TY - JOUR
T1 - Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: Novel inhibitors of protein kinases
AU - Brauers, G
AU - Edrada, R A
AU - Ebel, R
AU - Proksch, P
AU - Wray, V
AU - Berg, A
AU - Grafe, U
AU - Schachtele, C
AU - Totzke, F
AU - Finkenzeller, G
AU - Marme, D
AU - Kraus, J
AU - Munchbach, M
AU - Michel, M
AU - Bringmann, G
AU - Schaumann, K
PY - 2000/6
Y1 - 2000/6
N2 - An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6,8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the H-1 and C-13 NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.
AB - An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6,8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the H-1 and C-13 NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.
M3 - Article
SN - 0163-3864
VL - 63
SP - 739
EP - 745
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 6
ER -