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Unraveling the complexity of Echinacea fractions to identify alkylamides and ketones important for anti‐inflammatory bioactivity
Author(s) -
LaLone Carlie A.,
Rizshsky Ludmila,
Solco Avery,
Nikolau Basil,
Murphy Patricia,
Birt Diane F.
Publication year - 2009
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.23.1_supplement.104.5
Subject(s) - chemistry , fraction (chemistry) , fractionation , ketone , nitric oxide , anti inflammatory , echinacea (animal) , chromatography , high performance liquid chromatography , pharmacology , traditional medicine , organic chemistry , medicine
Third round fractions produced via bioactivity guided semi‐preparative reversed phase HPLC fractionation of Echinacea angustifolia were analyzed by GC‐MS to identify constituents important for the anti‐inflammatory properties of the botanical. Two fractions were of interest due to their ability to inhibit lipopolysaccharide induced PGE 2 production in RAW264.7 mouse macrophage cells and their GC‐MS chromatograms having peaks for known and synthetically available compounds. When identification and quantification from GC‐MS revealed that major constituents present in one fraction (1 µg/ml) were alkylamide 10 (0.15 µM) and ketone 23 (0.24 µM), and that the other fraction (1 µg/ml) consisted of alkylamide 11 (3.6 µM), these constituents were screened at the concentrations present in the fraction using the PGE 2 assay. The combination of alkylamide 10 and ketone 23 did not explain the bioactivity of its respective fraction, but alkylamide 11 was partially explanatory of the bioactivity, accounting for 30% reduction of PGE 2 production compared to 81% reduction of PGE 2 identified with the fraction. Chemically synthesized ketones 21 and 23 were also shown to individually inhibit PGE 2 and nitric oxide production at a concentration as low as 1µM, providing a basis to study these constituents further for anti‐inflammatory potential. Funding: 9 P50 AT004155‐06 from ODS/NCCAM, NIH. Grant Funding Source 9 P50 AT004155 ‐06 from ODS/NCCAM, NIH