Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

被引：37

作者：

Sueyoshi, Kosuke ^{[1
]}

Kaneda, Masato ^{[2
]}

Sumimoto, Shinpei ^{[3
]}

Oishi, Shinya ^{[2
]}

Fujii, Nobutaka ^{[2
]}

Suenaga, Kiyotake ^{[3
]}

Teruya, Toshiaki ^{[1
]}

机构：

[1] Univ Ryukyus, Fac Educ, 1 Senbaru, Nishihara, Okinawa 9030213, Japan

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[3] Keio Univ, Dept Chem, Kohoku Ku, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON | 2016年 / 72卷 / 35期

基金：

日本学术振兴会;

关键词：

Marine natural products; Okeania; Cyclic depsipeptide; Cytotoxicity; LYNGBYA-MAJUSCULA; BRINE SHRIMP; POTENT; DEPSIPEPTIDE; AURILIDE; KULOKEKAHILIDE-2; STEREOSTRUCTURE; LAGUNAMIDE; PEPTIDE; ANALOGS;

D O I：

10.1016/j.tet.2016.07.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC50 value of 263 nM. (C) 2016 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5472 / 5478

页数：7

相关论文

共 28 条

[1] C-13 CHEMICAL-SHIFTS OF SOME MODEL OLEFINS [J].

COUPERUS, PA ;

CLAGUE, ADH ;

VANDONGEN, JPCM .

ORGANIC MAGNETIC RESONANCE, 1976, 8 (08) :426-431

[2] Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula [J].

Edwards, DJ ;

Marquez, BL ;

Nogle, LM ;

McPhail, K ;

Goeger, DE ;

Roberts, MA ;

Gerwick, WH .

CHEMISTRY & BIOLOGY, 2004, 11 (06) :817-833

[3] CHEMICALLY RICH SPECIES OF TROPICAL MARINE CYANOBACTERIA OF THE GENUS OKEANIA GEN. NOV (OSCILLATORIALES, CYANOPROKARYOTA) [J].

Engene, Niclas ;

Paul, Valerie J. ;

Byrum, Tara ;

Gerwick, William H. ;

Thor, Andrea ;

Ellisman, Mark H. .

JOURNAL OF PHYCOLOGY, 2013, 49 (06) :1095-1106

[4]

Gerwick WH, 2001, ALKALOIDS, V57, P75, DOI 10.1016/S0099-9598(01)57003-0

[5] STRUCTURE OF CURACIN-A, A NOVEL ANTIMITOTIC, ANTIPROLIFERATIVE, AND BRINE SHRIMP TOXIC NATURAL PRODUCT FROM THE MARINE CYANOBACTERIUM LYNGBYA-MAJUSCULA [J].

GERWICK, WH ;

PROTEAU, PJ ;

NAGLE, DG ;

HAMEL, E ;

BLOKHIN, A ;

SLATE, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1243-1245

[6] Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula [J].

Han, BN ;

Gross, H ;

Goeger, DE ;

Mooberry, SL ;

Gerwick, WH .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04) :572-575

[7] Diverse Synthesis of Marine Cyclic Depsipeptide Lagunamide A and Its Analogues [J].

Huang, Wei ;

Ren, Rong-Guo ;

Dong, Han-Qing ;

Wei, Bang-Guo ;

Lin, Guo-Qiang .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) :10747-10762

[8] Polyene substrates with unusual methylation patterns to probe the active sites of three catalytic antibodies [J].

Kim, GT ;

Wenz, M ;

Park, JI ;

Hasserodt, J ;

Janda, KD .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (05) :1249-1262

[9] Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula [J].

Luesch, H ;

Yoshida, WY ;

Moore, RE ;

Paul, VJ ;

Corbett, TH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) :5418-5423

[10]

Mamer OA, 2000, METHOD ENZYMOL, V324, P3