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Mar Drugs
2023 Jan 31;212:. doi: 10.3390/md21020101.
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New Nostocyclophanes from Nostoc linckia.
Dai J
,
Philbin CS
,
Wakano C
,
Yoshida WY
,
Williams PG
.
Abstract
Six new nostocyclophanes and four known compounds have been isolated from Nostoc linckia (Nostocaceae) cyanobacterial strain UTEX B1932. The new compounds, nostocyclophanes E-J (1-6), were characterized by NMR and MS techniques. The known compounds were nostocyclophanes B-D, previously isolated from this strain, and dedichloronostocyclophane D. Structural modifications on the new [7.7]paracyclophane analogs 1-5, isolated from the 80% methanol fraction, range from simple changes such as the lack of methylation or halogenation to more unusual modifications such as those seen in nostocyclophane H (4), in which the exocyclic alkyl chains are of different length; this is the first time this modification has been observed in this family of natural products. In addition, nostocyclophane J (6) is a linear analog in which C-20 is chlorinated in preparation for the presumed enzymatic Friedel-Craft cyclization needed to form the final ring structure, analogous to the biosynthesis of the related cylindrocyclophanes. Nostocyclophane D, dedichloronostocyclophane D, and nostocyclophanes E-J demonstrated moderate to weak growth inhibition against MDA-MB-231 breast cancer cells.
CHE9974921 National Science Foundation, P41GM103484 National Institutes of Health, P41 GM103484 NIGMS NIH HHS , 1532310 National Science Foundation, W911NF-04-1-0344 United States Department of Defense
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