Plant-growth inhibitory activity of heliannuol derivatives

• Published in: Phytochemistry (Oxford) 2004-05, Vol.65 (10), p.1405-1411
• Main Authors: Doi, Fuminao, Ohara, Taiga, Ogamino, Takahisa, Sugai, Takeshi, Higashinakasu, Keiko, Yamada, Kosumi, Shigemori, Hideyuki, Hasegawa, Koji, Nishiyama, Shigeru
• Format: Article
• Language: English
• Subjects: Allelochemicals; Avena - drug effects; Avena - growth & development; Avena sativa; benzo(b)oxepin; bioassays; biochemical pathways; Biological and medical sciences; Bridged Bicyclo Compounds, Heterocyclic - isolation & purification; Bridged Bicyclo Compounds, Heterocyclic - pharmacology; Chemical agents; Chemical constitution; chemical structure; chromans; Compositae; Cotyledon - drug effects; Cotyledon - growth & development; Flowers - chemistry; Fundamental and applied biological sciences. Psychology; Heliannuol; heliannuols; Helianthus - chemistry; Helianthus annuus; Helianthus annuus L; Hypocotyl - drug effects; Hypocotyl - growth & development; isomers; Lepidium sativum; Lepidium sativum - drug effects; Lepidium sativum - growth & development; Molecular Conformation; Molecular Structure; phytochemicals; plant growth control; Plant Growth Regulators - isolation & purification; Plant Growth Regulators - pharmacology; Plant physiology and development; Plant Roots - drug effects; Plant Roots - growth & development; Plant-growth inhibition; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; sesquiterpenoids; Vegetative apparatus, growth and morphogenesis. Senescence
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2004.03.035

Chromane and tetrahydro-oxepin derivatives related to heliannuols were submitted to assessment of plant-growth inhibitory activity. In addition to (+)-, (−)- and (±)-heliannuol E, growth-inhibitory activities of five synthetic chromans and four tetrahydrobenzo[b]oxepins were examined against oat and cress. All heliannuol E isomers exhibited similar biological activities against cress, whereas when tested against oat roots, the unnatural optical isomer (+) showed no inhibitory activity. Four brominated chromans and two tetrahydrobenzo[b]oxepin derivatives also showed apparent inhibition against both cress and oat.