Two new pyrrolo-2-aminoimidazoles from a Myanmarese marine sponge, Clathria prolifera

So Yeun Woo, Nwet Nwet Win, Chin Piow Wong, Takuya Ito, Shotaro Hoshino, Hla Ngwe, Aung Aung Aye, Nang Mya Han, Huiping Zhang, Fumiaki Hayashi, Ikuro Abe, Hiroyuki Morita*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Marine organisms such as marine sponges and soft corals are valuable sources of pharmacologically active secondary metabolites. In our ongoing research on the discovery of new secondary metabolites from marine organisms, two new pyrrolo-2-aminoimidazoles, clathriroles A (1) and B (2), were isolated from the water-soluble portion prepared from the methanol and acetone (2:1) extract of the marine sponge, Clathria prolifera, collected in Myanmar. The chemical structures of the isolated compounds were determined using extensive spectroscopic techniques, including NMR, HRESIMS, IR, and optical rotation, and comparisons with the reported literature. The spectroscopic analyses of 1 and 2 suggested that 1 is an enantiomer of antifungal N-methylmanzacidin C isolated from the marine sponge Axinella brevistyla, whereas 2 is a diastereomer of manzacidin D at C-11 isolated from the marine sponge Astrosclera willeyana. To the best of our knowledge, this is the first report of the isolation of the pyrrolo-2-aminoimidazole compounds from C. prolifera. Furthermore, in contrast to the potency of N-methylmanzacidin C against Saccharomyces cerevisiae, the antifungal assay revealed that 1 and 2 lack any activity against this strain. Thus, these observations may suggest that the absolute configurations at both C-9 and C-11 play an important role in controlling the antifungal activity of this type of compound.

Original languageEnglish
Pages (from-to)803-807
Number of pages5
JournalNatural Medicines
Volume72
Issue number3
DOIs
StatePublished - 2018/06/01

Keywords

  • Alkaloids
  • Clathria prolifera
  • Marine sponge
  • Pyrrole derivatives
  • Saccharomyces cerevisiae

ASJC Scopus subject areas

  • Molecular Medicine

Fingerprint

Dive into the research topics of 'Two new pyrrolo-2-aminoimidazoles from a Myanmarese marine sponge, Clathria prolifera'. Together they form a unique fingerprint.

Cite this