Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites

Through bioassay-guided fractionation, 13 compounds ( 1 – 13 ) were isolated from the CH 2 Cl 2 /MeOH (1:1) extracts of the root bark of Newbouldia leavis and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives ( 1 – 7 , 12 – 13 ), one triterpeniod ( 8 ), and th...

Full description

Saved in:
Bibliographic Details
Published in:Medicinal chemistry research 2015, Vol.24 (3), p.965-969
Main Authors: Eyong, Kenneth O., Ketsemen, Herve L., Ghansenyuy, Salome Y., Folefoc, Gabriel N.
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Through bioassay-guided fractionation, 13 compounds ( 1 – 13 ) were isolated from the CH 2 Cl 2 /MeOH (1:1) extracts of the root bark of Newbouldia leavis and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives ( 1 – 7 , 12 – 13 ), one triterpeniod ( 8 ), and three steroids ( 9 – 11 ) were isolated. The stereochemistry of 3-hydroxy furonaphthoquinones isolated from this plant has been established for the first time as (2 S ,3 R ) on the basis of single X-ray crystal structure analysis and show marked 3 J H,H deviations from the Karplus curve from 1 H-NMR spectral analysis. The fractions together with three of the isolated compounds namely lapachol, 2-acetyl-naphtho [2,3- b ]furan-4,9-dione, and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3- b ]furan-4,9-dione were screened against Onchocerca ochengi parasites. Lapachol and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3- b ]furan-4,9-dione showed 100 % inhibition at a concentration of 5 μg/mL after 5 days.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-014-1173-z