Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: Novel inhibitors of protein kinases

G Brauers, R A Edrada, R Ebel, P Proksch, V Wray, A Berg, U Grafe, C Schachtele, F Totzke, G Finkenzeller, D Marme, J Kraus, M Munchbach, M Michel, G Bringmann, K Schaumann

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Abstract

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.

Original languageEnglish
Pages (from-to)739-745
Number of pages7
JournalJournal of Natural Products
Volume63
Issue number6
Publication statusPublished - Jun 2000

Cite this

Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: Novel inhibitors of protein kinases. / Brauers, G ; Edrada, R A ; Ebel, R ; Proksch, P ; Wray, V ; Berg, A ; Grafe, U ; Schachtele, C ; Totzke, F ; Finkenzeller, G ; Marme, D ; Kraus, J ; Munchbach, M ; Michel, M ; Bringmann, G ; Schaumann, K .

In: Journal of Natural Products, Vol. 63, No. 6, 06.2000, p. 739-745.

Research output: Contribution to journalArticle

Brauers, G, Edrada, RA, Ebel, R, Proksch, P, Wray, V, Berg, A, Grafe, U, Schachtele, C, Totzke, F, Finkenzeller, G, Marme, D, Kraus, J, Munchbach, M, Michel, M, Bringmann, G & Schaumann, K 2000, 'Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: Novel inhibitors of protein kinases', Journal of Natural Products, vol. 63, no. 6, pp. 739-745.
Brauers, G ; Edrada, R A ; Ebel, R ; Proksch, P ; Wray, V ; Berg, A ; Grafe, U ; Schachtele, C ; Totzke, F ; Finkenzeller, G ; Marme, D ; Kraus, J ; Munchbach, M ; Michel, M ; Bringmann, G ; Schaumann, K . / Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: Novel inhibitors of protein kinases. In: Journal of Natural Products. 2000 ; Vol. 63, No. 6. pp. 739-745.
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abstract = "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.",
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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

VL - 63

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JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

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ER -