Planta Med 2012; 78(10): 995-1001
DOI: 10.1055/s-0031-1298580
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Geranyl Flavonoid Derivatives from the Fresh Leaves of Artocarpus communis and Their Anti-inflammatory Activity

Chin-Lin Hsu
1   School of Nutrition, Chung Shan Medical University and Department of Nutrition, Chung Shan Medical University Hospital, Taichung, Taiwan
,
Fang-Rong Chang
2   Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Pei-Yu Tseng
1   School of Nutrition, Chung Shan Medical University and Department of Nutrition, Chung Shan Medical University Hospital, Taichung, Taiwan
,
Yi-Fen Chen
1   School of Nutrition, Chung Shan Medical University and Department of Nutrition, Chung Shan Medical University Hospital, Taichung, Taiwan
,
Mohamed El-Shazly
2   Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
3   Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Ain-Shams University, Cairo, Egypt
,
Ying-Chi Du
2   Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Song-Chwan Fang
4   Department of Food Nutrition, Chung Hwa University of Medical Technology, Tainan, Taiwan
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 01. August 2011
revised 02. April 2012

accepted 24. April 2012

Publikationsdatum:
22. Mai 2012 (online)

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Abstract

Breadfruit (Artocarpus communis) is a widely distributed crop in tropical and subtropical regions of the world. It is used in Southeast Asia and India to treat several inflammatory disorders. The aim of this study was to investigate the presence of anti-inflammatory flavonoids in A. communis leaves. Three new geranyl flavonoids, arcommunol C (1), arcommunol D (3), and 5′-geranyl-3,4,2′,4′-tetrahydroxychalcone (5), together with four known compounds, prostratol (2), arcommunol E (4), 3′-geranyl-3,4,2′,4′-tetrahydroxydihydrochalcone (6), and 3′-geranyl-3,4,2′,4′-tetrahydroxychalcone (7), were isolated from the leaves of A. communis. Compound 4 was isolated for the first time from natural sources. The anti-inflammatory activity of the isolated compounds (17) was evaluated by determining their inhibitory activity on the production of proinflammatory mediators in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 2, 3, and 4 suppressed the LPS-induced production of nitric oxide (NO) in RAW 264.7 cells with IC50 values of 8.13 ± 0.17, 18.45 ± 2.15, and 22.74 ± 1.74 µM, respectively. Furthermore, 2 decreased lipopolysaccharide (LPS)-mediated induction of protein expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW 264.7 cells. It was also found that 2 suppressed LPS-induced phosphorylation of JNK and p38 mitogen-activated protein kinase (MAPK) signaling.