Structure−Activity Relationship of Karrikin Germination Stimulants

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 15; pp. 8612 - 8617
• Main Authors: Flematti, Gavin R, Scaffidi, Adrian, Goddard-Borger, Ethan D, Heath, Charles H, Nelson, David C, Commander, Lucy E, Stick, Robert V, Dixon, Kingsley W, Smith, Steven M, Ghisalberti, Emilio L
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 11.08.2010; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Bioactive Constituents; bioactive properties; Biological and medical sciences; chemical analysis; chemical composition; Chemistry; Chemistry, Applied; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Furans - chemistry; Furans - pharmacology; Germination - drug effects; Life Sciences & Biomedicine; Molecular Structure; Physical Sciences; plant growth substances; Pyrans - chemistry; Pyrans - pharmacology; Science & Technology; seed germination; Seeds - drug effects; Seeds - physiology; smoke; Solanum - drug effects; Solanum - physiology; Structure-Activity Relationship; structure-activity relationships; Karrikinolide; smoke; seed dormancy; seed germination; germination stimulant; karrikin; SEED-GERMINATION; LIGHT; GIBBERELLIN; COMPOUND; BUTENOLIDE; SMOKE-WATER; GROWTH; Seeds; Structure activity relation; Germination
• ISSN: 0021-8561; 1520-5118; 1520-5118
• DOI: 10.1021/jf101690a

Karrikins (2H-furo[2,3-c]pyran-2-ones) are potent smoke-derived germination promoters for a diverse range of plant species but, to date, their mode of action remains unknown. This paper reports the structure−activity relationship of numerous karrikin analogues to increase understanding of the key structural features of the molecule that are required for biological activity. The results demonstrate that modification at the C5 position is preferred over modification at the C3, C4, or C7 positions for retaining the highest bioactivity.