Nhatrangins A and B, Aplysiatoxin-Related Metabolites from the Marine Cyanobacterium Lyngbya majuscula from Vietnam

被引:50
|
作者
Chlipala, George E. [1 ]
Tri, Pham Huu
Hung, Nguyen Van
Krunic, Aleksej [1 ]
Shim, Sang Hee [1 ]
Soejarto, D. Doel [1 ]
Orjala, Jimmy [1 ]
机构
[1] Univ Illinois, Dept Med Chem & Pharmacognosy, Chicago, IL 60612 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2010年 / 73卷 / 04期
关键词
COUPLING-CONSTANTS; NMR EXPERIMENTS; DEBROMOAPLYSIATOXIN;
D O I
10.1021/np100002q
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two polyketide metabolites, nhatrangins A (1) and B (2), were isolated from a Vietnamese collection of Lyngbya majuscula. These compounds are related to the aplysiatoxin series of metabolites, which have also been isolated from this species of marine cyanobacterium. The use of 900 MHz cryoprobe NMR allowed the elucidation of the 2D structure of 1 from approximately 0.3 mg of compound. LC-MS analysis was utilized to direct the isolation of additional material as well as the isolation of 2. Conformational analysis was completed using J-based coupling constant analysis and selective NOE experiments.
引用
收藏
页码:784 / 787
页数:4
相关论文
共 50 条
  • [41] 2 MALYNGAMIDES FROM THE CARIBBEAN CYANOBACTERIUM LYNGBYA-MAJUSCULA
    GERWICK, WH
    REYES, S
    ALVARADO, B
    PHYTOCHEMISTRY, 1987, 26 (06) : 1701 - 1704
  • [42] Two quinoline alkaloids from the Caribbean cyanobacterium Lyngbya majuscula
    Orjala, J
    Gerwick, WH
    PHYTOCHEMISTRY, 1997, 45 (05) : 1087 - 1090
  • [43] Biochemical Studies of the Lagunamides, Potent Cytotoxic Cyclic Depsipeptides from the Marine Cyanobacterium Lyngbya majuscula
    Tripathi, Ashootosh
    Fang, Wanru
    Leong, David Tai
    Tan, Lik Tong
    MARINE DRUGS, 2012, 10 (05): : 1126 - 1137
  • [44] Cloning and biochemical characterization of the hectochlorin biosynthetic gene cluster from the marine cyanobacterium Lyngbya majuscula
    Ramaswamy, Aishwarya V.
    Sorrels, Carla M.
    Gerwick, William H.
    JOURNAL OF NATURAL PRODUCTS, 2007, 70 (12): : 1977 - 1986
  • [46] Structure, synthesis, and biological properties of kalkitoxin, a novel neurotoxin from the marine cyanobacterium Lyngbya majuscula
    Wu, M
    Okino, T
    Nogle, LM
    Marquez, BL
    Williamson, RT
    Sitachitta, N
    Berman, FW
    Murray, TF
    McGough, K
    Jacobs, R
    Colsen, K
    Asano, T
    Yokokawa, F
    Shioiri, T
    Gerwick, WH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 12041 - 12042
  • [47] Three new malyngamides from a Papua new guinea collection of the marine cyanobacterium Lyngbya majuscula
    McPhail, KL
    Gerwick, WH
    JOURNAL OF NATURAL PRODUCTS, 2003, 66 (01): : 132 - 135
  • [48] Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula
    Han, BN
    Gross, H
    Goeger, DE
    Mooberry, SL
    Gerwick, WH
    JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04): : 572 - 575
  • [49] Total syntheses of lipopeptides derived from cyanobacterium Lyngbya majuscula: Sodium channel blockers from marine sources
    Paige, Mike
    Graf, Kristin M.
    Patel, Manoj K.
    Dakshanamurthy, Sivanesan
    Baheti, Aparna
    Wang, Kan
    Zhang, Li
    Brown, Milton L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [50] Pitiprolamide, a Proline-Rich Dolastatin 16 Analogue from the Marine Cyanobacterium Lyngbya majuscula from Guam
    Montaser, Rana
    Abboud, Khalil A.
    Paul, Valerie J.
    Luesch, Hendrik
    JOURNAL OF NATURAL PRODUCTS, 2011, 74 (01): : 109 - 112