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Abstract
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.
Acknowledgements
The authors would like to thank Dr. Dave Newman of the National Cancer Institute for numerous discussions and insights related to marine natural products and also Valdosta State University for support and resources. Some of this work was supported by an SBIR grant (from NOAA) to MIC Systems, Inc of Valdosta, Georgia. This work was also supported by NSF (CHE-99-09502), Florida State University, and the National High Magnetic Field Laboratory in Tallahassee, FL.
Notes
¶Also a member of the Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA.