Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros

被引:19
作者
Chianese, Giuseppina [1 ]
Silber, Johanna [1 ]
Luciano, Paolo [2 ]
Merten, Christian [3 ]
Erpenbeck, Dirk [4 ,5 ]
Topaloglu, Bulent [6 ]
Kaiser, Marcel [7 ,8 ]
Tasdemir, Deniz [1 ]
机构
[1] GEOMAR Helmholtz Ctr Ocean Res Kiel, Res Unit Marine Nat Prod Chem, GEOMAR Ctr Marine Biotechnol GEOMAR Biotech, D-24106 Kiel, Germany
[2] Univ Naples Federico II, Dept Pharm, I-80131 Naples, Italy
[3] Ruhr Univ Bochum, Lehrstuhl Organ Chem 2, D-44801 Bochum, Germany
[4] Ludwig Maximilians Univ Munchen, Dept Earth & Environm Sci, D-80333 Munich, Germany
[5] Ludwig Maximilians Univ Munchen, GeoBio Ctr, D-80333 Munich, Germany
[6] Istanbul Univ, Dept Marine Biol, Fac Fisheries, TR-34480 Istanbul, Turkey
[7] Swiss Trop & Publ Hlth Inst, Dept Med Parasitol & Infect Biol, CH-4002 Basel, Switzerland
[8] Univ Basel, CH-4003 Basel, Switzerland
来源
JOURNAL OF NATURAL PRODUCTS | 2017年 / 80卷 / 09期
关键词
TETRONIC ACIDS; GENUS IRCINIA; SESTERTERPENES; METABOLITES;
D O I
10.1021/acs.jnatprod.7b00543
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Chemical investigation of the marine sponge Ircinia oros yielded four linear furanosesterterpenoids, including the known metabolites ircinin-1 (1) and ircinin-2 (2) and two new compounds, ircinialactam E (3) and ircinialactam F (4). Their chemical structures were elucidated by using a combination of [alpha](D), NMR, HRMS, and FT-IR spectroscopy. The absolute configuration of C-18 in compounds 1-3 was identified as R by electronic circular dichroism (ECD) spectroscopy coupled with time-dependent density functional theory calculations. Compounds 1-4 showed moderate leishmanicidal, trypanocidal, and antiplasmodial activities (IC50 values 28-130 mu M). This is the second report of rare glycinyl lactam derivatives 3 and 4 from the genus Ircinia.
引用
收藏
页码:2566 / 2571
页数:6
相关论文
共 24 条
[1]   Sulawesins A-C, Furanosesterterpene Tetronic Acids That Inhibit USP7, from a Psammocinia sp Marine Sponge [J].
Afifi, Ahmed H. ;
Kagiyama, Ippei ;
El-Desoky, Ahmed H. ;
Kato, Hikaru ;
Mangindaan, Remy E. P. ;
de Voogd, Nicole J. ;
Ammar, Nagwa M. ;
Hifnawy, Mohammed S. ;
Tsukamoto, Sachiko .
JOURNAL OF NATURAL PRODUCTS, 2017, 80 (07) :2045-2050
[2]   Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites [J].
Atay, Irem ;
Kirmizibekmez, Hasan ;
Kaiser, Marcel ;
Akaydin, Galip ;
Yesilada, Erdem ;
Tasdemir, Deniz .
PHARMACEUTICAL BIOLOGY, 2016, 54 (09) :1808-1814
[3]   Ircinialactams: Subunit-selective glycine receptor modulators from Australian sponges of the family Irciniidae [J].
Balansa, Walter ;
Islam, Robiul ;
Fontaine, Frank ;
Piggott, Andrew M. ;
Zhang, Hua ;
Webb, Timothy I. ;
Gilbert, Daniel F. ;
Lynch, Joseph W. ;
Capon, Robert J. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (08) :2912-2919
[4]  
BERGQUIST PR, 1980, NEW ZEAL J ZOOL, V7, P1
[5]  
CAPON RJ, 1994, NAT PROD LETT, V4, P51
[6]   Ircinin-1 induces cell cycle arrest and apoptosis in SK-MEL-2 human melanoma cells [J].
Choi, HJ ;
Choi, YH ;
Yee, SB ;
Im, E ;
Jung, JH ;
Kim, ND .
MOLECULAR CARCINOGENESIS, 2005, 44 (03) :162-173
[7]   Inhibition of phospholipase A(2) activities and some inflammatory responses by the marine product ircinin [J].
Cholbi, R ;
Ferrandiz, ML ;
Terencio, MC ;
DeRosa, S ;
Alcaraz, MJ ;
Paya, M .
NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1996, 354 (05) :677-683
[8]   IRCININ-1 AND IRCININ-2 LINEAR SESTERTERPENES FROM MARINE SPONGE IRCINIA-OROS [J].
CIMINO, G ;
FATTORUSSO, E ;
MINALE, L ;
DESTEFAN.S .
TETRAHEDRON, 1972, 28 (02) :333-+
[9]   Granuloside, A Unique Linear Homosesterterpene from the Antarctic Nudibranch Charcotia granulosa [J].
Cutignano, Adele ;
Moles, Juan ;
Avila, Conxita ;
Fontana, Angelo .
JOURNAL OF NATURAL PRODUCTS, 2015, 78 (07) :1761-1764
[10]   Sulfated furanosesterterpenes from two sponges of the genus Ircinia [J].
DeRosa, S ;
Milone, A ;
DeGiulio, A ;
Crispino, A ;
Iodice, C .
NATURAL PRODUCT LETTERS, 1996, 8 (04) :245-251