A share of this work is part of the Ph.D. thesis of H. N., University of Trento, 2004.
Improved Anti-Inflammatory Activity of Three New Terpenoids Derived, by Systematic Chemical Modifications, from the Abundant Triterpenes of the Flowery Plant Calendula officinalis†
Version of Record online: 18 MAY 2005
Copyright © 2005 Verlag Helvetica Chimica Acta AG, Zürich
Chemistry & Biodiversity
Volume 2, Issue 5, pages 657–671, May 2005
How to Cite
Neukirch, H., D'Ambrosio, M., Sosa, S., Altinier, G., Della Loggia, R. and Guerriero, A. (2005), Improved Anti-Inflammatory Activity of Three New Terpenoids Derived, by Systematic Chemical Modifications, from the Abundant Triterpenes of the Flowery Plant Calendula officinalis. Chemistry & Biodiversity, 2: 657–671. doi: 10.1002/cbdv.200590042
- Issue online: 18 MAY 2005
- Version of Record online: 18 MAY 2005
- Manuscript Received: 21 SEP 2004
Rings A, D and E of faradiol (1), and ring E of both arnidiol (10) and calenduladiol (4) have been subjected to various selective chemical manipulations to modify polarity, water affinity, H-bonding, sterics, and number of aromatic groups of these anti-inflammatory natural compounds. A total of 15 new and four known pentacyclic triterpenoids have been obtained in this way. Some 13 terpenoids were evaluated for their topical anti-inflammatory activities with respect to inhibition of croton oil induced ear oedema in mouse. Three derivatives of 1, the C(16) benzyl ether 15, the C(30) aldehyde 24, and the C(30) primary alcohol 25 showed significantly improved anti-inflammatory potencies, which is relevant for (future) structure–activity-relationship (SAR) studies.