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Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production.
J Nat Prod. 2006 Apr; 69(4):719-21.JN

Abstract

A new prenylated chalcone, 3' ',3' '-dimethylpyrano[3',4']2,4,2'-trihydroxychalcone (1), was isolated from the heartwood of Artocarpus communis. Two flavonoid derivatives, (-)-cycloartocarpin (9) and (-)-cudraflavone A (10), were isolated as new isomers. In addition, eight known flavonoids, isobacachalcone (2), morachalcone A (3), gemichalcones B (4) and C (5), artocarpin (6), cudraflavone C (7), licoflavone C (8), and (2S)-euchrenone a(7) (11), were isolated and identified from this plant for the first time. Compounds 1-4, 6, and 11 exhibited potent inhibitory activity on nitric oxide production in RAW264.7 LPS-activated mouse macrophage cells with IC(50) values of 18.8, 6.4, 16.4, 9.3, 18.7, and 12.3 microM, respectively. The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments.

Authors+Show Affiliations

College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16643064

Citation

Han, Ah-Reum, et al. "Prenylated Flavonoids From the Heartwood of Artocarpus Communis With Inhibitory Activity On Lipopolysaccharide-induced Nitric Oxide Production." Journal of Natural Products, vol. 69, no. 4, 2006, pp. 719-21.
Han AR, Kang YJ, Windono T, et al. Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production. J Nat Prod. 2006;69(4):719-21.
Han, A. R., Kang, Y. J., Windono, T., Lee, S. K., & Seo, E. K. (2006). Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production. Journal of Natural Products, 69(4), 719-21.
Han AR, et al. Prenylated Flavonoids From the Heartwood of Artocarpus Communis With Inhibitory Activity On Lipopolysaccharide-induced Nitric Oxide Production. J Nat Prod. 2006;69(4):719-21. PubMed PMID: 16643064.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production. AU - Han,Ah-Reum, AU - Kang,You-Jin, AU - Windono,Tri, AU - Lee,Sang Kook, AU - Seo,Eun-Kyoung, PY - 2006/4/29/pubmed PY - 2006/6/22/medline PY - 2006/4/29/entrez SP - 719 EP - 21 JF - Journal of natural products JO - J Nat Prod VL - 69 IS - 4 N2 - A new prenylated chalcone, 3' ',3' '-dimethylpyrano[3',4']2,4,2'-trihydroxychalcone (1), was isolated from the heartwood of Artocarpus communis. Two flavonoid derivatives, (-)-cycloartocarpin (9) and (-)-cudraflavone A (10), were isolated as new isomers. In addition, eight known flavonoids, isobacachalcone (2), morachalcone A (3), gemichalcones B (4) and C (5), artocarpin (6), cudraflavone C (7), licoflavone C (8), and (2S)-euchrenone a(7) (11), were isolated and identified from this plant for the first time. Compounds 1-4, 6, and 11 exhibited potent inhibitory activity on nitric oxide production in RAW264.7 LPS-activated mouse macrophage cells with IC(50) values of 18.8, 6.4, 16.4, 9.3, 18.7, and 12.3 microM, respectively. The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/16643064/Prenylated_flavonoids_from_the_heartwood_of_Artocarpus_communis_with_inhibitory_activity_on_lipopolysaccharide_induced_nitric_oxide_production_ DB - PRIME DP - Unbound Medicine ER -