Merocyclophanes A and B, antiproliferative cyclophanes from the cultured terrestrial Cyanobacterium Nostoc sp.

Abstract:

:The cell extract of a cultured terrestrial Nostoc sp. (UIC 10062), obtained from a sample collected at Grand Mere State Park in Michigan, displayed antiproliferative activity against the HT-29 human colon cancer cell line. Bioactivity-guided fractionation of the cell extract, combined with LC-MS analysis, led to the isolation of two cyclophanes, named merocyclophanes A and B (1 and 2). Their structures were determined by various spectroscopic techniques including HRESIMS, and 1D and 2D NMR analyses. The stereoconfiguration was assigned on the basis of X-ray crystallographic and CD analyses. The structures of merocyclophanes A and B (1 and 2) established a hitherto unknown [7.7]paracyclophane skeleton in nature, as characterized by α-branched methyls at C-1/14. Merocyclophanes A and B (1 and 2) displayed antiproliferative activity against the HT-29 human colon cancer cell line with IC₅₀ values of 3.3 and 1.7 μM, respectively.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Kang HS,Santarsiero BD,Kim H,Krunic A,Shen Q,Swanson SM,Chai H,Kinghorn AD,Orjala J

doi

10.1016/j.phytochem.2012.03.005

subject

Has Abstract

pub_date

2012-07-01 00:00:00

pages

109-15

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(12)00137-9

journal_volume

79

pub_type

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