Chemical constituents from the leaves of Boehmeria rugulosa with antidiabetic and antimicrobial activities.
Three new flavonoid glycosides, named chalcone-6'-hydroxy-2',3,4-trimethoxy-4'-O-beta-D-glucopyranoside (1), isoflavone-3',4',5,6-tetrahydroxy-7-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranoside] (2), and isoflavone-3',4',5,6-tetrahydroxy-7-O-[beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranoside] (3), were isolated from the leaves of Boehmeria rugulosa, together with five known compounds, beta-sitosterol, quercetin, 3,4-dimethoxy-omega-(2'-piperidyl)-acetophenone (4), boehmeriasin A (5), and quercetin-7-O-beta-D-glucopyranoside. The structures of the isolated compounds were determined by means of chemical and spectral data including 2D NMR experiments. The ethanolic extract of leaves showed significant hypoglycemic activity on alloxan-induced diabetic mice. Glibenclamide, an oral hypoglycemic agent (5 mg/kg, p.o.), was used as a positive control. The ethanolic extract of the plant as well as the isolated compounds 1-3 (25 microg/ml) showed potent antimicrobial activity against two bacterial species (Staphylococcus aureus and Streptococcus mutans) and three fungus pathogens (Microsporum gypseum, Microsporum canis, and Trichophyton rubrum). The activities of the isolated compounds 1-3 have been compared with positive controls, novobiocin, and erythromycin (15 microg/ml).
Semwal
Deepak Kumar
DK
Department of Chemistry, H N B Garhwal University, Srinagar, Uttarakhand, India. dr_dks.1983@yahoo.co.in
Rawat
Usha
U
Semwal
Ravindra
R
Singh
Randhir
R
Krishan
Pawan
P
Singh
Manjeet
M
Singh
Gur Jas Preet
GJ
D000496:Alloxan / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D032402:Boehmeria / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007194:India; D008751:Methylene Blue; D051379:Mice; D008826:Microbial Sensitivity Tests; D008864:Microsporum / Q000187:drug effects; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D013210:Staphylococcus / Q000187:drug effects; D013291:Streptococcus / Q000187:drug effects; D014249:Trichophyton / Q000187:drug effects
D000890:Anti-Infective Agents; D005419:Flavonoids; D006027:Glycosides; D007004:Hypoglycemic Agents; D000496:Alloxan; D008751:Methylene Blue