Haliclonadiamine Derivatives and 6-epi-Monanchorin from the Marine Sponge Halichondria panicea Collected at Iriomote Island

J Nat Prod. 2016 Apr 22;79(4):1149-54. doi: 10.1021/acs.jnatprod.6b00095. Epub 2016 Apr 1.

Abstract

Four new haliclonadiamine analogues, (10Z,12E)-haliclonadiamine (1), (10E,12Z)-haliclonadiamine (2), and halichondriamines A (3) and B (4), were isolated from the Okinawan marine sponge Halichondria panicea together with haliclonadiamine (5) and papuamine (6). The structures of 1-4 were elucidated on the basis of their spectroscopic data by comparisons with those for 5 and 6. Further separation of the remaining fraction led to the isolation of a new bicyclic guanidine alkaloid, 6-epi-monanchorin (7), along with monanchorin (8). Compound 7 is the epimer of 8 at the 6 position. Compounds 1-6 inhibited the growth of Mycobacterium smegmatis with inhibition zones of 12, 7, 8, 7, 16, and 12 mm at 10 μg/disc, respectively. Compounds 2-4 exhibited weak cytotoxicities against the Huh-7 (hepatoma) human cancer cell line and were 2-fold less active than 5 and 6. Compounds 7 and 8 were not active against M. smegmatis at 20 μg/disc or the cancer cell line at 10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / isolation & purification*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Carcinoma, Hepatocellular / drug therapy
  • Drug Screening Assays, Antitumor
  • Guanidine
  • Guanidines / chemistry
  • Guanidines / isolation & purification*
  • Guanidines / pharmacology
  • Humans
  • Japan
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium smegmatis / drug effects
  • Porifera / chemistry*

Substances

  • 6-epi-monanchorin
  • Alkaloids
  • Antineoplastic Agents
  • Bridged Bicyclo Compounds, Heterocyclic
  • Guanidines
  • haliclonadiamine
  • monanchorin
  • Guanidine