Naphthalenone derivatives from Berrya ammonilla with inhibitory activity on superoxide generation and elastase release by neutrophils

JJ Chen; SK Chien; T Chou; TL Hwang; DC Wei; IS Chen; SZ Yang; HC Liao; CC Ho

doi:10.1055/s-0030-1264645

Planta Medica, Inhaltsverzeichnis

Naphthalenone derivatives from Berrya ammonilla with inhibitory activity on superoxide generation and elastase release by neutrophils

JJ Chen ¹, SK Chien ¹, T Chou ², TL Hwang ³, DC Wei ¹, IS Chen ², SZ Yang ⁴, HC Liao ¹, CC Ho ¹

¹Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, No. 20, Weishin Rd., Yanpu Shiang, Pingtung 907, Taiwan
²Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
³Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan
⁴Department of Forest Resource, Management and Technology, National Pingtung University of Science and Technology, Pingtung 912, Taiwan

Abstract

Berrya ammonilla Roxb. (Tiliaceae) is a large tree, distributed in southern India, Ceylon, Philippines, and Taiwan [1]. The plants of the family Tiliaceae are rich in flavonoids with flavones, flavanones, flavans, and biflavans as the major

constituents, some of which have demonstrated cytotoxic and antiplatelet aggregation activities. In our studies on constituents of Formosan plants for in vitro inhibitory activity on neutrophil proinflammatory responses, B. ammonilla has been found to be an active species. Five new naphthalenone derivatives, berryammone A (1), berryammone B (2), berryammone C (3), 6-O-methylberryammone C (4), and 4-O-methylberryammone C (5) and eleven known compounds (6–16) have been isolated and identified from the stem of B. ammonilla. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 2, 3, 5, (+)-pinoresinol (6), and 3-epi-betulinic acid (12) exhibited inhibition (IC50 ≤1.58µg/mL) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, and 5 also inhibited fMLP/CB induced elastase release with IC₅₀values ≤1.21µg/mL.

Fig.1

Acknowledgements: This work was supported by grant from the National Science Council of the Republic of China.

References: 1. Robson, N.K.B. Tiliaceae in Flora of Taiwan. 2nd edition. Editorial Committee of the Flora of Taiwan, Taipei, Taiwan: 1996; Vol. 3: 694–714.