New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscula

被引:47
|
作者
Kan, Y [1 ]
Sakamoto, B
Fujita, T
Nagai, H
机构
[1] Suntory Inst Bioorgan Res, Osaka 6188503, Japan
[2] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2000年 / 63卷 / 12期
关键词
D O I
10.1021/np000250t
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Isomalyngamides A and B (1, 2) were isolated and characterized from a collection of the cyanobacterium Lyngbya majuscula from Hawaiian waters. These compounds represent a new type of malyngamide, similar to malyngamides Q and R, in which the conformation of the chloromethylene group is opposite from the majority of previously reported malyngamides. The geometry of the chloromethylene moiety was elucidated from the long-range coupling constants ((3)J(C-H)) Obtained from editing-HETLOC and phase-sensitive HMBC experiments. Isomalyngamides A and B (1, 2) showed lethal toxicity to crayfish.
引用
收藏
页码:1599 / 1602
页数:4
相关论文
共 50 条
  • [31] Malyngamide 4, a new lipopeptide from the Red Sea marine cyanobacterium Moorea producens (formerly Lyngbya majuscula)
    Shaala, Lamiaa A.
    Youssef, Diaa T. A.
    McPhail, Kerry L.
    Elbandy, Mohamed
    PHYTOCHEMISTRY LETTERS, 2013, 6 (02) : 183 - 188
  • [32] Synthesis of lagunamides: Antimalarial and cytotoxic natural products from the marine cyanobacterium lyngbya majuscula
    Banasik, Brent
    Wang, Lee
    Bergdahl, Mikael B.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [33] Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula
    Lai, J.-Y.
    Yu, J.
    Mekonnen, B.
    Falck, J. R.
    Tetrahedron Letters, 37 (40):
  • [34] Malyngolide Dimer, a Bioactive Symmetric Cyclodepside from the Panamanian Marine Cyanobacterium Lyngbya majuscula
    Gutierrez, Marcelino
    Tidgewell, Kevin
    Capson, Todd L.
    Engene, Niclas
    Almanza, Alejandro
    Schemies, Joerg
    Jung, Manfred
    Gerwick, William H.
    JOURNAL OF NATURAL PRODUCTS, 2010, 73 (04): : 709 - 711
  • [35] Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula
    Edwards, DJ
    Marquez, BL
    Nogle, LM
    McPhail, K
    Goeger, DE
    Roberts, MA
    Gerwick, WH
    CHEMISTRY & BIOLOGY, 2004, 11 (06): : 817 - 833
  • [36] Absolute configuration and total synthesis of (+)-curacin A, an antiproliferative agent from the cyanobacterium Lyngbya majuscula
    White, JD
    Kim, TS
    Nambu, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (01) : 103 - 111
  • [37] Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula
    Yokokawa, F
    Sameshima, H
    Shioiri, T
    TETRAHEDRON LETTERS, 2001, 42 (25) : 4171 - 4174
  • [38] Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula
    Luesch, H
    Yoshida, WY
    Moore, RE
    Paul, VJ
    Mooberry, SL
    JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05): : 611 - 615
  • [39] Lyngbyabellin B, a toxic and antifungal secondary metabolite from the marine cyanobacterium Lyngbya majuscula
    Milligan, KE
    Marquez, BL
    Williamson, RT
    Gerwick, WH
    JOURNAL OF NATURAL PRODUCTS, 2000, 63 (10): : 1440 - 1443
  • [40] Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula
    Lai, JY
    Yu, JR
    Mekonnen, B
    Falck, JR
    TETRAHEDRON LETTERS, 1996, 37 (40) : 7167 - 7170