Unraveling Structures Containing Highly Conjugated Pyrrolo[4,3,2-de]quinoline Cores That Are Deficient in Diagnostic Proton NMR Signals

This study began with the goal of identifying additional constituents from Zyzzya fuliginosa extracts obtained from an Indo-Pacific sponge (coll. no. 06132). The previous work identified several red and green pyrroloiminiquinones (aka pyrrolo­[4,3,2-de]­quinolines), and this reinvestigation provided...

Full description

Saved in:
Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-01, Vol.83 (1), p.174-178
Main Authors: McCauley, Erin P, Smith, Gavin C, Crews, Phillip
Format: Article
Language:English
Subjects:
Animals
Magnetic Resonance Spectroscopy
Molecular Structure
Porifera - chemistry
Protons
Quinolines - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:This study began with the goal of identifying additional constituents from Zyzzya fuliginosa extracts obtained from an Indo-Pacific sponge (coll. no. 06132). The previous work identified several red and green pyrroloiminiquinones (aka pyrrolo­[4,3,2-de]­quinolines), and this reinvestigation provided two additional analogues, a blue compound named zyzzamine A (1) and a green compound named zyzzamine B (2). The relatively low ratio of H/[sum­(CNO)] = 0.71 or 0.76 of this pair greatly complicated the final steps of compound characterization and required the use of five 2D NMR strategies and MS2 data sets.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.9b01111