RRC ID 40083
Author Oya A, Tanaka N, Kusama T, Kim SY, Hayashi S, Kojoma M, Hishida A, Kawahara N, Sakai K, Gonoi T, Kobayashi J.
Title Prenylated benzophenones from Triadenum japonicum.
Journal J Nat Prod
Abstract Six new prenylated benzophenones, (-)-nemorosonol (1) and trijapins A-E (2-6), were isolated from the aerial parts of Triadenum japonicum. (-)-Nemorosonol (1) and trijapins A-C (2-4) have a common tricyclo[4.3.1.0(3,7)]decane skeleton, while 1 is an enantiomer of (+)-nemorosonol previously isolated from Clusia nemorosa. The absolute configuration of (-)-nemorosonol (1) was assigned by ECD spectroscopy. Trijapins A-C (2-4) are analogues of 1 possessing an additional tetrahydrofuran ring. Trijapins D (5) and E (6) are prenylated benzophenones with a 1,2-dioxane moiety and a hydroperoxy group, respectively. (-)-Nemorosonol (1) exhibited antimicrobial activity against Escherichia coli (MIC, 8 μg/mL), Staphylococcus aureus (MIC, 16 μg/mL), Bacillus subtilis (MIC, 16 μg/mL), Micrococcus luteus (MIC, 32 μg/mL), Aspergillus niger (IC50, 16 μg/mL), Trichophyton mentagrophytes (IC50, 8 μg/mL), and Candida albicans (IC50, 32 μg/mL), while trijapin D (5) showed antimicrobial activity against C. albicans (IC50, 8 μg/mL).
Volume 78(2)
Pages 258-64
Published 2015-2-27
DOI 10.1021/np500827h
PMID 25602977
MeSH Anti-Bacterial Agents / chemistry Anti-Bacterial Agents / isolation & purification* Anti-Bacterial Agents / pharmacology Aspergillus niger / drug effects Bacillus subtilis / drug effects Benzophenones / chemistry Benzophenones / isolation & purification* Benzophenones / pharmacology Candida albicans / drug effects Escherichia coli / drug effects Hypericum / chemistry* Japan Microbial Sensitivity Tests Micrococcus luteus / drug effects Molecular Structure Plant Components, Aerial / chemistry Prenylation Staphylococcus aureus / drug effects Stereoisomerism Trichophyton / drug effects
IF 3.782
Times Cited 20
WOS Category PLANT SCIENCES PHARMACOLOGY & PHARMACY CHEMISTRY, MEDICINAL
Resource
Pathogenic microorganisms NA