Langkolide, a 32-Membered Macrolactone Antibiotic Produced by Streptomyces sp Acta 3062

被引:20
作者
Helaly, Soleiman E. [2 ,3 ]
Kulik, Andreas [4 ]
Zinecker, Heidi [5 ,6 ,7 ]
Ramachandaran, Kamalanathan [1 ]
Tan, Geok Yuan Annie [1 ]
Imhoff, Johannes F. [5 ,6 ]
Suessmuth, Roderich D. [2 ]
Fiedler, Hans-Peter [4 ]
Sabaratnam, Vikineswary [1 ]
机构
[1] Univ Malaya, Inst Biol Sci, Kuala Lumpur 50603, Malaysia
[2] Tech Univ Berlin, Inst Chim, D-10623 Berlin, Germany
[3] S Valley Univ, Dept Chem, Aswan 81528, Egypt
[4] Univ Tubingen, Inst Mikrobiol, D-72076 Tubingen, Germany
[5] IFM GEOMAR, Kieler Wirkstoff Zentrum, D-24105 Kiel, Germany
[6] IFM GEOMAR, Leibniz Inst Meereswissensch, D-24105 Kiel, Germany
[7] Univ Bonn, Inst Pharmazeut, Bonn, Germany
来源
JOURNAL OF NATURAL PRODUCTS | 2012年 / 75卷 / 06期
关键词
UNIVERSAL NMR DATABASES; STEREOCHEMICAL ASSIGNMENT; DESERTOMYCIN/OASOMYCIN CLASS; NATURAL-PRODUCTS; IMMUNOSUPPRESSIVE MACROLIDE; BIOSYNTHETIC CAPACITIES; NOCARDIA-BRASILIENSIS; SECONDARY METABOLITES; C21-C38; PORTION; BRASILINOLIDE-A;
D O I
10.1021/np200580g
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new 32-membered macrolactone antibiotic, named langkolide, was isolated from the mycelium of Streptomyces sp. Acta 3062. The langkolide structure was determined by HR-MS and 1D and 2D NMR as a 32-membered macrolactone connected from an overhanging polyketide tail to a naphthoquinone unit mediated by two carbohydrate moieties. The producing strain was isolated from a rhizosphere soil of Clitorea sp. collected at Burau Bay, Langkawi, Malaysia, and was characterized by its morphological and chemotaxonomic features in addition to its 16S rRNA gene sequence. It was identified as a member of the Streptomyces galbus clade. Langkolide exhibited various bioactivities including antimicrobial and antiproliferative activities. Furthermore, langkolide inhibited human recombinant phosphodiesterase 4 with an IC50 value of 0.48 mu M.
引用
收藏
页码:1018 / 1024
页数:7
相关论文
共 45 条
  • [1] A high throughput luminescent assay for glycogen synthase kinase-3β inhibitors
    Baki, Andrea
    Bielik, Attila
    Molnar, Laszlo
    Szendrei, Gyorgyi
    Keseru, Gyorgy M.
    [J]. ASSAY AND DRUG DEVELOPMENT TECHNOLOGIES, 2007, 5 (01) : 75 - 83
  • [2] Barbara L.T.P., 1976, INT J SYST BACTERIOL, V26, P319
  • [3] Stereochemistry of the core structure of the mycolactones
    Benowitz, AB
    Fidanze, S
    Small, PLC
    Kishi, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) : 5128 - 5129
  • [4] RHODINOSE, EINE TRIDESOXY-HEXOSE
    BROCKMANN, H
    WAEHNELDT, T
    [J]. NATURWISSENSCHAFTEN, 1963, 50 (02) : 43 - &
  • [5] MYCOTICIN, A NEW ANTIFUNGAL ANTIBIOTIC .1. PRELIMINARY PAPER
    BURKE, RC
    SWARTZ, JH
    CHAPMAN, SS
    HUANG, WY
    [J]. JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1954, 23 (03) : 163 - 168
  • [6] Chun J., 2001, PHYDIT VERSION 3 1
  • [7] EzTaxon: a web-based tool for the identification of prokaryotes based on 16S ribosomal RNA gene sequences
    Chun, Jongsik
    Lee, Jae-Hak
    Jung, Yoonyoung
    Kim, Myungjin
    Kim, Seil
    Kim, Byung Kwon
    Lim, Young-Woon
    [J]. INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY, 2007, 57 : 2259 - 2261
  • [8] STREPTOMYCES-BUNGOENSIS SP-NOV
    EGUCHI, T
    TAKADA, N
    NAKAMURA, S
    TANAKA, T
    MAKINO, T
    OSHIMA, Y
    [J]. INTERNATIONAL JOURNAL OF SYSTEMATIC BACTERIOLOGY, 1993, 43 (04): : 794 - 798
  • [9] Complete structure of the mycolactones
    Fidanze, S
    Song, FB
    Szlosek-Pinaud, M
    Small, PLC
    Kishi, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) : 10117 - 10118
  • [10] Fiedler H.P., 1993, NAT PROD LETT, V2, P119