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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>
Chang Shin Yoon,Hyoung Kyu Kim,Natalia P. Mishchenko,Elena A. Vasileva,Sergey A. Fedoreyev,Olga P. Shestak,Nadezhda N. Balaneva,Vyacheslav L. Novikov,Valentin A. Stonik,한진 대한독성 유전단백체 학회 2019 Molecular & cellular toxicology Vol.15 No.4
Backgrounds: Echinochrome A (6-ethyl-2,3,5,7,8-pentahydroxy- 1,4-naphthoquinone) is a common naphthoquinone pigment found in the shells, spines, and coelomic fluid of sea urchins. We previously reported that echinochrome A has a cardioprotective function as an antioxidant against reactive oxygen species (ROS) induced by tert-Butyl hydroperoxide and doxorubicin. Methods: In the current study, we evaluated the antioxidant activity, ATP production, and oxygen consumption rate (OCR) of seven echinochrome structural analogs (spinochromes) in AC16 human cardiomyocyte cells. The compounds included in the study had various substituents including hydroxyl (Sp B and Sp E), amino (Echm A), methoxyl (TriMeEch A), pentyl (No. 284), and hydroxypentyl (No. 285). We also investigated the effects of one dimeric spinochrome (Binaphthoquinone). Results: Spinochromes exhibited enhanced antioxidant activity and ATP production. Interestingly, the hydroxylated compounds significantly enhanced the OCR and had a cardiomyocyte protective effect in the presence of doxorubicin. Conclusion: Our findings indicate that echinochrome A structural analogs may have therapeutic potential for cardio-protection.
Jin, Jun-O,Park, Hae-Young,Xu, Qi,Park, Joo-In,Zvyagintseva, Tatyana,Stonik, Valentin A.,Kwak, Jong-Young American Society of Hematology 2009 Blood Vol.113 No.23
<B>Abstract</B><P>Dendritic cells (DCs) are the most potent antigen-presenting cells for naive T cells. In this study, scavenger receptor class A type I and type II (SR-A) were shown to be expressed by peripheral blood DCs (PBDCs) and monocyte-derived DCs (MDDCs). In addition, the binding of anti-SR-A antibody to these cells was lower in the presence of fucoidan, an SR-A agonist. Treatment of these DCs with fucoidan or anti-SR-A antibody markedly increased the surface expression of costimulatory molecules CD83 and major histocompatibility complex class II on the CD11chighCD123low myeloid subset of PBDCs. Furthermore, fucoidan-treated PBDCs produced tumor necrosis factor-α (TNF-α) but not IL-12p70. In addition, fucoidan-induced maturation was eliminated by pretreatment with TNF-α-neutralizing antibody. Finally, interferon-γ secretion and T-cell proliferation were enhanced by coculture of T cells with fucoidan-matured PBDCs. Specific inhibitors of p38 MAPK and glycogen synthase kinase 3 suppressed TNF-α production and maturation of fucoidan-treated PBDCs. Moreover, MDDCs lacking SR-A failed to up-regulate CD83 expression, TNF-α production, and phosphorylation of p38 MAPK and glycogen synthase kinase 3-β in the presence of fucoidan. Taken together, these results suggest that ligation of SR-A leads to induction of TNF-α, which subsequently induces PBDC maturation, thereby leading to enhanced T-cell stimulatory capacity.</P>
Makarieva, Tatyana N.,Tabakmaher, Ksenya M.,Guzii, Alla G.,Denisenko, Vladimir A.,Dmitrenok, Pavel S.,Shubina, Larisa K.,Kuzmich, Alexandra S.,Lee, Hyi-Seung,Stonik, Valentin A. American Chemical Society and American Society of 2011 Journal of natural products Vol.74 No.9
<P>New unusual polycyclic guanidine alkaloids monanchocidins B–E (<B>2</B>–<B>5</B>) along with monanchocidin A (<B>1</B>), which we recently described, were isolated from the Far-Eastern marine sponge <I>Monanchora pulchra</I>. Their structures were established using spectroscopic data and chemical transformations. Compounds <B>1</B>–<B>5</B> show potent cytotoxic activities against HL-60 human leukemia cells with IC<SUB>50</SUB> values of 540, 200, 110, 830, and 650 nM, respectively.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2011/jnprdf.2011.74.issue-9/np200452m/production/images/medium/np-2011-00452m_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np200452m'>ACS Electronic Supporting Info</A></P>
New Derivatives of Natural Acyclic Guanidine Alkaloids with TRPV Receptor-Regulating Properties
Ogurtsova, Ekaterina K.,Makarieva, Tatyana N.,Korolkova, Yuliya V.,Andreev, Yaroslav A.,Mosharova, Irina V.,Denisenko, Vladimir A.,Dmitrenok, Pavel S.,Lee, Yeon-Ju,Grishin, Eugene V.,Stonik, Valentin NATURAL PRODUCT COMMUNICATIONS 2015 Natural product communications Vol.10 No.7