Anti-mycobacterial alkaloids, cyclic 3-alkyl pyridinium dimers, from the Indonesian marine sponge Haliclona sp

Bioorg Med Chem Lett. 2017 Aug 1;27(15):3503-3506. doi: 10.1016/j.bmcl.2017.05.067. Epub 2017 May 23.

Abstract

Three new dimeric 3-alkyl pyridinium alkaloids, named haliclocyclamines A-C (1-3), were isolated together with five known congeners, cyclostellettamines A (4), B (5), C (6), E (7), and F (8), from the Indonesian marine sponge Haliclona sp. The structures of 1-3 were assigned based on their spectroscopic data (1D and 2D NMR, HRFABMS, ESIMS/MS, UV, and IR). Compounds 1-8 exhibited antimicrobial activities against Mycobacterium smegmatis with inhibition zones of 17, 10, 13, 14, 8, 8, 12, and 12mm, respectively, at 10μg/disc. Compounds 3 and 8 also modestly inhibited the activity of vaccinia H-1-related phosphatase (VHR), a dual-specificity phosphatase, at 17-18μM.

Keywords: 3-Alkyl pyridinium alkaloid; Haliclocyclamine; Marine sponge Haliclona sp.; Mycobacterium smegmatis; Vaccinia H-1-related phosphatase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Haliclona / chemistry*
  • Indonesia
  • Mycobacterium Infections, Nontuberculous / drug therapy
  • Mycobacterium Infections, Nontuberculous / microbiology*
  • Mycobacterium smegmatis / drug effects*
  • Pyridinium Compounds / chemistry
  • Pyridinium Compounds / isolation & purification
  • Pyridinium Compounds / pharmacology*

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Pyridinium Compounds