A New Sesquiterpenoid and Bioactive Constituents of Curcuma zedoaria
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A NEW SESQUITERPENOID AND BIOACTIVE CONSTITUENTS OF Curcuma zedoaria
Jen-Wen Hsiao,1 Li-Chai Chen,2* Chien-Liang Lin,3 Tsung-Hsien Chang,4 Chun-Lin Chen,5 Ping-Jyun Sung,6 Ming-Jen Cheng,7* Ching-Ju Hung,8* and Jih-Jung Chen9,10*
A new sesquiterpenoid derivative, 13-hydroxy-1-oxocurzerenone (1), has been isolated from the rhizomes of Curcuma zedoaria, together with seven known compounds, 1-oxocurzerenone (2), curcolone (3), curcumenone (4), procurcumenol (5), curcumenol (6), zerumin A (7), and labda-8(17),12-diene-15,16-dial (8). The structure of the new compound 1 was determined through spectroscopic and MS analyses. Among the isolates, 13-hydroxy-1-oxocurzerenone (1), procurcumenol (5), and zerumin A (7) exhibited cytotoxicities, with IC50 values of 3.48, 12.36, and 14.08 μM, respectively, against the DLD-1 cell line. Curcumenone (4) and curcumenol (6) showed cytotoxic effects, with IC50 values of 8.97 and 10.26 μM, respectively, against the MCF-7 cell line. In addition, 13-hydroxy-1-oxocurzerenone (1), 1-oxocurzerenone (2), zerumin A (7), and labda-8(17),12-diene-15,16-dial (8) showed potent inhibition, with IC50 values of 4.63, 6.48, 16.57, and 18.45 μM, respectively, against LPS-induced NO generation. Keywords: Curcuma zedoaria, Zingiberaceae, rhizomes, sesquiterpenoid, 13-hydroxy-1-oxocurzerenone, cytotoxic activity, anti-inflammatory activity. Curcuma zedoaria (Christm.) Roscoe (Zingiberaceae) is a perennial rhizomatous herb, distributed in Bangladesh, Sri Lanka, and India, and is also widely cultivated in China, Japan, Brazil, Nepal, and Thailand [1]. Previous chemical studies of this plant have reported the isolation of several components including sesquiterpenoids [1–5], steroids [1], curcuminoids [1, 2], benzenoids [2], and their derivatives. This plant also exhibits diverse biological activities, including antiplatelet aggregating [1], cytotoxic [2], antibabesial [3], anti-inflammatory [4], and antifungal [5] activities. The current phytochemical investigation of the rhizomes of this plant has led to the isolation of a new sesquiterpenoid derivative, 13-hydroxy-1-oxocurzerenone (1), along with seven known compounds. The structural elucidation of 1 and the cytotoxic and anti-inflammatory properties of 1–8 are described herein. Extensive fractionation of the EtOAc soluble portion of a MeOH extract of rhizomes of Curcuma zedoaria using silica gel column chromatography (CC) and preparative TLC afforded compounds 1–8.
1) Department of Pharmacy, Pingtung Christian Hospital, 900, Pingtung, Taiwan; 2) Department of Pharmacy, Tajen University, 907, Pingtung, Taiwan; 3) Department of Pharmacy, FooYin University Hospital, 928, Pingtung, Taiwan; 4) Institute of Microbiology and Immunology, National Defense Medical Center, 114, Taipei, Taiwan; 5) Department of Biological Sciences, National Sun Yat-Sen University, 804, Kaohsiung, Taiwan; 6) National Museum of Marine Biology and Aquarium, 944, Pingtung, Taiwan; 7) Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (F
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