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Cytotoxic Sesquiterpenoids and Diarylheptanoids from the Rhizomes of Curcuma elata Roxb.

Ratchanaporn Chokchaisiri, Prapapan Pimkaew, Pawinee Piyachaturawat, Rattana Chalermglin and Apichart Suksamrarn

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand

Department of Chemistry, School of Science, University of Phayao, Maeka, Muang, Phayao 56000, Thailand

Toxicology Graduate Program

Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand

Department of Chemistry, Faculty of Science and Technology, Rajabhat Chandrakasem University, Bangkok 10900, Thailand

Abstract: The present study was aimed to investigate the chemical constituents of Curcuma elata Roxb. (Zingiberaceae) rhizomes originating in Thailand. Ten sesquiterpenes, germacrone (1), curzerenone (2), isofuranodienone (3), furanodienone (4), curdione (5), neocurdione (6), zederone (7), curcumenone (8), 13- hydroxygermacrone (9) and zedoarondiol (10), and four diarylheptanoids, 3-hydroxy- 5-platyphyllone (11), (3S)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (12), centrolobol (13) and (3 S )- 1- (3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (14) were isolated for the first time from the rhizomes of this plant. The structures of the isolated compounds were identified by comparison of the spectroscopic and physical data with those of the reported values and the stereochemistry at the asymmetric carbon was determined by the modified Mosher’s method and, in some cases, was confirmed by comparison of optical rotation data with literature. Compounds 12 and 13 exhibited strong cytotoxic activity against KB cell line, whereas compounds 4, 9 and 12-14 showed strong cytoxicity against NCI-H187 cell line.

Keywords: Curcuma elata ; Zingiberaceae; sesquiterpenoids ; diarylheptanoids; cytotoxicity . © 2014 ACG Publications. All rights reserved.