Isolation of (-)(2S)-5,6,7,3',5'-pentahydroxyflavanone-7-O-β-D-glucopyranoside, from Lippia graveolens H.B.K. var. berlandieri Schauer, a new anti-inflammatory and cytotoxic flavanone.
A new flavanone glycoside, (-)(2S)-5,6,7,3',5'-pentahydroxyflavanone-7-O-β-D-glucopyranoside (1), was isolated from the stems of Lippia graveolens H.B.K. (Verbenaceae). The structure of 1 was elucidated based on spectral analysis and chemical transformations. The treatment of 1 with acetic anhydride and pyridine afforded the corresponding per-acetylated derivative 2, while an acid hydrolysis reaction of 1 afforded a 5,6,7,3',5'-pentahydroxy flavanone (3). Additionally, the anti-inflammatory and cytotoxic activities of 1, 2 and 3 were determined.
Gonzalez-Guëreca
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MC
Instituto Politecnico Nacional, Dgo, Mexico.
Soto-Hernandez
M
M
Martinez-Vazquez
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M
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification*; D045744:Cell Line, Tumor; D002642:Chick Embryo; D004354:Drug Screening Assays, Antitumor; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D006801:Humans; D032411:Lippia / Q000737:chemistry*; D008297:Male; D051379:Mice; D015394:Molecular Structure; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry
C554705:(-)(2S)-5,6,7,3',5'-pentahydroxyflavanone-7-O-beta-D-glucopyranoside; D000893:Anti-Inflammatory Agents; D000972:Antineoplastic Agents, Phytogenic; D044950:Flavanones; D005960:Glucosides