Flavonoids and Phenolic Compounds from Rosmarinus officinalis

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 9; pp. 5363 - 5367
• Main Authors: Bai, Naisheng, He, Kan, Roller, Marc, Lai, Ching-Shu, Shao, Xi, Pan, Min-Hsiung, Ho, Chi-Tang
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 12-05-2010
• Subjects: anti-inflammatory activity; Aroma and flavouring agent industries; Bioactive Constituents; Biological and medical sciences; Cell Line, Tumor; cell proliferation; cytotoxicity; flavonoids; Flavonoids - isolation & purification; food analysis; food composition; Food industries; functional foods; Fundamental and applied biological sciences. Psychology; human cell lines; Humans; Magnetic Resonance Spectroscopy; phenolic compounds; Phenols - isolation & purification; rosemary; Rosmarinus - chemistry; Rosmarinus officinalis; Spectrometry, Mass, Electrospray Ionization; anti-inflammatory; 6′′-O-(E)-feruloylhomoplantaginin; human cancer cell lines (HepG2, COLO 205, HL-60); flavonoids; Rosmarinus officinalis; Human; Antiinflammatory agent; Spice; Malignant tumor; Flavonoid; In vitro; Polyphenol; Cell line; 6-O-(E)-feruloylhomoplantaginin; Labiatae; Dicotyledones; Angiospermae; Phenols; Rosemary; Spermatophyta; Cancer
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf100332w

A new flavonoid, 6′′-O-(E)-feruloylhomoplantaginin (1), and 14 known compounds, 6′′-O-(E)-feruloylnepitrin (2), 6′′-O-(E)-p-coumaroylnepitrin (3), 6-methoxyluteolin 7-glucopyranoside (4), luteolin 3′-O-β-d-glucuronide (5), luteolin 3′-O-(3′′-O-acetyl)-β-d-glucuronide (6), kaempferol (7), luteolin (8), genkwanin (9), and ladanein (10), together with 1-O-feruloyl-β-d-glucopyranose (11), 1-O-(4-hydroxybenzoyl)-β-d-glucopyranose (12), rosmarinic acid (13), carnosic acid (14), and carnosol (15), were isolated from the leaves of Rosmarinus officinalis. The structures were established on the basis of NMR spectroscopic methods supported by HRMS. All isolated compounds were tested for cytotoxicity in human cancer cell lines (HepG2, COLO 205, and HL-60) and for anti-inflammatory activities in lipopolysaccharide (LPS)-treated RAW 264.7 macrophage cells. Among them, compounds 14 and 15 were modestly active in the inhibition of nitrite production in macrophages, followed by compounds 8 and 5. Compounds 14 and 15 were more effective as an antiproliferative agent in HL-60 cells with IC50 values of 1.7 and 5.5 μM, followed by compounds 8 and 7 with IC50 of 39.6 and 82.0 μM, respectively. In addition, compounds 14 and 15 showed potent antiproliferative effects on COLO 205 cells with IC50 values of 32.8 and 29.9 μM, respectively.