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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
.
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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
Braffman,
Structural basis for an unprecedented enzymatic alkylation in cylindrocyclophane biosynthesis.
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Braffman,
Structural basis for an unprecedented enzymatic alkylation in cylindrocyclophane biosynthesis.
2022,
Pubmed
Lee,
Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: proof of concept.
1999,
Pubmed
Luesch,
Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.
2001,
Pubmed
May,
Merocyclophanes C and D from the Cultured Freshwater Cyanobacterium Nostoc sp. (UIC 10110).
2017,
Pubmed
Nakamura,
Cylindrocyclophane biosynthesis involves functionalization of an unactivated carbon center.
2012,
Pubmed
Nakamura,
A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis.
2017,
Pubmed
Preisitsch,
Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2.
2016,
Pubmed
Preisitsch,
Cylindrofridins A-C, Linear Cylindrocyclophane-Related Alkylresorcinols from the Cyanobacterium Cylindrospermum stagnale.
2016,
Pubmed
Salvador-Reyes,
Biological targets and mechanisms of action of natural products from marine cyanobacteria.
2015,
Pubmed
Schultz,
Biocatalytic Friedel-Crafts Alkylation Using a Promiscuous Biosynthetic Enzyme.
2019,
Pubmed
Thanh,
A new [7.7]paracyclophane from Vietnamese marine snail Planaxis sulcatus (Born, 1780).
2020,
Pubmed
van Santen,
The Natural Products Atlas 2.0: a database of microbially-derived natural products.
2022,
Pubmed
