The structure elucidation of isomalyngamide K from the marine cyanobacterium Lyngbya majuscula by experimental and DFT computational methods

被引:9
作者
Han, Bingnan [2 ]
Reinscheid, Uwe M. [3 ]
Gerwick, William H. [4 ]
Gross, Harald [1 ]
机构
[1] Univ Bonn, Inst Pharmaceut Biol, D-53115 Bonn, Germany
[2] Zhejiang Univ, Dept Ocean Sci & Engn, Hangzhou 310028, Zhejiang, Peoples R China
[3] Max Planck Inst Biophys Chem, D-37077 Gottingen, Germany
[4] Univ Calif San Diego, Sch Pharm & Pharmaceut Sci, Ctr Marine Biotechnol & Biomed, Scripps Inst Oceanog & Skaggs, La Jolla, CA 92093 USA
关键词
Lyngbya majuscula; Malyngamide; Vinyl-chloride; NMR; OFT; NEW-GUINEA COLLECTION; HARE BURSATELLA-LEACHII; MALYNGAMIDES; METABOLITES; ACID;
D O I
10.1016/j.molstruc.2011.01.012
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The 2Z-isomer of malyngamide K has been isolated along with the known compounds malyngamide C, deoxy-C and K, and characterized from a Papua New Guinea field collection of the cyanobacterium Lyngbya majuscula. The planar structure was deduced by 10 and 20 NMR spectroscopic and mass spectral data interpretation. The absolute configurations were determined on the basis of spectroscopic techniques, chemical degradation and OFT theoretical calculations. (c) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:109 / 113
页数:5
相关论文
共 27 条
[1]   STRUCTURE OF MALYNGAMIDE-C [J].
AINSLIE, RD ;
BARCHI, JJ ;
KUNIYOSHI, M ;
MOORE, RE ;
MYNDERSE, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2859-2862
[2]   A new biologically active malyngamide from a New Zealand collection of the sea hare Bursatella leachii [J].
Appleton, DR ;
Sewell, MA ;
Berridge, MV ;
Copp, BR .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (04) :630-631
[3]   Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods [J].
Bifulco, Giuseppe ;
Dambruoso, Paolo ;
Gomez-Paloma, Luigi ;
Riccio, Raffaele .
CHEMICAL REVIEWS, 2007, 107 (09) :3744-3779
[4]  
BLUNT JW, 2005, MARINLIT DATABASE
[5]   (-)-TRANS-7(S)-METHOXYTETRADEC-4-ENOIC ACID AND RELATED AMIDES FROM MARINE CYANOPHYTE LYNGBYA-MAJUSCULA [J].
CARDELLINA, JH ;
DALIETOS, D ;
MARNER, FJ ;
MYNDERSE, JS ;
MOORE, RE .
PHYTOCHEMISTRY, 1978, 17 (12) :2091-2095
[6]   New Cerebrosides from Euphorbia peplis L.:: Antimicrobial activity evaluation [J].
Cateni, F ;
Zilic, J ;
Falsone, G ;
Scialino, G ;
Banfi, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (24) :4345-4350
[7]   Total synthesis of malyngamide M and isomalyngamide M [J].
Chen, Jie ;
Shi, Zi-Fa ;
Zhou, Ling ;
Xie, An-Le ;
Cao, Xiao-Ping .
TETRAHEDRON, 2010, 66 (19) :3499-3507
[8]   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
[9]   Stereostructure Assignment of Medium-Sized Rings through an NMR-Computational Combined Approach. Application to the New Germacranes Ketopelenolides C and D [J].
Fattorusso, Ernesto ;
Luciano, Paolo ;
Romano, Adriana ;
Taglialatela-Scafati, Orazio ;
Appendino, Giovanni ;
Borriello, Marianna ;
Fattorusso, Caterina .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (12) :1988-1992
[10]  
Frisch MJ, 2003, GAUSSIAN 03 REVISION