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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  
1   Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Sheng-Kan Chien  
2   Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan
,
Tsong-Long Hwang
3   Graduate Institute of Natural Products, Chang Gung University, Taoyuan, Taiwan
,
Dau-Chang Wei
2   Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan
,
Ih-Sheng Chen
1   Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Ping-Jyun Sung
4   National Museum of Marine Biology and Aquarium, Pingtung, Taiwan
,
Ming-Jen Cheng
5   Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan
,
Sheng-Zehn Yang
6   Department of Forest Resource, Management and Technology, National Pingtung University of Science and Technology, Pingtung, Taiwan
,
Ken-Ming Chang
1   Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Jih-Jung Chen
2   Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan
› Author Affiliations
Further Information

Publication History

received 16 January 2012
revised 21 March 2012

accepted 25 March 2012

Publication Date:
12 April 2012 (online)

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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

These authors contributed equally to this work.


Supporting Information

 

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