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Molecules 2014, 19(12), 20521-20535; doi:10.3390/molecules191220521

Biflavans, Flavonoids, and a Dihydrochalcone from the Stem Wood of Muntingia calabura and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses

1
Chung-Jen Junior College of Nursing, Health Sciences and Management, Chiayi 600, Taiwan
2
Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan
3
Department of Pharmacy, Tajen University, Pingtung 907, Taiwan
4
Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan
*
Authors to whom correspondence should be addressed.
Received: 28 October 2014 / Revised: 24 November 2014 / Accepted: 4 December 2014 / Published: 8 December 2014
(This article belongs to the Collection Bioactive Compounds)
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Abstract

Muntingia calabura (Tiliaceae) is commercially used in healthcare for the improvement of hypertension, myocardial infarction, spasm, and inflammatory conditions. Its fruits can be processed into jam and the leaves can be used for making tea. In the work reported herein a new biflavan, (M),(2S),(2''S)-,(P),(2S),(2''S)-7,8,3',4',5',7'',8'',3''',4''',5'''-decamethoxy-5,5'' biflavan (1), a new flavone, 4'-hydroxy-7,8,3',5'-tetramethoxyflavone (2), and a new dihydrochalcone, (R)-2',β-dihydroxy-3',4'-dimethoxydihydrochalcone (3), have been isolated from the stem wood of M. calabura, together with 12 known compounds (415). The structures of these new compounds were elucidated by the interpretations of extensive spectroscopic data. Among the isolated compounds, 5-hydroxy-7-methoxyflavone (5), quercetin (6), and (2S)-7-hydroxyflavanone (10) exhibited potent inhibition of fMLP-induced superoxide anion generation by human neutrophils, with IC50 values of 1.77 ± 0.70, 3.82 ± 0.46, and 4.92 ± 1.71 μM, respectively. View Full-Text
Keywords: Muntingia calabura; Tiliaceae; biflavan; flavone; dihydrochalcone; structure elucidation; anti-inflammatory activity Muntingia calabura; Tiliaceae; biflavan; flavone; dihydrochalcone; structure elucidation; anti-inflammatory activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Kuo, W.-L.; Liao, H.-R.; Chen, J.-J. Biflavans, Flavonoids, and a Dihydrochalcone from the Stem Wood of Muntingia calabura and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses. Molecules 2014, 19, 20521-20535.

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