Orthoquinone and Naphthalenone Derivatives from Berrya ammonilla and Their Anti-Inflammatory Activity

Tsung-Hsien Chou; Sheng-Kan Chien; Tsong-Long Hwang; Dau-Chang Wei; Ih-Sheng Chen; Ping-Jyun Sung; Ming-Jen Cheng; Sheng-Zehn Yang; Ken-Ming Chang; Jih-Jung Chen

doi:10.1055/s-0031-1298460

Planta Medica, Inhaltsverzeichnis

Planta Med 2012; 78(09): 919-925
DOI: 10.1055/s-0031-1298460

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Orthoquinone and Naphthalenone Derivatives from Berrya ammonilla and Their Anti-Inflammatory Activity

Tsung-Hsien Chou

¹Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Sheng-Kan Chien

²Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan

,

Tsong-Long Hwang

³Graduate Institute of Natural Products, Chang Gung University, Taoyuan, Taiwan

,

Dau-Chang Wei

²Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan

,

Ih-Sheng Chen

¹Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Ping-Jyun Sung

⁴National Museum of Marine Biology and Aquarium, Pingtung, Taiwan

,

Ming-Jen Cheng

⁵Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan

,

Sheng-Zehn Yang

⁶Department of Forest Resource, Management and Technology, National Pingtung University of Science and Technology, Pingtung, Taiwan

,

Ken-Ming Chang

¹Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Jih-Jung Chen

²Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan

› Institutsangaben

Abstract

A new orthoquinone, berryammone A (1), and four new naphthalenone derivatives, berryammone B (2), berryammone C (3), 6-O-methylberryammone C (4), and 4-O-methylberryammone C (5), have been isolated from the stem of Berrya ammonilla, together with eleven known compounds (6–16). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolates, compounds 1–3, 5, (+)-pinoresinol (6), and betulinic acid (12) exhibited inhibition (IC₅₀ ≤ 4.41 µM) 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 IC₅₀ values ≤ 3.95 µM.

Key words

Berrya ammonilla - Tiliaceae - orthoquinone - naphthalenone - anti-inflammatory activity

Volltext

Referenzen

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