Coscinolactams A and B: new nitrogen-containing sesterterpenoids from the marine sponge Coscinoderma mathewsi exerting anti-inflammatory properties

被引：22

作者：

De Marino, Simona ^{[1
]}

Festa, Carmen ^{[1
]}

D'Auria, Maria Valeria ^{[1
]}

Bourguet-Kondracki, Marie-Lise ^{[2
]}

Petek, Sylvain ^{[3
]}

Debitus, Cecile ^{[4
]}

Maria Andres, Rosa ^{[5
]}

Carmen Terencio, Maria ^{[5
]}

Paya, Miguel ^{[5
]}

Zampella, Angela ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, Via D Montesano 49, I-80131 Naples, Italy

[2] MNHN, Lab Chim & Biochim Substances Nat, F-75005 Paris, France

[3] IRD, UMR152, Noumea, New Caledonia

[4] IRD, UMR152, Papeete, Tahiti, France

[5] Univ Valencia, Fac Farm, Dept Farmacol, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 2009年 / 65卷 / 15期

关键词：

CONTAINING CLERODANE DITERPENOIDS; INHIBITORS; ECHINOPHYLLINS; SUVANINE; POTENT; ASSAY;

D O I：

10.1016/j.tet.2009.02.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Investigation of the marine sponge Coscinoderma mathewsi led to the isolation of two novel nitrogen-containing cheilanthane sesterterpenoids, coscinolactams A and B, together with known suvanine. The structures were elucidated by extensive spectroscopic measurements including NOE experiments to deduce the stereochemistry. The natural compounds, as well as a semisynthetic derivative, showed moderate anti-inflammatory activity measured as their capability to inhibit PGE(2) and NO production. The suvanine aldehyde derivative 4 inhibited inducible nitric oxide protein expression with an IC50 value of 7.3 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2905 / 2909

页数：5

相关论文

共 21 条

[11] TUMOR INHIBITORS .82. BRUCEANTIN, A NEW POTENT ANTILEUKEMIC SIMAROUBOLIDE FROM BRUCEA-ANTIDYSENTERICA [J].

KUPCHAN, SM ;

BRITTON, RW ;

ZIEGLER, MF ;

SIGEL, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :178-179

[12] Sesterterpene sulfates as isocitrate lyase inhibitors from tropical sponge Hippospongia sp. [J].

Lee, Hyi-Seung ;

Lee, Tae-Hoon ;

Yang, Seung Hwan ;

Shin, Hee Jae ;

Shin, Jongheon ;

Oh, Ki-Bong .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) :2483-2486

[13] Coscinosulfate, a CDC25 phosphatase inhibitor from the sponge Coscinoderma mathewsi [J].

Loukaci, A ;

Le Saout, I ;

Samadi, M ;

Leclerc, S ;

Damiens, E ;

Meijer, L ;

Debitus, C ;

Guyot, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (11) :3049-3054

[14] SUVANINE, A NOVEL SESTERTERPENE FROM AN IRCINIA MARINE SPONGE [J].

MANES, LV ;

NAYLOR, S ;

CREWS, P ;

BAKUS, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :284-286

[15] CHEMISTRY AND REVISED STRUCTURE OF SUVANINE [J].

MANES, LV ;

CREWS, P ;

KERNAN, MR ;

FAULKNER, DJ ;

FRONCZEK, FR ;

GANDOUR, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :570-575

[16] A FLUOROMETRIC ASSAY FOR THE MEASUREMENT OF NITRITE IN BIOLOGICAL SAMPLES [J].

MISKO, TP ;

SCHILLING, RJ ;

SALVEMINI, D ;

MOORE, WM ;

CURRIE, MG .

ANALYTICAL BIOCHEMISTRY, 1993, 214 (01) :11-16

[17] Spongolactams, farnesyl transferase inhibitors from a marine sponge: Isolation through an LC/MS-Guided assay, structures, and semisyntheses [J].

Mori, Daisuke ;

Kimura, Yuko ;

Kitamura, Shigeyuki ;

Sakagami, Youji ;

Yoshioka, Yukio ;

Shintani, Tomoaki ;

Okamoto, Tetsuji ;

Ojika, Makoto .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7190-7198

[18] Inhibition and kinetics of Mycobacterium tuberculosis and Mycobacterium smegmatis mycothiol-S-conjugate amidase by natural product inhibitors [J].

Nicholas, GM ;

Eckman, LL ;

Newton, GL ;

Fahey, RC ;

Ray, S ;

Bewley, CA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (04) :601-608

[19] Involvement of secretory phospholipase A(2) activity in the zymosan rat air pouch model of inflammation [J].

Paya, M ;

Terencio, MC ;

Ferrandiz, ML ;

Alcaraz, MJ .

BRITISH JOURNAL OF PHARMACOLOGY, 1996, 117 (08) :1773-1779

[20] STRUCTURE-BASED DESIGN OF THE FIRST POTENT AND SELECTIVE INHIBITOR OF HUMAN NONPANCREATIC SECRETORY PHOSPHOLIPASE-A(2) [J].

SCHEVITZ, RW ;

BACH, NJ ;

CARLSON, DG ;

CHIRGADZE, NY ;

CLAWSON, DK ;

DILLARD, RD ;

DRAHEIM, SE ;

HARTLEY, LW ;

JONES, ND ;

MIHELICH, ED ;

OLKOWSKI, JL ;

SNYDER, DW ;

SOMMERS, C ;

WERY, JP .

NATURE STRUCTURAL BIOLOGY, 1995, 2 (06) :458-465