Niizalactams A-C, Multicyclic Macrolactams Isolated from Combined Culture of Streptomyces with Mycolic Acid-Containing Bacterium

被引:61
|
作者
Hoshino, Shotaro [1 ]
Okada, Masahiro [1 ]
Wakirnoto, Toshiyuki [1 ]
Zhang, Huiping [2 ]
Hayashi, Fumiaki [2 ]
Onaka, Hiroyasu [3 ]
Abe, Ikuro [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
[2] RIKEN Ctr Life Sci Technol, Tsurumi Ku, Yokohama, Kanagawa 2300045, Japan
[3] Univ Tokyo, Grad Sch Agr & Life Sci, Bunkyo Ku, Tokyo 1138657, Japan
来源
JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 12期
关键词
ABSOLUTE-CONFIGURATION; DISCOVERY; BIOSYNTHESIS; ANTIBIOTICS; METABOLITES; POLYKETIDE; OXYLIPINS; ALCOHOLS; GENOME; NMR;
D O I
10.1021/acs.jnatprod.5b00804
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A terrestrial bacterium, Streptomyces sp. NZ-6, produced niizalactams A-C (1-3), unprecedented di- and tricyclic macrolactams, by coculturing with the mycolic acid-containing bacterium Tsukamurella pulmonis TP-B0596. Their complete structures, including absolute configurations, were elucidated on, the basis of spectroscopic data and chemical derivatization. Their unique skeletons are proposed to be biosynthesized from a common 26-membered macrolactam intermediate by S(N)2 cyclization or an intramolecular Diels-Alder reaction.
引用
收藏
页码:3011 / 3017
页数:7
相关论文
共 19 条
  • [1] Umezawamides, new bioactive polycyclic tetramate macrolactams isolated from a combined-culture of Umezawaea sp and mycolic acid-containing bacterium
    Hoshino, Shotaro
    Wong, Chin Piow
    Ozeki, Masahiro
    Zhang, Huiping
    Hayashi, Fumiaki
    Awakawa, Takayoshi
    Asamizu, Shumpei
    Onaka, Hiroyasu
    Abe, Ikuro
    JOURNAL OF ANTIBIOTICS, 2018, 71 (07): : 653 - 657
  • [2] Mirilactams C-E, Novel Polycyclic Macrolactams Isolated from Combined-Culture of Actinosynnema mirum NBRC 14064 and Mycolic Acid-Containing Bacterium
    Hoshino, Shotaro
    Ozeki, Masahiro
    Wong, Chin Piow
    Zhang, Huiping
    Hayashi, Fumiaki
    Awakawa, Takayoshi
    Morita, Hiroyuki
    Onaka, Hiroyasu
    Abe, Ikuro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2018, 66 (06) : 660 - 667
  • [3] Umezawamides, new bioactive polycyclic tetramate macrolactams isolated from a combined-culture of Umezawaea sp. and mycolic acid-containing bacterium
    Shotaro Hoshino
    Chin Piow Wong
    Masahiro Ozeki
    Huiping Zhang
    Fumiaki Hayashi
    Takayoshi Awakawa
    Shumpei Asamizu
    Hiroyasu Onaka
    Ikuro Abe
    The Journal of Antibiotics, 2018, 71 : 653 - 657
  • [4] Chojalactones A-C, Cytotoxic Butanolides Isolated from Streptomyces sp Cultivated with Mycolic Acid Containing Bacterium
    Hoshino, Shotaro
    Wakimoto, Toshiyuki
    Onaka, Hiroyasu
    Abe, Ikuro
    ORGANIC LETTERS, 2015, 17 (06) : 1501 - 1504
  • [5] Killing of Mycolic Acid-Containing Bacteria Aborted Induction of Antibiotic Production by Streptomyces in Combined-Culture
    Asamizu, Shumpei
    Ozaki, Taro
    Teramoto, Kanae
    Satoh, Katsuya
    Onaka, Hiroyasu
    PLOS ONE, 2015, 10 (11):
  • [6] Arcyriaflavin E, a new cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823
    Hoshino, Shotaro
    Zhang, Lihan
    Awakawa, Takayoshi
    Wakimoto, Toshiyuki
    Onaka, Hiroyasu
    Abe, Ikuro
    JOURNAL OF ANTIBIOTICS, 2015, 68 (05): : 342 - 344
  • [7] Arcyriaflavin E, a new cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823
    Shotaro Hoshino
    Lihan Zhang
    Takayoshi Awakawa
    Toshiyuki Wakimoto
    Hiroyasu Onaka
    Ikuro Abe
    The Journal of Antibiotics, 2015, 68 : 342 - 344
  • [8] Catenulobactins A and B, Heterocyclic Peptides from Culturing Catenuloplanes sp with a Mycolic Acid-Containing Bacterium
    Hoshino, Shotaro
    Ozeki, Masahiro
    Awakawa, Takayoshi
    Morita, Hiroyuki
    Onaka, Hiroyasu
    Abe, Ikuro
    JOURNAL OF NATURAL PRODUCTS, 2018, 81 (09): : 2106 - 2110
  • [9] Dispelling the "Nocardia amarae" myth:: a phylogenetic and phenotypic study of mycolic acid-containing actinomycetes isolated from activated sludge foam
    Stainsby, FM
    Soddell, J
    Seviour, R
    Upton, J
    Goodfellow, M
    WATER SCIENCE AND TECHNOLOGY, 2002, 46 (1-2) : 81 - 90
  • [10] Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.
    An, Joon Soo
    Kim, Myoun-Su
    Han, Jaeho
    Jang, Sung Chul
    Im, Ji Hyeon
    Cui, Jinsheng
    Lee, Yeonjin
    Nam, Sang-Jip
    Shin, Jongheon
    Lee, Sang Kook
    Yoon, Yeo Joon
    Oh, Dong-Chan
    JOURNAL OF NATURAL PRODUCTS, 2022, 85 (04): : 804 - 814