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Rö,nsberg, David,Debbab, Abdessamad,Má,ndi, Attila,Vasylyeva, Vera,Bö,hler, Philip,Stork, Bjö,rn,Engelke, Laura,Hamacher, Alexandra,Sawadogo, Richard,Diederich, Marc,Wray, Vict American Chemical Society 2013 Journal of organic chemistry Vol.78 No.24
<P>Four tetrahydroxanthone dimers (<B>1</B>–<B>4</B>) and four biogenetically related monomers (<B>5</B>–<B>8</B>), including the new derivatives <B>4</B>–<B>6</B>, were isolated from the endophyte Phomopsis longicolla. The absolute configurations of <B>2</B>–<B>4</B> were established for the first time by TDDFT electronic circular dichroism calculations, and that of phomoxanthone A (<B>1</B>) was revised by X-ray crystallography. Phomoxanthone A (<B>1</B>) showed the strongest pro-apoptotic activity when tested against a panel of human cancer cell lines, including cisplatin-resistant cells, whereas it was up to 100-fold less active against healthy blood cells. It was also the most potent activator of murine T lymphocytes, NK cells, and macrophages, suggesting an activation of the immune system in parallel to its pro-apoptotic activity. This dual effect in combating cancer cells could help in fighting resistance during chemotherapy. Preliminary structure–activity studies of isolated compounds and derivatives obtained by semisynthesis (<B>9a</B>–<B>11</B>) hinted at the location of the biaryl axis and the presence of acetyl groups as important structural elements for the biological activity of the studied tetrahydroxanthones.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2013/joceah.2013.78.issue-24/jo402066b/production/images/medium/jo-2013-02066b_0011.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo402066b'>ACS Electronic Supporting Info</A></P>
Protein Kinase and HDAC Inhibitors from the Endophytic Fungus <i>Epicoccum nigrum</i>
El Amrani, Mustapha,Lai, Daowan,Debbab, Abdessamad,Aly, Amal H.,Siems, Karsten,Seidel, Carole,Schnekenburger, Michael,Gaigneaux, Anthoula,Diederich, Marc,Feger, Daniel,Lin, Wenhan,Proksch, Peter American Chemical Society and American Society of 2014 Journal of natural products Vol.77 No.1
<P>A chemical investigation of the endophytic fungus <I>Epicoccum nigrum</I> isolated from leaves of <I>Mentha suaveolens</I> collected in Morocco resulted in the isolation of five new polyketides, epicocconigrones A and B (<B>1</B> and <B>2</B>), 3-methoxyepicoccone B (<B>3</B>), 3-methoxyepicoccone (<B>4</B>), and 2,3,4-trihydroxy-6-(methoxymethyl)-5-methylbenzaldehyde (<B>5</B>), together with five known compounds (<B>6</B>–<B>10</B>). The structures of the new compounds were unambiguously determined by extensive analysis of the 1D and 2D NMR and mass spectroscopic data. Compounds <B>1</B> and <B>10</B> showed potent inhibition of at least 15 protein kinases with IC<SUB>50</SUB> values ranging from 0.07 to 9.00 μM. Moreover, compounds <B>1</B> and <B>10</B> inhibited histone deacetylase (HDAC) activities with IC<SUB>50</SUB> values of 9.8 and 14.2 μM, respectively. A preliminary structure–activity relationship is discussed. Interestingly, compounds <B>1</B> and <B>10</B> exert mainly cytostatic effects in human lymphoma RAJI and U-937 cell lines.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2014/jnprdf.2014.77.issue-1/np4005745/production/images/medium/np-2013-005745_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np4005745'>ACS Electronic Supporting Info</A></P>