Pursuing sesterterpene lactams in Australian Irciniidae sponges

Pritesh Prasad; Ailian Zhang; Angela A Salim; Robert J Capon

doi:10.1016/j.fitote.2017.09.003

Pursuing sesterterpene lactams in Australian Irciniidae sponges

Fitoterapia. 2018 Apr:126:83-89. doi: 10.1016/j.fitote.2017.09.003. Epub 2017 Sep 6.

Authors

Pritesh Prasad¹, Ailian Zhang², Angela A Salim¹, Robert J Capon³

Affiliations

¹ Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Queensland 4072, Australia.
² School of Forestry and Biotechnology, Zhejiang A & F University, Lin'an, Zhejiang 311300, People's Republic of China.
³ Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Queensland 4072, Australia. Electronic address: r.capon@uq.edu.au.

PMID: 28888966
DOI: 10.1016/j.fitote.2017.09.003

Abstract

Chemical investigation of two Irciniidae sponges collected by hand (SCUBA) from Australian near shore waters, afforded six new examples of a rare class of sesterterpene lactam; ircinialactams B (1), G (2), H (5), and I (6), and 8-hydroxyircinialactams C (3) and G (4); together with the new biosynthetically related lactone, ircinialactone A (7). Also isolated were seven biosynthetically related known Irciniidae metabolites; ircinialactams A (8) and C (9), (7E,12E,20Z,18S)-variabilin (10), (7Z,12Z,20Z,18S)-variabilin (11), (7E,12Z,20Z,18S)-variabilin (12), (7Z,12E,20Z,18S)-variabilin (13) and irciniafuran A (14). The structure elucidation of 1-14 was achieved by detailed spectroscopic analysis, and consideration of a plausible biosynthetic relationship linking Irciniidae sesterterpene β-furans, lactams and lactones.

Keywords: Irciniidae; Lactam; Marine natural product; Sesterterpene; Sponge; Tetronic acid.

MeSH terms

Animals
Lactams / chemistry*
Lactams / isolation & purification
Molecular Structure
New South Wales
Porifera / chemistry*
Proteins / chemistry
Sesterterpenes / chemistry*
Sesterterpenes / isolation & purification

Substances

Lactams
Proteins
Sesterterpenes
variabilin