least 20 different structures of bryostatin have been reported in the literature. This work suggests that these variations may be products of the chemical environment in which the bryozoa Bugula neritina resides and are not the result of genetic variations within Bugula.
Manning
Thomas J
TJ
Chemistry Department, Valdosta State University, Valdosta, GA 31698, USA. tmanning@valdosta.edu
Rhodes
Emily
E
Land
Michael
M
Parkman
Render
R
Sumner
Brandy
B
Lam
Tukiet T
TT
Marshall
Alan G
AG
Phillips
Dennis
D
D000818:Animals; D054713:Bryostatins; D002013:Bryozoa / Q000737:chemistry* / Q000378:metabolism; D002712:Chlorides; D003198:Computer Simulation; D017753:Ecosystem; D005290:Ferric Compounds / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D018942:Macrolides / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet; D014025:Titanium / Q000737:chemistry; D014466:Ultraviolet Rays
D054713:Bryostatins; D002712:Chlorides; D005290:Ferric Compounds; D018942:Macrolides; C009495:titanium dioxide; C046785:bryostatin 1; D007455:Iodine; D014025:Titanium; C024555:ferric chloride