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Shubina, Larisa K.,Makarieva, Tatyana N.,Denisenko, Vladimir A.,Dmitrenok, Pavel S.,Dyshlovoy, Sergey A.,von Amsberg, Gunhild,Glazunov, Valery P.,Silchenko, Artem S.,Stonik, Inna V.,Lee, Hyi-Seung NATURAL PRODUCT COMMUNICATIONS 2016 Natural product communications Vol.11 No.9
<P>As a result of the first study on secondary metabolites from the cosmopolitan bioluminescent marine tube polychaete Chaetopterus variopedatus, a new bicyclic guanidine alkaloid, 6-epi-monanchorin (1), along with the previously known monanchorin (2) were isolated. The structure of 1 was elucidated by spectroscopic and chemical methods, including a cleavage of the C-1-O-7 bond to obtain a secondary alcohol (3), which was used to determine the absolute configurations by Mosher's method. It was found that 1 and 2 were mainly accumulated in a secreted mucus special organ of the worm (food net), where green and blue-green microalgae were detected. A biosynthetic pathway to 6-epi-monanchorin and monanchorin from dietary polyenic fatty acid precursors was proposed.</P>
Guzii, Alla G.,Makarieva, Tatyana N.,Denisenko, Vladimir A.,Dmitrenok, Pavel S.,Kuzmich, Aleksandra S.,Dyshlovoy, Sergey A.,von Amsberg, Gunhild,Krasokhin, Vladimir B.,Stonik, Valentin A. American Chemical Society 2016 ORGANIC LETTERS Vol.18 No.14
<P>Melonoside A (<B>1</B>), the first representative of a new class of ω-glycosylated fatty acid amides, was isolated from the Far Eastern marine sponge <I>Melonanchora kobjakovae</I>. The structure of <B>1</B>, including absolute configuration, was established using detailed analysis of 1D and 2D NMR, CD, and mass spectra as well as chemical transformations. Compound <B>1</B> induces autophagy of human cisplatin-resistant germinal tumor cells NCCIT-R.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2016/orlef7.2016.18.issue-14/acs.orglett.6b01678/production/images/medium/ol-2016-01678y_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol6b01678'>ACS Electronic Supporting Info</A></P>