10.1021/np900661g.s001
Hyukjae Choi
Hyukjae
Choi
Niclas Engene
Niclas
Engene
Jennifer E. Smith
Jennifer E.
Smith
Linda B. Preskitt
Linda B.
Preskitt
William H. Gerwick
William H.
Gerwick
Crossbyanols A−D, Toxic Brominated Polyphenyl Ethers from the Hawai’ian Bloom-Forming Cyanobacterium <i>Leptolyngbya crossbyana</i>
American Chemical Society
2010
toxicity phenomenon
IC 50 2.8 ppm
marine cyanobacterium Leptolyngbya crossbyana forms
Hawai
antibiotic activity
Crossbyanol
crossbyanol
MIC value
Brominated Polyphenyl Ethers
HMBC
NMR
MS data
brine shrimp toxicity
MRSA
heptabrominated polyphenolic ethers
subtending corals
2010-04-23 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Crossbyanols_A_D_Toxic_Brominated_Polyphenyl_Ethers_from_the_Hawai_ian_Bloom_Forming_Cyanobacterium_i_Leptolyngbya_crossbyana_i_/2774854
Periodically, the marine cyanobacterium <i>Leptolyngbya crossbyana</i> forms extensive blooms on Hawai’ian coral reefs and results in significant damage to the subtending corals. Additionally, corals near mats of this cyanobacterium, but not directly overgrown, have been observed to undergo bleaching. Therefore, samples of this cyanobacterium were chemically investigated for bioactive secondary metabolites that might underlie this toxicity phenomenon. <sup>1</sup>H NMR spectroscopy-guided fractionation led to the isolation of four heptabrominated polyphenolic ethers, crossbyanols A−D (<b>1</b>−<b>4</b>). Structure elucidation of these compounds was made challenging by their very low proton to carbon (H/C) ratio, but was completed by combining standard NMR and MS data with 2 Hz-optimized HMBC data. Derivatization of crossbyanol A as the diacetate assisted in the assignment of its structure. Crossbyanol B (<b>2</b>) showed antibiotic activity with an MIC value of 2.0−3.9 μg/mL against methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) and relatively potent brine shrimp toxicity (IC<sub>50</sub> 2.8 ppm).