C-methylated and C-prenylated isoflavonoids from root extract of Desmodium uncinatum

• Published in: Phytochemistry (Oxford) Vol. 68; no. 5; pp. 646 - 651
• Main Authors: Guchu, Salome M., Yenesew, Abiy, Tsanuo, Muniru K., Gikonyo, Nicholas K., Pickett, John A., Hooper, Antony M., Hassanali, Ahmed
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.03.2007; Elsevier
• Subjects: Biochemistry & Molecular Biology; Biological and medical sciences; Biotechnology; Chemical constitution; chemical structure; Desmodium uncinatum; Edudiol; Fabaceae; Fabaceae - chemistry; Fabaceae - physiology; Flavonoids - chemistry; Flavonoids - isolation & purification; Fundamental and applied biological sciences. Psychology; Genetic engineering; Genetic technics; Germination; Germination stimulation; Isoflavanones; Isoflavonoids; Life Sciences & Biomedicine; Methods. Procedures. Technologies; Methylation; Models, Molecular; Molecular Conformation; plant extracts; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant physiology and development; Plant Roots - chemistry; Plant Sciences; Protein Prenylation; Pterocarpans; root systems; Science & Technology; seed germination; Seeds - physiology; spectral analysis; Striga hermonthica; Transgenic animals and transgenic plants; Transgenic plants; Uncinacarpan; uncinanone; Uncinanone D; Uncinanone E; Germination stimulation; Uncinanone E; Isoflavanones; Uncinanone D; Pterocarpans; Striga hermonthica; Uncinacarpan; Isoflavonoids; Edudiol; Desmodium uncinatum; Fabaceae; edudiol; STRIGA-HERMONTHICA; germination stimulation; STEM; SPP; pterocarpans; isoflavanones; isoflavonoids; MAIZE; uncinacarpan; uncinanone D; uncinanone E; Seeds; Root; Germination; Stimulation; Desmodium; Leguminosae; Dicotyledones; Seed; Angiospermae; Diterpene; Isolation; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2006.11.035

Three isoflavonoids, uncinacarpan ( 1), uncinanone D ( 3) and uncinanone E ( 4), along with three known compounds were isolated from the roots of Desmodium uncinatum, which induced germination of Striga hermonthica seeds. The isolated compounds were characterised by spectroscopic methods. A pterocarpan, 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (named uncinacarpan) and two isoflavanones, 5,7-dihydroxy-2′,3′,4′-trimethoxy-6-(3-methylbut-2-enyl)isoflavanone (named uncinanone D) and 5,4′-dihydroxy-7,2′-dimethoxy-6-methylisoflavanone (named uncinanone E), were isolated from the CH 2Cl 2 root extract of Desmodium uncinatum (Jacq.) DC and characterised by spectroscopic methods. In addition, a rare pterocarpan edudiol and two known abietane diterpenes, 7-oxo-15-hydroxydehydroabietic acid and 7-hydroxycallitrisic acid were identified. The fraction of the root extract that was analysed induced germination of Striga hermonthica seeds, but none of the isolated compounds showed this activity.