Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei

• Published in: Tetrahedron Vol. 67; no. 29; pp. 5346 - 5359
• Main Authors: Sugamoto, Kazuhiro, Matsusita, Yoh-ichi, Matsui, Kana, Kurogi, Chiaki, Matsui, Takanao
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.07.2011; Elsevier
• Subjects: [1,3]-Sigmatropic rearrangement; Angelica; Angelica keiskei; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiinfectives and antibacterials; Bacteria; Bearing; Biological and medical sciences; Chemistry; Chemistry, Organic; Derivatives; Exact sciences and technology; General pharmacology; Geranylated chalcone; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Medical sciences; Organic chemistry; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Physical Sciences; Prenylated chalcone; Preparations and properties; Science & Technology; Synthesis (chemistry); Tetrahedrons; Asia; Japan; Angelica keiskei; [1,3]-Sigmatropic rearrangement; Antibacterial activity; Prenylated chalcone; Geranylated chalcone; 4-HYDROXYDERRICIN; ALLYL PHENYL ETHERS; XANTHOANGELOL; CHEMICAL-COMPONENTS; BAVACHALCONE; FLAVANONES; ISOBAVACHALCONE; RESACETOPHENONE; ROOT BARK; CONSTITUENTS; Sigmatropic reaction; Pharmacognosy; Isoprenoid; Flavonoid; Medicinal plant; Folk medicine; Gram positive bacteria; Dicotyledones; Angiospermae; Plant origin; Spermatophyta; Umbelliferae; Antibacterial agent; Chemical synthesis
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.04.104

Chalcones bearing prenyl or geranyl groups from Angelica keiskei, such as 4-hydroxyderricin ( 1a), xanthoangelol ( 1e), xanthoangelol F ( 1f), xanthoangelol H ( 2), deoxyxanthoangelol H ( 3), and deoxydihydroxanthoangelol H ( 4) and their derivatives were synthesized. From the evaluation of antibacterial activity of the synthesized chalcones, 1a, isobavachalcone ( 1b), 1e, 1f, bavachalcone ( 5a), and broussochalcone B ( 5b) were found to inhibit Gram-positive bacteria. [Display omitted]