Prev. Article Next Article Table of Contents

Article

Sesquiterpene Lactones as Allelochemicals

Francisco A. Macías,*^† Adriana Fernández,^† Rosa M. Varela,^† José M. G. Molinillo,^† Ascensión Torres,^† and Pedro L. C. A. Alves^‡

Grupo de Alelopata, Departamento de Qumica Orgnica, Facultad de Ciencias, Universidad de Cdiz, Avda. Repblica Saharaui, Apdo. 40, 11510 Puerto Real, Spain, and Departamento de Biologia Aplicada Agropecuria, FCAV, Universidade Estadual Paulista/UNESP, CEP 14884-900, Jaboticabal, So Paulo, Brazil

J. Nat. Prod., 2006, 69 (5), pp 795–800

DOI: 10.1021/np060056s

Publication Date (Web): April 27, 2006

To whom correspondence should be addressed. Tel: +34.956.016370. Fax: +34.956.016193. E-mail: famacias@uca.es.

†

Universidad de Cádiz.

‡

Universidade Estadual Paulista.

Abstract

Six new sesquiterpene lactones, annuolide H (3), helivypolides F, H−J (4, 11−13), and helieudesmanolide A (6), together with known compounds, were isolated from polar bioactive fractions of Helianthus annuus cv. SH-222 and Stella fresh leaf water extracts. Spectroscopic analysis of the new data for 1,2-anhydroniveusin A and 1-methoxy-4,5-dihydroniveusin A corrects some previous assignments. The compounds were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species (STS) (Lepidium sativum, Allium cepa, Lactuca sativa, Lycopersicon esculentum, and Triticum aestivum) from 5 × 10^-4 to 10^-5 M. The most phytotoxic compounds were helivypolide F and 15-hydroxy-3-dehydrodeoxyfruticin, both of which have a carbonyl group at C-3 conjugated with two double bonds.